Title: Cheshire B&B: Find the Best Bed and Breakfast from CA $400 | Expedia.ca [Hotels in Cheshire](https://expedia.ca/Cheshire-Hotels.d183057.Travel-Guide-Hotels)[Vacation Rentals in Cheshire](https://expedia.ca/Cheshire-Vacation-Rentals.d183057.Travel-Guide-VacationRentals)[Flights to Cheshire](https://expedia.ca/Cheap-Flights-To-Cheshire.d183057.Travel-Guide-Flights)[Cheshire Car Rentals](https://expedia.ca/Car-Rentals-In-Cheshire.d183057.Car-Rental-Guide)[Cheshire Vacation Packages](https://expedia.ca/Cheshire.d183057.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/ab039a4411a79c16e7c533ffaba43069.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Tai Bui # Find a Bed and Breakfast in Cheshire from CA $400 ![](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 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=183057&startDate=2025-10-17&endDate=2025-10-19&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=183057&startDate=2025-10-24&endDate=2025-10-26&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=183057&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=183057&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Cheshire B&B ![Room, 1 King Bed, Patio, Ground Floor (7)](https://images.trvl-media.com/lodging/32000000/31960000/31958900/31958886/c76f25a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/32000000/31960000/31958900/31958886/5ee4b9df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/32000000/31960000/31958900/31958886/f87cac33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![36-inch Smart TV with cable channels, TV, Netflix](https://images.trvl-media.com/lodging/32000000/31960000/31958900/31958886/6b4787fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Homestead Madison Center 10/10 Exceptional (87) "This is our 2nd year staying at the Homestead B & B. We absolutely love it here! Great food, amenities galore, and just an awesome getaway!" CA $390 CA $433 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Old-Saybrook-Hotels-The-Homestead.h31958886.Hotel-Information) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/31000000/30050000/30043400/30043334/a616a4b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/31000000/30050000/30043400/30043334/8566427f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/31000000/30050000/30043400/30043334/983938c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/31000000/30050000/30043400/30043334/a18e931d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Bevin House Bed & Breakfast East Hampton 9.6/10 Exceptional (78) "The staff was super friendly and welcoming. The house was beautiful and the grounds full of things to explore. The breakfast was presently with panache and tasted great. We swam in the pool, ate at local restaurants, pet a turkey, and visited the local winery. I would highly recommend this establishment. " CA $360 CA $400 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Hartford-Hotels-The-Bevin-House-Bed-Breakfast.h30043334.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/102000000/101880000/101878900/101878830/056c3b04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/102000000/101880000/101878900/101878830/5aa07695.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/102000000/101880000/101878900/101878830/ecd1ecf3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/102000000/101880000/101878900/101878830/cb2d285a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stylish 3000 Square-Feet Private Floor Luxury Oasis in a Commercial Space Hamden CA $882 CA $1,367 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Hamden-Hotels-2500-SF-Loft-You-Own-Full-Floor-Luxury-Oasis-In-A-Commercial-Space.h101878830.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=2025-10-26&endDate=2025-10-27®ionId=183057&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%2FCheshire-Bed-And-Breakfast.d183057-aaBedAndBreakfast.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FCheshire-Bed-And-Breakfast.d183057-aaBedAndBreakfast.Travel-Guide-Accommodation) ## Top Cheshire Hotel Reviews ![Best Western Hartford Hotel & Suites](//images.trvl-media.com/lodging/1000000/20000/12200/12156/cfbe36c4_y.jpg) ### Best Western Hartford Hotel & Suites 10/10 Excellent "Very good pricing" [](https://expedia.ca/Hartford-Hotels-Best-Western-Hartford-Hotel-Suites.h12156.Hotel-Information) ![Woodspring Suites Newington - Hartford South](//images.trvl-media.com/lodging/106000000/105290000/105285500/105285488/3fbd5164_y.jpg) ### Woodspring Suites Newington - Hartford South 10/10 Excellent "Clean room, clean sheets and towels. Lobby and elevator clean. Nice staff all around" [](https://expedia.ca/Newington-Hotels-Woodspring-Suites-Newington-Hartford-South.h105285488.Hotel-Information) ![Hyatt Place Milford / New Haven](//images.trvl-media.com/lodging/2000000/1570000/1562800/1562702/0336d577_y.jpg) ### Hyatt Place Milford / New Haven 10/10 Excellent "Overall good" [](https://expedia.ca/New-Haven-Hotels-Hyatt-Place-Milford-New-Haven.h1562702.Hotel-Information) ![La Quinta Inn & Suites by Wyndham New Haven](//images.trvl-media.com/lodging/1000000/10000/1300/1241/92ca5e77_y.jpg) ### La Quinta Inn & Suites by Wyndham New Haven 10/10 Excellent "good" [](https://expedia.ca/New-Haven-Hotels-La-Quinta-Inn-Suites-By-Wyndham-New-Haven.h1241.Hotel-Information) ![New Haven Hotel](//images.trvl-media.com/lodging/1000000/40000/36800/36721/dd69cbb4_y.jpg) ### New Haven Hotel 10/10 Excellent "There is no breakfast possibility offered😟" [](https://expedia.ca/New-Haven-Hotels-New-Haven-Hotel.h36721.Hotel-Information) ![Best Western Executive Hotel Of New Haven - West Haven](//images.trvl-media.com/lodging/1000000/30000/23300/23217/b63e42e2_y.jpg) ### Best Western Executive Hotel Of New Haven - West Haven 10/10 Excellent "Very neat and tidy, in and around the property. All basic necessities available. Good value for money. " [](https://expedia.ca/New-Haven-Hotels-Best-Western-Executive-Hotel-Of-New-Haven-West-Haven.h23217.Hotel-Information) ![Wyndham Southbury](//images.trvl-media.com/lodging/16000000/15660000/15651900/15651820/412fe155_y.jpg) ### Wyndham Southbury 10/10 Excellent "The hotel was easily accessible from the main highways. Nice location. " [](https://expedia.ca/Danbury-Hotels-Wyndham-Southbury.h15651820.Hotel-Information) ![Hotel Marcel New Haven, Tapestry Collection By Hilton](//images.trvl-media.com/lodging/72000000/71430000/71427300/71427300/1699c03c_y.jpg) ### Hotel Marcel New Haven, Tapestry Collection By Hilton 10/10 Excellent "Value " [](https://expedia.ca/New-Haven-Hotels-Hotel-Marcel-New-Haven.h71427300.Hotel-Information) ![The Capitol Hotel](//images.trvl-media.com/lodging/1000000/10000/6800/6777/2c26b973_y.jpg) ### The Capitol Hotel 10/10 Excellent "We had a great room with a beautiful view of the Hartford Capital! Room was ckean and comfortable and clean. Staff was friendly. Would recommend. " [](https://expedia.ca/Hartford-Hotels-The-Capitol-Hotel.h6777.Hotel-Information) ## Find out more about Cheshire ## Cheshire B&B information | Number of reviews | 165 | | --- | --- | | Accommodation | 9 B&B | | Lowest Price | CA $400 | | Highest Price | CA $1,367 | ## Frequently asked questions ### Searching for B&Bs in Cheshire? > If you want to find a place to stay with fewer rooms than the traditional hotel and a cozy environment, a B&B may be the perfect thing for your getaway to Cheshire. While you're here, you can get to know Cheshire by exploring its natural beauty. Consider a stop by Roaring Brook Park and Drazen Orchards. ### How do you know if a B&B is a good option for your stay? > With attentive service, opportunities to mingle with other guests, and top-rated breakfasts, B&Bs all have a one-of-a-kind environment. ### What are the best B&Bs in Cheshire? > Here are some well-liked B&Bs in the surrounding area: [Jay's Ranch](https://www.expedia.ca/Hamden-Hotels-Jays-Ranch.h93133074.Hotel-Information): 3 rooms. 10.6 mi (17.1 km) from the heart of Cheshire.[Higganum House B&B](https://www.expedia.ca/Higganum-Hotels-Higganum-House-BB.h114814862.Hotel-Information): 4 rooms. 18.1 mi (29.1 km) from the heart of downtown. Enjoy the private yard and unique décor. [Sunny Peace Homestay](https://www.expedia.ca/Harwinton-Hotels-Sunny-Peace.h109140360.Hotel-Information): 2 rooms. Located 18.2 mi (29.3 km) from the core of Cheshire. ### When should I book my B&B in Cheshire? > When you're dreaming of a getaway to Cheshire, be sure to take into account the year-round temperatures. The hottest months are usually July and August with an average temp of 70°F, while the coldest months are January and February with an average of 33°F. Average annual precipitation for Cheshire is 54 inches. ### What is there to do in Cheshire? > If you're looking to find something to do during your travels, you might consider checking out Barker Character, Comic and Cartoon Museum and Cheshire Hollow Farm. You might put Roaring Brook Park and Maplecroft Plaza Shopping Center on your list if you want to see more of the area. ### How can I get to and around Cheshire? > Planning your excursions in and around Cheshire is easier with these transportation options. Fly into Oxford, CT (OXC-Waterbury - Oxford), which is located 12 mi (19.3 km) away from the heart of the city. You can also search for flights into New Haven, CT (HVN-Tweed - New Haven Regional), which is 16.5 mi (26.6 km) away. 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