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Search B&B in Cheshire

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Compare 10 B&B in Cheshire with updated reviews, rates, and availability.

Jay's Ranch
Terrace/patio

Jay's Ranch

3.5 star property
7.8 out of 10, Good, (36)
"Best stay ever !!! Felt like I was family , she cooked us breakfast in the morning and also offered lunch and dinner , and also addressed that every Wednesday was laundry day and it was included with our stay, and told us if we pay for two days that we have the option to stay the third day free of charge "
The price is AED 273
AED 305 total
includes taxes & fees
4 Dec - 5 Dec
Jay's Ranch
The Bevin House Bed & Breakfast
Exterior detail

The Bevin House Bed & Breakfast

3.5 star property
9.6 out of 10, Exceptional, (70)
"Our room was beautiful, spacious and clean, with a wonderful bathroom. The innkeeper was friendly and very helpful and provided a delicious breakfast."
The price is AED 815
AED 895 total
includes taxes & fees
17 Dec - 18 Dec
The Bevin House Bed & Breakfast
The Homestead
Exterior

The Homestead

3.0 star property
10.0 out of 10, Exceptional, (70)
"Great people and accommodations "
The price is AED 1,033
AED 1,147 total
includes taxes & fees
10 Dec - 11 Dec
The Homestead
Sunny Peace Homestay
Exterior

Sunny Peace Homestay

3.0 star property
The price is AED 463
AED 520 total
includes taxes & fees
28 Nov - 29 Nov
Sunny Peace Homestay
The Connecticut River Valley Inn
Lobby sitting area

The Connecticut River Valley Inn

3.5 star property
9.4 out of 10, Exceptional, (24)
"The Inn and the innkeepers were lovely. The decor is quirky and elegant at the same time. Every convince is thought of. The fireplace in every room is a fabulous touch. We can’t wait to visit again soon"
The Connecticut River Valley Inn
Thimble Islands Bed & Breakfast
Front of property

Thimble Islands Bed & Breakfast

3.5 star property
10.0 out of 10, Exceptional, (4)
"Property was first class inside and out. The view was breath taking The owners made us feel at home and did not want to leave ! Already thinking about next trip back."
Thimble Islands Bed & Breakfast
2500 SF Loft: You Own Full Floor Luxury Oasis in a Commercial Space
Interior

2500 SF Loft: You Own Full Floor Luxury Oasis in a Commercial Space

The price is AED 1,102
AED 1,760 total
includes taxes & fees
2 Dec - 3 Dec
2500 SF Loft: You Own Full Floor Luxury Oasis in a Commercial Space
Green Acres B&B
Exterior

Green Acres B&B

3.0 star property
9.8 out of 10, Exceptional, (150)
"Gracious hosts, many amenities and the best breakfast!"
Green Acres B&B
Captain Josiah Cowles Place
Exterior

Captain Josiah Cowles Place

3.0 star property
10.0 out of 10, Exceptional, (19)
"This is a beautiful old home (c 1730), that is now used as an Inn-B&B establishment. It is very beautiful, clean and the owners provided a great breakfast and great hospitality ....which included the owners hand made Maple syrup made from the owners' Sugar Maples on the property. It was quite an experience, a real treat to be vacationing for a night in a home/Inn that was built before the Revolutionary War was even thought of and on the National Registry of Historic Homes/Buildings......It...
Captain Josiah Cowles Place
Silas W Robbins House
Exterior

Silas W Robbins House

2.0 star property
10.0 out of 10, Exceptional, (43)
"Beautiful place with a comfortable and relaxing atmosphere. Dimitri was gracious and knowledgeable about the house and town history. Loved it!!!"
Silas W Robbins House
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.
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Other property types in Cheshire

New Haven Village Suites
Front of property

New Haven Village Suites

3.0 star property
7.6 out of 10, Good, (1966)
"Convenient location, helpful staff, comfortable bed. Thanks!"
The price is AED 364
AED 405 total
includes taxes & fees
3 Dec - 4 Dec
New Haven Village Suites
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Pool

Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

10.0 out of 10, Exceptional, (126)
"We stayed here for an anniversary weekend away and found the property and neighborhood to be amazing. We enjoyed the hot tub, pool and firepit and went kayaking in the afternoon. Enjoyed amazing sunsets from the deck; Adam gave us spot-on restaurant recommendations. I don't know if the supply of snacks is standard or an anniversary "special", but all in all this place was a wonderful find. Thank you!!"
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Luxury Furnished Apartments by Hyatus Downtown at Yale
Room

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 star property
9.8 out of 10, Exceptional, (34)
"Great location! Clean building And modern. "
Luxury Furnished Apartments by Hyatus Downtown at Yale
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.

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 well-liked B&Bs in the surrounding area: Jay’s Ranch: 3 rooms. 10.6 mi (17.1 km) from the heart of Cheshire.Thimble Islands Bed & Breakfast: 2 rooms. Located 18.5 mi (29.8 km) from the core of Cheshire. Enjoy the free cooked breakfast and designer toiletries.
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 Drazen Orchards and Barker Character, Comic and Cartoon Museum. You might put Maplecroft Plaza Shopping Center and Bartlem Park 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. If you’d like to venture out around the area, you may want to rent a car for your trip.