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 [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248635975869849&startDate=2025-10-31&endDate=2025-11-02&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [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 one month [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=553248635975869849&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248635975869849&startDate=2025-12-19&endDate=2025-12-21&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) ![Aerial view](https://images.trvl-media.com/lodging/8000000/7760000/7754000/7753947/b28516d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, bed sheets](https://images.trvl-media.com/lodging/8000000/7760000/7754000/7753947/fd1046f8.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) ### Locust Tree Bed and Breakfast LLC East Canaan 9.0/10 Wonderful (406) "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 Oct 22 - Oct 23 [](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) ![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) ![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) ![Interior](https://images.trvl-media.com/lodging/13000000/12990000/12986600/12986517/cabd45f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Truman Gillet House Bed & Breakfast Granby 9.6/10 Exceptional (96) "Pleasant hosts, quiet area, big soaking sub, we enjoyed our stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) michelle CA $196 CA $218 total includes taxes & fees Oct 22 - Oct 23 [](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) ![Library](https://images.trvl-media.com/lodging/96000000/96000000/95991200/95991149/e7ac793d.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) ![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 (147) "A wonderful facility, lovely breakfast and way way more than you would expect in every catagory." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steve CA $231 CA $265 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Norfolk-Hotels-Blackberry-River-Inn.h95991149.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) ![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) ![45-inch flat-screen TV with digital channels, streaming services](https://images.trvl-media.com/lodging/106000000/105820000/105813900/105813835/683afd1c.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 $209 CA $234 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Sheffield-Hotels-Wilder-House-Berkshires.h105813835.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) ![Porch](https://images.trvl-media.com/lodging/1000000/50000/42300/42279/99af973d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/50000/42300/42279/5cb24d7d.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) ### Simsbury 1820 House Simsbury Center 9.2/10 Wonderful (1001) "A beautiful place to enjoy the many sights of the area from." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $229 CA $288 total includes taxes & fees Nov 2 - Nov 3 [](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) ![Garden](https://images.trvl-media.com/lodging/2000000/1160000/1159100/1159082/5a1ddd61.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) ![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) ### 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 $404 CA $449 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Torrington-Hotels-Manor-House-Inn.h1159082.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=2025-11-04&endDate=2025-11-05®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 ![Homewood Suites by Hilton Hartford-Farmington](//images.trvl-media.com/lodging/1000000/210000/203500/203496/4f26a2b3_y.jpg) ### Homewood Suites by Hilton Hartford-Farmington 10/10 Excellent "The only problem is the potholes and deep drains on the entrance and exit that have not been repaired for the last year. " [](https://expedia.ca/Hartford-Hotels-Homewood-Suites-By-Hilton-Hartford-Farmington.h203496.Hotel-Information) ![The Farmington Inn & Suites](//images.trvl-media.com/lodging/1000000/20000/10200/10185/1c89931a_y.jpg) ### The Farmington Inn & Suites 10/10 Excellent "Very clean rooms. Wait staff at the cafe was always replenishing items that ran out during breakfast. Very friendly staff." [](https://expedia.ca/Hartford-Hotels-The-Farmington-Inn-Suites.h10185.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 "Friendly and helpful staff. Clean room. Safe and well maintained environment. " [](https://expedia.ca/Hartford-Hotels-Fairfield-Inn-Suites-By-Marriott-Plainville.h9965.Hotel-Information) ![Simsbury Inn](//images.trvl-media.com/lodging/1000000/20000/16800/16756/ceb52ab8_y.jpg) ### Simsbury Inn 10/10 Excellent "Great stay, location, and service!!" [](https://expedia.ca/Weatogue-Hotels-Simsbury-Inn.h16756.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 "Excellent location and value" [](https://expedia.ca/Hartford-Hotels-Avon-Old-Farms-Hotel.h2635.Hotel-Information) ![Blackberry River Inn](//images.trvl-media.com/lodging/96000000/96000000/95991200/95991149/50a90cdd_y.jpg) ### Blackberry River Inn 10/10 Excellent "A wonderful facility, lovely breakfast and way way more than you would expect in every catagory." [](https://expedia.ca/Norfolk-Hotels-Blackberry-River-Inn.h95991149.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 "Walls are thin but it was clean and safe with friendly staff." [](https://expedia.ca/Torrington-Hotels-Americas-Best-Value-Inn-Torrington-CT.h5738.Hotel-Information) ![Delamar West Hartford](//images.trvl-media.com/lodging/19000000/18170000/18166800/18166744/d809cec2_y.jpg) ### Delamar West Hartford 10/10 Excellent "Great as usual " [](https://expedia.ca/Hartford-Hotels-Delamar-West-Hartford.h18166744.Hotel-Information) ![Days Inn by Wyndham Torrington](//images.trvl-media.com/lodging/1000000/50000/50000/49932/dd052437_y.jpg) ### Days Inn by Wyndham Torrington 8/10 Good "Convenient location. Everything was good, not great. Met expectations for the price and location. Solid three stars all-around. Room was comfortable, but a bit small. No dresser or drawers. Front desk staff was friendly, but overworked. Nobody there when we went to check in an when we went back the next morning to get a room key fixed. Overall condition is a bit tired, but they said that renovations are underway." [](https://expedia.ca/Torrington-Hotels-Days-Inn-By-Wyndham-Torrington.h49932.Hotel-Information) ## Find out more about Winchester ## Winchester B&B information | Number of reviews | 1,788 | | --- | --- | | Accommodation | 9 B&B | | Lowest Price | CA $169 | | Highest Price | CA $449 | ## 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 Platt Hill State Park 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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