Title: Book the Best BOUTIQUE Hotels in Winchester in 2025 | 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) # Find Boutique Hotels in Winchester, MA from CA $216 ![](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 Boutique Hotels Tonight [Oct 18 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-10-18&endDate=2025-10-19&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 19 - Oct 20](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-10-19&endDate=2025-10-20&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-10-24&endDate=2025-10-26&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-10-31&endDate=2025-11-02&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Winchester Boutique Hotels ![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) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/16100/16067/a1ab1c31.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) ### Copley Square Hotel, a FOUND Hotel Back Bay 8.6/10 Excellent (3883) "Great hotel, great location, great staff! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Armen CA $185 CA $216 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Boston-Hotels-Copley-Square-Hotel.h16067.Hotel-Information) ![Peruvian cuisine](https://images.trvl-media.com/lodging/11000000/10120000/10118700/10118614/e4d256d2.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) ![Front of property - evening/night](https://images.trvl-media.com/lodging/11000000/10120000/10118700/10118614/6d541773.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 (4536) "Great hotel in a great location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael J. CA $249 CA $355 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Boston-Hotels-The-Godfrey-Hotel-Boston.h10118614.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) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/10000/4100/4054/100a8c35.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 (1011) "Cute room, kind staff, great location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Loren CA $209 CA $284 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Boston-Hotels-Staypineapple.h4054.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 (1333) "Great staff and location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carlton CA $303 CA $410 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Boston-Hotels-Hotel-AKA-Boston-Common.h867308.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) ![Suite (Loft)](https://images.trvl-media.com/lodging/1000000/900000/895000/894999/9d9b005b.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) ### Hotel Commonwealth Fenway–Kenmore 9.4/10 Exceptional (1796) "Great stay !" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Donna CA $256 CA $364 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Boston-Hotels-Hotel-Commonwealth.h894999.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) ![Property grounds](https://images.trvl-media.com/lodging/1000000/20000/15200/15159/47d0a7af.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/15200/15159/5402cae6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Bostonian Boston Government Center 8.4/10 Very good (1961) "The hotel was in a great walking location to many sites and restaurants." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) rob CA $209 CA $292 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Boston-Hotels-The-Bostonian-Boston.h15159.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) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/990000/981000/980972/2b12d9c2.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) ![Reception](https://images.trvl-media.com/lodging/1000000/990000/981000/980972/4aca5a8c.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 (1135) "Super close to TD garden, friendly service beautiful rooms " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Heather CA $249 CA $339 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Boston-Hotels-Kimpton-Onyx-Hotel.h980972.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) ![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) ![Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds](https://images.trvl-media.com/lodging/1000000/20000/12700/12660/43efca49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Colonnade Hotel Back Bay Back Bay 9.2/10 Wonderful (2226) "Great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alisa CA $315 CA $416 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Boston-Hotels-The-Colonnade-Hotel-Back-Bay.h12660.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/1000000/470000/464700/464632/2e88bc42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee service](https://images.trvl-media.com/lodging/1000000/470000/464700/464632/5ff7a744.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/470000/464700/464632/ab96e8b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/470000/464700/464632/89b97ef5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Hotel Marblehead Marblehead 9.2/10 Wonderful (423) "Loved our stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christopher CA $222 CA $248 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Boston-Hotels-The-Hotel-Marblehead.h464632.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) ![Front of property](https://images.trvl-media.com/lodging/2000000/1120000/1118900/1118893/c0bfcdbe.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) ![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) ### Eurostars The Boxer West End 8.6/10 Excellent (1328) "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 $308 CA $387 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Boston-Hotels-The-Boxer.h1118893.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=2025-11-01&endDate=2025-11-02®ionId=175481&adults=2&specialized_stays_group_explore=boutique_property&sort=RECOMMENDED&openPlayBack=true) ## Top Winchester Hotel Reviews ![The Dagny Boston](//images.trvl-media.com/lodging/1000000/160000/151300/151201/4c15d693_y.jpg) ### The Dagny Boston 10/10 Excellent "Lumpy mattress but fabulous shower. Street noise at night" [](https://expedia.ca/Boston-Hotels-Hilton-Boston-DowntownFaneuil-Hall.h151201.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 "I stayed here with three of my friends for a weekend birthday trip, and we absolutely loved our experience! Our room was clean, spacious, and very comfortable, it’s perfect for a group stay. The staff were friendly and accommodating from the start, allowing us to store our luggage both before check-in and after check-out, which made exploring the city so much easier. We really appreciated the complimentary coffee and water stations, such a thoughtful touch and the cozy sitting area just past the lobby was perfect for relaxing and chatting before heading out. The location couldn’t be better: it’s within walking distance of the train station and many of Boston’s main attractions, yet it still feels peaceful and tucked away from the city noise. For the price, you truly can’t beat the convenience and comfort this hotel offers. Overall, we had a fantastic stay and would definitely return on our next trip to Boston! " [](https://expedia.ca/Boston-Hotels-Club-Quarters-Hotel-In-Boston.h66938.Hotel-Information) ![Hilton Boston Park Plaza](//images.trvl-media.com/lodging/1000000/10000/4300/4215/82ab675e_y.jpg) ### Hilton Boston Park Plaza 10/10 Excellent "Clean rooms central location" [](https://expedia.ca/Boston-Hotels-Boston-Park-Plaza.h4215.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 "Location is very convenient to theatre district for a venue I was attending. Hotel is very clean and the staff is polite and welcoming. The restaurant, Ruka, is wonderful. " [](https://expedia.ca/Boston-Hotels-The-Godfrey-Hotel-Boston.h10118614.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 "Great hotel. Perfect. " [](https://expedia.ca/Boston-Hotels-Harborside-Inn-Of-Boston.h202814.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 "Love this hotel!!!" [](https://expedia.ca/Boston-Hotels-Copley-Square-Hotel.h16067.Hotel-Information) ## Frequently asked questions ### What's there to see and do in Winchester? > After you've decided where to stay in family-friendly Winchester, figure out some fun things to do on your trip. Major sights and activities around Winchester include TD Garden, Fenway Park, and New England Aquarium. While you're here, make sure you don't miss Encore Boston Harbor, Harvard Square, and Boston Harbor. ### What kind of weather should I plan for when I travel to Winchester? > Understanding the weather in Winchester will help you enjoy your stay to the fullest. The hottest months are usually July and August with an average temp of 69°F, while the coldest months are January and February with an average of 33°F. The snowiest months in Winchester are January, February, March, and April, with each month seeing an average of 5 inches of snowfall. ### What's the best way to get to my boutique hotel in Winchester? > You have a few options for getting to and around Winchester. The closest major airport is Bedford, MA (BED-Laurence G. Hanscom Field), which is located 7.7 mi (12.3 km) from the heart of the city, but Boston, MA (BNH-Boston Harbor Seaplane Base) may also be an option. 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