Title: Cheshire B&B: Find the Best Bed and Breakfast from CA $382 | 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) ![Castle Craig at Hubbard Park, Meriden, CT. easily replaceable sky. with a clean, classic view of the tower. Very recognizable image of this historic structure.](https://images.trvl-media.com/place/183057/92c74fd9-1a45-4931-a43e-251e181e803f.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find a Bed and Breakfast in Cheshire from CA $382 - ![](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 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) In two weeks [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=183057&startDate=2025-12-12&endDate=2025-12-14&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=183057&startDate=2025-12-26&endDate=2025-12-28&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=183057&startDate=2026-01-23&endDate=2026-01-25&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Cheshire B&B ![Exterior](https://images.trvl-media.com/lodging/94000000/93140000/93133100/93133074/190efae8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee/tea maker, electric kettle](https://images.trvl-media.com/lodging/94000000/93140000/93133100/93133074/79349d1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed](https://images.trvl-media.com/lodging/94000000/93140000/93133100/93133074/6f34105d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business Room | Bathroom](https://images.trvl-media.com/lodging/94000000/93140000/93133100/93133074/9dd943d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Jay's Ranch Hamden 7.6/10 Good (47) "Im so happy I found this place to stay. Meets all my needs and great service !!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Diana [](https://www.expedia.ca/Hamden-Hotels-Jays-Ranch.h93133074.Hotel-Information) ![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) ![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) ![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) ### The Homestead Madison Center 10/10 Exceptional (89) "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!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cynthia CA $377 CA $418 total includes taxes & fees Dec 17 - Dec 18 [](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) ![Meeting facility](https://images.trvl-media.com/lodging/31000000/30050000/30043400/30043334/983938c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Executive lounge](https://images.trvl-media.com/lodging/31000000/30050000/30043400/30043334/a35721c0.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) ### The Bevin House Bed & Breakfast East Hampton 9.6/10 Exceptional (81) "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. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Juliette CA $344 CA $382 total includes taxes & fees Dec 4 - Dec 5 [](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/cb2d285a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/102000000/101880000/101878900/101878830/e5e2d941.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) ### Stylish 3000 Square-Feet Private Floor Luxury Oasis in a Commercial Space Hamden CA $885 CA $1,361 total includes taxes & fees Nov 30 - Dec 1 [](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=2025-12-11&endDate=2025-12-12®ionId=183057&adults=2&lodging=BED_AND_BREAKFAST&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=AA_BF_PROMO_183057) ![](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](https://images.trvl-media.com/lodging/1000000/20000/12200/12156/cfbe36c4_y.jpg) ### Best Western Hartford Hotel & Suites 10/10 Excellent "great front desk service" [](https://expedia.ca/Hartford-Hotels-Best-Western-Hartford-Hotel-Suites.h12156.Hotel-Information) ![Hampton Inn & Suites Hartford/East Hartford](https://images.trvl-media.com/lodging/3000000/2950000/2943100/2943093/5cf369a5_y.jpg) ### Hampton Inn & Suites Hartford/East Hartford 10/10 Excellent "Fun staff" [](https://expedia.ca/Hartford-Hotels-Hampton-Inn-Suites-HartfordEast-Hartford.h2943093.Hotel-Information) ![New Haven Hotel](https://images.trvl-media.com/lodging/1000000/40000/36800/36721/d665dc9c_y.jpg) ### New Haven Hotel 10/10 Excellent "Spotless and spacious room. Exceptional front desk staff. Great location a short walk from Yale University. Welcoming lobby with mini-shop for snacks, drinks, necessities. Beer, wine, other beverages in lobby. We loved our stay here!" [](https://expedia.ca/New-Haven-Hotels-New-Haven-Hotel.h36721.Hotel-Information) ![Avon Old Farms Hotel](https://images.trvl-media.com/lodging/1000000/10000/2700/2635/d997675e_y.jpg) ### Avon Old Farms Hotel 10/10 Excellent "Beautiful room and property. Had a wonderful time! Definitely will stay again. " [](https://expedia.ca/Hartford-Hotels-Avon-Old-Farms-Hotel.h2635.Hotel-Information) ![Holiday Inn Cheshire - Southington by IHG](https://images.trvl-media.com/lodging/2000000/1810000/1802800/1802750/a3c0d287_y.jpg) ### Holiday Inn Cheshire - Southington by IHG 10/10 Excellent "I didn't know about breakfast" [](https://expedia.ca/New-Haven-Hotels-Holiday-Inn-Cheshire-Southington.h1802750.Hotel-Information) ![Motel 6 New Haven - Branford, CT](https://images.trvl-media.com/lodging/1000000/60000/50400/50320/c15293e5_y.jpg) ### Motel 6 New Haven - Branford, CT 10/10 Excellent "Stay here because it’s clean and the price is right for the money you can’t beat it plus you have excellent food at Capones restaurant 100 feet away for your convenience " [](https://expedia.ca/New-Haven-Hotels-Motel-6-New-Haven-Branford.h50320.Hotel-Information) ![Omni New Haven Hotel at Yale](https://images.trvl-media.com/lodging/1000000/50000/50000/49957/7466af25_y.jpg) ### Omni New Haven Hotel at Yale 10/10 Excellent "Yale visit" [](https://expedia.ca/New-Haven-Hotels-Omni-New-Haven-Hotel-At-Yale.h49957.Hotel-Information) ![Wyndham Southbury](https://images.trvl-media.com/lodging/16000000/15660000/15651900/15651820/412fe155_y.jpg) ### Wyndham Southbury 10/10 Excellent "I booked this to host a touring music artist and the value was great and worked well to provide a solid night's rest for a touring musician I will use this hotel again for the same purpose." [](https://expedia.ca/Danbury-Hotels-Wyndham-Southbury.h15651820.Hotel-Information) ![Hampton Inn by Hilton Shelton](https://images.trvl-media.com/lodging/1000000/210000/200400/200381/e6ef0843_y.jpg) ### Hampton Inn by Hilton Shelton 10/10 Excellent "Cleaning was top notch. Im super picky when it comes to hotel rooms and I had no complaints. Staff was so nice!" [](https://expedia.ca/New-Haven-Hotels-Hampton-Inn-By-Hilton-Shelton.h200381.Hotel-Information) ## Find out more about Cheshire ## Cheshire B&B information | Number of reviews | 217 | | --- | --- | | Accommodation | 9 B&B | | Lowest Price | CA $382 | | Highest Price | CA $1,361 | ## 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 Drazen Orchards and Bartlem Park. ### 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 B&Bs in the surrounding area: [Jay's Ranch](https://www.expedia.ca/Hamden-Hotels-Jays-Ranch.h93133074.Hotel-Information): 3 rooms. Situated 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. [Stylish 3000 Square-Feet Private Floor Luxury Oasis in a Commercial Space](https://www.expedia.ca/Hamden-Hotels-2500-SF-Loft-You-Own-Full-Floor-Luxury-Oasis-In-A-Commercial-Space.h101878830.Hotel-Information): Located 11.3 mi (18.2 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 Maplecroft Plaza Shopping Center and Drazen Orchards 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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