Title: Winchester Villas from CA $158 | 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) ![Default HTG hotel image](https://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Winchester Villa Rentals from CA $158 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 In two weeks [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-10-17&endDate=2025-10-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-10-31&endDate=2025-11-02&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-11-28&endDate=2025-11-30&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Dec 26 - Dec 28](https://www.expedia.ca/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) ## Browse Select Winchester Villas We don't have any properties that match your exact search [See all properties in Winchester](https://expedia.ca/Hotel-Search?startDate=2025-10-18&endDate=2025-10-19®ionId=175481&adults=2) ## Recommended hotels in Winchester ![Exterior](https://images.trvl-media.com/lodging/2000000/1150000/1145300/1145259/31868feb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1150000/1145300/1145259/4aea60d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1150000/1145300/1145259/e425e9d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Economy Double Room, Ensuite](https://images.trvl-media.com/lodging/2000000/1150000/1145300/1145259/f81a74b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Oasis Guest House Fenway–Kenmore 9.6/10 Exceptional (1294) "Clean room, excellent staff and great location." CA $264 CA $303 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Boston-Hotels-Oasis-Guest-House.h1145259.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) ![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) ![Building design](https://images.trvl-media.com/lodging/1000000/20000/15800/15746/7fdd8c83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/20000/15800/15746/3da48020.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Found Hotel Boston Common Bay Village 8.4/10 Very good (1227) "For a quick getaway this place was absolutely perfect! It was in a very convenient location and everywhere was easy to walk to. " CA $290 CA $338 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Boston-Hotels-Found-Hotel-Boston-Common.h15746.Hotel-Information) ![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) ![Terrace/patio](https://images.trvl-media.com/lodging/19000000/18100000/18090400/18090311/ded31790.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/19000000/18100000/18090400/18090311/e6f5d3e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed (VIP)](https://images.trvl-media.com/lodging/19000000/18100000/18090400/18090311/c90a145e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### YOTEL Boston Seaport District 8.6/10 Excellent (2259) "Staff were extremely friendly and helpful Food was great " CA $301 CA $408 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Boston-Hotels-YOTEL-Boston.h18090311.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/56000000/55430000/55422000/55421972/e8e42358.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ballroom](https://images.trvl-media.com/lodging/56000000/55430000/55422000/55421972/4d183864.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/56000000/55430000/55422000/55421972/ef05180d.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 Seaport District 9.2/10 Wonderful (2572) "Great place to stay" CA $294 CA $342 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Boston-Hotels-Hampton-Inn-Boston-Seaport.h55421972.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/30000/26200/26176/f37fab18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/30000/26200/26176/217aab42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/30000/26200/26176/88b533e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/26200/26176/3cddef07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn at Historic Concord Concord 8.6/10 Excellent (1002) "I booked it. Confirmed nuber and cc charged PROPERTY WAS CLOSED" CA $152 CA $170 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Boston-Hotels-Historic-Concord-Suites.h26176.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1460000/1450100/1450057/73cb3288.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily to-go breakfast for a fee](https://images.trvl-media.com/lodging/2000000/1460000/1450100/1450057/ce2ce7cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, down comforters, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/2000000/1460000/1450100/1450057/2d4804d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1460000/1450100/1450057/60cb4bac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Westin Boston Seaport District Seaport District 9.0/10 Wonderful (2206) "Great hotel" CA $288 CA $384 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Boston-Hotels-The-Westin-Boston-Seaport-District.h1450057.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1490000/1482500/1482493/8aea9ff9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1490000/1482500/1482493/ac01edf4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/2000000/1490000/1482500/1482493/5ebb4acf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Studio, 1 King Bed with Sofa bed, Kitchen](https://images.trvl-media.com/lodging/2000000/1490000/1482500/1482493/67115820.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Copley House Back Bay 9.0/10 Wonderful (1847) "Great overnight stay especially if visiting Fenway Park" CA $226 CA $260 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Boston-Hotels-Copley-House.h1482493.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) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/80000/79900/79888/40a54799.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/80000/79900/79888/f8efea04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/80000/79900/79888/b4b93ddd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Seaport Hotel Boston Seaport District 9.6/10 Exceptional (3461) "Excellent property, we really enjoyed the dining options nearby." CA $265 CA $316 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Boston-Hotels-Seaport-Hotel-Boston.h79888.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) ![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) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/16100/16067/a1ab1c31.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) ### Copley Square Hotel, a FOUND Hotel Back Bay 8.6/10 Excellent (3829) "Nice place with nice staff." CA $284 CA $330 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Boston-Hotels-Copley-Square-Hotel.h16067.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/800000/796200/796159/da61c38e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sundeck](https://images.trvl-media.com/lodging/1000000/800000/796200/796159/fff59724.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ballroom](https://images.trvl-media.com/lodging/1000000/800000/796200/796159/5a4906c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/800000/796200/796159/f3392579.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Nantasket Beach Resort Nantasket Beach 8.6/10 Excellent (1000) "Great little place. " CA $165 CA $214 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Boston-Hotels-Nantasket-Beach-Resort.h796159.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/1000000/460000/458300/458272/3cbb9fa5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/1000000/460000/458300/458272/344bfc3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/460000/458300/458272/06d533cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/460000/458300/458272/41356953.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Boston - Revere Revere 7.4/10 Good (1001) "Hotel was great! Staff were very nice! " CA $141 CA $158 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Boston-Hotels-Quality-Inn-Boston-Revere.h458272.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/57000000/56290000/56289400/56289302/9e29ca3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/57000000/56290000/56289400/56289302/0e1c57a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/57000000/56290000/56289400/56289302/647818b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/57000000/56290000/56289400/56289302/61a7306f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Homewood Suites by Hilton Boston Seaport District Seaport District 9.2/10 Wonderful (1294) "Loved our stay" CA $317 CA $364 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Boston-Hotels-Homewood-Suites-By-Hilton-Boston-Seaport.h56289302.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/160000/151300/151201/242d7352.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/160000/151300/151201/3521e55a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, down comforters, pillowtop beds](https://images.trvl-media.com/lodging/1000000/160000/151300/151201/8fdf5334.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) ### The Dagny Boston Downtown Boston 9.4/10 Exceptional (6535) "Amazing hotel and location " CA $313 CA $413 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Boston-Hotels-Hilton-Boston-DowntownFaneuil-Hall.h151201.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/850000/845600/845522/d5f6b947.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard, One Full Bed](https://images.trvl-media.com/lodging/1000000/850000/845600/845522/25cd1f6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Traditional Room, 1 Queen Bed](https://images.trvl-media.com/lodging/1000000/850000/845600/845522/b167dd69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/850000/845600/845522/ca8cb62e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charlesmark Hotel Back Bay 8.8/10 Excellent (1077) "While small rooms, it was a perfect location for our trip. " CA $260 CA $301 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Boston-Hotels-Charlesmark-Hotel.h845522.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/990000/981000/980972/259b527d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/990000/981000/980972/f440e3c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/990000/981000/980972/4aca5a8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Room, 1 King Bed](https://images.trvl-media.com/lodging/1000000/990000/981000/980972/c8dcbaea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pennyweight Hotel Boston, Curio Collection by Hilton West End 8.2/10 Very good (1128) "Super close to TD garden, friendly service beautiful rooms " CA $283 CA $379 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Boston-Hotels-Kimpton-Onyx-Hotel.h980972.Hotel-Information) ![4 restaurants, breakfast served](https://images.trvl-media.com/lodging/69000000/68020000/68014400/68014393/bc3320d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/69000000/68020000/68014400/68014393/4fa70e94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/69000000/68020000/68014400/68014393/0063ecca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/69000000/68020000/68014400/68014393/1ac58b6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Omni Boston Hotel at the Seaport Seaport District 9.2/10 Wonderful (4091) "Great place to stay! great food on property " CA $334 CA $445 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Boston-Hotels-Omni-Boston-Hotel-At-The-Seaport.h68014393.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) ![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) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/2900/2898/592d909a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Midtown Hotel Back Bay 7.4/10 Good (1008) "Nice room, friendly staff and good location!" CA $317 CA $364 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Boston-Hotels-Midtown-Hotel.h2898.Hotel-Information) ![Standard Room, 1 King Bed](https://images.trvl-media.com/lodging/2000000/1060000/1056700/1056601/96689681.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1060000/1056700/1056601/005c6b1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed | Terrace/patio](https://images.trvl-media.com/lodging/2000000/1060000/1056700/1056601/e0a39a9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds](https://images.trvl-media.com/lodging/2000000/1060000/1056700/1056601/2cf106fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Nantasket Beach Hotel Hull 9.2/10 Wonderful (1001) "Always a great relaxing stay here!" CA $187 CA $205 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Boston-Hotels-Nantasket-Beach-Hotel.h1056601.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) ![Accessible Two Queen Beds with Bathtub](https://images.trvl-media.com/lodging/47000000/46530000/46521400/46521349/6e0a2d35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/47000000/46530000/46521400/46521349/7512691e.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) ### Hyatt Place Boston/Seaport District Seaport District 9.4/10 Exceptional (2136) "It was a great place to stay!" CA $347 CA $405 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Boston-Hotels-Hyatt-Place-BostonSeaport-District.h46521349.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) ![Ballroom](https://images.trvl-media.com/lodging/1000000/10000/4300/4215/d4a5b47e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Presidential Suite, 1 Bedroom | Living area](https://images.trvl-media.com/lodging/1000000/10000/4300/4215/573419fc.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 Bay Village 8.4/10 Very good (3143) "Great place to stay" CA $319 CA $429 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Boston-Hotels-Boston-Park-Plaza.h4215.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=2025-10-18&endDate=2025-10-19®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 Back Bay](//images.trvl-media.com/lodging/97000000/97000000/96998900/96998829/90056141_y.jpg) ### citizenM Boston Back Bay 10/10 Excellent "Great location and great vibes" [](https://expedia.ca/Boston-Hotels-CitizenM-Boston-Back-Bay.h96998829.Hotel-Information) ![The Arcadian Hotel](//images.trvl-media.com/lodging/32000000/31100000/31097800/31097754/f8ad7683_y.jpg) ### The Arcadian Hotel 10/10 Excellent "Great service" [](https://expedia.ca/Boston-Hotels-Arcadian-Hotel-Brookline.h31097754.Hotel-Information) ![Midtown Hotel](//images.trvl-media.com/lodging/1000000/10000/2900/2898/e6722cab_y.jpg) ### Midtown Hotel 10/10 Excellent "The staff, from an original phone call, with a question, until check out could not have been more amazing. Personable, professional, friendly, and enthusiastic are just of the few ways I would describe them. From the moment we arrived until we left we were engaged in an amazing way. We loved Betsy Lynn at the desk and her colleague, Vereema. Next time I am Boston we will choose to stay at the Midtown for the staff alone, although the beds and room were extremely comfortable. I cannot wait to see the finished renovation." [](https://expedia.ca/Boston-Hotels-Midtown-Hotel.h2898.Hotel-Information) ![Seaport Hotel Boston](//images.trvl-media.com/lodging/1000000/80000/79900/79888/fa9777a9_y.jpg) ### Seaport Hotel Boston 10/10 Excellent "Loved the large harbor view king room. Easy and pleasant check in. Room ready early. Housekeeping staff were terrific- friendly and helpful. Everything immaculate. Only the shower tile floor shows wear. Enjoyed the harbor area- good dining options, walked to the port (a little long with luggage but doable)—-we were cruising so hotel is well situated for the port and airport. Boston traffic is pretty bad, so Ubers to the Back Bay or Cambridge take a while! Pick your hotel close to where you need or want to be!" [](https://expedia.ca/Boston-Hotels-Seaport-Hotel-Boston.h79888.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 "We loved our stay at CitizenM. " [](https://expedia.ca/Boston-Hotels-CitizenM-Boston-North-Station.h33870542.Hotel-Information) ![The Dagny Boston](//images.trvl-media.com/lodging/1000000/160000/151300/151201/4c15d693_y.jpg) ### The Dagny Boston 10/10 Excellent "Amazing hotel and location " [](https://expedia.ca/Boston-Hotels-Hilton-Boston-DowntownFaneuil-Hall.h151201.Hotel-Information) ![Copley Square Hotel, a FOUND Hotel](//images.trvl-media.com/lodging/1000000/20000/16100/16067/dbccf1fb_y.jpg) ### Copley Square Hotel, a FOUND Hotel 10/10 Excellent "Historic aged hotel, so our expectations were more than served. Highly recommend for access to the city and all sites during traveling." [](https://expedia.ca/Boston-Hotels-Copley-Square-Hotel.h16067.Hotel-Information) ![Sheraton Boston, a Marriott Hotel](//images.trvl-media.com/lodging/1000000/30000/22100/22046/dfa592c9_y.jpg) ### Sheraton Boston, a Marriott Hotel 10/10 Excellent "All good" [](https://expedia.ca/Boston-Hotels-Sheraton-Boston.h22046.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 girls at the front desk were super friendly and helpful. Room was simple but clean. Located close to places to eat and historic sites. " [](https://expedia.ca/Boston-Hotels-Harborside-Inn-Of-Boston.h202814.Hotel-Information) ## Find out more about Winchester ## Winchester Villas information | Number of reviews | 43,249 | | --- | --- | | Accommodation | 2 Villas | | Lowest Price | CA $158 | | Highest Price | CA $445 | ## 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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