Title: Holiday Rentals Winchester from £118: Find Short-Term Rentals & Holiday Accommodations | Expedia.co.uk [Winchester Travel Guide](https://expedia.co.uk/Winchester.dx175481)[Hotels in Winchester](https://expedia.co.uk/Winchester-Hotels.d175481.Travel-Guide-Hotels)[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) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Holiday Rentals in Winchester - ![](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 ## Check prices for these dates Tonight [1 Nov - 2 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=175481&startDate=2025-11-01&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [2 Nov - 3 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=175481&startDate=2025-11-02&endDate=2025-11-03&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [7 Nov - 9 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=175481&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [14 Nov - 16 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=175481&startDate=2025-11-14&endDate=2025-11-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Holiday Rentals in Winchester ![Deluxe Studio | 1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/46000000/45800000/45791600/45791512/5a1c0f00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Apartment | Private kitchen | Fridge, microwave, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/46000000/45800000/45791600/45791512/5c22409f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/46000000/45800000/45791600/45791512/f74aa0fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Apartment, 1 Double Bed with Sofa bed | Private kitchen | Fridge, microwave, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/46000000/45800000/45791600/45791512/342a0357.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Temple Place Suites Downtown Boston 7.0/10 Good (307) "Very convenient place to stay, near transportation and waking distance to historic points and shopping. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carolina £126 includes taxes & fees 1 Dec - 2 Dec [](https://www.expedia.co.uk/Boston-Hotels-Temple-Place-Suites.h45791512.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/3000000/2680000/2673500/2673422/846eaaee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hiking](https://images.trvl-media.com/lodging/3000000/2680000/2673500/2673422/552e92d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/3000000/2680000/2673500/2673422/w637h436x0y0-f81097e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Room, 2 Queen Beds | Desk, iron/ironing board, free Internet, bed sheets](https://images.trvl-media.com/lodging/3000000/2680000/2673500/2673422/1d3abb35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Crescent Suites Hotel South Side 9.6/10 Exceptional (1120) "Great Hotel. Super friendly staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael £124 includes taxes & fees 23 Nov - 24 Nov [](https://www.expedia.co.uk/Boston-Hotels-Crescent-Suites-Hotel.h2673422.Hotel-Information) ![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/77000000/76170000/76165700/76165648/w837h480x0y0-3c5d7594.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Double Room | Living area](https://images.trvl-media.com/lodging/77000000/76170000/76165700/76165648/1df69efb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/77000000/76170000/76165700/76165648/w843h480x0y0-ebedf864.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Double Room, Shared Bathroom | Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/77000000/76170000/76165700/76165648/b3807f6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Premier Suites - Bay Village Bay Village 6.4/10 (241) "Clean room, good location, check in check out easily!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) HIEN T £154 includes taxes & fees 20 Nov - 21 Nov [](https://www.expedia.co.uk/Boston-Hotels-Premier-Suites-Bay-Village.h76165648.Hotel-Information) ![Desk, laptop workspace, free WiFi, bed sheets](https://images.trvl-media.com/lodging/93000000/92430000/92423000/92422919/55a7f850.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, free WiFi, bed sheets](https://images.trvl-media.com/lodging/93000000/92430000/92423000/92422919/7e78cb5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hair dryer, towels](https://images.trvl-media.com/lodging/93000000/92430000/92423000/92422919/a6a4dfac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/93000000/92430000/92423000/92422919/aa08e294.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bay Village Suites Bay Village 6.4/10 (239) "Great location nice neighborhood " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jose [](https://www.expedia.co.uk/Boston-Hotels-Rooms-At-Premier-Suites-Bay-Village.h92422919.Hotel-Information) ![Deluxe Studio Suite (2nd Floor - Unit 202) | 1 bedroom, individually furnished, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/96000000/95350000/95348100/95348090/aa77b438.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/96000000/95350000/95348100/95348090/2ec5ebb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/96000000/95350000/95348100/95348090/b68b988b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Staircase](https://images.trvl-media.com/lodging/96000000/95350000/95348100/95348090/w6052h4023x0y0-a9f7e4a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Maverick Suites at 28 Fenway Fenway–Kenmore 8.8/10 Excellent (307) "Great location! Clean and charming!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lee £163 includes taxes & fees 30 Nov - 1 Dec [](https://www.expedia.co.uk/Boston-Hotels-28-Fenway.h95348090.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/41000000/40220000/40217700/40217649/65d878ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Individually furnished, laptop workspace, free cots/infant beds, WiFi](https://images.trvl-media.com/lodging/41000000/40220000/40217700/40217649/9d234e98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/41000000/40220000/40217700/40217649/e57df49b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![55-inch flat-screen TV with cable channels, TV](https://images.trvl-media.com/lodging/41000000/40220000/40217700/40217649/f7c8df6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 907 Main Hotel Central Square, Sonder by Marriott Bonvoy Central Square 8.2/10 Very good (533) "beautiful stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary L £118 includes taxes & fees 23 Nov - 24 Nov [](https://www.expedia.co.uk/Boston-Hotels-Sonder-907-Main.h40217649.Hotel-Information) ![Lobby lounge](https://images.trvl-media.com/lodging/23000000/22790000/22788600/22788576/eaf6c86d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Apartment, 2 Bedrooms, Balcony, City View | View from room](https://images.trvl-media.com/lodging/23000000/22790000/22788600/22788576/1b8fe5c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Apartment, 1 Bedroom | Living area | Smart TV](https://images.trvl-media.com/lodging/23000000/22790000/22788600/22788576/1efec715.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Apartment, 1 Queen Bed with Sofa bed | Private kitchen | Full-sized fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/23000000/22790000/22788600/22788576/d9d7b4dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Global Luxury Suites Downtown Boston Chinatown 8.0/10 Very good (617) "The property looks much better inside than out Was just a couple of blocks to get to boston commons and T transportation. Staff was really nice " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Teresa [](https://www.expedia.co.uk/Boston-Hotels-Global-Luxury-Suites-Downtown-Boston.h22788576.Hotel-Information) ![Interior entrance](https://images.trvl-media.com/lodging/90000000/89430000/89420300/89420220/41817f87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room | 1 bedroom, desk, laptop workspace, iron/ironing board](https://images.trvl-media.com/lodging/90000000/89430000/89420300/89420220/398cbf5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/90000000/89430000/89420300/89420220/56552ba9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room | 1 bedroom, desk, laptop workspace, iron/ironing board](https://images.trvl-media.com/lodging/90000000/89430000/89420300/89420220/fa1bc1da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Maverick Suites at 89 Marion Coolidge Corner South Side 8.4/10 Very good (262) "Great location for the event we were going to and very clean. Unfortunately the experience was marred by loud construction across the street occurring early in the morning. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristine £152 includes taxes & fees 30 Nov - 1 Dec [](https://www.expedia.co.uk/Boston-Hotels-89-Marion.h89420220.Hotel-Information) ![Individually furnished, laptop workspace, iron/ironing board, bed sheets](https://images.trvl-media.com/lodging/21000000/20300000/20296000/20295998/5ce8baff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Mini-fridge, microwave, electric kettle, cookware/dishes/utensils](https://images.trvl-media.com/lodging/21000000/20300000/20296000/20295998/07d4dfbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Individually furnished, laptop workspace, iron/ironing board, bed sheets](https://images.trvl-media.com/lodging/21000000/20300000/20296000/20295998/1bfee967.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/21000000/20300000/20296000/20295998/3d6292d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### No. 284 Back Bay Hotel, Sonder by Marriott Bonvoy Back Bay 9.2/10 Wonderful (946) "Fantastic location, clean and tidy room, easy self check-in and check-out, great communication from Sonder. Very pleased." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cathy £153 includes taxes & fees 16 Nov - 17 Nov [](https://www.expedia.co.uk/Boston-Hotels-No-284.h20295998.Hotel-Information) ![42-inch TV with satellite channels](https://images.trvl-media.com/lodging/89000000/88180000/88179900/88179829/bf03eabd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, stovetop, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/89000000/88180000/88179900/88179829/bb9bfcd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![42-inch TV with satellite channels](https://images.trvl-media.com/lodging/89000000/88180000/88179900/88179829/f70f107d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/89000000/88180000/88179900/88179829/6bdc1239.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Maverick Suites at 400 Columbus Ave South End 7.2/10 Good (128) "Good location -comfortable " ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) David £155 includes taxes & fees 30 Nov - 1 Dec [](https://www.expedia.co.uk/Boston-Hotels-400-Columbus-Avenue.h88179829.Hotel-Information) ![Rooftop terrace](https://images.trvl-media.com/lodging/60000000/59300000/59296500/59296491/a5dc30b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/60000000/59300000/59296500/59296491/606054a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/60000000/59300000/59296500/59296491/742d229a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Apartment, 1 Bedroom | Private kitchen | Full-sized fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/60000000/59300000/59296500/59296491/2b67c0b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Global Luxury Suites East Boston East Boston 6.8/10 (171) "I will not be staying there again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Malcolm £161 includes taxes & fees 26 Nov - 27 Nov [](https://www.expedia.co.uk/Boston-Hotels-Global-Luxury-Suites-East-Boston.h59296491.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/24000000/23400000/23391100/23391094/385a9f3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/24000000/23400000/23391100/23391094/240d30d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![42-inch flat-screen TV with digital channels, TV, streaming services](https://images.trvl-media.com/lodging/24000000/23400000/23391100/23391094/bd370fc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Individually furnished, desk, iron/ironing board, free cots/infant beds](https://images.trvl-media.com/lodging/24000000/23400000/23391100/23391094/144e4d8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sonder by Marriott Bonvoy Pierce Boston Apartments Fenway Fenway–Kenmore 8.8/10 Excellent (275) "Easy check in and clean property with in unit laundry" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sarah £159 includes taxes & fees 1 Dec - 2 Dec [](https://www.expedia.co.uk/Boston-Hotels-Sonder-Pierce-Boston.h23391094.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/90000000/89670000/89660600/89660519/0dd63623.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Studio (Unit 7) | Terrace/patio](https://images.trvl-media.com/lodging/90000000/89670000/89660600/89660519/44b2972c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Studio (Unit 9) | Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/90000000/89670000/89660600/89660519/33c8997c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Economy Studio (Unit 12) | Private kitchen | Mini-fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/90000000/89670000/89660600/89660519/1068f50a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Maverick Suites at 40 Temple St Beacon Hill 7.6/10 Good (102) "Great place to stay, in such a good location with everything you need nearby. Definitely recommend 😌" ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Jordan Elizabeth Marie £176 includes taxes & fees 30 Nov - 1 Dec [](https://www.expedia.co.uk/Boston-Hotels-40-Temple-St.h89660519.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/90000000/89760000/89756300/89756238/2e7614de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee/tea maker, paper towels](https://images.trvl-media.com/lodging/90000000/89760000/89756300/89756238/a0babb8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/90000000/89760000/89756300/89756238/7f1f7cfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/90000000/89760000/89756300/89756238/3f6f337b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Maverick Suites at 245 Newbury St Back Bay 8.2/10 Very good (150) "Clean. Great location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jake £159 includes taxes & fees 30 Nov - 1 Dec [](https://www.expedia.co.uk/Boston-Hotels-245-Newbury-St.h89756238.Hotel-Information) ![City Studio | 1 bedroom, Egyptian cotton sheets, premium bedding, memory-foam beds](https://images.trvl-media.com/lodging/106000000/105960000/105956000/105955992/4cdc32d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Apartment | Living area | 24-inch Smart TV with digital channels](https://images.trvl-media.com/lodging/106000000/105960000/105956000/105955992/2d8ce635.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Apartment | 1 bedroom, Egyptian cotton sheets, premium bedding, memory-foam beds](https://images.trvl-media.com/lodging/106000000/105960000/105956000/105955992/677325f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/106000000/105960000/105956000/105955992/w1437h1080x242y0-1fcb4236.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Chester Hotel South End 8.4/10 Very good (25) "The property was spacious and clean. We enjoyed our stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bryan £291 includes taxes & fees 6 Nov - 7 Nov [](https://www.expedia.co.uk/Boston-Hotels-The-Chester.h105955992.Hotel-Information) ![Apartment, 2 Bedrooms | Private kitchen | Mini-fridge, microwave, cookware/dishes/utensils, paper towels](https://images.trvl-media.com/lodging/79000000/78430000/78423000/78422939/07b376b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Studio | Individually decorated, individually furnished, laptop workspace](https://images.trvl-media.com/lodging/79000000/78430000/78423000/78422939/8315a4e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, 2 Bedrooms | Living area | 30-inch flat-screen TV with satellite channels, TV](https://images.trvl-media.com/lodging/79000000/78430000/78423000/78422939/c849e9a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room | Individually decorated, individually furnished, laptop workspace](https://images.trvl-media.com/lodging/79000000/78430000/78423000/78422939/b61106da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Maverick Suites at 402 Columbus Ave South End 8.0/10 Very good (65) "Loved how cozy and clean it was. Location was great, near many points of interest. Parking at an extra fee, but plenty of street parking in the area. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Isaiah Joel Santa £164 includes taxes & fees 30 Nov - 1 Dec [](https://www.expedia.co.uk/Boston-Hotels-402-Columbus-Ave.h78422939.Hotel-Information) ![Apartment | 1 bedroom, premium bedding, desk, iron/ironing board](https://images.trvl-media.com/lodging/23000000/22220000/22214100/22214064/156ba4d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Comfort Studio | 1 bedroom, premium bedding, desk, iron/ironing board](https://images.trvl-media.com/lodging/23000000/22220000/22214100/22214064/c76735bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Studio Suite | 1 bedroom, premium bedding, desk, iron/ironing board](https://images.trvl-media.com/lodging/23000000/22220000/22214100/22214064/10554b31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment | Living area | 42-inch flat-screen TV with satellite channels, TV, fireplace](https://images.trvl-media.com/lodging/23000000/22220000/22214100/22214064/0a6e2b49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charlesgate Suites Fenway–Kenmore 9.4/10 Exceptional (197) "Excellent location near Boston University, bars, restaurants, etc and just a few minute walk to Fenway. We had the downstairs suite which was extremely roomy and had a full kitchen. While there was no front desk, the reservation team was responsive, polite and helpful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Wendy £295 includes taxes & fees 30 Nov - 1 Dec [](https://www.expedia.co.uk/Boston-Hotels-The-Gryphon-House.h22214064.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/84000000/83400000/83395100/83395011/7e426cd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![40-inch flat-screen TV with digital channels, TV, streaming services](https://images.trvl-media.com/lodging/84000000/83400000/83395100/83395011/1814a3d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Queen Bed (Mobility Accessible, Transfer Shower) | 1 bedroom, individually decorated, individually furnished](https://images.trvl-media.com/lodging/84000000/83400000/83395100/83395011/d99b4d39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Suite, 1 Queen Bed with Sofa bed | Living room | 40-inch flat-screen TV with digital channels, TV, streaming services](https://images.trvl-media.com/lodging/84000000/83400000/83395100/83395011/152a4311.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sonder by Marriott Bonvoy The Magnolia Apartments Back Bay Back Bay 8.8/10 Excellent (77) "Excellent location in the heart of shops. Quiet and clean location. Highly recommend and would definitely stay again ❤️." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michelle £144 includes taxes & fees 1 Dec - 2 Dec [](https://www.expedia.co.uk/Boston-Hotels-Sonder-The-Magnolia.h83395011.Hotel-Information) ![Luxury Suite 2 | Living area | Smart TV, Netflix, Hulu, streaming services](https://images.trvl-media.com/lodging/104000000/103780000/103772900/103772852/e7938c37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Rooftop terrace](https://images.trvl-media.com/lodging/104000000/103780000/103772900/103772852/305fc3b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Suite 2 | Living area | Smart TV, Netflix, Hulu, streaming services](https://images.trvl-media.com/lodging/104000000/103780000/103772900/103772852/5706fa36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Suite 4 | Living area | Smart TV, Netflix, Hulu, streaming services](https://images.trvl-media.com/lodging/104000000/103780000/103772900/103772852/1eaf1ab5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Monty Boston Downtown Boston 9.4/10 Exceptional (26) "Beautiful and comfortable. Plenty of room and good location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary £607 includes taxes & fees 9 Nov - 10 Nov [](https://www.expedia.co.uk/Boston-Hotels-The-Monty-Boston.h103772852.Hotel-Information) ![Apartment | 1 bedroom, desk, laptop workspace, free WiFi](https://images.trvl-media.com/lodging/115000000/114400000/114397800/114397715/5e32bb52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment | 1 bedroom, desk, laptop workspace, free WiFi](https://images.trvl-media.com/lodging/115000000/114400000/114397800/114397715/722951b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment | 1 bedroom, desk, laptop workspace, free WiFi](https://images.trvl-media.com/lodging/115000000/114400000/114397800/114397715/fa86d68e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment | 1 bedroom, desk, laptop workspace, free WiFi](https://images.trvl-media.com/lodging/115000000/114400000/114397800/114397715/864a41d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Furnished Apartments near Encore Boston Everett 8.4/10 Very good (6) "Great place. Very clean. Great communication." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michele £188 includes taxes & fees 2 Nov - 3 Nov [](https://www.expedia.co.uk/Boston-Hotels-Furnished-Apartments-Near-Encore-Boston.h114397715.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=2025-11-15&endDate=2025-11-16®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-Holiday-Rentals.d175481.Travel-Guide-HolidayRentals)[Sign up, it's free](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Holiday-Rentals.d175481.Travel-Guide-HolidayRentals) ## Top Winchester Hotel Reviews ![Encore Boston Harbor](//images.trvl-media.com/lodging/38000000/37060000/37057200/37057112/9dbd3cd5_y.jpg) ### Encore Boston Harbor 10/10 Excellent "Perfectly clean and beautiful room. Entire resort is clean. Service is excellent. Quality is very high. The casino is pretty big. Plenty of table games open. Lots of slots. Drink service was fast and friendly. Restaurants were modern and classy." [](https://expedia.co.uk/Boston-Hotels-Encore-Boston-Harbor.h37057112.Hotel-Information) ![citizenM Boston North Station](//images.trvl-media.com/lodging/34000000/33880000/33870600/33870542/0eda38d5_y.jpg) ### citizenM Boston North Station 10/10 Excellent "Everything was amazing, I’d definitely stay again" [](https://expedia.co.uk/Boston-Hotels-CitizenM-Boston-North-Station.h33870542.Hotel-Information) ![The Godfrey Hotel Boston](//images.trvl-media.com/lodging/11000000/10120000/10118700/10118614/e4d256d2_y.jpg) ### The Godfrey Hotel Boston 10/10 Excellent "Good service, great room and location was great " [](https://expedia.co.uk/Boston-Hotels-The-Godfrey-Hotel-Boston.h10118614.Hotel-Information) ![Hilton Boston Logan Airport](//images.trvl-media.com/lodging/1000000/290000/281600/281536/23c65d09_y.jpg) ### Hilton Boston Logan Airport 10/10 Excellent "Clean room, great staff" [](https://expedia.co.uk/Boston-Hotels-Hilton-Boston-Logan-Airport.h281536.Hotel-Information) ![Hilton Boston Park Plaza](//images.trvl-media.com/lodging/1000000/10000/4300/4215/82ab675e_y.jpg) ### Hilton Boston Park Plaza 10/10 Excellent "Beautiful " [](https://expedia.co.uk/Boston-Hotels-Boston-Park-Plaza.h4215.Hotel-Information) ![Seaport Hotel Boston](//images.trvl-media.com/lodging/1000000/80000/79900/79888/fa9777a9_y.jpg) ### Seaport Hotel Boston 10/10 Excellent "Clean room and staff was great" [](https://expedia.co.uk/Boston-Hotels-Seaport-Hotel-Boston.h79888.Hotel-Information) ![Hampton Inn Boston - Logan Airport](//images.trvl-media.com/lodging/1000000/580000/578500/578419/w3839h2488x0y0-d5429574_y.jpg) ### Hampton Inn Boston - Logan Airport 10/10 Excellent "Staff went out of their way to help. Clean room and very comfortable." [](https://expedia.co.uk/Boston-Hotels-Hampton-Inn-Boston-Logan-Airport.h578419.Hotel-Information) ![citizenM Boston Back Bay](//images.trvl-media.com/lodging/97000000/97000000/96998900/96998829/90056141_y.jpg) ### citizenM Boston Back Bay 10/10 Excellent "I enjoying the hotel. Lots of dining options within walking distance. " [](https://expedia.co.uk/Boston-Hotels-CitizenM-Boston-Back-Bay.h96998829.Hotel-Information) ![Harborside Inn Of Boston](//images.trvl-media.com/lodging/1000000/210000/202900/202814/b3140789_y.jpg) ### Harborside Inn Of Boston 10/10 Excellent "The staff was super friendly, clean rooms, very neat hotel, walkable to several things in the city, subway stop right outside. Neighborhood was safe and quiet. Will definitely stay again. " [](https://expedia.co.uk/Boston-Hotels-Harborside-Inn-Of-Boston.h202814.Hotel-Information) ## Find out more about Winchester **Everything you need to know about** **Winchester** **holiday rentals** Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winchester holiday rental for you. At Expedia, you can take your pick from private holiday homes, [apartments](https://www.expedia.co.uk/aa/Apartments), cottages, [apart-hotels](https://www.expedia.co.uk/aa/ApartHotels), cabins, [villas](https://www.expedia.co.uk/aa/Villas)... The list goes on, and on… and on! There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winchester holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.  **Winchester holiday rentals: An excellent choice for every season** Whenever you want to travel, a warm welcome awaits you in Winchester. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in .  Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winchester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winchester holiday rentals we have selected for you start as low as £118 per night. Entering your travel dates in the search wizard you might find even better deals! **How to find incredible deals on Winchester rentals** At Expedia, we put the best Winchester holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.  To find some top Winchester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winchester holiday. If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winchester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.  ## Explore a world of travel with Expedia - Trending destinations on Expedia.co.uk - All accommodation types in Winchester ### Trending destinations on Expedia.co.uk - [Holiday Rentals in the Cotswold](https://www.expedia.co.uk/lp/b/vr/cotswold) - [Holiday Rentals in Lake District](https://www.expedia.co.uk/lp/b/vr/lake-district) - [Devon Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Devon.d6046196.Holiday-Rental-Destinations) - [Norfolk Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Norfolk.d6046223.Holiday-Rental-Destinations) - [Bedfordshire Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Bedfordshire.d6046189.Holiday-Rental-Destinations) - [Dorset Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Dorset.d6046198.Holiday-Rental-Destinations) - [Northumberland Holiday Rentals](https://www.expedia.com/Destinations-In-Northumberland.d6046225.Vacation-Rental-Destinations) - [Herefordshire Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Herefordshire.d6046203.Holiday-Rental-Destinations) - [Essex Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Essex.d6046201.Holiday-Rental-Destinations) - [Cumbria Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Cumbria.d6046194.Holiday-Rental-Destinations) - [Yorkshire Holiday Rentals](https://www.expedia.co.uk/Yorkshire-Holiday-Rentals.d6342462.Travel-Guide-HolidayRentals) - [South Wales Holiday Rentals](https://www.expedia.co.uk/South-Wales-Holiday-Rentals.d6054274.Travel-Guide-HolidayRentals) - [North Wales Holiday Rentals](https://www.expedia.co.uk/North-Wales-Holiday-Rentals.d6054276.Travel-Guide-HolidayRentals) - [London Holiday Rentals](https://www.expedia.co.uk/London-Holiday-Rentals.d178279.Travel-Guide-HolidayRentals) - [York Holiday Rentals](https://www.expedia.co.uk/York-Holiday-Rentals.d5489.Travel-Guide-HolidayRentals) - [Blackpool Holiday Rentals](https://www.expedia.co.uk/Blackpool-Holiday-Rentals.d619.Travel-Guide-HolidayRentals) - [Isle of Wight Holiday Rentals](https://www.expedia.com/Destinations-In-Isle-Of-Wight.d6046218.Vacation-Rental-Destinations) - [Scarborough Holiday Rentals](https://www.expedia.co.uk/Scarborough-Holiday-Rentals.d5680.Travel-Guide-HolidayRentals) - [Edinburgh Holiday Rentals](https://www.expedia.co.uk/Edinburgh-Holiday-Rentals.d6069845.Travel-Guide-HolidayRentals) - [Bath Holiday Rentals](https://www.expedia.co.uk/Bath-Holiday-Rentals.d6084496.Travel-Guide-HolidayRentals) - [Bournemouth Holiday Rentals](https://www.expedia.co.uk/Bournemouth-Holiday-Rentals.d654.Travel-Guide-HolidayRentals) - [England Holiday Rentals](https://www.expedia.co.uk/Destinations-In-England.d11218.Holiday-Rental-Destinations) - [Scotland Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Scotland.d11219.Holiday-Rental-Destinations) - [Cornwall Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Cornwall.d6046193.Holiday-Rental-Destinations) - [Wales Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Wales.d11220.Holiday-Rental-Destinations) - [Northern Ireland Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Northern-Ireland.d11221.Holiday-Rental-Destinations) - [Houseboats in Winchester](https://expedia.co.uk/Winchester-Houseboats.d175481-aaHouseboats.Travel-Guide-Accommodation) ## Frequently asked questions ### Can I find holiday rentals in Winchester? > Yes, there are holiday rentals in Winchester close to Winter Pond, or you can select a more secluded option if you're looking for a relaxing stay. Winchester is known for its football matches and lake views. ### What are some of the best holiday rentals that Winchester has to offer? > [Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC](https://www.expedia.co.uk/Boston-Hotels-Unit-1-Beautiful-Large-3-Bedroom2-Bathroom-Apartment-With-All-Amenities.h33506871.Hotel-Information) : This holiday home rental outside of Winchester is equipped with a patio, air conditioning and laundry facilities to help you feel comfortable during your stay. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. ### What can I see and do in Winchester? > While exploring the area, visit family-friendly sights like Winter Pond, or get outside and enjoy nature at Boston Common. TD Garden and Fenway Park are other popular places to visit in the area. ### What are holiday rentals like in Winchester? > Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winchester. Holiday rentals offer amenities such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about cleanliness, a holiday rental can provide a sense of safety away from shared hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for family trips. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels when you book in the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,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)