Title: Winchester B&B: Find the Best Bed and Breakfast from CA $225 | 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) ![](https://images.trvl-media.com/place/175481/5b3e907d-d662-4314-947e-70c644534c55.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 [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) In two weeks [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2026-02-13&endDate=2026-02-15&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2026-02-27&endDate=2026-03-01&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2026-03-27&endDate=2026-03-29&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/e935fa7f.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) ![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/124000000/123170000/123166200/123166125/940c4785.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 8.4/10 Very good (16 reviews) "The property was very clean and well maintained with spacious showers and a tv in your room. There are fresh towels as well as a free continental breakfast. The location has many restaurants/convenient stores not far away as well. Definitely recommend " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tyler CA $83 CA $96 total includes taxes & fees Mar 1 - Mar 2 [](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/112000000/111430000/111428500/111428434/4c5471b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Double Room | Interior](https://images.trvl-media.com/lodging/112000000/111430000/111428500/111428434/75a704bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, free WiFi](https://images.trvl-media.com/lodging/112000000/111430000/111428500/111428434/a17581c7.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 8.8/10 Excellent (19 reviews) "The entire place looks really amazing!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeremiah CA $86 CA $99 total includes taxes & fees Feb 1 - Feb 2 [](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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1150000/1145300/1145268/6c141328.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/2000000/1150000/1145300/1145268/9e8a5760.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 (1,001 reviews) "Outstanding location, pleasant facilities and staff, decent breakfast choices. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary CA $205 CA $236 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Boston-Hotels-The-College-Club-Of-Boston.h1145268.Hotel-Information) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/52000000/51880000/51876500/51876423/33110329.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/52000000/51880000/51876500/51876423/46c702a8.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) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/52000000/51880000/51876500/51876423/c8695da5.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 (61 reviews) "Great location and wonderful host" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert M. CA $127 CA $232 total includes taxes & fees Feb 3 - Feb 4 [](https://www.expedia.ca/Boston-Hotels-The-Pistachio-Room.h51876423.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/124000000/123090000/123086900/123086868/w987h712x22y16-3f0ec4ba.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/124000000/123090000/123086900/123086868/62a060c5.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 8.8/10 Excellent (6 reviews) "Very neat house " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nikhil CA $96 CA $111 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Boston-Hotels-Homestay-Near-Downtown-Boston.h123086868.Hotel-Information) ![King Luxury Suite Overlooking the Bay](https://images.trvl-media.com/lodging/13000000/12370000/12363500/12363414/390d6f57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/13000000/12370000/12363500/12363414/dadfe6c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Suite w/ Hot Tub and Fireplace](https://images.trvl-media.com/lodging/13000000/12370000/12363500/12363414/907b6e14.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/c75ebbed.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 (305 reviews) "The room was perfect, the house was perfect. The continental breakfast was poor. Oatmeal, Grits, pancakes, fresh fruit, banana " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chisulo CA $201 CA $225 total includes taxes & fees Feb 3 - Feb 4 [](https://www.expedia.ca/Boston-Hotels-The-Beacon-Waterfront-Inn.h12363414.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) ![Reception](https://images.trvl-media.com/lodging/1000000/980000/977400/977322/ccd05b4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Buffet](https://images.trvl-media.com/lodging/1000000/980000/977400/977322/3466e8e2.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) ### Irving House At Harvard [](https://www.expedia.ca/Boston-Hotels-Irving-House-At-Harvard.h977322.Hotel-Information) Mid-Cambridge 9.0/10 Wonderful (1,000 reviews) "Staff still worked and fed us through a huge snow storm. Really appreciated that" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Keoki CA $197 CA $226 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Boston-Hotels-Irving-House-At-Harvard.h977322.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/46000000/45020000/45019700/45019626/49c793d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/46000000/45020000/45019700/45019626/48f965fe.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) ### Daniels House Inn [](https://www.expedia.ca/Boston-Hotels-Daniels-House.h45019626.Hotel-Information) Salem 9.4/10 Exceptional (101 reviews) "Clearly a well managed historic inn. Gorgeous, comfortable, unique, in a very walkable area. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) April CA $280 CA $280 total includes taxes & fees Feb 22 - Feb 23 [](https://www.expedia.ca/Boston-Hotels-Daniels-House.h45019626.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/10300/10270/w2000h2936x0y64-1c599ade.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![West House Classic Suite, 1 Queen Bed, Private Bathroom](https://images.trvl-media.com/lodging/1000000/20000/10300/10270/775720ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/1000000/20000/10300/10270/29b4f786.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV](https://images.trvl-media.com/lodging/1000000/20000/10300/10270/84639258.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 (1,000 reviews) "This place was great. We loved our stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jared CA $243 CA $271 total includes taxes & fees Feb 7 - Feb 8 [](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/df4209be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1160000/1153700/1153660/033f0b58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Food and drink](https://images.trvl-media.com/lodging/2000000/1160000/1153700/1153660/585b10da.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 reviews) "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 $263 CA $294 total includes taxes & fees Feb 3 - Feb 4 [](https://www.expedia.ca/Boston-Hotels-North-Bridge-Inn.h1153660.Hotel-Information) ![Basic Quadruple Room](https://images.trvl-media.com/lodging/126000000/125060000/125050200/125050198/8b3dd660.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Basic Double or Twin Room | Bathroom](https://images.trvl-media.com/lodging/126000000/125060000/125050200/125050198/dc4fbf84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Basic Double or Twin Room | Interior](https://images.trvl-media.com/lodging/126000000/125060000/125050200/125050198/ebb85b41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Basic Quadruple Room | Interior](https://images.trvl-media.com/lodging/126000000/125060000/125050200/125050198/7be976af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Homestay Near Near Savin Hill Area [](https://www.expedia.ca/Boston-Hotels-Homestay-Near-Near-Savin-Hill-Area.h125050198.Hotel-Information) Dorchester 2.0/10 (1 review) "The guy change the house and location at an interval I didn't have no option. He kept sending encrypted access code for the check in. He masked to send ID to he's WhatsApp. He doesn't reply on time. I told him parking spot is important for me while there wasn't none at the place he changed me to. For very long waiting I was having the the obligation to find another place. When I try to reach out to him he even don't read the message. I don't recommend this hoster. It was a bad experience and a... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jules Andre CA $94 CA $109 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Boston-Hotels-Homestay-Near-Near-Savin-Hill-Area.h125050198.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=2026-02-14&endDate=2026-02-15®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 ![The Godfrey Hotel Boston](https://images.trvl-media.com/lodging/11000000/10120000/10118700/10118614/e4d256d2_y.jpg) ### The Godfrey Hotel Boston 10/10 Excellent "The hotel staff was excellent. Friendly, courteous, and professional. The room that I stayed in was spotless. " [](https://expedia.ca/Boston-Hotels-The-Godfrey-Hotel-Boston.h10118614.Hotel-Information) ![Hyatt Place Boston/Seaport District](https://images.trvl-media.com/lodging/47000000/46530000/46521400/46521349/5fe1e844_y.jpg) ### Hyatt Place Boston/Seaport District 10/10 Excellent "Very nice hotel and friendly staff. Hotel was clean and comfortable. Breakfast was not the best powdered eggs is definitely a no no and sausages was just okay need to upgrade breakfast " [](https://expedia.ca/Boston-Hotels-Hyatt-Place-BostonSeaport-District.h46521349.Hotel-Information) ![Omni Boston Hotel at the Seaport](https://images.trvl-media.com/lodging/69000000/68020000/68014400/68014393/26d11bc3_y.jpg) ### Omni Boston Hotel at the Seaport 10/10 Excellent "All good!" [](https://expedia.ca/Boston-Hotels-Omni-Boston-Hotel-At-The-Seaport.h68014393.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 "very nice view and very easy quick check in" [](https://expedia.ca/Boston-Hotels-CitizenM-Boston-Back-Bay.h96998829.Hotel-Information) ![Encore Boston Harbor](https://images.trvl-media.com/lodging/38000000/37060000/37057200/37057112/9dbd3cd5_y.jpg) ### Encore Boston Harbor 10/10 Excellent "GREAT LOCATION" [](https://expedia.ca/Boston-Hotels-Encore-Boston-Harbor.h37057112.Hotel-Information) ![The Dagny Boston](https://images.trvl-media.com/lodging/1000000/160000/151300/151201/4c15d693_y.jpg) ### The Dagny Boston 10/10 Excellent "Very clean, friendly staff, awesome gym. " [](https://expedia.ca/Boston-Hotels-Hilton-Boston-DowntownFaneuil-Hall.h151201.Hotel-Information) ![Hilton Boston Logan Airport](https://images.trvl-media.com/lodging/1000000/290000/281600/281536/23c65d09_y.jpg) ### Hilton Boston Logan Airport 10/10 Excellent "My favorite hotel! So convenient! Great restaurant! " [](https://expedia.ca/Boston-Hotels-Hilton-Boston-Logan-Airport.h281536.Hotel-Information) ![The Langham, Boston](https://images.trvl-media.com/lodging/1000000/10000/2600/2558/9a3ebe8a_y.jpg) ### The Langham, Boston 10/10 Excellent "Very nice hotel with excellent staff." [](https://expedia.ca/Boston-Hotels-The-Langham.h2558.Hotel-Information) ![citizenM Boston North Station](https://images.trvl-media.com/lodging/34000000/33880000/33870600/33870542/0eda38d5_y.jpg) ### citizenM Boston North Station 10/10 Excellent "Very clean and well maintained. Staff was friendly and attentive. " [](https://expedia.ca/Boston-Hotels-CitizenM-Boston-North-Station.h33870542.Hotel-Information) ## Find out more about Winchester ## Winchester B&B information | Number of reviews | 3,516 | | ----------------- | ------- | | Accommodation | 29 B&B | | Lowest Price | CA $225 | | Highest Price | CA $294 | ## 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) - [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) - 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