Title: Winchester B&B: Find the Best Bed and Breakfast from CA $197 | 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 # Find a Bed and Breakfast in Winchester from CA $197 - ![](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 [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-12-19&endDate=2025-12-21&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-12-26&endDate=2025-12-28&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2026-01-09&endDate=2026-01-11&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2026-02-06&endDate=2026-02-08&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winchester bed & breakfast ![Classic Triple Room | Interior](https://images.trvl-media.com/lodging/124000000/123170000/123166200/123166125/6d80ec6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Triple Room | Interior](https://images.trvl-media.com/lodging/124000000/123170000/123166200/123166125/e935fa7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Triple Room | Bathroom](https://images.trvl-media.com/lodging/124000000/123170000/123166200/123166125/08ce5fd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Triple Room](https://images.trvl-media.com/lodging/124000000/123170000/123166200/123166125/cd92220b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Homestay In Boston - [](https://www.expedia.ca/Boston-Hotels-Homestay-In-Boston.h123166125.Hotel-Information) Dorchester 10/10 Exceptional (1) "Very clean and cozy" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Vladimir CA $86 CA $99 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Boston-Hotels-Homestay-In-Boston.h123166125.Hotel-Information) ![Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111430000/111428500/111428434/14f525ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111430000/111428500/111428434/5ef8720e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111430000/111428500/111428434/4c5471b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/112000000/111430000/111428500/111428434/9c240fde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Homestay In Fields Corner Area Boston [](https://www.expedia.ca/Boston-Hotels-Homestay-In-Fields-Corner-Area-Boston.h111428434.Hotel-Information) Dorchester 10/10 Exceptional (1) "Great house!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Liang CA $81 CA $94 total includes taxes & fees Jan 2 - Jan 3, 2026 [](https://www.expedia.ca/Boston-Hotels-Homestay-In-Fields-Corner-Area-Boston.h111428434.Hotel-Information) ![Miscellaneous](https://images.trvl-media.com/lodging/2000000/1150000/1145300/1145268/7eb70e08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/2000000/1150000/1145300/1145268/92cc92c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Double Room, Ensuite (Two Full Beds)](https://images.trvl-media.com/lodging/2000000/1150000/1145300/1145268/f7cefa8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Double Room, Ensuite (Two Full Beds)](https://images.trvl-media.com/lodging/2000000/1150000/1145300/1145268/f350449a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The College Club of Boston [](https://www.expedia.ca/Boston-Hotels-The-College-Club-Of-Boston.h1145268.Hotel-Information) Back Bay 9.4/10 Exceptional (1001) "So pretty decoration for Christmas " ![Japan](https://a.travel-assets.com/egds/marks/flags/jp.svg) Kumiyo CA $210 CA $241 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Boston-Hotels-The-College-Club-Of-Boston.h1145268.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/124000000/123090000/123086900/123086868/62a060c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Towels, soap, shampoo, toilet paper](https://images.trvl-media.com/lodging/124000000/123090000/123086900/123086868/b7731ffe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, free WiFi](https://images.trvl-media.com/lodging/124000000/123090000/123086900/123086868/w987h712x22y16-40401b18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Television](https://images.trvl-media.com/lodging/124000000/123090000/123086900/123086868/1197f5e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Homestay Near Downtown Boston [](https://www.expedia.ca/Boston-Hotels-Homestay-Near-Downtown-Boston.h123086868.Hotel-Information) Dorchester CA $106 CA $122 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Boston-Hotels-Homestay-Near-Downtown-Boston.h123086868.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/1000000/980000/977400/977322/1f468c7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/980000/977400/977322/fc9d6dfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/980000/977400/977322/0ea091f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Economy Room, 2 Single Beds, Shared Bathroom](https://images.trvl-media.com/lodging/1000000/980000/977400/977322/bd0accdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Irving House At Harvard [](https://www.expedia.ca/Boston-Hotels-Irving-House-At-Harvard.h977322.Hotel-Information) Mid-Cambridge 9.0/10 Wonderful (1006) "Clean, affordable, historic building, little libraries in every room" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Josh CA $172 CA $197 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Boston-Hotels-Irving-House-At-Harvard.h977322.Hotel-Information) ![King Luxury Suite Overlooking the Bay](https://images.trvl-media.com/lodging/13000000/12370000/12363500/12363414/bc04ac14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Suite w/ Hot Tub and Fireplace](https://images.trvl-media.com/lodging/13000000/12370000/12363500/12363414/abd1dd37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![King Luxury Suite Overlooking the Bay](https://images.trvl-media.com/lodging/13000000/12370000/12363500/12363414/021114f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Suite w/ Hot Tub and Fireplace | Bathroom](https://images.trvl-media.com/lodging/13000000/12370000/12363500/12363414/49b9d077.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Beacon Waterfront Inn [](https://www.expedia.ca/Boston-Hotels-The-Beacon-Waterfront-Inn.h12363414.Hotel-Information) Hull 9.4/10 Exceptional (301) "Beautiful spacious room " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maryann CA $205 CA $229 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Boston-Hotels-The-Beacon-Waterfront-Inn.h12363414.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/52000000/51880000/51876500/51876423/3189ffae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/52000000/51880000/51876500/51876423/97cdf100.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/52000000/51880000/51876500/51876423/f9d27d3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/52000000/51880000/51876500/51876423/cd4359db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Pistachio Room at TPH - Boston [](https://www.expedia.ca/Boston-Hotels-The-Pistachio-Room.h51876423.Hotel-Information) Brighton 9.6/10 Exceptional (60) "Great location and wonderful host" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert M. CA $130 CA $237 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Boston-Hotels-The-Pistachio-Room.h51876423.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/46000000/45020000/45019700/45019626/a825dfb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/46000000/45020000/45019700/45019626/66de39e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/46000000/45020000/45019700/45019626/d2cd9637.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/46000000/45020000/45019700/45019626/c516227c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Daniels House Inn [](https://www.expedia.ca/Boston-Hotels-Daniels-House.h45019626.Hotel-Information) Salem 9.4/10 Exceptional (100) "This property is amazing. The home and rooms are clean, comfortable and beautiful. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rachel CA $317 CA $317 total includes taxes & fees Jan 9 - Jan 10, 2026 [](https://www.expedia.ca/Boston-Hotels-Daniels-House.h45019626.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/1000000/20000/10300/10270/312989ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily cooked-to-order breakfast](https://images.trvl-media.com/lodging/1000000/20000/10300/10270/241e8c87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee/tea maker](https://images.trvl-media.com/lodging/1000000/20000/10300/10270/9045dc2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Individually decorated, individually furnished, iron/ironing board](https://images.trvl-media.com/lodging/1000000/20000/10300/10270/c4f603c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Salem Inn [](https://www.expedia.ca/Boston-Hotels-The-Salem-Inn.h10270.Hotel-Information) Salem 9.2/10 Wonderful (1000) "Very clean and lovely atmosphere! Definitely grateful to stay here so I could walk everywhere! All the cool places are in walking distance." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chelsey CA $248 CA $277 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Boston-Hotels-The-Salem-Inn.h10270.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/2000000/1160000/1153700/1153660/c56c123e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/2000000/1160000/1153700/1153660/53429d6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/2000000/1160000/1153700/1153660/0b73197a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, coffee/tea maker](https://images.trvl-media.com/lodging/2000000/1160000/1153700/1153660/32429dd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### North Bridge Inn [](https://www.expedia.ca/Boston-Hotels-North-Bridge-Inn.h1153660.Hotel-Information) Concord 8.4/10 Very good (349) "Hot breakfast, attentive staff, proximity to a lot of history including Boston" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Martin CA $269 CA $300 total includes taxes & fees Dec 20 - Dec 21 [](https://www.expedia.ca/Boston-Hotels-North-Bridge-Inn.h1153660.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=2025-12-27&endDate=2025-12-28®ionId=175481&adults=2&lodging=BED_AND_BREAKFAST&sort=RECOMMENDED&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-Bed-And-Breakfast.d175481-aaBedAndBreakfast.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Bed-And-Breakfast.d175481-aaBedAndBreakfast.Travel-Guide-Accommodation) ## Top Winchester Hotel Reviews ![Hilton Boston Logan Airport](https://images.trvl-media.com/lodging/1000000/290000/281600/281536/23c65d09_y.jpg) ### Hilton Boston Logan Airport 10/10 Excellent "It’s very convenient when you have an early flight in the am. " [](https://expedia.ca/Boston-Hotels-Hilton-Boston-Logan-Airport.h281536.Hotel-Information) ![citizenM Boston Back Bay](https://images.trvl-media.com/lodging/97000000/97000000/96998900/96998829/90056141_y.jpg) ### citizenM Boston Back Bay 10/10 Excellent "We had a great stay. The location was perfect, bed was super comfy and bar area great to rewind in at the end of the day." [](https://expedia.ca/Boston-Hotels-CitizenM-Boston-Back-Bay.h96998829.Hotel-Information) ![Harborside Inn Of Boston](https://images.trvl-media.com/lodging/1000000/210000/202900/202814/b3140789_y.jpg) ### Harborside Inn Of Boston 10/10 Excellent "The staff was very friendly and helpful. There is a restaurant connected to the hotel. Food and staff there were excellent " [](https://expedia.ca/Boston-Hotels-Harborside-Inn-Of-Boston.h202814.Hotel-Information) ![Seaport Hotel Boston](https://images.trvl-media.com/lodging/1000000/80000/79900/79888/fa9777a9_y.jpg) ### Seaport Hotel Boston 10/10 Excellent "As expected" [](https://expedia.ca/Boston-Hotels-Seaport-Hotel-Boston.h79888.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 "Yyy" [](https://expedia.ca/Boston-Hotels-The-Godfrey-Hotel-Boston.h10118614.Hotel-Information) ![Omni Parker House ](https://images.trvl-media.com/lodging/1000000/30000/23500/23415/c414a1f3_y.jpg) ### Omni Parker House 10/10 Excellent "The location was extremely convenient. Room was huge. Front desk staff was very helpful checking in and out" [](https://expedia.ca/Boston-Hotels-Boston-Omni-Parker-House-Hotel.h23415.Hotel-Information) ![The Dagny Boston](https://images.trvl-media.com/lodging/1000000/160000/151300/151201/4c15d693_y.jpg) ### The Dagny Boston 10/10 Excellent "We intentionally stay at the Dagny Boston for so many reasons, but top of my list is the absolutely delightful friendliness we experience with EVERYONE on staff at the hotel. From being greeted at the door in arrival to the smiles from housekeeping staff, everyone is WONDERFUL!!! Thank you so much for a fabulous stay!!!!" [](https://expedia.ca/Boston-Hotels-Hilton-Boston-DowntownFaneuil-Hall.h151201.Hotel-Information) ![Hilton Boston Park Plaza](https://images.trvl-media.com/lodging/1000000/10000/4300/4215/6e9f8959_y.jpg) ### Hilton Boston Park Plaza 10/10 Excellent "Amazing hotel I love the gym and the facilities!" [](https://expedia.ca/Boston-Hotels-Boston-Park-Plaza.h4215.Hotel-Information) ![The Charles Hotel](https://images.trvl-media.com/lodging/1000000/20000/15900/15861/66098bc6_y.jpg) ### The Charles Hotel 10/10 Excellent "Everything was great" [](https://expedia.ca/Boston-Hotels-The-Charles-Hotel.h15861.Hotel-Information) ## Find out more about Winchester ## Winchester B&B information | Number of reviews | 3,502 | | ----------------- | ------- | | Accommodation | 29 B&B | | Lowest Price | CA $197 | | Highest Price | CA $317 | ## Frequently asked questions ### Searching for B&Bs in Winchester? ### How do you know if a B&B is the right choice for your stay? ### What are the best B&Bs in Winchester? ### When should I stay at a B&B in Winchester? ### What is there to do in Winchester? ### How can I get to and around Winchester? ## 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) - 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