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Check prices for these dates

Compare 8 B&B in Cheshire with updated reviews, rates, and availability.

Jay's Ranch

4.0 star property
7.6 out of 10, Good, (40)
"Quiet and safe "
Jay's Ranch

The Homestead

3.0 star property
10.0 out of 10, Exceptional, (79)
"Beautiful and comfortable b+b. Well thought out amenities such as comfortable bed, fluffy towels, great breakfast options and snacks. The innkeepers friendly and made sure we were well taken care of during our stay "
The price is SAR 1,266
SAR 1,405 total
includes taxes & fees
1 Jun - 2 Jun
The Homestead

The Bevin House Bed & Breakfast

3.5 star property
9.6 out of 10, Exceptional, (73)
"I really wanted to see the goats as silly as that sounds and had a great time doing it."
The price is SAR 1,027
SAR 1,140 total
includes taxes & fees
3 Jun - 4 Jun
The Bevin House Bed & Breakfast

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

The price is SAR 2,626
SAR 3,979 total
includes taxes & fees
1 Jun - 2 Jun
Stylish 3000 Square-Feet Private Floor Luxury Oasis in a Commercial Space

Thimble Islands Bed & Breakfast

3.5 star property
10.0 out of 10, Exceptional, (4)
Thimble Islands Bed & Breakfast

Sunny Peace Homestay

2.0 star property
9.4 out of 10, Exceptional, (3)
"Stayed there for business. Cute bed and breakfast! She made me tea when I got there late. Angie was a sweetheart Will def stay every time I have a shift at the hospital! "
Sunny Peace Homestay

The Connecticut River Valley Inn

3.5 star property
9.4 out of 10, Exceptional, (24)
"Charming Inn, "
The Connecticut River Valley Inn

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

Higganum House B&B

3.0 star property
Higganum House 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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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?
Check out this B&B in the area: Jay’s Ranch: 3 rooms. 10.6 mi (17.1 km) from the heart 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. If you’d like to venture out around the area, you may want to rent a car for your trip.