A stone tower with a metal gate, surrounded by trees and a stone wall.

Find a Bed and Breakfast in Cheshire from CA $275

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Check prices for these dates

Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10

Our top choices for Cheshire bed & breakfast

A house with a stone staircase leading to a door, surrounded by lush greenery and a well-maintained garden.

1. Sunny Peace Homestay

Sunny Peace Homestay
3.0 star property
Harwinton
9.0 out of 10, Wonderful, (19 reviews)
"When I arrived after dark, it was hard to tell if I was at the right house. The bedroom was clean and quiet. Appears to be a shared bathroom but lucky one of the two bedrooms were vacant. Good for a quick stay."
United States
Dean
The price is CA $169
CA $276 total
includes taxes & fees
Dec 12 - Dec 13
Sunny Peace Homestay
View from room

2. The Connecticut River Valley Inn

The Connecticut River Valley Inn
3.5 star property
Glastonbury
9.4 out of 10, Exceptional, (29 reviews)
"This is an exceptionally nice place to stay. The hosts are warm and attentive and the property is first class in every way."
United States
Robert
The price is CA $442
CA $508 total
includes taxes & fees
Nov 28 - Nov 29
The Connecticut River Valley Inn
A red door with a 'Gone to the Beach' sign, a wicker chair, a table with a plate of food and drinks, and a potted plant.

3. The Homestead

The Homestead
3.0 star property
Madison Center
10.0 out of 10, Exceptional, (114 reviews)
"Beautiful and unique inn with great staff."
United States
Anita C
The price is CA $299
CA $332 total
includes taxes & fees
Nov 12 - Nov 13
The Homestead
A hallway with a patterned carpet, a chandelier, and bookshelves on either side.

4. The Bevin House Bed & Breakfast

The Bevin House Bed & Breakfast
3.5 star property
East Hampton
9.6 out of 10, Exceptional, (92 reviews)
"The house was beautiful! The innkeeper Amanda made an excellent breakfast and was friendly and knowledgeable about the property. The house renovations fit in with the period of the house, but provided modern convenience. It was a joy to stay there"
United States
Eric
The price is CA $335
CA $372 total
includes taxes & fees
Nov 18 - Nov 19
The Bevin House Bed & Breakfast
Exterior

5. Silas W Robbins House

Silas W Robbins House
2.0 star property
Old Wethersfield Historic District
10.0 out of 10, Exceptional, (50 reviews)
"the hostess did a great job and the breakfasts were amazing"
United States
James
The price is CA $634
CA $729 total
includes taxes & fees
Dec 6 - Dec 7
Silas W Robbins House
A building with a grey exterior, a front door, and a small porch with steps.

6. Peaceful Modern Private Room with Comfort & Charm

Peaceful Modern Private Room with Comfort & Charm
Harwinton
8.4 out of 10, Very good, (6 reviews)
"We had a very comfortable stay . Communication with our host was easy & prompt. We would stay again “"
United States
Laurel B.
The price is CA $224
CA $275 total
includes taxes & fees
Dec 6 - Dec 7
Peaceful Modern Private Room with Comfort & Charm
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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Top Cheshire Hotel Reviews

New Haven Hotel

New Haven Hotel

10/10 Excellent
"Stayed overnight with my children. The property was clean, comfortable, and beautifully decorated. Staff were super helpful. Would definitely recommend."
Kristen 1-night trip
Posted 3 hours ago
New Haven Hotel

Find out more about Cheshire

Cheshire B&B information

Number of reviews
285
Accommodation
12 B&B
Lowest Price
CA $275
Highest Price
CA $729

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?
Below is a B&B in the area: Sunny Peace Homestay: 2 rooms. Situated 18.2 mi (29.3 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 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.

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