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Check prices for these dates

Next weekend
14 Feb - 16 Feb
In two weeks
21 Feb - 23 Feb
In one month
7 Mar - 9 Mar
In two months
4 Apr - 6 Apr

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

The Homestead
Exterior

The Homestead

3.0 star property
10.0 out of 10, Exceptional, (77)
"Charming in every aspect. Highly recommend, Hosts are wonderful people."
The price is AED 837
AED 929 total
includes taxes & fees
7 Mar - 8 Mar
The Homestead
Sunny Peace Homestay
Exterior

Sunny Peace Homestay

3.0 star property
9.0 out of 10, Wonderful, (2)
"A beautiful home in the woods of Northwest Connecticut. Quiet. Responsive and pleasant customer service. "
The price is AED 463
AED 532 total
includes taxes & fees
10 Feb - 11 Feb
Sunny Peace Homestay
Jay's Ranch
Terrace/patio

Jay's Ranch

4.0 star property
7.8 out of 10, Good, (37)
"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 "
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 779
AED 865 total
includes taxes & fees
10 Feb - 11 Feb
The Bevin House Bed & Breakfast
Stylish 3000 Square-Feet Private Floor Luxury Oasis in a Commercial Space
Interior

Stylish 3000 Square-Feet Private Floor Luxury Oasis in a Commercial Space

The price is AED 2,571
AED 3,918 total
includes taxes & fees
9 Feb - 10 Feb
Stylish 3000 Square-Feet Private Floor Luxury Oasis in a Commercial Space
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
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
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
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
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, (2002)
"The room layout, amenities and cleanliness were excellent. Think about adding a continental breakfast."
The price is AED 324
AED 373 total
includes taxes & fees
18 Feb - 19 Feb
New Haven Village Suites
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, (38)
"Great location. Nice place. Noisy neighbors though"
Luxury Furnished Apartments by Hyatus Downtown at Yale
A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!
Exterior image

A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!

10.0 out of 10, Exceptional, (24)
"The house is an architectural gem with plenty of space for the family. We enjoyed the fireplace in the evenings."
A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!
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: Sunny Peace Homestay: 2 rooms. 18.2 mi (29.3 km) from the downtown core. Jay’s Ranch: 3 rooms. Situated 10.6 mi (17.1 km) from the heart of Cheshire. Stylish 3000 Square-Feet Private Floor Luxury Oasis in a Commercial Space: 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 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.