Title: Book the Best BOUTIQUE Hotels in Winter Hill in 2025 | Expedia.ca [Winter Hill Travel Guide](https://expedia.ca/Boston-Winter-Hill.dx553248635976476697)[Vacation Rentals in Boston](https://expedia.ca/Boston-Vacation-Rentals.d178239.Travel-Guide-VacationRentals)[Flights to Boston](https://expedia.ca/Cheap-Flights-To-Boston.d178239.Travel-Guide-Flights)[Things to do in Boston](https://expedia.ca/Things-To-Do-In-Boston.d178239.Travel-Guide-Activities)[Winter Hill Car Rentals](https://expedia.ca/Car-Rentals-In-Winter-Hill.d553248635976476697.Car-Rental-Guide)[Winter Hill Vacations](https://expedia.ca/Winter-Hill.d553248635976476697.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/boutique.jpeg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Boutique Hotels in Winter Hill, MA from CA $174 - ![](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 Winter Hill Boutique Hotels Tonight [Nov 7 - Nov 8](https://www.expedia.ca/Hotel-Search?regionId=553248635976476697&startDate=2025-11-07&endDate=2025-11-08&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 8 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=553248635976476697&startDate=2025-11-08&endDate=2025-11-09&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=553248635976476697&startDate=2025-11-07&endDate=2025-11-09&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=553248635976476697&startDate=2025-11-14&endDate=2025-11-16&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Winter Hill Boutique Hotels ![Peruvian cuisine](https://images.trvl-media.com/lodging/11000000/10120000/10118700/10118614/e4d256d2.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) ![Interior detail](https://images.trvl-media.com/lodging/11000000/10120000/10118700/10118614/3c267db5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/11000000/10120000/10118700/10118614/3fa1f257.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Godfrey Hotel Boston Downtown Boston 9.4/10 Exceptional (4631) "Great location, awesome staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jorge CA $136 CA $224 total includes taxes & fees Nov 26 - Nov 27 [](https://www.expedia.ca/Boston-Hotels-The-Godfrey-Hotel-Boston.h10118614.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) ![Restaurant](https://images.trvl-media.com/lodging/1000000/20000/16100/16067/c2b6fbff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Copley Square Hotel, a FOUND Hotel Back Bay 8.6/10 Excellent (3853) "Amazing hotel! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jessica CA $160 CA $186 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Boston-Hotels-Copley-Square-Hotel.h16067.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/900000/895000/894999/6b079723.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/900000/895000/894999/cfd3fcf9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/900000/895000/894999/72c68b3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite (Loft)](https://images.trvl-media.com/lodging/1000000/900000/895000/894999/9d9b005b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Commonwealth Fenway–Kenmore 9.4/10 Exceptional (1848) "Great staff, quiet and clean rooms" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jamie CA $161 CA $253 total includes taxes & fees Nov 26 - Nov 27 [](https://www.expedia.ca/Boston-Hotels-Hotel-Commonwealth.h894999.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) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/4100/4054/b57212de.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) ![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) ### Staypineapple, A Delightful Hotel, South End South End 8.8/10 Excellent (1000) "Lovely hotel in Boston . Great welcoming and helpful staff and quirky, bright rooms . Great location - metro system nearby but we walked everywhere . Great bar and restaurant too" ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Steve CA $148 CA $213 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Boston-Hotels-Staypineapple.h4054.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/2000000/1120000/1118900/1118893/db81308e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, individually decorated, desk](https://images.trvl-media.com/lodging/2000000/1120000/1118900/1118893/4774d7cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily cooked-to-order breakfast for a fee](https://images.trvl-media.com/lodging/2000000/1120000/1118900/1118893/1c9bd2a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1120000/1118900/1118893/188173d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Eurostars The Boxer West End 8.6/10 Excellent (1333) "I like the small cozy property and convenience to walk to a lot of bars and restaurants " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James CA $226 CA $291 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/Boston-Hotels-The-Boxer.h1118893.Hotel-Information) ![View from room](https://images.trvl-media.com/lodging/1000000/20000/15200/15159/680c86ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/20000/15200/15159/ad5ebe4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/1000000/20000/15200/15159/47d0a7af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/20000/15200/15159/f5ab7f9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Bostonian Boston Government Center 8.2/10 Very good (1936) "Easy check in and nice staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steve CA $175 CA $252 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Boston-Hotels-The-Bostonian-Boston.h15159.Hotel-Information) ![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) ![Reception](https://images.trvl-media.com/lodging/1000000/850000/845600/845522/19eac2a5.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 (1112) "Comfortable room, great location. Great staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cynthia CA $151 CA $174 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Boston-Hotels-Charlesmark-Hotel.h845522.Hotel-Information) ![Seasonal outdoor pool, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/1000000/20000/12700/12660/f43e7537.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lounge](https://images.trvl-media.com/lodging/1000000/20000/12700/12660/04a71950.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/1000000/20000/12700/12660/5268c493.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/1000000/20000/12700/12660/b832589e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Colonnade Hotel Back Bay Back Bay 9.2/10 Wonderful (2252) "This was a good value hotel with nice amenities in an excellent location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elizabeth CA $268 CA $361 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Boston-Hotels-The-Colonnade-Hotel-Back-Bay.h12660.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/1000000/870000/867400/867308/bf7a8409.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![City view](https://images.trvl-media.com/lodging/1000000/870000/867400/867308/5a237597.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/870000/867400/867308/1565ba4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/870000/867400/867308/e7578f6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel AKA Boston Common Downtown Boston 9.0/10 Wonderful (1384) "Modern hotel centrally located in Boston." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael CA $273 CA $376 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Boston-Hotels-Hotel-AKA-Boston-Common.h867308.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) ![Reception](https://images.trvl-media.com/lodging/1000000/990000/981000/980972/4aca5a8c.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) ![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 (1142) "Great location" ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Peter CA $191 CA $272 total includes taxes & fees Nov 27 - Nov 28 [](https://www.expedia.ca/Boston-Hotels-Kimpton-Onyx-Hotel.h980972.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=2025-11-21&endDate=2025-11-22®ionId=553248635976476697&adults=2&specialized_stays_group_explore=boutique_property&sort=RECOMMENDED&openPlayBack=true) ## Top Winter Hill Hotel Reviews ![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 "The room was spacious clean and the staff was great . Parking was not the best we had to park across the street and it was a pain. Shopping and dinning was great . We took the train into lil Italy loved that part. " [](https://expedia.ca/Boston-Hotels-Copley-Square-Hotel.h16067.Hotel-Information) ![The Dagny Boston](//images.trvl-media.com/lodging/1000000/160000/151300/151201/4c15d693_y.jpg) ### The Dagny Boston 10/10 Excellent "The room was very clean. The staff was knowledgeable and very helpful. The location was perfect for our needs. " [](https://expedia.ca/Boston-Hotels-Hilton-Boston-DowntownFaneuil-Hall.h151201.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 "Friendly staff. Nice, clean boutique hotel. Great location. Would stay there again." [](https://expedia.ca/Boston-Hotels-Harborside-Inn-Of-Boston.h202814.Hotel-Information) ![The Godfrey Hotel Boston](//images.trvl-media.com/lodging/11000000/10120000/10118700/10118614/e4d256d2_y.jpg) ### The Godfrey Hotel Boston 10/10 Excellent "Room was great with a nice skyline view. Staff were very friendly. Candy cart was a nice touch. Ate at attached restaurant and was a great meal with even better drinks. Super short walk to opera house. Great breakfast and coffee morning after. Will defiantly plan another stay/Theatre visit. " [](https://expedia.ca/Boston-Hotels-The-Godfrey-Hotel-Boston.h10118614.Hotel-Information) ![Club Quarters Hotel Faneuil Hall, Boston](//images.trvl-media.com/lodging/1000000/70000/67000/66938/1b7afb42_y.jpg) ### Club Quarters Hotel Faneuil Hall, Boston 10/10 Excellent "Good location" [](https://expedia.ca/Boston-Hotels-Club-Quarters-Hotel-In-Boston.h66938.Hotel-Information) ## Frequently asked questions ### What's there to see and do in Winter Hill? > After you've decided where you'd like to stay, consider what to do for fun during your trip. Top activities and sights around Winter Hill include TD Garden, Fenway Park, and New England Aquarium. You might also want to see noteworthy spots like Encore Boston Harbor, Harvard Square, and Faneuil Hall Marketplace during your trip. ### What's the best way to get to my boutique hotel in Winter Hill? > You have a few options for getting to Winter Hill. The nearest major airport is Boston, MA (BNH-Boston Harbor Seaplane Base), which is located 4.1 mi (6.5 km) away, but Logan International Airport (BOS) may also be an option. 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