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Compare 9 B&B in Cheshire with updated reviews, rates, and availability.

Jay's Ranch
Room
Jay's Ranch
3.0 star property
7.0 out of 10, Good, (6)
"Had a wonderful time "
The price is SAR 262
SAR 296 total
includes taxes & fees
18 Jum. II - 19 Jum. II
Jay's Ranch
The Homestead
Exterior
The Homestead
3.0 star property
10.0 out of 10, Exceptional, (63)
"Excellent accommodations and Host. "
The price is SAR 1,571
SAR 1,744 total
includes taxes & fees
17 Jum. II - 18 Jum. II
The Homestead
The Bevin House Bed & Breakfast
Exterior detail
The Bevin House Bed & Breakfast
3.5 star property
9.6 out of 10, Exceptional, (65)
"Avery amazing house and what a breakfast!"
The price is SAR 801
SAR 882 total
includes taxes & fees
27 Jum. II - 28 Jum. II
The Bevin House Bed & Breakfast
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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
King/Queen suits available Guest House quiet & serene
Room
King/Queen suits available Guest House quiet & serene
King/Queen suits available Guest House quiet & serene
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 SAR 2,626
SAR 3,760 total
includes taxes & fees
17 Jum. II - 18 Jum. II
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
9.6 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
9.8 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
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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.

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, (1845)
"We stayed only one night as planned. The property is in need of renovation, more than just paint. Our room had a musty smell and the carpets were worn out. The people working there were great. I hope they can rejuvenate this area. "
The price is SAR 363
SAR 403 total
includes taxes & fees
15 Raj. - 16 Raj.
New Haven Village Suites
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Property grounds
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
10.0 out of 10, Exceptional, (113)
"Was looking for a coastal retreat to enjoy a couple days with my daughter who lives near this location. This property had everything from a super clean, cozy studio with fridge and counters filled with surprising treats, incredible hot tub with lights in the trees, pool to cool off and little private beach to launch a paddlleboard and kayak, or hang out at night with a burn pit. If you are just a beach person and want toes in the sand and to swim in the ocean, this area is not for 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
10.0 out of 10, Exceptional, (21)
"Better than most hotels nearby"
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.
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 Cheshire Hollow Farm and Drazen Orchards. 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.

Recent reviews of Cheshire hotels
Expedia verified reviews

Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

5/5 Excellent
Good hotel near Yale
"Great service from the staff and very comfortable and clean room. The hotel is a newer property very close to Yale University."
A verified traveler stayed at Cambria Hotel New Haven University Area
Posted 1 day ago
Cambria Hotel New Haven University Area