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Check prices for these dates

Next weekend
28 Nov - 30 Nov
In two weeks
5 Dec - 7 Dec
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19 Dec - 21 Dec
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16 Jan - 18 Jan

Browse Select Cheshire B&B

Exterior
Harbour House Inn

Harbour House Inn

3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53)
"We had a wonderful stay! Brandi is a wonderful host, super friendly and full of helpful information! The afternoon cookies and morning breakfast were delicious! Will definitely stay again next time we’re in the area!! "
United States
Lorie
The price is ₹22,346
₹23,620 total
includes taxes & fees
25 Nov - 26 Nov
Harbour House Inn
Garden
Shaker Mill Inn

Shaker Mill Inn

2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (435)
"Nice place, easy check in"
United States
Robert
The price is ₹9,286
₹10,187 total
includes taxes & fees
18 Nov - 19 Nov
Shaker Mill Inn
Front of property
UU Rowe Camp and Conference Center

UU Rowe Camp and Conference Center

2.0 star property
Rowe
The price is ₹13,222
₹13,976 total
includes taxes & fees
18 Nov - 19 Nov
UU Rowe Camp and Conference Center
Terrace/patio
The Trail in Adams - Berkshires’ Art Hotel

The Trail in Adams - Berkshires’ Art Hotel

2.5 star property
Adams
8.8 out of 10, Excellent, (141)
"Staff was great, very clean, Breakfast was terrific"
United States
michael
The price is ₹15,419
₹17,223 total
includes taxes & fees
18 Nov - 19 Nov
The Trail in Adams - Berkshires’ Art Hotel
Front of property
Chambery Inn

Chambery Inn

3.0 star property
Lee
9.6 out of 10, Exceptional, (372)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
Chambery Inn
Front of property – evening/night
Devonfield Inn B&B

Devonfield Inn B&B

4.0 star property
Lee
10.0 out of 10, Exceptional, (133)
"The inn has an excellent location and amenities."
United States
Christopher
Devonfield Inn B&B
Porch
Lakehouse Inn

Lakehouse Inn

4.0 star property
Lee
9.6 out of 10, Exceptional, (289)
"Lovely location on a lake, quiet, simple, clean rooms, great breakfast included. "
United States
Roberta
The price is ₹15,272
₹17,912 total
includes taxes & fees
20 Nov - 21 Nov
Lakehouse Inn
Exterior
The Inn at Stockbridge

The Inn at Stockbridge

4.0 star property
Lee
9.8 out of 10, Exceptional, (98)
"Well-run and elegant property. "
United States
Steven
The price is ₹22,256
₹26,104 total
includes taxes & fees
20 Nov - 21 Nov
The Inn at Stockbridge
Front of property
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 star property
Lenox
9.0 out of 10, Wonderful, (1002)
"Overall a really fun place to stay. Rooms were good quality and the staff was welcoming and helpful."
United States
Jacob
The price is ₹11,430
₹16,237 total
includes taxes & fees
18 Nov - 19 Nov
The Cornell Inn, Lenox & The Berkshires
Property grounds
Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast

3.5 star property
Lenox
7.8 out of 10, Good, (500)
"We had the smallest room on the property.very quaint and clean. Nicest staff great place to stay."
United States
Lisa
The price is ₹12,004
₹13,409 total
includes taxes & fees
19 Nov - 20 Nov
Whistler's Inn Bed & Breakfast
Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi
33 Main

33 Main

4.0 star property
Lenox
10.0 out of 10, Exceptional, (74)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is ₹37,831
₹42,258 total
includes taxes & fees
25 Nov - 26 Nov
33 Main
Loft, Private Bathroom (Skylight Loft) | 1 bedroom, premium bedding, iron/ironing board, rollaway beds
Brook Farm Inn

Brook Farm Inn

3.5 star property
Lenox
9.4 out of 10, Exceptional, (162)
"Comfortable, quiet, convenient location, very friendly staff. "
United States
Susan
Brook Farm Inn
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

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"Great stay!"
Ann 1-night trip
Posted 3 days ago
The Yankee, Trademark Collection by Wyndham

Find out more about Cheshire

Cheshire B&B information

Number of reviews
2,588
Accommodation
24 B&B
Lowest Price
₹10,187
Highest Price
₹42,258

Frequently asked questions

Searching for B&Bs in Cheshire?
If you want to find some accommodation with fewer rooms than the traditional hotel and an intimate environment, a B&B might be a great fit for your trip to Cheshire. When you want to explore some of the destination's attractions, Mount Greylock State Reservation is worth a visit.
Why should you consider a B&B versus a traditional hotel?
B&Bs all have a unique charm — whether it's a cosy reading space or a beautiful breakfast room, the quaint details are what make bed and breakfasts the perfect escape.
What are the best B&Bs in Cheshire?
Below are some well-liked B&Bs in the area: Harbour House Inn: 6 rooms. 1.2 mi (2 km) from the heart of Cheshire. Enjoy the free full breakfast and unique decor. The Cornell Inn, Lenox & The Berkshires: 14.8 mi (23.9 km) from the city centre. Enjoy the free full breakfast and unique decor. Chambery Inn: 9 rooms. Situated 18.1 mi (29.1 km) from the heart of Cheshire. Enjoy the private garden and snack bar/deli. Whistler's Inn Bed & Breakfast: 14 rooms. Located 15.1 mi (24.2 km) from the core of Cheshire. Enjoy the private garden and unique decor.
When is the best time to book my B&B in Cheshire?
When you're planning your stay in Cheshire, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August, with an average temperature of 17°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Cheshire are January, March, February and November, with each month seeing an average of 17 cm of snowfall.
What is there to do in Cheshire?
When you want to explore some things to do in Cheshire, consider a visit to Mount Greylock State Reservation. You might also consider a trip to sites such as Mount Greylock State Reservation Visitor Center or Mount Greylock if you have time to see more of the area.
How can I get to and around Cheshire?
Mapping out your trip in and around Cheshire is easy with these transportation options. Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 11.5 mi (18.5 km) from the city centre. Otherwise, look for flights into Hudson, NY (HCC-Columbia County), which is 33.6 mi (54 km) away. If you'd like to explore around the area, you may want a rental car for your journey.

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