Title: Book the Best Winchester CASINO Hotels & Resorts in 2026 | 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) ![Winchester Town Hall at 71 Mt Vernon Street in historic town center of Winchester, Middlesex County, Massachusetts MA, USA. ](https://images.trvl-media.com/place/175481/5b3e907d-d662-4314-947e-70c644534c55.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Casino Hotels in Winchester, MA from CA $128 - ![](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 availability on Winchester Casino Hotels Tonight [Dec 7 - Dec 8](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-12-07&endDate=2025-12-08&adults=2&amenities=CASINO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 8 - Dec 9](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-12-08&endDate=2025-12-09&adults=2&amenities=CASINO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-12-12&endDate=2025-12-14&adults=2&amenities=CASINO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-12-19&endDate=2025-12-21&adults=2&amenities=CASINO&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Winchester Casino Hotels ![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) ![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) ![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 8.2/10 Very good (1263) "I always like staying here " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sonia CA $137 CA $159 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Boston-Hotels-Found-Hotel-Boston-Common.h15746.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/16100/16067/a1ab1c31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Copley Square Hotel, a FOUND Hotel Back Bay 8.6/10 Excellent (3905) "Great for a short stay option. We stayed 2 days and it was perfect for our needs. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rocco CA $110 CA $128 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Boston-Hotels-Copley-Square-Hotel.h16067.Hotel-Information) ![Meeting facility](https://images.trvl-media.com/lodging/39000000/38770000/38766200/38766175/dbe625a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/39000000/38770000/38766200/38766175/49683728.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) ![Lobby](https://images.trvl-media.com/lodging/39000000/38770000/38766200/38766175/e6d81cec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Moxy Boston Downtown Bay Village 8.8/10 Excellent (1009) "Great place to stay. Good location, good service, nice rooms, very good price" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rigoberto CA $109 CA $183 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Boston-Hotels-Moxy-Boston-Downtown.h38766175.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/3000000/2320000/2311800/2311712/c2e44637.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) ![Water view](https://images.trvl-media.com/lodging/3000000/2320000/2311800/2311712/c9a6a0ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Couples treatment rooms, sauna, steam room, Turkish bath](https://images.trvl-media.com/lodging/3000000/2320000/2311800/2311712/d6523d8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Battery Wharf Hotel, Boston Waterfront North End 8.8/10 Excellent (1741) "Beautiful hotel and close to everything " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) jeannette CA $173 CA $258 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Boston-Hotels-Battery-Wharf-Hotel.h2311712.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/25700/25655/fa173b31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Suite, 1 King Bed](https://images.trvl-media.com/lodging/1000000/30000/25700/25655/f1b3dec8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, open 10:00 AM to 9:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/1000000/30000/25700/25655/08fc63c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/30000/25700/25655/3fb712f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wyndham Boston Beacon Hill West End 7.8/10 Good (2037) "Check in staff was awesome" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joseph CA $191 CA $223 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Boston-Hotels-Wyndham-Boston-Beacon-Hill.h25655.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/550000/543800/543784/fa5d7891.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/550000/543800/543784/0d5ffb85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/550000/543800/543784/bc294af0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Blackout drapes, soundproofing, iron/ironing board](https://images.trvl-media.com/lodging/1000000/550000/543800/543784/240a5ed6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites Logan International Airport Revere 9.0/10 Wonderful (2198) "The room was clean and the staff was very friendly " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Troyce CA $128 CA $151 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Boston-Hotels-Comfort-Inn-Suites-Logan-International-Airport.h543784.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/891000/890954/2242b90c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/900000/891000/890954/b8f10c35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, laptop workspace, iron/ironing board](https://images.trvl-media.com/lodging/1000000/900000/891000/890954/564924ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/900000/891000/890954/9718d6ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SpringHill Suites by Marriott Boston Peabody Peabody 7.8/10 Good (1114) "Clean room, friendly staff, and lots of amenities." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rachel CA $128 CA $143 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Boston-Hotels-SpringHill-Suites-By-Marriott-Boston-Peabody.h890954.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/2600/2558/9a3ebe8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, brunch served; Italian cuisine ](https://images.trvl-media.com/lodging/1000000/10000/2600/2558/b09a9741.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Club Room, 1 King Bed, Park View | Park view](https://images.trvl-media.com/lodging/1000000/10000/2600/2558/9dd85bb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/2600/2558/0f2f31a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Langham, Boston Downtown Boston 9.6/10 Exceptional (1002) "Great hotel" ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Caren Christina CA $504 CA $587 total includes taxes & fees Jan 2 - Jan 3, 2026 [](https://www.expedia.ca/Boston-Hotels-The-Langham.h2558.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/400/395/de8ba46e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room (Mansion)](https://images.trvl-media.com/lodging/1000000/10000/400/395/178a98f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/400/395/357d5388.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ballroom](https://images.trvl-media.com/lodging/1000000/10000/400/395/d23d79f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Newbury Boston Back Bay 9.2/10 Wonderful (545) "Excellent hotel. " ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Anne CA $558 CA $723 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Boston-Hotels-The-Newbury-Boston.h395.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/24800/24732/b06ec1c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, minibar, in-room safe](https://images.trvl-media.com/lodging/1000000/30000/24800/24732/2200c59e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/1000000/30000/24800/24732/0bb4dd98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/30000/24800/24732/91120a91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Eliot Hotel Back Bay 9.6/10 Exceptional (1005) "Great location in Boston, lovely rooms, staff super nice and helpful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anne CA $367 CA $427 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Boston-Hotels-The-Eliot-Hotel.h24732.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=2025-12-22&endDate=2025-12-23®ionId=175481&adults=2&amenities=CASINO&sort=RECOMMENDED&openPlayBack=true) ## Top Winchester Hotel Reviews ## Frequently asked questions ### Searching for casino hotels in Winchester? ### When should I take my casino trip to Winchester? ### What is there to do in Winchester? ### What are my transportation options for my casino getaway to Winchester? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [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) - [Hotels with a Pool in Arlington ](https://www.expedia.ca/Arlington-Hotels-Hotel-With-Pool.0-0-d74693-tHotelwithPool.Travel-Guide-Filter-Hotels) - 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