Title: Winchester Villas from CA $115 | Expedia.ca [Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d175481.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d175481.Travel-Guide-VacationRentals)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d175481.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/Winchester.d175481.Destination-Travel-Guides) ![Skyline of Boston](https://images.trvl-media.com/place/162713/d94e6534-0d00-46ec-b964-4dc54f45df9d.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Ana Lei # Search Winchester Villa Rentals from CA $115 - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](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 Next weekend [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2026-01-16&endDate=2026-01-18&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2026-01-23&endDate=2026-01-25&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2026-02-06&endDate=2026-02-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) No exact matches found, but these alternatives could be just right ## Recommended hotels in Winchester ![View from property](https://images.trvl-media.com/lodging/97000000/97000000/96998900/96998829/61974d0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/97000000/97000000/96998900/96998829/d17a08ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/97000000/97000000/96998900/96998829/98af3a24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed (High Floor)](https://images.trvl-media.com/lodging/97000000/97000000/96998900/96998829/44395d4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### citizenM Boston Back Bay [](https://www.expedia.ca/Boston-Hotels-CitizenM-Boston-Back-Bay.h96998829.Hotel-Information) 9.4/10 Exceptional (2188) "Great stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alexander CA $148 CA $173 total includes taxes & fees Jan 14 - Jan 15 [](https://www.expedia.ca/Boston-Hotels-CitizenM-Boston-Back-Bay.h96998829.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/1000000/20000/15800/15746/f7a78de2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Building design](https://images.trvl-media.com/lodging/1000000/20000/15800/15746/7fdd8c83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 Queen Bed](https://images.trvl-media.com/lodging/1000000/20000/15800/15746/5e10c317.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/20000/15800/15746/5e786b7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Found Hotel Boston Common [](https://www.expedia.ca/Boston-Hotels-Found-Hotel-Boston-Common.h15746.Hotel-Information) 8.4/10 Very good (1287) "Nice place to stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brenda CA $105 CA $123 total includes taxes & fees Feb 2 - Feb 3 [](https://www.expedia.ca/Boston-Hotels-Found-Hotel-Boston-Common.h15746.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/2900/2898/a8ad449d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/1000000/10000/2900/2898/a2b908c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/10000/2900/2898/0f2e267f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/10000/2900/2898/e6722cab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Midtown Hotel MOD Collection by Sonesta [](https://www.expedia.ca/Boston-Hotels-Midtown-Hotel.h2898.Hotel-Information) 7.4/10 Good (1004) "Clean, newly renovated, in-room Keurig and fridge, friendly staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Judith [](https://www.expedia.ca/Boston-Hotels-Midtown-Hotel.h2898.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/4300/4215/82ab675e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/4300/4215/6e9f8959.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/4300/4215/3aa5107f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ballroom](https://images.trvl-media.com/lodging/1000000/10000/4300/4215/6238869c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Boston Park Plaza [](https://www.expedia.ca/Boston-Hotels-Boston-Park-Plaza.h4215.Hotel-Information) 8.4/10 Very good (3101) "Great staff and a beautiful room. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elizabeth CA $124 CA $201 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Boston-Hotels-Boston-Park-Plaza.h4215.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/16100/16067/dbccf1fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/20000/16100/16067/e1a64100.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, blackout drapes, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/1000000/20000/16100/16067/ce275009.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/1000000/20000/16100/16067/213feb43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Copley Square Hotel, a FOUND Hotel [](https://www.expedia.ca/Boston-Hotels-Copley-Square-Hotel.h16067.Hotel-Information) 8.6/10 Excellent (3911) "Great location, clean and comfy room, friendly staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Zachary CA $111 CA $129 total includes taxes & fees Jan 18 - Jan 19 [](https://www.expedia.ca/Boston-Hotels-Copley-Square-Hotel.h16067.Hotel-Information) ![Superior Suite (Bath in Room) | Terrace/patio](https://images.trvl-media.com/lodging/31000000/30090000/30080300/30080227/72455221.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee shop](https://images.trvl-media.com/lodging/31000000/30090000/30080300/30080227/8ac4fbcd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/31000000/30090000/30080300/30080227/fac562db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/31000000/30090000/30080300/30080227/c80dc7a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Revolution Hotel [](https://www.expedia.ca/Boston-Hotels-The-Revolution-Hotel.h30080227.Hotel-Information) 9.0/10 Wonderful (2380) "Great stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sue CA $99 CA $115 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Boston-Hotels-The-Revolution-Hotel.h30080227.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/11000000/10120000/10118700/10118614/db3fd34b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Peruvian cuisine](https://images.trvl-media.com/lodging/11000000/10120000/10118700/10118614/eb7322a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Peruvian cuisine](https://images.trvl-media.com/lodging/11000000/10120000/10118700/10118614/c254df3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/11000000/10120000/10118700/10118614/3c267db5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Godfrey Hotel Boston [](https://www.expedia.ca/Boston-Hotels-The-Godfrey-Hotel-Boston.h10118614.Hotel-Information) 9.4/10 Exceptional (4842) "Great place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nick A CA $134 CA $220 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Boston-Hotels-The-Godfrey-Hotel-Boston.h10118614.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/17900/17845/w2557h3837x3y3-ca2d3d94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/17900/17845/1db57cc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Executive Room, Terrace | Living area](https://images.trvl-media.com/lodging/1000000/20000/17900/17845/17c5a38e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Presidential Suite](https://images.trvl-media.com/lodging/1000000/20000/17900/17845/866dc285.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Regency Boston [](https://www.expedia.ca/Boston-Hotels-Hyatt-Regency-Boston.h17845.Hotel-Information) 9.0/10 Wonderful (1770) "Wonderful stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) sujata CA $176 CA $254 total includes taxes & fees Jan 31 - Feb 1 [](https://www.expedia.ca/Boston-Hotels-Hyatt-Regency-Boston.h17845.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/39000000/38770000/38766200/38766175/62c9d5b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, blackout drapes, free cribs/infant beds](https://images.trvl-media.com/lodging/39000000/38770000/38766200/38766175/8d14bce6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/39000000/38770000/38766200/38766175/cfaa2fff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Serves breakfast, lunch, and dinner](https://images.trvl-media.com/lodging/39000000/38770000/38766200/38766175/b8807d89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Moxy Boston Downtown [](https://www.expedia.ca/Boston-Hotels-Moxy-Boston-Downtown.h38766175.Hotel-Information) 8.8/10 Excellent (1011) "Friendly staff, excellent customer service, clean rooms and spacious enough for two. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stacey CA $113 CA $188 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Boston-Hotels-Moxy-Boston-Downtown.h38766175.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/1000000/160000/151300/151201/w6386h4263x7y0-3eb965d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Library](https://images.trvl-media.com/lodging/1000000/160000/151300/151201/9c0dae36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/1000000/160000/151300/151201/328c763f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/160000/151300/151201/80b97ccf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Dagny Boston [](https://www.expedia.ca/Boston-Hotels-Hilton-Boston-DowntownFaneuil-Hall.h151201.Hotel-Information) 9.4/10 Exceptional (6935) "Great rooms - great staff - great location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steven CA $187 CA $267 total includes taxes & fees Jan 11 - Jan 12 [](https://www.expedia.ca/Boston-Hotels-Hilton-Boston-DowntownFaneuil-Hall.h151201.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/47000000/46530000/46521400/46521349/5fe1e844.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/47000000/46530000/46521400/46521349/b025cdc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/47000000/46530000/46521400/46521349/6f0677c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/47000000/46530000/46521400/46521349/ee0d02d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Place Boston/Seaport District [](https://www.expedia.ca/Boston-Hotels-Hyatt-Place-BostonSeaport-District.h46521349.Hotel-Information) 9.4/10 Exceptional (2250) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nancy CA $187 CA $218 total includes taxes & fees Jan 18 - Jan 19 [](https://www.expedia.ca/Boston-Hotels-Hyatt-Place-BostonSeaport-District.h46521349.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/34000000/33880000/33870600/33870542/7c57b7a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/34000000/33880000/33870600/33870542/f2f31351.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/34000000/33880000/33870600/33870542/c37d2403.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Room, 1 King Bed (View)](https://images.trvl-media.com/lodging/34000000/33880000/33870600/33870542/23e9f070.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### citizenM Boston North Station [](https://www.expedia.ca/Boston-Hotels-CitizenM-Boston-North-Station.h33870542.Hotel-Information) 9.4/10 Exceptional (4241) "Great stay! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) REBECCA CA $161 CA $187 total includes taxes & fees Jan 18 - Jan 19 [](https://www.expedia.ca/Boston-Hotels-CitizenM-Boston-North-Station.h33870542.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/12000000/11270000/11264000/11263952/2d0dd8e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/12000000/11270000/11264000/11263952/a95c70b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/12000000/11270000/11264000/11263952/d6de0f74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/12000000/11270000/11264000/11263952/116c5658.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Aloft by Marriott, Boston Seaport District [](https://www.expedia.ca/Boston-Hotels-Aloft-Boston-Seaport-District.h11263952.Hotel-Information) 9.0/10 Wonderful (1397) "Clean room, great bar and breakfast options and good location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bianca CA $143 CA $207 total includes taxes & fees Jan 11 - Jan 12 [](https://www.expedia.ca/Boston-Hotels-Aloft-Boston-Seaport-District.h11263952.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/80000/79900/79888/fa9777a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/80000/79900/79888/3a90f50b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/80000/79900/79888/e07ab872.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/1000000/80000/79900/79888/dea35c86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Seaport Hotel Boston [](https://www.expedia.ca/Boston-Hotels-Seaport-Hotel-Boston.h79888.Hotel-Information) 9.6/10 Exceptional (3874) "Great accommodations and friendly staff!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nicholas CA $167 CA $242 total includes taxes & fees Jan 18 - Jan 19 [](https://www.expedia.ca/Boston-Hotels-Seaport-Hotel-Boston.h79888.Hotel-Information) ![BBQ/picnic area](https://images.trvl-media.com/lodging/3000000/2320000/2311800/2311712/3c399d30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/3000000/2320000/2311800/2311712/82f65e6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cafe](https://images.trvl-media.com/lodging/3000000/2320000/2311800/2311712/3e3b7a7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2320000/2311800/2311712/4f982a48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Battery Wharf Hotel, Boston Waterfront [](https://www.expedia.ca/Boston-Hotels-Battery-Wharf-Hotel.h2311712.Hotel-Information) 8.8/10 Excellent (1757) "We stay here every visit to Boston. Pet friendly for our dogs, great location and nice accommodations and staff " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Peter CA $165 CA $248 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Boston-Hotels-Battery-Wharf-Hotel.h2311712.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/210000/202900/202814/f403d96c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/210000/202900/202814/fa2751b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/210000/202900/202814/754f64e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lounge](https://images.trvl-media.com/lodging/1000000/210000/202900/202814/65e6256b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Harborside Inn Of Boston [](https://www.expedia.ca/Boston-Hotels-Harborside-Inn-Of-Boston.h202814.Hotel-Information) 9.2/10 Wonderful (6125) "Well located for those sightseeing in Boston. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Albert CA $148 CA $173 total includes taxes & fees Jan 18 - Jan 19 [](https://www.expedia.ca/Boston-Hotels-Harborside-Inn-Of-Boston.h202814.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/20000/16700/16680/0ed5a88d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/16700/16680/e7ad1586.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Banquet hall](https://images.trvl-media.com/lodging/1000000/20000/16700/16680/6cfad146.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges, rooftop bar](https://images.trvl-media.com/lodging/1000000/20000/16700/16680/2b0d79ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Revere Hotel Boston Common [](https://www.expedia.ca/Boston-Hotels-Revere-Hotel-Boston-Common.h16680.Hotel-Information) 9.0/10 Wonderful (1928) "Great place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sheri CA $170 CA $254 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Boston-Hotels-Revere-Hotel-Boston-Common.h16680.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) ![Premium bedding, down comforters, pillowtop beds, desk](https://images.trvl-media.com/lodging/1000000/10000/4100/4054/99039e28.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) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/4100/4054/b57212de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Staypineapple, A Delightful Hotel, South End [](https://www.expedia.ca/Boston-Hotels-Staypineapple.h4054.Hotel-Information) 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 CA $82 CA $136 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Boston-Hotels-Staypineapple.h4054.Hotel-Information) ![Rooftop terrace](https://images.trvl-media.com/lodging/19000000/18100000/18090400/18090311/0ab5b9a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, memory foam beds, in-room safe, laptop workspace](https://images.trvl-media.com/lodging/19000000/18100000/18090400/18090311/827459a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/19000000/18100000/18090400/18090311/245fc311.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach/ocean view](https://images.trvl-media.com/lodging/19000000/18100000/18090400/18090311/e67c2116.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### YOTEL Boston [](https://www.expedia.ca/Boston-Hotels-YOTEL-Boston.h18090311.Hotel-Information) 8.6/10 Excellent (2377) "Nice hotel great location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) MARK CA $125 CA $210 total includes taxes & fees Jan 11 - Jan 12 [](https://www.expedia.ca/Boston-Hotels-YOTEL-Boston.h18090311.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/56000000/55430000/55422000/55421972/ef05180d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/56000000/55430000/55422000/55421972/e8e42358.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/56000000/55430000/55422000/55421972/c304377b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/56000000/55430000/55422000/55421972/4f4d7c0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Boston Seaport District [](https://www.expedia.ca/Boston-Hotels-Hampton-Inn-Boston-Seaport.h55421972.Hotel-Information) 9.2/10 Wonderful (2781) "Excellent hotel and stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ana CA $175 CA $204 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Boston-Hotels-Hampton-Inn-Boston-Seaport.h55421972.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.ca/Hotel-Search?startDate=2026-01-23&endDate=2026-01-24®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.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Villas.d175481-aaVillas.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Villas.d175481-aaVillas.Travel-Guide-Accommodation) ## Top Winchester Hotel Reviews ![citizenM Boston North Station](https://images.trvl-media.com/lodging/34000000/33880000/33870600/33870542/0eda38d5_y.jpg) ### citizenM Boston North Station 10/10 Excellent "Amazing rooms! Amazing views! But most importantly amazing customer services 10/10\. Exceeded my expectations. " [](https://expedia.ca/Boston-Hotels-CitizenM-Boston-North-Station.h33870542.Hotel-Information) ![The Revolution Hotel](https://images.trvl-media.com/lodging/31000000/30090000/30080300/30080227/cce5d2b3_y.jpg) ### The Revolution Hotel 10/10 Excellent "." [](https://expedia.ca/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 "Really nice hotel, great clean rooms, nice bath, super location, staff were great" [](https://expedia.ca/Boston-Hotels-Hyatt-Regency-Boston.h17845.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.ca/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.ca/Boston-Hotels-The-Godfrey-Hotel-Boston.h10118614.Hotel-Information) ![Omni Boston Hotel at the Seaport](https://images.trvl-media.com/lodging/69000000/68020000/68014400/68014393/26d11bc3_y.jpg) ### Omni Boston Hotel at the Seaport 10/10 Excellent "Amazing hotel" [](https://expedia.ca/Boston-Hotels-Omni-Boston-Hotel-At-The-Seaport.h68014393.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" [](https://expedia.ca/Boston-Hotels-Hilton-Boston-Back-Bay.h5928.Hotel-Information) ![The Westin Copley Place, Boston, a Marriott Hotel](https://images.trvl-media.com/lodging/1000000/10000/4500/4443/ac4901eb_y.jpg) ### The Westin Copley Place, Boston, a Marriott Hotel 10/10 Excellent "Room was great and staff very helpful" [](https://expedia.ca/Boston-Hotels-The-Westin-Copley-Place.h4443.Hotel-Information) ![Omni Parker House ](https://images.trvl-media.com/lodging/1000000/30000/23500/23415/c414a1f3_y.jpg) ### Omni Parker House 10/10 Excellent "Check in was easy and the room was very nice." [](https://expedia.ca/Boston-Hotels-Boston-Omni-Parker-House-Hotel.h23415.Hotel-Information) ## Find out more about Winchester ## Winchester Villas information | Number of reviews | 56,160 | | ----------------- | -------- | | Accommodation | 3 Villas | | Lowest Price | CA $115 | | Highest Price | CA $267 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [Aparthotels in Arlington ](https://www.expedia.ca/Arlington-Apart-Hotels.d74693-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Arlington ](https://www.expedia.ca/Arlington-Bed-And-Breakfast.d74693-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Boutique Hotels in Arlington ](https://www.expedia.ca/Arlington-Hotels-Boutique-Hotel.0-0-d74693-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Casino Hotels in Arlington ](https://www.expedia.ca/Arlington-Hotels-Casino-Hotel.0-0-d74693-tCasinoHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Arlington ](https://www.expedia.ca/Arlington-Hotels-Cheap-Hotels.0-0-d74693-tCheapHotels.Travel-Guide-Filter-Hotels) - 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