Title: Hotels in Winchester, MA - Best Winchester Hotels from £64 - Fully Refundable Options - Expedia.co.uk [Winchester Travel Guide](https://expedia.co.uk/Winchester.dx175481)[Holiday Rentals in Winchester](https://expedia.co.uk/Winchester-Holiday-Rentals.d175481.Travel-Guide-HolidayRentals)[Winchester Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Winchester.d175481.Car-Hire-Guide)[Winchester Holidays](https://expedia.co.uk/Winchester.d175481.Holidays-City-Breaks) ![Winchester Town Hall at 71 Mt Vernon Street in historic town center of Winchester, Middlesex County, Massachusetts MA, USA. ](https://images.trvl-media.com/place/175481/5b3e907d-d662-4314-947e-70c644534c55.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find hotels in Winchester, MA from £64 - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Go beyond your typical stay in Winchester Spa [](https://www.expedia.co.uk/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-01-23&d1=2026-01-23&endDate=2026-01-25&d2=2026-01-25&amenities=SPA_ON_SITE) Pool [](https://www.expedia.co.uk/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-01-23&d1=2026-01-23&endDate=2026-01-25&d2=2026-01-25&amenities=POOL) Apart hotel [](https://www.expedia.co.uk/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-01-23&d1=2026-01-23&endDate=2026-01-25&d2=2026-01-25&lodging=APART_HOTEL) Family friendly [](https://www.expedia.co.uk/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-01-23&d1=2026-01-23&endDate=2026-01-25&d2=2026-01-25&travelerType=family_friendly) Hot tub [](https://www.expedia.co.uk/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-01-23&d1=2026-01-23&endDate=2026-01-25&d2=2026-01-25&amenities=HOT_TUB) Apart­ment [](https://www.expedia.co.uk/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-01-23&d1=2026-01-23&endDate=2026-01-25&d2=2026-01-25&lodging=APARTMENT) Pet friendly [](https://www.expedia.co.uk/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-01-23&d1=2026-01-23&endDate=2026-01-25&d2=2026-01-25&amenities=PETS) Sea view [](https://www.expedia.co.uk/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-01-23&d1=2026-01-23&endDate=2026-01-25&d2=2026-01-25&amenities=OCEAN_VIEW) Condo [](https://www.expedia.co.uk/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-01-23&d1=2026-01-23&endDate=2026-01-25&d2=2026-01-25&lodging=CONDO) Waterpark [](https://www.expedia.co.uk/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-01-23&d1=2026-01-23&endDate=2026-01-25&d2=2026-01-25&amenities=WATER_PARK) House­boat [](https://www.expedia.co.uk/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-01-23&d1=2026-01-23&endDate=2026-01-25&d2=2026-01-25&lodging=HOUSE_BOAT) ## Check prices for these dates Tonight [9 Jan - 10 Jan](https://www.expedia.co.uk/Hotel-Search?regionId=175481&startDate=2026-01-09&endDate=2026-01-10&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [10 Jan - 11 Jan](https://www.expedia.co.uk/Hotel-Search?regionId=175481&startDate=2026-01-10&endDate=2026-01-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [9 Jan - 11 Jan](https://www.expedia.co.uk/Hotel-Search?regionId=175481&startDate=2026-01-09&endDate=2026-01-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [16 Jan - 18 Jan](https://www.expedia.co.uk/Hotel-Search?regionId=175481&startDate=2026-01-16&endDate=2026-01-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winchester hotels ![Terrace/patio](https://images.trvl-media.com/lodging/39000000/38980000/38980000/38979980/895877cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed, Refrigerator | Living area | 42-inch flat-screen TV with satellite channels, TV](https://images.trvl-media.com/lodging/39000000/38980000/38980000/38979980/b99bbada.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/39000000/38980000/38980000/38979980/fea8bce5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/39000000/38980000/38980000/38979980/86ae4f86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Boston Woburn [](https://www.expedia.co.uk/Boston-Hotels-Hampton-Inn-Woburn-Boston.h38979980.Hotel-Information) Woburn 9.0/10 Wonderful (1370) "Very good room and great breakfast!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rodrigo £86 includes taxes & fees 6 Feb - 7 Feb [](https://www.expedia.co.uk/Boston-Hotels-Hampton-Inn-Woburn-Boston.h38979980.Hotel-Information) ![Free daily buffet breakfast ](https://images.trvl-media.com/lodging/1000000/30000/23200/23170/d8d2abf3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/23200/23170/0f245c4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/30000/23200/23170/2ba9e68f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/23200/23170/f25454be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus New Englander [](https://www.expedia.co.uk/Boston-Hotels-Best-Western-Plus-New-Englander.h23170.Hotel-Information) Woburn 8.6/10 Excellent (1004) "Clean room, great and attentive staff, good breakfast !" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Adriana £73 includes taxes & fees 16 Jan - 17 Jan [](https://www.expedia.co.uk/Boston-Hotels-Best-Western-Plus-New-Englander.h23170.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/30000/24600/24545/10a49135.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/30000/24600/24545/b24b174a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/24600/24545/7abf11b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/24600/24545/2f902750.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sheraton Boston Needham Hotel [](https://www.expedia.co.uk/Boston-Hotels-Sheraton-Boston-Needham-Hotel.h24545.Hotel-Information) Needham 8.8/10 Excellent (1532) "Comfortable bed, quiet and great staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shauna £78 includes taxes & fees 22 Jan - 23 Jan [](https://www.expedia.co.uk/Boston-Hotels-Sheraton-Boston-Needham-Hotel.h24545.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/60000000/59840000/59831600/59831559/648e971c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/60000000/59840000/59831600/59831559/1d94a443.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/60000000/59840000/59831600/59831559/02f201ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, laptop workspace, blackout curtains](https://images.trvl-media.com/lodging/60000000/59840000/59831600/59831559/622d5d47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Watertown Boston [](https://www.expedia.co.uk/Boston-Hotels-Hampton-Inn-Suites-Watertown-Boston.h59831559.Hotel-Information) Watertown 9.4/10 Exceptional (1003) "The environment was nice, the room felt new, and the breakfast was very nice. We really enjoyed our stay." ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Jing £88 includes taxes & fees 18 Jan - 19 Jan [](https://www.expedia.co.uk/Boston-Hotels-Hampton-Inn-Suites-Watertown-Boston.h59831559.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/1000000/800000/796200/796159/bb22da0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ballroom](https://images.trvl-media.com/lodging/1000000/800000/796200/796159/5a4906c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/800000/796200/796159/c5791e43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/800000/796200/796159/9babae6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Nantasket Beach Resort [](https://www.expedia.co.uk/Boston-Hotels-Nantasket-Beach-Resort.h796159.Hotel-Information) Nantasket Beach 8.6/10 Excellent (1000) "Great room off season, great view of the ocean. Have stayed before and will be back!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patricia £110 includes taxes & fees 25 Jan - 26 Jan [](https://www.expedia.co.uk/Boston-Hotels-Nantasket-Beach-Resort.h796159.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/52000000/51270000/51263700/51263672/89b219e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/52000000/51270000/51263700/51263672/daeb0fc2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/52000000/51270000/51263700/51263672/fb438a59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/52000000/51270000/51263700/51263672/5666f87b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Boston Brookline, MA [](https://www.expedia.co.uk/Boston-Hotels-Hilton-Garden-Inn-Boston-Brookline.h51263672.Hotel-Information) Brookline 9.0/10 Wonderful (1000) "Clean, convenient location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tony £112 includes taxes & fees 25 Jan - 26 Jan [](https://www.expedia.co.uk/Boston-Hotels-Hilton-Garden-Inn-Boston-Brookline.h51263672.Hotel-Information) ![Courtyard](https://images.trvl-media.com/lodging/1000000/570000/565100/565095/4d49894a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/570000/565100/565095/243a6731.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/570000/565100/565095/34975101.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/570000/565100/565095/c1946c03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sonesta ES Suites Andover Boston [](https://www.expedia.co.uk/Andover-Hotels-Sonesta-ES-Suites-Andover-Boston.h565095.Hotel-Information) Andover 8.8/10 Excellent (1002) "The nicest hotel in the area. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Edna £92 includes taxes & fees 11 Jan - 12 Jan [](https://www.expedia.co.uk/Andover-Hotels-Sonesta-ES-Suites-Andover-Boston.h565095.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/30000000/29870000/29866100/29866090/c39bbe4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/30000000/29870000/29866100/29866090/d9276788.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/30000000/29870000/29866100/29866090/85d3579c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/30000000/29870000/29866100/29866090/9ba9146b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Whitney Hotel [](https://www.expedia.co.uk/Boston-Hotels-The-Whitney-Hotel.h29866090.Hotel-Information) Beacon Hill 9.6/10 Exceptional (501) "Our second stay there, love it" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steve £236 includes taxes & fees 26 Jan - 27 Jan [](https://www.expedia.co.uk/Boston-Hotels-The-Whitney-Hotel.h29866090.Hotel-Information) ![Lobby sitting area](https://images.trvl-media.com/lodging/32000000/31100000/31097800/31097754/dc8963ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/32000000/31100000/31097800/31097754/0ff2e99d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/32000000/31100000/31097800/31097754/ec5d67d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Individually furnished, free WiFi, bed sheets](https://images.trvl-media.com/lodging/32000000/31100000/31097800/31097754/54c45291.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Arcadian Hotel [](https://www.expedia.co.uk/Boston-Hotels-Arcadian-Hotel-Brookline.h31097754.Hotel-Information) Brookline 8.0/10 Very good (3880) "Great Hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Naika £102 includes taxes & fees 16 Jan - 17 Jan [](https://www.expedia.co.uk/Boston-Hotels-Arcadian-Hotel-Brookline.h31097754.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/26000000/25110000/25108500/25108453/73538c60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/26000000/25110000/25108500/25108453/26261323.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/26000000/25110000/25108500/25108453/2116de49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, blackout curtains, iron/ironing board](https://images.trvl-media.com/lodging/26000000/25110000/25108500/25108453/dd4d4a9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Chelmsford by IHG [](https://www.expedia.co.uk/Chelmsford-Hotels-Holiday-Inn-Express-Chelmsford.h25108453.Hotel-Information) Chelmsford 8.8/10 Excellent (1003) "Great place to stay comfortably " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rene £88 includes taxes & fees 22 Jan - 23 Jan [](https://www.expedia.co.uk/Chelmsford-Hotels-Holiday-Inn-Express-Chelmsford.h25108453.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/1000000/10000/4100/4054/4ee2b5dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/4100/4054/b57212de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/10000/4100/4054/59f7788e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down duvets, pillow-top beds, desk](https://images.trvl-media.com/lodging/1000000/10000/4100/4054/99039e28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Staypineapple, A Delightful Hotel, South End [](https://www.expedia.co.uk/Boston-Hotels-Staypineapple.h4054.Hotel-Information) South End 9.0/10 Wonderful (1001) "Friendly and helpful staff, clean hotel and cute decor. Also, a great bar downstairs! " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Jasmyn £72 includes taxes & fees 1 Feb - 2 Feb [](https://www.expedia.co.uk/Boston-Hotels-Staypineapple.h4054.Hotel-Information) ![Coffee service](https://images.trvl-media.com/lodging/1000000/30000/25800/25755/24932924.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/25800/25755/85454a8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/25800/25755/51852890.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/30000/25800/25755/26940b02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Quinta Inn & Suites by Wyndham Boston-Andover [](https://www.expedia.co.uk/Andover-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Boston-Andover.h25755.Hotel-Information) Andover 8.2/10 Very good (1970) "Nice room, free breakfast, staff very joyful " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kai £82 includes taxes & fees 1 Feb - 2 Feb [](https://www.expedia.co.uk/Andover-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Boston-Andover.h25755.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20400/20351/b04e2b5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dinner served](https://images.trvl-media.com/lodging/1000000/30000/20400/20351/ecfcd4d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Double Double | Individually furnished, desk, laptop workspace, blackout curtains](https://images.trvl-media.com/lodging/1000000/30000/20400/20351/654ed3da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/20400/20351/d5aec2a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lakeside Inn [](https://www.expedia.co.uk/Boston-Hotels-Lakeside-Inn.h20351.Hotel-Information) Wakefield 7.6/10 Good (2325) "Another great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brian £65 includes taxes & fees 26 Jan - 27 Jan [](https://www.expedia.co.uk/Boston-Hotels-Lakeside-Inn.h20351.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/130000/126800/126766/d3be416a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/130000/126800/126766/b9939440.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down duvets, desk, blackout curtains](https://images.trvl-media.com/lodging/1000000/130000/126800/126766/9def59a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down duvets, desk, blackout curtains](https://images.trvl-media.com/lodging/1000000/130000/126800/126766/25fbd437.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Place Boston/Medford [](https://www.expedia.co.uk/Boston-Hotels-Hyatt-Place-BostonMedford.h126766.Hotel-Information) Medford 8.4/10 Very good (1613) "Amazing stay and friendly staff! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Caterin £91 includes taxes & fees 17 Jan - 18 Jan [](https://www.expedia.co.uk/Boston-Hotels-Hyatt-Place-BostonMedford.h126766.Hotel-Information) ![Daily full breakfast (USD 17 per person)](https://images.trvl-media.com/lodging/1000000/20000/10700/10664/e89debc2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/10700/10664/41a30495.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/10700/10664/30da9526.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/10700/10664/ce7aefee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Boston/Waltham [](https://www.expedia.co.uk/Boston-Hotels-Hilton-Garden-Inn-BostonWaltham.h10664.Hotel-Information) Waltham 8.8/10 Excellent (1003) "Very clean room, quiet, we got the items we needed and had a very comfortable stay for the weekend!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alison £61 includes taxes & fees 6 Feb - 7 Feb [](https://www.expedia.co.uk/Boston-Hotels-Hilton-Garden-Inn-BostonWaltham.h10664.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/76000000/75900000/75893900/75893900/5c57af4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/76000000/75900000/75893900/75893900/083db75f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Italian cuisine](https://images.trvl-media.com/lodging/76000000/75900000/75893900/75893900/8201aecc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/76000000/75900000/75893900/75893900/33401160.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cambria Hotel Boston Somerville [](https://www.expedia.co.uk/Boston-Hotels-Cambria-Hotel-Boston-Somerville.h75893900.Hotel-Information) Spring Hill 9.6/10 Exceptional (1001) "Amazing hotel! Cozy lobby, friendly and helpful staff, clean and spacious room, valet parking. All around great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sandra £106 includes taxes & fees 2 Feb - 3 Feb [](https://www.expedia.co.uk/Boston-Hotels-Cambria-Hotel-Boston-Somerville.h75893900.Hotel-Information) ![Lobby sitting area](https://images.trvl-media.com/lodging/38000000/37210000/37207600/37207595/f4ef6c3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/38000000/37210000/37207600/37207595/738242f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast meal](https://images.trvl-media.com/lodging/38000000/37210000/37207600/37207595/3860e92d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/38000000/37210000/37207600/37207595/e3b4439e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn & Suites by Marriott Boston Logan Airport/Chelsea [](https://www.expedia.co.uk/Boston-Hotels-Fairfield-Inn-Suites-By-Marriott-Boston-Logan-AirportChelsea.h37207595.Hotel-Information) Chelsea 9.0/10 Wonderful (1001) "Very friendly staff and close to everything I wanted to see" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rachel ann £84 includes taxes & fees 25 Jan - 26 Jan [](https://www.expedia.co.uk/Boston-Hotels-Fairfield-Inn-Suites-By-Marriott-Boston-Logan-AirportChelsea.h37207595.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/28000000/27120000/27111700/27111655/36e1822d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/28000000/27120000/27111700/27111655/7388ff95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/28000000/27120000/27111700/27111655/295d4607.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/28000000/27120000/27111700/27111655/5eac132a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel 1868 [](https://www.expedia.co.uk/Boston-Hotels-Hotel-1868.h27111655.Hotel-Information) Agassiz 9.4/10 Exceptional (1000) "Clean rooms, great gym, friendly and helpful staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jose £85 includes taxes & fees 18 Jan - 19 Jan [](https://www.expedia.co.uk/Boston-Hotels-Hotel-1868.h27111655.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/11000000/10120000/10118300/10118255/f7f0b149.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property – evening/night](https://images.trvl-media.com/lodging/11000000/10120000/10118300/10118255/92e6efb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/11000000/10120000/10118300/10118255/b449b276.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, blackout curtains, iron/ironing board](https://images.trvl-media.com/lodging/11000000/10120000/10118300/10118255/ddf88a9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Porter Square Hotel [](https://www.expedia.co.uk/Boston-Hotels-Porter-Square-Hotel.h10118255.Hotel-Information) North Cambridge 9.2/10 Wonderful (1001) "This was a good place for a stay in a convenient location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Corey £85 includes taxes & fees 11 Jan - 12 Jan [](https://www.expedia.co.uk/Boston-Hotels-Porter-Square-Hotel.h10118255.Hotel-Information) ![Desk, laptop workspace, blackout curtains, iron/ironing board](https://images.trvl-media.com/lodging/1000000/550000/544800/544728/e81e653a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property – evening/night](https://images.trvl-media.com/lodging/1000000/550000/544800/544728/w3840h2557x0y3-f1135124.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/1000000/550000/544800/544728/89b9be47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![42-inch flat-screen TV with satellite channels, TV](https://images.trvl-media.com/lodging/1000000/550000/544800/544728/w3836h2560x4y0-6112db77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sonesta Simply Suites Boston Burlington [](https://www.expedia.co.uk/Boston-Hotels-Sonesta-Simply-Suites-Boston-Burlington.h544728.Hotel-Information) Burlington 9.0/10 Wonderful (158) "Good rooms, helpful staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Abhir £69 includes taxes & fees 16 Jan - 17 Jan [](https://www.expedia.co.uk/Boston-Hotels-Sonesta-Simply-Suites-Boston-Burlington.h544728.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.co.uk/Hotel-Search?startDate=2026-01-23&endDate=2026-01-24®ionId=175481&adults=2&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.co.uk/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Hotels.d175481.Travel-Guide-Hotels)[ Sign up, it's free ](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Hotels.d175481.Travel-Guide-Hotels) ## Stay near popular Winchester attractions ### Winter Pond Enjoy an outing to Winter Pond during your stay in Winchester. Discover the top-notch restaurants and acclaimed art galleries in this vibrant area. [See properties](https://www.expedia.co.uk/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621561930456) ## Learn more about Winchester Stroll along the shores of Mystic Lake, where locals gather for picnics and kayaking on sunny afternoons. History buffs can explore the Wright-Locke Farm, learning about sustainable agriculture while kids enjoy the farm animals and nature trails. [See all hotels in Winchester](https://www.expedia.co.uk/Hotel-Search?startDate=2026-01-23&endDate=2026-01-24&adults=2®ionId=175481) ![Winchester Town Hall at 71 Mt Vernon Street in historic town center of Winchester, Middlesex County, Massachusetts MA, USA. ](https://images.trvl-media.com/place/175481/5b3e907d-d662-4314-947e-70c644534c55.jpg?impolicy=fcrop&w=900&h=600&p=1&q=high) ## Top Winchester Hotel Reviews ![Harborside Inn Of Boston](https://images.trvl-media.com/lodging/1000000/210000/202900/202814/b3140789_y.jpg) ### Harborside Inn Of Boston 10/10 Excellent "everything was great!" [](https://expedia.co.uk/Boston-Hotels-Harborside-Inn-Of-Boston.h202814.Hotel-Information) ![Hilton Boston Back Bay](https://images.trvl-media.com/lodging/1000000/10000/6000/5928/f418fbdd_y.jpg) ### Hilton Boston Back Bay 10/10 Excellent "Great breakfast, comfortable rooms." [](https://expedia.co.uk/Boston-Hotels-Hilton-Boston-Back-Bay.h5928.Hotel-Information) ![Hyatt Place Boston/Seaport District](https://images.trvl-media.com/lodging/47000000/46530000/46521400/46521349/5fe1e844_y.jpg) ### Hyatt Place Boston/Seaport District 10/10 Excellent "Everything was great, room was nice and clean, staff was very accommodating and helpful " [](https://expedia.co.uk/Boston-Hotels-Hyatt-Place-BostonSeaport-District.h46521349.Hotel-Information) ![The Godfrey Hotel Boston](https://images.trvl-media.com/lodging/11000000/10120000/10118700/10118614/e4d256d2_y.jpg) ### The Godfrey Hotel Boston 10/10 Excellent "Excellent downtown location, valet parking, restaurants in and around the hotel, clean room, super friendly staff… George Howell coffee shop connected to hotel 👌 " [](https://expedia.co.uk/Boston-Hotels-The-Godfrey-Hotel-Boston.h10118614.Hotel-Information) ![The Revolution Hotel](https://images.trvl-media.com/lodging/31000000/30090000/30080300/30080227/cce5d2b3_y.jpg) ### The Revolution Hotel 10/10 Excellent "CC" [](https://expedia.co.uk/Boston-Hotels-The-Revolution-Hotel.h30080227.Hotel-Information) ![Hyatt Regency Boston](https://images.trvl-media.com/lodging/1000000/20000/17900/17845/24991d94_y.jpg) ### Hyatt Regency Boston 10/10 Excellent "The room was spacious! Great housekeeping. The location is also great! " [](https://expedia.co.uk/Boston-Hotels-Hyatt-Regency-Boston.h17845.Hotel-Information) ![citizenM Boston North Station](https://images.trvl-media.com/lodging/34000000/33880000/33870600/33870542/0eda38d5_y.jpg) ### citizenM Boston North Station 10/10 Excellent "The hotel was so modern and sleek! The bed and comforter were so comfortable! I would recommend to everyone! " [](https://expedia.co.uk/Boston-Hotels-CitizenM-Boston-North-Station.h33870542.Hotel-Information) ![Encore Boston Harbor](https://images.trvl-media.com/lodging/38000000/37060000/37057200/37057112/9dbd3cd5_y.jpg) ### Encore Boston Harbor 10/10 Excellent "Everything was great " [](https://expedia.co.uk/Boston-Hotels-Encore-Boston-Harbor.h37057112.Hotel-Information) ![The Lenox Hotel Boston](https://images.trvl-media.com/lodging/1000000/10000/6500/6446/db068914_y.jpg) ### The Lenox Hotel Boston 10/10 Excellent "I had an early flight in! I was exhausted, I called the Lenox and they allowed me early check in as a room was available! My 2nd time here and have not been disappointed! Honestly, my favorite hotel in Boston!" [](https://expedia.co.uk/Boston-Hotels-The-Lenox-Hotel-Boston.h6446.Hotel-Information) ## More cheap stays in Winchester ![Sonesta Simply Suites Boston Burlington](https://images.trvl-media.com/lodging/1000000/550000/544800/544728/a4844b99_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Sonesta Simply Suites Boston Burlington 130 Middlesex Tpke Burlington MA £69 16 Jan - 17 Jan includes taxes & fees 8.8/10 Excellent! (157 reviews) [](https://expedia.co.uk/Boston-Hotels-Sonesta-Simply-Suites-Boston-Burlington.h544728.Hotel-Information) ![Ramada by Wyndham Boston](https://images.trvl-media.com/lodging/1000000/10000/300/293/b875dc04_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Ramada by Wyndham Boston 800 Morrissey Blvd Boston MA £73 6 Feb - 7 Feb includes taxes & fees 6.8/10 (1,597 reviews) [](https://expedia.co.uk/Boston-Hotels-Ramada-By-Wyndham-Boston.h293.Hotel-Information) ![Hampton Inn & Suites Boston/Waltham](https://images.trvl-media.com/lodging/22000000/21910000/21904300/21904239/841c68d6_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hampton Inn & Suites Boston/Waltham 135 2nd Ave Waltham MA £81 19 Jan - 20 Jan includes taxes & fees 9.2/10 Wonderful! (1,608 reviews) [](https://expedia.co.uk/Boston-Hotels-Hampton-Inn-Suites-BostonWaltham.h21904239.Hotel-Information) ![Hampton Inn Boston Logan Airport Chelsea](https://images.trvl-media.com/lodging/49000000/48880000/48879900/48879812/bfe287d7_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hampton Inn Boston Logan Airport Chelsea 200 2nd Street Chelsea MA £81 11 Jan - 12 Jan includes taxes & fees 9/10 Wonderful! (2,723 reviews) [](https://expedia.co.uk/Boston-Hotels-Hampton-Inn-Boston-Logan-Airport-Chelsea.h48879812.Hotel-Information) ![enVision Hotel Boston Everett](https://images.trvl-media.com/lodging/18000000/17520000/17515300/17515205/09904e53_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### enVision Hotel Boston Everett 1834 Revere Beach Pkwy Everett MA £82 12 Jan - 13 Jan includes taxes & fees 8.4/10 Very Good! (1,002 reviews) [](https://expedia.co.uk/Boston-Hotels-EnVision-Hotel-Boston-Everett.h17515205.Hotel-Information) ![Comfort Inn & Suites Logan International Airport](https://images.trvl-media.com/lodging/1000000/550000/543800/543784/fa5d7891_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Comfort Inn & Suites Logan International Airport 85 American Legion Hwy Revere MA £87 25 Jan - 26 Jan includes taxes & fees 8.8/10 Excellent! (2,238 reviews) [](https://expedia.co.uk/Boston-Hotels-Comfort-Inn-Suites-Logan-International-Airport.h543784.Hotel-Information) ## Find out more about Winchester ### Top reasons to visit Winchester - **Scenic Outdoor Activities:** Winchester offers a variety of outdoor pursuits, including lovely parks and recreational areas perfect for families. - **Rich Historical Sites:** Explore charming attractions like the Winchester Discovery Centre and historic landmarks, including Winchester Cathedral. - **Vibrant Local Culture:** Wander through picturesque streets and immerse yourself in the friendly atmosphere of the town. - **Diverse Accommodation Options:** Choose from hotels and charming B&Bs, catering to all travellers, including pet-friendly and LGBTQIA-friendly stays. - **Convenient Location:** Winchester is ideally situated for day trips and easy access to nearby skiing and shopping. ### Find great hotels near Winchester Discover a range of accommodation options in Winchester, Massachusetts, perfect for every type of traveller. Whether you're seeking a convenient hotel for business or a charming bed & breakfast for a relaxing getaway, Winchester offers pet-friendly and LGBTQIA welcoming stays. From budget-friendly options to more luxurious experiences, you'll find the ideal place to unwind and explore this delightful town. - **[citizenM Boston North Station: ](https://www.expedia.co.uk/Boston-Hotels-CitizenM-Boston-North-Station.h33870542.Hotel-Information)** Emphasising a modern and innovative design, citizenM Boston North Station is a 4-star hotel that caters to business travellers seeking a vibrant and inclusive atmosphere. Located 4.3km from Winchester, this hotel is proud to welcome the LGBTQIA community and offers dedicated facilities such as a 24-hour business centre, meeting rooms, and coworking spaces. With a commitment to comfort, citizenM ensures guests enjoy contemporary rooms equipped with all the essentials for a productive stay, making it an excellent choice for professionals on the go. - **[Extended Stay America Suites - Boston - Saugus: ](https://www.expedia.co.uk/Boston-Hotels-WoodSpring-Suites-Boston-North.h19848478.Hotel-Information)** For those looking for adventure, Extended Stay America Suites - Boston - Saugus, situated 3.7km from Winchester, offers a unique blend of excitement and comfort. This pet-friendly accommodation is welcoming to the LGBTQIA community and provides opportunities for outdoor activities such as scooter rentals, ice skating, and horse riding nearby. The hotel features essential amenities for longer stays, making it ideal for guests who wish to explore the surrounding area while enjoying a home-like atmosphere. - **[Hyatt Regency Boston/Cambridge: ](https://www.expedia.co.uk/Boston-Hotels-Hyatt-Regency-BostonCambridge.h16079.Hotel-Information)** A refined choice for both business and leisure travellers, Hyatt Regency Boston/Cambridge is located 4.3km from Winchester. This 4-star hotel offers a seamless blend of professionalism and pet-friendly policies, welcoming the LGBTQIA community with open arms. Guests can benefit from conference spaces and other business amenities while enjoying the hotel's luxurious features. With a commitment to service and comfort, Hyatt Regency is perfect for those seeking an elegant environment paired with the convenience of being close to the vibrant city life. ### Where to stay near Winchester Winchester, Massachusetts, offers a delightful blend of outdoor activities and cultural experiences, making it ideal for family vacations. Explore the charming streets of Winchester city and immerse yourself in its friendly atmosphere. Just a short walk away, you can discover the vibrant local culture and historical sights. Whether you're wandering through picturesque neighbourhoods or enjoying the lush parks, Winchester promises an enriching getaway for all ages. - **[Boston: ](https://www.expedia.co.uk/Boston-Hotels.d178239.Travel-Guide-Hotels)** A vibrant metropolis located 5.0km from Winchester, Boston is renowned for its rich history and cultural diversity. Visitors can immerse themselves in a plethora of experiences, from educational institutions to lively music concerts and expansive shopping malls. The city’s landmarks, such as historic sports stadiums and conference venues, offer a glimpse into its sporting heritage and community events. With traveller numbers peaking in the summer and autumn, Boston is a bustling hub for family adventures and cultural exploration. - **[Woburn: ](https://www.expedia.co.uk/Woburn-Hotels.d10373.Travel-Guide-Hotels)** Situated a mere 1.2km from Winchester, Woburn is a charming city that attracts visitors throughout the year. Known for its family-friendly atmosphere and cultural experiences, Woburn boasts an array of shopping centres and educational venues. Its local attractions include beach areas and event conference venues, providing a perfect backdrop for leisure and entertainment. Peak travel seasons in April, July, and September bring a lively atmosphere, making Woburn an inviting destination for all. - **[West Medford: ](https://www.expedia.co.uk/West-Medford-Boston-Hotels.0-n173092-0.Travel-Guide-Filter-Hotels)** Just 1.2km from Winchester, West Medford is a picturesque neighbourhood known for its cultural and outdoor experiences. The area draws seasonal visitors, particularly in spring and late autumn. With a blend of educational institutions and shopping areas, West Medford offers a relaxed yet vibrant atmosphere. Notable landmarks include historic buildings and modern colleges, making it an intriguing destination for those interested in history and education, as well as outdoor pursuits. ### Things to do near Winchester Winchester, Massachusetts, is perfect for outdoor and cultural family vacations. Visitors can enjoy various activities, including educational experiences, shopping at the local mall, and skiing at nearby fields. For those looking for a day trip, Winchester offers a charming blend of leisure and exploration, making it an ideal destination for a delightful getaway. **Shopping** In Winchester, you can enjoy shopping at [Burlington Mall](https://www.expedia.co.uk/Burlington-Mall-Hotels.0-l6163632-0.Travel-Guide-Filter-Hotels), just 2.5km away, offering a vibrant mix of businesses and family entertainment. [Harvard Square](https://www.expedia.co.uk/Harvard-Square-Hotels.0-l6070079-0.Travel-Guide-Filter-Hotels) and [Boston Public Market](https://www.expedia.co.uk/Boston-Public-Market-Hotels.0-l553248621533117592-0.Travel-Guide-Filter-Hotels), both within 6-4.3km, provide a lively city atmosphere for unique gifts, perfect for a memorable shopping experience. **Recreation** [Agganis Arena](https://www.expedia.co.uk/Agganis-Arena-Hotels.0-l6229782-0.Travel-Guide-Filter-Hotels) offers an energetic atmosphere with various sports events, perfect for those seeking excitement. The [House of Blues Boston](https://www.expedia.co.uk/House-Of-Blues-Boston-Hotels.0-l6160608-0.Travel-Guide-Filter-Hotels) and [Hatch Shell](https://www.expedia.co.uk/Hatch-Shell-Hotels.0-l6192284-0.Travel-Guide-Filter-Hotels) provide vibrant music experiences, allowing you to unwind and enjoy live performances in a lively setting, just a short distance from Winchester. **Adventure** Horn Pond, located 1.2km from Winchester, offers a tranquil outdoor experience, perfect for leisurely walks and picnics. The Courageous Sailing Center, 4.3km away, provides thrilling water sports adventures. For scenic hiking, explore the Irish Heritage Trail, situated 5.0km from Winchester, showcasing beautiful landscapes. **Nightlife** In Winchester, the [LEGOLAND® Discovery Center](https://www.expedia.co.uk/LEGOLAND-Discovery-Center-Hotels.0-l553248621561930613-0.Travel-Guide-Filter-Hotels) provides a fun-filled arcadeAdventureZone perfect for families. For a cultural evening, the Somerville Theatre offers a blend of entertainment and romance. Enjoy a relaxed drink at Cambridge Common, an inviting pub ideal for lively conversation and a romantic atmosphere. ### Booking tips and Expedia advantages for Winchester For a budget-friendly visit to Winchester, Massachusetts, consider travelling during the off-peak months of December to February, when accommodation prices are lower. Sundays tend to be the least expensive days to stay, while Saturdays are pricier. Use Expedia's search tool to sort options by budget and package deals that combine hotels, flights, and activities for additional savings. Look for hotel deals and minute offers to maximise your budget. Don't forget to explore free local attractions to enrich your experience without overspending. - **The most and least expensive months on average to stay in a hotel:** The cheapest months to stay in Winchester are December to February, where the prices are slightly lower. This is in comparison to May and September to October, where prices are slightly higher. - **The most and least expensive days on average to stay in a hotel:** The least expensive day to stay in Winchester is Sunday. The most expensive day to stay in Winchester is Saturday. - **Find cheap hotels on Expedia:** Utilise Expedia's search tool to refine your preferences, such as budget, preferred location, and desired hotel type. To discover the most affordable options and offers, arrange the price filter from lowest to highest. - **Consider bundling your trip:** You can save money by combining your hotel stay in Winchester with your flights and activities through an Expedia package. ### Find the best attractions near Winchester Winchester, Massachusetts, is an ideal destination for outdoor enthusiasts and culture seekers alike, offering a family-friendly atmosphere. Visitors can explore notable attractions such as the Winchester Discovery Centre, Winchester Cathedral, and the historic Winchester Castle, along with the Great Hall. These sites provide a rich blend of history and urban parks, ensuring a fulfilling experience for travellers looking to immerse themselves in local culture and heritage. - **[Fenway Park: ](https://www.expedia.co.uk/Fenway-Park-Hotels.0-l6023384-0.Travel-Guide-Filter-Hotels)** Experience the rich history and vibrant atmosphere of one of America’s oldest ballparks, home to the Boston Red Sox. Enjoy a game or take a guided tour to learn about its iconic features and the passionate sports culture surrounding it. - **[Harvard University: ](https://www.expedia.co.uk/Harvard-University-Hotels.0-l6034936-0.Travel-Guide-Filter-Hotels)** Visit the world-renowned institution, steeped in tradition and academic excellence. Stroll through its picturesque campus, admire historic buildings, and soak up the intellectual culture that has shaped many leaders. - **[TD Garden: ](https://www.expedia.co.uk/TD-Garden-Hotels.0-l6070137-0.Travel-Guide-Filter-Hotels)** Discover this premier venue that hosts major sporting events and concerts, offering a dynamic atmosphere. Whether attending a game or a concert, you'll feel the energy of Boston's business and entertainment scene. ### Best time to go to Winchester The best time to visit Winchester can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Winchester falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Winchester falls in January, visitor numbers are average and weather is mostly sunny with light rain. | **![calendar](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)Pricing** | | ---------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------- | ------------------------------------------------------------------------------------------------------------- | | January | 28.6°F (-1.9°C) | Light Rain | Mostly Sunny | Average | Slightly Low | | February | 29.8°F (-1.2°C) | Light Rain | Mostly Cloudy | Slightly Low | Slightly Low | | March | 36.9°F (2.7°C) | Light Rain | Mostly Sunny | Average | Average | | April | 47.7°F (8.7°C) | Light Rain | Mostly Sunny | Slightly High | Average | | May | 58.3°F (14.6°C) | Light Rain | Mostly Sunny | Average | Slightly High | | June | 66.4°F (19.1°C) | Light Rain | Mostly Sunny | Average | Average | | July | 73.6°F (23.1°C) | Light Rain | Mostly Sunny | Slightly High | Average | | August | 72.3°F (22.4°C) | Light Rain | Mostly Sunny | Average | Average | | September | 65.3°F (18.5°C) | Light Rain | Mostly Sunny | Slightly High | Slightly High | | October | 54.9°F (12.7°C) | Light Rain | Mostly Sunny | Average | Slightly High | | November | 43.3°F (6.3°C) | Light Rain | Mostly Sunny | Slightly Low | Average | | December | 35.1°F (1.7°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly Low | ### The nearest major airports for your trip to Winchester For your visit to Winchester, Massachusetts, the primary airport is Boston Logan International Airport ([BOS](https://www.expedia.co.uk/Logan-Intl-Airport-Hotels.0-aBOS-0.Travel-Guide-Filter-Hotels)), situated 5.6km away. Nearby excellent hotels include the 5-star [Encore Boston Harbor](https://www.expedia.co.uk/Boston-Hotels-Encore-Boston-Harbor.h37057112.Hotel-Information), 1.9km from the airport, and both [The Langham](https://www.expedia.co.uk/Boston-Hotels-The-Langham.h2558.Hotel-Information) and [Boston Harbor Hotel](https://www.expedia.co.uk/Boston-Hotels-Boston-Harbor-Hotel.h26146.Hotel-Information), each 1.2km from BOS. Another option is Providence T.F. Green Airport ([PVD](https://www.expedia.co.uk/TF-Green-Airport-Hotels.0-aPVD-0.Travel-Guide-Filter-Hotels)), located 51.9km away, with the [Omni Providence Hotel](https://www.expedia.co.uk/Providence-Hotels-Omni-Providence-Hotel.h24536.Hotel-Information), [Renaissance Providence Downtown Hotel](https://www.expedia.co.uk/Providence-Hotels-Renaissance-Providence-Downtown-Hotel.h1636958.Hotel-Information), and [Graduate by Hilton Providence](https://www.expedia.co.uk/Providence-Hotels-Graduate-Providence.h20009389.Hotel-Information), all approximately 4.3km from the airport. Additionally, Manchester-Boston Regional Airport ([MHT](https://www.expedia.co.uk/Manchester-Boston-Regional-Airport-Hotels.0-aMHT-0.Travel-Guide-Filter-Hotels)) is 22.4km away, with hotels like [The Grand at Bedford Village Inn](https://www.expedia.co.uk/Manchester-Hotels-The-Bedford-Village-Inn.h1211321.Hotel-Information) and [DoubleTree by Hilton Manchester Downtown](https://www.expedia.co.uk/Manchester-Hotels-DoubleTree-By-Hilton-Manchester-Downtown.h19860.Hotel-Information), both 2.5km from MHT. ## Frequently asked questions ### When is the best time to go to Winchester? > As you delve into the peak season, which spans from April to June, you'll find that Winchester attracts a diverse array of visitors keen to experience its rich history and charming atmosphere. The city buzzes with activity during this time, with various events, such as the famous Winchester Science Festival, drawing in crowds and adding to the lively ambiance. > > > For those who relish outdoor adventures, spring is a delightful time to enjoy Winchester's scenic parks and the surrounding countryside. The mild weather allows for comfortable walks along the River Itchen or a leisurely bike ride through the nearby South Downs National Park. The blossoming flora enhances the beauty of your surroundings, providing a great backdrop for memorable photos. > > > If you're looking for a more budget-friendly option, consider visiting in November. While the weather may be cooler, with temperatures averaging around 5 to 10°C, the city is less crowded, allowing for a more intimate experience. You can still enjoy the historical sites without the hustle and bustle of peak tourist season. ### Can I cancel my hotel reservation on Expedia? ### How can I save on a Winchester hotel booking with Expedia? ### How much is the nightly rate at a Winchester hotel? ## Explore a world of travel with Expedia - Accommodation - Flights - Packages - Cars - Holiday Homes - Other - More ways to book - [3 Star Hotels in Somerville ](https://www.expedia.co.uk/3Star-Somerville-Hotels.s30-0-d55192.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Lexington ](https://www.expedia.co.uk/4Star-Lexington-Hotels.s40-0-d8601.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Belmont ](https://www.expedia.co.uk/5Star-Belmont-Hotels.s50-0-d78656.Travel-Guide-Filter-Hotels) - [Hotels near Alewife Station ](https://www.expedia.co.uk/Alewife-Station-Hotels.d6210670.Travel-Guide-Hotels) - [Arlington Hotels ](https://www.expedia.co.uk/Arlington-Hotels.d74693.Travel-Guide-Hotels) - [Belmont Hotels ](https://www.expedia.co.uk/Belmont-Hotels.d78656.Travel-Guide-Hotels) - 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