Castle Craig at Hubbard Park, Meriden, CT. easily replaceable sky. with a clean, classic view of the tower. Very recognizable image of this historic structure.

Find a Bed and Breakfast in Cheshire from CA $146

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Check prices for these dates

Next weekend
Jun 26 - Jun 28
In two weeks
Jul 3 - Jul 5
In one month
Jul 17 - Jul 19
In two months
Aug 14 - Aug 16

Our top choices for Cheshire bed & breakfast

Exterior

Jay's Ranch

Jay's Ranch
4.0 star property
Hamden
7.6 out of 10, Good, (47 reviews)
"I only stayed for one night , but the house is spotless and I was served a nice breakfast too. I also enjoyed the room. wish I could have stayed longer! "
United States
Daniela
The price is CA $96
CA $146 total
includes taxes & fees
Jun 29 - Jun 30
Jay's Ranch
Exterior

Silas W Robbins House

Silas W Robbins House
2.0 star property
Old Wethersfield Historic District
10.0 out of 10, Exceptional, (43 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 $628
CA $722 total
includes taxes & fees
Jun 19 - Jun 20
Silas W Robbins House
Deluxe Room, 1 King Bed, Fireplace, Garden Area | View from room

The Connecticut River Valley Inn

The Connecticut River Valley Inn
3.5 star property
Glastonbury
9.4 out of 10, Exceptional, (26 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 $437
CA $503 total
includes taxes & fees
Jun 28 - Jun 29
The Connecticut River Valley Inn
Library

The Bevin House Bed & Breakfast

The Bevin House Bed & Breakfast
3.5 star property
East Hampton
9.6 out of 10, Exceptional, (85 reviews)
"Wonderful stay. Excellent staff that treats the guest like family and friends. "
United States
Liliana
The price is CA $327
CA $363 total
includes taxes & fees
Jul 2 - Jul 3
The Bevin House Bed & Breakfast
Exterior detail

Peaceful Modern B&B with Comfort & Charm

Peaceful Modern B&B with Comfort & Charm
Harwinton
9.0 out of 10, Wonderful, (2 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 $207
CA $266 total
includes taxes & fees
Jun 23 - Jun 24
Peaceful Modern B&B with Comfort & Charm
Room, 1 King Bed, Patio, Ground Floor (2) | Terrace/patio

The Homestead

The Homestead
3.0 star property
Madison Center
10.0 out of 10, Exceptional, (92 reviews)
"Beautiful property- wonderful staff- clean, comfortable and relaxed feeling with a lovely breakfast 😄"
United States
Anthony
The price is CA $497
CA $551 total
includes taxes & fees
Jun 17 - Jun 18
The Homestead
Garden

Sunny Peace Homestay

Sunny Peace Homestay
3.0 star property
Harwinton
9.4 out of 10, Exceptional, (8 reviews)
"Angela is very respectful and generous to her guests."
United States
Jean
The price is CA $1,064
CA $1,224 total
includes taxes & fees
Jun 28 - Jun 29
Sunny Peace Homestay
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

Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

10/10 Excellent
"Clean room and pleasant staff. Very quiet stay. We would book again in the near future. The parking was a little tight on a Friday night."
Myrna 3-night trip
Posted 1 hour ago
Best Western Executive Hotel Of New Haven - West Haven

Find out more about Cheshire

Cheshire B&B information

Number of reviews
162
Accommodation
12 B&B
Lowest Price
CA $146
Highest Price
CA $1,224

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?
Here are some B&Bs in the surrounding area: Jay's Ranch: 3 rooms. Situated 10.6 mi (17.1 km) from the heart of Cheshire. Peaceful Modern B&B with Comfort & Charm: 18.2 mi (29.3 km) from the heart of downtown. Sunny Peace Homestay: 2 rooms. Located 18.2 mi (29.3 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 Cheshire Hollow Farm and Drazen Orchards. You might put Maplecroft Plaza Shopping Center and Roaring Brook 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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