Title: Winchester B&B: Find the Best Bed and Breakfast from CA $169 | Expedia.ca [Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d553248635975869849.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d553248635975869849.Travel-Guide-VacationRentals)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d553248635975869849.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/Winchester.d553248635975869849.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 a Bed and Breakfast in Winchester from CA $169 - ![](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 [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=553248635975869849&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=553248635975869849&startDate=2025-11-14&endDate=2025-11-16&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=553248635975869849&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248635975869849&startDate=2025-12-26&endDate=2025-12-28&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Winchester B&B ![Terrace/patio](https://images.trvl-media.com/lodging/8000000/7760000/7754000/7753947/fb8a0016.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/8000000/7760000/7754000/7753947/9c157bdc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/8000000/7760000/7754000/7753947/9fc87fbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/8000000/7760000/7754000/7753947/b28516d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Locust Tree Bed and Breakfast LLC East Canaan 9.0/10 Wonderful (410) "Peaceful area and great staff; Thank you for the service and experience " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andre CA $147 CA $169 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Torrington-Hotels-Locust-Tree-Bed-And-Breakfast-LLC.h7753947.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/13000000/12990000/12986600/12986517/6b073b81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/13000000/12990000/12986600/12986517/cabd45f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Traditional Studio Suite, Multiple Beds | Bathroom](https://images.trvl-media.com/lodging/13000000/12990000/12986600/12986517/77eb1bd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, individually decorated, individually furnished](https://images.trvl-media.com/lodging/13000000/12990000/12986600/12986517/c1a6e504.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Truman Gillet House Bed & Breakfast Granby 9.6/10 Exceptional (98) "It was a lovely stay overnight with a delicious homemade breakfast. Very clean and hosts were so nice." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lynn CA $196 CA $218 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Hartford-Hotels-Truman-Gillet-House-Bed-Breakfast.h12986517.Hotel-Information) ![Library](https://images.trvl-media.com/lodging/96000000/96000000/95991200/95991149/50a90cdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/96000000/96000000/95991200/95991149/d4318cc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Library](https://images.trvl-media.com/lodging/96000000/96000000/95991200/95991149/e7ac793d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/96000000/96000000/95991200/95991149/6349c6d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Blackberry River Inn Norfolk 9.4/10 Exceptional (151) "The highlight of our 10 day trip through the northeast" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) bruce CA $230 CA $265 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Norfolk-Hotels-Blackberry-River-Inn.h95991149.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/1000000/50000/42300/42279/6326a611.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/50000/42300/42279/7e4b3c86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Queen with Sofa Bed](https://images.trvl-media.com/lodging/1000000/50000/42300/42279/c37c5ed2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/1000000/50000/42300/42279/99af973d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Simsbury 1820 House Simsbury Center 9.2/10 Wonderful (1003) "Staff are super friendly and kind, the room is clean " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Roisin CA $209 CA $264 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Hartford-Hotels-Simsbury-1820-House.h42279.Hotel-Information) ![Interior detail](https://images.trvl-media.com/lodging/2000000/1160000/1159100/1159082/dee42d8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1160000/1159100/1159082/2ff2ecab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1160000/1159100/1159082/016e08a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/2000000/1160000/1159100/1159082/5a622627.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Manor House Inn Norfolk 9.4/10 Exceptional (138) "Excellent bed and breakfast, room was clean and comfortable." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kevin CA $403 CA $448 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Torrington-Hotels-Manor-House-Inn.h1159082.Hotel-Information) ![Wilder House Berkshires Room 3](https://images.trvl-media.com/lodging/106000000/105820000/105813900/105813835/f0c223e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![45-inch flat-screen TV with digital channels, streaming services](https://images.trvl-media.com/lodging/106000000/105820000/105813900/105813835/8660fa49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/106000000/105820000/105813900/105813835/f8f74b93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/106000000/105820000/105813900/105813835/7fea6163.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wilder House Berkshires Sheffield 9.8/10 Exceptional (37) "Highly recommend this beautiful bed & breakfast! The room was wonderful and overlooked the property, the breakfast was delicious, and the hospitality was amazing. I had a fantastic stay, and will definitely stay at The Wilder House again when I'm in the area." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marina CA $220 CA $246 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Sheffield-Hotels-Wilder-House-Berkshires.h105813835.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=2025-11-16&endDate=2025-11-17®ionId=553248635975869849&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.d553248635975869849-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.d553248635975869849-aaBedAndBreakfast.Travel-Guide-Accommodation) ## Top Winchester Hotel Reviews ![The Farmington Inn & Suites](//images.trvl-media.com/lodging/1000000/20000/10200/10185/1c89931a_y.jpg) ### The Farmington Inn & Suites 10/10 Excellent "Clean room, great staff, large room in a welcoming hotel. This was much more than I expected. We'd gladly stay here again." [](https://expedia.ca/Hartford-Hotels-The-Farmington-Inn-Suites.h10185.Hotel-Information) ![Delamar West Hartford](//images.trvl-media.com/lodging/19000000/18170000/18166800/18166744/d809cec2_y.jpg) ### Delamar West Hartford 10/10 Excellent "Valet+Welcome Proseccos & Bottled Water=👍" [](https://expedia.ca/Hartford-Hotels-Delamar-West-Hartford.h18166744.Hotel-Information) ![Avon Old Farms Hotel](//images.trvl-media.com/lodging/1000000/10000/2700/2635/d997675e_y.jpg) ### Avon Old Farms Hotel 10/10 Excellent "We did not have breakfast. The staff was friendly. However, they should stock more complimentary items such as hot tea and not just say "oh, we are out". " [](https://expedia.ca/Hartford-Hotels-Avon-Old-Farms-Hotel.h2635.Hotel-Information) ![Home2 Suites by Hilton Bristol](//images.trvl-media.com/lodging/95000000/94950000/94946700/94946614/74bd7e00_y.jpg) ### Home2 Suites by Hilton Bristol 10/10 Excellent "Room was immaculate. Nice spacious lobby with plenty of areas to sit. Nice outdoor enclosed patio in the back to hang out. Breakfast was very good, egg bites, turkey bacon, waffle machine, yogurt and many more options. " [](https://expedia.ca/Bristol-Hotels-Home2-Suites-By-Hilton-Bristol.h94946614.Hotel-Information) ![Blackberry River Inn](//images.trvl-media.com/lodging/96000000/96000000/95991200/95991149/50a90cdd_y.jpg) ### Blackberry River Inn 10/10 Excellent "Charming place. No tv. Small room. Good breakfast. " [](https://expedia.ca/Norfolk-Hotels-Blackberry-River-Inn.h95991149.Hotel-Information) ![Extended Stay America Suites Hartford Farmington](//images.trvl-media.com/lodging/1000000/160000/151100/151013/02939ae3_y.jpg) ### Extended Stay America Suites Hartford Farmington 10/10 Excellent "Thank Staff was Great! Very very nice and attentive. Room very clean, Quiet we rested well! The Great was awesome and exit was wonderful. Parking was smoothe. We’ll return to enjoy another quiet night get away. " [](https://expedia.ca/Hartford-Hotels-Extended-Stay-America-Suites-Hartford-Farmington.h151013.Hotel-Information) ![Sheraton Hartford Hotel at Bradley Airport](//images.trvl-media.com/lodging/1000000/10000/4700/4632/c8edc11d_y.jpg) ### Sheraton Hartford Hotel at Bradley Airport 10/10 Excellent "Very safe, convenient, clean place to stay; current construction caused confusion trying to unload and check-in with blocked drive in. Remodeling also put undue pressure on wait staff with temporary dining area. However, staff at checkin and especially in the restaurant are super competent and super friendly." [](https://expedia.ca/Hartford-Hotels-Sheraton-Hartford-Hotel-At-Bradley-Airport.h4632.Hotel-Information) ![Americas Best Value Inn Torrington CT](//images.trvl-media.com/lodging/1000000/10000/5800/5738/a9b48332_y.jpg) ### Americas Best Value Inn Torrington CT 10/10 Excellent "Excellent parking." [](https://expedia.ca/Torrington-Hotels-Americas-Best-Value-Inn-Torrington-CT.h5738.Hotel-Information) ![Fairfield Inn & Suites by Marriott Plainville](//images.trvl-media.com/lodging/1000000/10000/10000/9965/01d5897d_y.jpg) ### Fairfield Inn & Suites by Marriott Plainville 10/10 Excellent "Nice hotel. Breakfast quality very good" [](https://expedia.ca/Hartford-Hotels-Fairfield-Inn-Suites-By-Marriott-Plainville.h9965.Hotel-Information) ## Find out more about Winchester ## Winchester B&B information | Number of reviews | 1,797 | | --- | --- | | Accommodation | 9 B&B | | Lowest Price | CA $169 | | Highest Price | CA $448 | ## Frequently asked questions ### Searching for B&Bs in Winchester? > Whether you're on a romantic trip and want to stay somewhere quiet and intimate, or you're a solo traveler hoping to get some tips from locals, a B&B can be a good choice for many different types of travelers. If your ideal vacation to Winchester includes spending lots of time outside, Walker Field and Rowley Fields are good spots to enjoy the scenery. ### Why consider B&Bs instead of traditional hotels? > Every B&B has a unique charm. Whether it's a picturesque garden or a sunlit breakfast nook to enjoy your morning cup of coffee, the small details are what make bed and breakfasts a home away from home. ### What are the best bed and breakfasts in Winchester? > Here are some well-liked B&Bs in the area: [Simsbury 1820 House](https://www.expedia.ca/Hartford-Hotels-Simsbury-1820-House.h42279.Hotel-Information): 16.5 mi (26.5 km) from the heart of Winchester. Enjoy the designer toiletries and bars. [Blackberry River Inn](https://www.expedia.ca/Norfolk-Hotels-Blackberry-River-Inn.h95991149.Hotel-Information): 14 rooms. 8.3 mi (13.3 km) from the downtown core. Enjoy the free cooked breakfast and outdoor pool. [Locust Tree Bed and Breakfast LLC](https://www.expedia.ca/Torrington-Hotels-Locust-Tree-Bed-And-Breakfast-LLC.h7753947.Hotel-Information): 7 rooms. Situated 11.5 mi (18.5 km) from the heart of Winchester. [Wilder House Berkshires](https://www.expedia.ca/Sheffield-Hotels-Wilder-House-Berkshires.h105813835.Hotel-Information): 5 rooms. 17.2 mi (27.7 km) from the heart of downtown. Enjoy the free cooked breakfast and unique décor. [Truman Gillet House Bed & Breakfast](https://www.expedia.ca/Hartford-Hotels-Truman-Gillet-House-Bed-Breakfast.h12986517.Hotel-Information): 2 rooms. Located 15.9 mi (25.6 km) from the core of Winchester. Enjoy the free full breakfast and unique décor. ### What's the best time of year to stay at a B&B in Winchester? > When you're planning your stay in Winchester, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 67°F, while the coldest months are January and February with an average of 30°F. The snowiest months in Winchester are January, February, March, and April, with each month seeing an average of 6 inches of snowfall. ### What is there to do in Winchester? > Spend some time exploring Highland Lake and Walker Field if you're hoping to see some of the area's natural features. You might put Burr Pond State Park and Winchester Historical Society on your list if you want to see more of the area. ### How can I get to and around Winchester? > Mapping out your trip in and around Winchester is easy with these transportation options. Fly into Bradley Intl. Airport (BDL), which is located 21.9 mi (35.2 km) away from the heart of the city. Otherwise, you can search for flights to Westfield, MA (BAF-Barnes Municipal), which is 25.8 mi (41.5 km) away. 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