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

Find a Bed and Breakfast in Cheshire from CA $282

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Check prices for these dates

Next weekend
Oct 2 - Oct 4
In two weeks
Oct 9 - Oct 11
In one month
Oct 23 - Oct 25
In two months
Nov 20 - Nov 22

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
9.6 out of 10, Exceptional, (14 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 $185
CA $294 total
includes taxes & fees
Sep 28 - Sep 29
Sunny Peace Homestay
A building with a grey exterior, a front door, and a small porch with steps.

2. 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 $221
CA $282 total
includes taxes & fees
Sep 27 - Sep 28
Peaceful Modern Private Room with Comfort & Charm

3. Silas W Robbins House

Silas W Robbins House
2.0 star property
Old Wethersfield Historic District
10.0 out of 10, Exceptional, (46 reviews)
"Beautiful place with a comfortable and relaxing atmosphere. Dimitri was gracious and knowledgeable about the house and town history. Loved it!!!"
United States
Cynthia
The price is CA $635
CA $730 total
includes taxes & fees
Sep 27 - Sep 28
Silas W Robbins House
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.

4. The Homestead

The Homestead
3.0 star property
Madison Center
10.0 out of 10, Exceptional, (108 reviews)
"Charming Inn with great staff and an amazing breakfast."
United States
Sherry
The price is CA $342
CA $380 total
includes taxes & fees
Sep 28 - Sep 29
The Homestead

5. The Connecticut River Valley Inn

The Connecticut River Valley Inn
3.5 star property
Glastonbury
9.4 out of 10, Exceptional, (28 reviews)
"Lovely gardens and pool"
United States
Julie
The price is CA $442
CA $509 total
includes taxes & fees
Oct 2 - Oct 3
The Connecticut River Valley Inn
A hallway with a patterned carpet, a chandelier, and bookshelves on either side.

6. The Bevin House Bed & Breakfast

The Bevin House Bed & Breakfast
3.5 star property
East Hampton
9.6 out of 10, Exceptional, (90 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 $359
CA $399 total
includes taxes & fees
Sep 28 - Sep 29
The Bevin House Bed & Breakfast
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

8/10 Good
"The staff members at check-in & check-out were warmly professional and attentive. What a gorgeous & spacious living room area with appealing decor. The breakfast options were fantastic for self-serve options. The room was immaculate. Two points that led me to rate it a 4.7 out of 5 = the extremely hard bed & non-working light & electric fixtures on the side of the bed by the window."
Maria Luisa 1-night trip
Posted 6 hours ago
New Haven Hotel

Find out more about Cheshire

Cheshire B&B information

Number of reviews
178
Accommodation
12 B&B
Lowest Price
CA $282
Highest Price
CA $730

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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