Title: Holiday Rentals Winchester from £101: 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) ![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) # 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 [17 Dec - 18 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=175481&startDate=2025-12-17&endDate=2025-12-18&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [18 Dec - 19 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=175481&startDate=2025-12-18&endDate=2025-12-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [19 Dec - 21 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=175481&startDate=2025-12-19&endDate=2025-12-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [26 Dec - 28 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=175481&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winchester holiday rentals ![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/93000000/92430000/92423000/92422919/41f2434e.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) ![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) ### Bay Village Suites [](https://www.expedia.co.uk/Boston-Hotels-Rooms-At-Premier-Suites-Bay-Village.h92422919.Hotel-Information) Bay Village 6.4/10 (251) "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) ![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) ![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) ![Standard Studio (Unit 9) | Private kitchen | Mini-fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/90000000/89670000/89660600/89660519/41ff46e8.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 [](https://www.expedia.co.uk/Boston-Hotels-40-Temple-St.h89660519.Hotel-Information) 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 [](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/b86b51c3.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) ![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) ### Maverick Suites at 245 Newbury St [](https://www.expedia.co.uk/Boston-Hotels-245-Newbury-St.h89756238.Hotel-Information) Back Bay 8.2/10 Very good (154) "Room was clean and a good size. Location was perfect - walking distance to where I needed to be. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steven [](https://www.expedia.co.uk/Boston-Hotels-245-Newbury-St.h89756238.Hotel-Information) ![Deluxe Studio Suite (2nd Floor - Unit 202) | Individually furnished, iron/ironing board, free WiFi, bed sheets](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/96000000/95350000/95348100/95348090/5e51303d.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) ![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 [](https://www.expedia.co.uk/Boston-Hotels-28-Fenway.h95348090.Hotel-Information) Fenway–Kenmore 8.8/10 Excellent (326) "Good place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elijah £136 includes taxes & fees 18 Dec - 19 Dec [](https://www.expedia.co.uk/Boston-Hotels-28-Fenway.h95348090.Hotel-Information) ![Deluxe Studio | Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/46000000/45800000/45791600/45791512/5a1c0f00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Double Room | Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/46000000/45800000/45791600/45791512/f8b6e982.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) ![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) ### Temple Place Suites [](https://www.expedia.co.uk/Boston-Hotels-Temple-Place-Suites.h45791512.Hotel-Information) Downtown Boston 7.0/10 Good (326) "Pretty clean room, good location, resonable price." ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Beiyu £124 includes taxes & fees 18 Dec - 19 Dec [](https://www.expedia.co.uk/Boston-Hotels-Temple-Place-Suites.h45791512.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) ![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) ![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) ![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) ### Maverick Suites at 400 Columbus Ave [](https://www.expedia.co.uk/Boston-Hotels-400-Columbus-Avenue.h88179829.Hotel-Information) South End 7.4/10 Good (133) "Good location, compact room with everything you need. Very convenient self-service token-operated washing machine and dryer. Worth the price. No elevators, and bed is a bit small." ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Fanny Pei Yee [](https://www.expedia.co.uk/Boston-Hotels-400-Columbus-Avenue.h88179829.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 | Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/77000000/76170000/76165700/76165648/a3efc44d.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 | Living area](https://images.trvl-media.com/lodging/77000000/76170000/76165700/76165648/1df69efb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Premier Suites - Bay Village [](https://www.expedia.co.uk/Boston-Hotels-Premier-Suites-Bay-Village.h76165648.Hotel-Information) Bay Village 6.4/10 (252) "Clean room, good location, check in check out easily!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) HIEN T £101 includes taxes & fees 18 Dec - 19 Dec [](https://www.expedia.co.uk/Boston-Hotels-Premier-Suites-Bay-Village.h76165648.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) ![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) ![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) ### Global Luxury Suites Downtown Boston [](https://www.expedia.co.uk/Boston-Hotels-Global-Luxury-Suites-Downtown-Boston.h22788576.Hotel-Information) Chinatown 8.0/10 Very good (632) "This unit and location was perfect for my trip! Super close to many of the attractions that we wanted to visit. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lily £115 includes taxes & fees 18 Dec - 19 Dec [](https://www.expedia.co.uk/Boston-Hotels-Global-Luxury-Suites-Downtown-Boston.h22788576.Hotel-Information) ![City Studio | 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) ![Exterior](https://images.trvl-media.com/lodging/106000000/105960000/105956000/105955992/w1437h1080x242y0-1fcb4236.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/e3ac04a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Apartment | 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) ### The Chester Hotel [](https://www.expedia.co.uk/Boston-Hotels-The-Chester.h105955992.Hotel-Information) South End 8.6/10 Excellent (28) "The property was spacious and clean. We enjoyed our stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bryan £247 includes taxes & fees 6 Jan - 7 Jan 2026 [](https://www.expedia.co.uk/Boston-Hotels-The-Chester.h105955992.Hotel-Information) ![Desk, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/107000000/106220000/106214600/106214509/w1432h1080x244y0-f97316a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106220000/106214600/106214509/w1434h1080x243y0-a618f581.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106220000/106214600/106214509/w1443h1080x235y0-0b8745bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106220000/106214600/106214509/w1432h1080x244y0-d71b136a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Chester: Urban Chic Retreat In South End [](https://www.expedia.co.uk/Boston-Hotels-The-Chester-Urban-Chic-Retreat-In-South-End.h106214509.Hotel-Information) South End 10/10 Exceptional (1) "We had a great stay in Boston and the Chester was perfect for our trip. First time in Boston so we did a lot of the usual things, but this location was great to easily connect with bus and train options as we decided not to rent a vehicle. Space was comfortable for group of three - lots of shops and restaurants in the area. We were touring a lot, so didn’t spend a lot of time in the unit, but it was very comfortable and would definitely come back again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chad T. £274 includes taxes & fees 18 Dec - 19 Dec [](https://www.expedia.co.uk/Boston-Hotels-The-Chester-Urban-Chic-Retreat-In-South-End.h106214509.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/90000000/89810000/89806200/89806138/38511c45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/90000000/89810000/89806200/89806138/c7e28698.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/90000000/89810000/89806200/89806138/975d5cbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/90000000/89810000/89806200/89806138/f782cc4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Location Studio In Downtown Boston [](https://www.expedia.co.uk/Boston-Hotels-Best-Location-Studio-In-Downtown-Boston.h89806138.Hotel-Information) Downtown Boston 10/10 Exceptional (1) "In town to celebrate a special event." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Pam P. £163 includes taxes & fees 18 Dec - 19 Dec [](https://www.expedia.co.uk/Boston-Hotels-Best-Location-Studio-In-Downtown-Boston.h89806138.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/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/115000000/114400000/114397800/114397715/722951b0.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/eab62aac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Furnished Apartments near Encore Boston [](https://www.expedia.co.uk/Boston-Hotels-Furnished-Apartments-Near-Encore-Boston.h114397715.Hotel-Information) Everett 8.4/10 Very good (8) "Great place. Very clean. Great communication." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michele £168 includes taxes & fees 18 Dec - 19 Dec [](https://www.expedia.co.uk/Boston-Hotels-Furnished-Apartments-Near-Encore-Boston.h114397715.Hotel-Information) ![1 bedroom, WiFi](https://images.trvl-media.com/lodging/93000000/92510000/92502800/92502721/56692a27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, toaster](https://images.trvl-media.com/lodging/93000000/92510000/92502800/92502721/58f027ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/93000000/92510000/92502800/92502721/492d50de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, toaster](https://images.trvl-media.com/lodging/93000000/92510000/92502800/92502721/4140283f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern North End Studio [](https://www.expedia.co.uk/Boston-Hotels-Modern-North-End-Studio.h92502721.Hotel-Information) North End 9.0/10 Wonderful (10) "Convenient location. Great restaurants. Perfect apatment for a couple. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Holly V. £250 includes taxes & fees 29 Dec - 30 Dec [](https://www.expedia.co.uk/Boston-Hotels-Modern-North-End-Studio.h92502721.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/93000000/92370000/92364800/92364708/0191ba06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/93000000/92370000/92364800/92364708/be1b485a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Towels, soap, shampoo](https://images.trvl-media.com/lodging/93000000/92370000/92364800/92364708/8f14882d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/93000000/92370000/92364800/92364708/4fac5973.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Walk to Boston Common, Safe & Central Stay [](https://www.expedia.co.uk/Boston-Hotels-Walk-To-Boston-Common.h92364708.Hotel-Information) Beacon Hill 7.2/10 Good (17) "Property was excellent. Transportation was easy and communication with host was great. Thanks for a great vacation in beautiful Boston." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) john £224 includes taxes & fees 8 Jan - 9 Jan 2026 [](https://www.expedia.co.uk/Boston-Hotels-Walk-To-Boston-Common.h92364708.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/73000000/72690000/72689800/72689792/50790669.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/73000000/72690000/72689800/72689792/810b1ae6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, Internet](https://images.trvl-media.com/lodging/73000000/72690000/72689800/72689792/fb45de89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/73000000/72690000/72689800/72689792/1cca5427.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Studio Steps from Boston Common and Theaters [](https://www.expedia.co.uk/Boston-Hotels-Cozy-Studio-Steps-From-Boston-Common-And-Theaters.h72689792.Hotel-Information) Bay Village 7.4/10 Good (10) "Was clean and the location was perfect for my stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Laurie F. £184 includes taxes & fees 18 Dec - 19 Dec [](https://www.expedia.co.uk/Boston-Hotels-Cozy-Studio-Steps-From-Boston-Common-And-Theaters.h72689792.Hotel-Information) ![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/104000000/103110000/103106200/103106122/12b94653.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/104000000/103110000/103106200/103106122/31b86770.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/104000000/103110000/103106200/103106122/62b779f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/104000000/103110000/103106200/103106122/d04e748e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Perfect One Bedroom Stay In Downtown Boston! [](https://www.expedia.co.uk/Boston-Hotels-Perfect-One-Bedroom-Stay-In-Downtown-Boston.h103106122.Hotel-Information) Downtown Boston 8.6/10 Excellent (17) "Temple Place Suites was a great place to stay for our few days in Boston. We loved being across from Boston Commons, near great bakerys and cafes. It was a comfortable apartment with great space and plenty of amenities. Staff was great at communicating about check in, building codes and check out. Wished there were dish towels and wash cloths. Otherwise, it was great!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christine £166 includes taxes & fees 18 Dec - 19 Dec [](https://www.expedia.co.uk/Boston-Hotels-Perfect-One-Bedroom-Stay-In-Downtown-Boston.h103106122.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/103000000/102370000/102364000/102363922/7173e9ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/103000000/102370000/102364000/102363922/b1c18589.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/103000000/102370000/102364000/102363922/c07cefd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/103000000/102370000/102364000/102363922/bcf61f13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Perfetto North End 1brm [](https://www.expedia.co.uk/Boston-Hotels-Perfetto-North-End-1brm.h102363922.Hotel-Information) North End 10/10 Exceptional (11) "The location was perfect - we would stay here again.The description and pictures are accurate." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kenna E. £277 includes taxes & fees 28 Dec - 29 Dec [](https://www.expedia.co.uk/Boston-Hotels-Perfetto-North-End-1brm.h102363922.Hotel-Information) ![TV, offices](https://images.trvl-media.com/lodging/90000000/89810000/89806200/89806135/98fb199d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/90000000/89810000/89806200/89806135/d112c10b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/90000000/89810000/89806200/89806135/ba77e7a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/90000000/89810000/89806200/89806135/e687838b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Come Visit Boston and Stay In Our Homey Studio [](https://www.expedia.co.uk/Boston-Hotels-Come-Visit-Boston-And-Stay-In-Our-Homey-Studio.h89806135.Hotel-Information) Downtown Boston 8.8/10 Excellent (3) "Great central location! Tiny but super !would come back . Great food , bars, brewery , breakfast at our doorstep. By the park too!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dean and Courtenay M. £163 includes taxes & fees 24 Dec - 25 Dec [](https://www.expedia.co.uk/Boston-Hotels-Come-Visit-Boston-And-Stay-In-Our-Homey-Studio.h89806135.Hotel-Information) ![Smart TV, books](https://images.trvl-media.com/lodging/74000000/73130000/73124700/73124640/2cff64bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/74000000/73130000/73124700/73124640/70eef4dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, memory-foam beds, blackout curtains, iron/ironing board](https://images.trvl-media.com/lodging/74000000/73130000/73124700/73124640/ef3bcee3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/74000000/73130000/73124700/73124640/7b30d7b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### King Bed Loft in the Heart of Downtown Boston [](https://www.expedia.co.uk/Boston-Hotels-King-Bed-Loft-In-The-Heart-Of-Downtown-Boston.h73124640.Hotel-Information) Downtown Boston 10/10 Exceptional (37) "It was my first time staying here, and the room was very clean and fresh. The staff were extremely friendly and helpful, and the facilities were perfect. I will definitely stay here again, and I highly recommend it to anyone." ![Japan](https://a.travel-assets.com/egds/marks/flags/jp.svg) MINEKI £277 includes taxes & fees 27 Dec - 28 Dec [](https://www.expedia.co.uk/Boston-Hotels-King-Bed-Loft-In-The-Heart-Of-Downtown-Boston.h73124640.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/79000000/78770000/78763900/78763861/127156b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78770000/78763900/78763861/ba0817f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/79000000/78770000/78763900/78763861/9dd306c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/79000000/78770000/78763900/78763861/44314df0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### ♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥ [](https://www.expedia.co.uk/Boston-Hotels-Historic-StudioMinutes-To-SalemBeachesOld-Town-MarbleheadPrivate-Parking.h78763861.Hotel-Information) Marblehead 10/10 Exceptional (70) "The property was in a great location and within walking distance of restaurants and activities. Would definitely stay here again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Pamela O. £168 includes taxes & fees 18 Dec - 19 Dec [](https://www.expedia.co.uk/Boston-Hotels-Historic-StudioMinutes-To-SalemBeachesOld-Town-MarbleheadPrivate-Parking.h78763861.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=2025-12-31&endDate=2026-01-01®ionId=175481&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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 ![The Arcadian Hotel](https://images.trvl-media.com/lodging/32000000/31100000/31097800/31097754/f8ad7683_y.jpg) ### The Arcadian Hotel 10/10 Excellent "Very clean and the staff was friendly. Parking is a little tricky but that's to be expected. Would definitely go back. " [](https://expedia.co.uk/Boston-Hotels-Arcadian-Hotel-Brookline.h31097754.Hotel-Information) ![Harborside Inn Of Boston](https://images.trvl-media.com/lodging/1000000/210000/202900/202814/b3140789_y.jpg) ### Harborside Inn Of Boston 10/10 Excellent "The room was larger than expected - clean and well located. Parking was discounted but a little distance from the hotel " [](https://expedia.co.uk/Boston-Hotels-Harborside-Inn-Of-Boston.h202814.Hotel-Information) ![citizenM Boston Back Bay](https://images.trvl-media.com/lodging/97000000/97000000/96998900/96998829/90056141_y.jpg) ### citizenM Boston Back Bay 10/10 Excellent "Great stay " [](https://expedia.co.uk/Boston-Hotels-CitizenM-Boston-Back-Bay.h96998829.Hotel-Information) ![Encore Boston Harbor](https://images.trvl-media.com/lodging/38000000/37060000/37057200/37057112/9dbd3cd5_y.jpg) ### Encore Boston Harbor 10/10 Excellent "Didn't have breakfast" [](https://expedia.co.uk/Boston-Hotels-Encore-Boston-Harbor.h37057112.Hotel-Information) ![Boston Harbor Hotel](https://images.trvl-media.com/lodging/1000000/30000/26200/26146/37dc487b_y.jpg) ### Boston Harbor Hotel 10/10 Excellent "The staff and room were excellent." [](https://expedia.co.uk/Boston-Hotels-Boston-Harbor-Hotel.h26146.Hotel-Information) ![Copley Square Hotel, a FOUND Hotel](https://images.trvl-media.com/lodging/1000000/20000/16100/16067/72cd2881_y.jpg) ### Copley Square Hotel, a FOUND Hotel 10/10 Excellent "Thanks for the great room!" [](https://expedia.co.uk/Boston-Hotels-Copley-Square-Hotel.h16067.Hotel-Information) ![Seaport Hotel Boston](https://images.trvl-media.com/lodging/1000000/80000/79900/79888/fa9777a9_y.jpg) ### Seaport Hotel Boston 10/10 Excellent "The staff was incredibly friendly. That bed was comfy. The room was clean. It was in a great location. The pool and fitness center were fantastic. We loved it." [](https://expedia.co.uk/Boston-Hotels-Seaport-Hotel-Boston.h79888.Hotel-Information) ![The Dagny Boston](https://images.trvl-media.com/lodging/1000000/160000/151300/151201/4c15d693_y.jpg) ### The Dagny Boston 10/10 Excellent "Beautiful hotel in a perfect location. The staff was friendly and efficient. We will definitely stay again. " [](https://expedia.co.uk/Boston-Hotels-Hilton-Boston-DowntownFaneuil-Hall.h151201.Hotel-Information) ![Hilton Boston Park Plaza](https://images.trvl-media.com/lodging/1000000/10000/4300/4215/6e9f8959_y.jpg) ### Hilton Boston Park Plaza 10/10 Excellent "Yes the room was very clean and comfortable. " [](https://expedia.co.uk/Boston-Hotels-Boston-Park-Plaza.h4215.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 £101 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? ### What are some of the best holiday rentals that Winchester has to offer? ### What can I see and do in Winchester? ### What are holiday rentals like in Winchester? ![](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. 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