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Check prices for these dates

Next weekend
31 Oct - 2 Nov
In two weeks
7 Nov - 9 Nov
In one month
21 Nov - 23 Nov
In two months
19 Dec - 21 Dec

B&B in Cheshire

Exterior
Harbour House Inn
Harbour House Inn
3.5 star property
9.4 out of 10, Exceptional, (52)
"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 AED 963
AED 1,018 total
includes taxes & fees
27 Oct - 28 Oct
Harbour House Inn
Garden
Shaker Mill Inn
Shaker Mill Inn
2.5 star property
9.6 out of 10, Exceptional, (430)
"Very casual and easy check in and out; lovely and substantial breakfast"
United States
Jamie
The price is AED 408
AED 448 total
includes taxes & fees
4 Nov - 5 Nov
Shaker Mill Inn
Terrace/patio
The Trail in Adams - Berkshires’ Art Hotel
The Trail in Adams - Berkshires’ Art Hotel
2.5 star property
8.8 out of 10, Excellent, (138)
"We had an excellent experience. The location was convenient for our needs, clean, and tastefully done. It's excellent value for the area. It must be said that a younger traveller will probably be more comfortable with the low-touch approach (text check in, code-locked doors), but they've clearly made an effort to be more accessible to a traveler looking for something more traditional. "
United States
Jonathan
The price is AED 638
AED 713 total
includes taxes & fees
27 Oct - 28 Oct
The Trail in Adams - Berkshires’ Art Hotel
Front of property
The Cornell Inn, Lenox & The Berkshires
The Cornell Inn, Lenox & The Berkshires
3.5 star property
9.0 out of 10, Wonderful, (1000)
"Overall a really fun place to stay. Rooms were good quality and the staff was welcoming and helpful."
United States
Jacob
The price is AED 469
AED 667 total
includes taxes & fees
27 Oct - 28 Oct
The Cornell Inn, Lenox & The Berkshires
Front of property
UU Rowe Camp and Conference Center
UU Rowe Camp and Conference Center
2.0 star property
The price is AED 547
AED 578 total
includes taxes & fees
1 Nov - 2 Nov
UU Rowe Camp and Conference Center
Porch
Lakehouse Inn
Lakehouse Inn
4.0 star property
9.6 out of 10, Exceptional, (285)
"Lovely location on a lake, quiet, simple, clean rooms, great breakfast included. "
United States
Roberta
The price is AED 672
AED 788 total
includes taxes & fees
2 Nov - 3 Nov
Lakehouse Inn
Front of property
Chambery Inn
Chambery Inn
3.0 star property
9.6 out of 10, Exceptional, (370)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
Chambery Inn
Interior
The Red Door B&B
The Red Door B&B
3.0 star property
10.0 out of 10, Exceptional, (5)
"Centrally located. Lovely hosts. Only three bedrooms so we got to know the other guests. The breakfasts were works of art as well as delicious."
United States
Anonymous traveler
The Red Door B&B
Property grounds
Whistler's Inn Bed & Breakfast
Whistler's Inn Bed & Breakfast
3.5 star property
7.8 out of 10, Good, (499)
"We had the smallest room on the property.very quaint and clean. Nicest staff great place to stay."
United States
Lisa
The price is AED 491
AED 548 total
includes taxes & fees
30 Oct - 31 Oct
Whistler's Inn Bed & Breakfast
Exterior
The Inn at Stockbridge
The Inn at Stockbridge
4.0 star property
9.8 out of 10, Exceptional, (98)
"Well-run and elegant property. "
United States
Steven
The price is AED 1,274
AED 1,494 total
includes taxes & fees
2 Nov - 3 Nov
The Inn at Stockbridge
Front of property - evening/night
Devonfield Inn B&B
Devonfield Inn B&B
4.0 star property
10.0 out of 10, Exceptional, (132)
"The inn has an excellent location and amenities."
United States
Christopher
Devonfield Inn B&B
3 bedrooms, bed sheets
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
The price is AED 762
AED 1,118 total
includes taxes & fees
27 Oct - 28 Oct
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Business center
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
9.2 out of 10, Wonderful, (108)
"Wonderful! Owner/host Diane was friendly, helpful, knowledgeable. Breakfasts awesome with great choices daily. Place was spotless, cozy and classic. So glad we stayed there. "
United States
Robert
The price is AED 1,137
AED 1,375 total
includes taxes & fees
9 Nov - 10 Nov
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Loft, Private Bathroom (Skylight Loft) | 1 bedroom, premium bedding, iron/ironing board, rollaway beds
Brook Farm Inn
Brook Farm Inn
3.5 star property
9.4 out of 10, Exceptional, (161)
"Inn was gorgeous and staff exceptional!"
United States
Joyce
Brook Farm Inn
Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi
33 Main
33 Main
4.0 star property
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 AED 1,689
AED 1,887 total
includes taxes & fees
24 Nov - 25 Nov
33 Main
Aerial view
Inn at Silver Maple Farm
Inn at Silver Maple Farm
3.0 star property
9.8 out of 10, Exceptional, (97)
"Great stay, comfortable place"
United States
barry
The price is AED 584
AED 654 total
includes taxes & fees
23 Nov - 24 Nov
Inn at Silver Maple Farm
1 bedroom, WiFi, bed sheets
Elegant Carriage House room with a queen bed and private patio.
Elegant Carriage House room with a queen bed and private patio.
The price is AED 821
AED 1,191 total
includes taxes & fees
28 Oct - 29 Oct
Elegant Carriage House room with a queen bed and private patio.
1 bedroom, WiFi, bed sheets, wheelchair access
Experience Timeless Elegance in The Edith Wharton Room!
Experience Timeless Elegance in The Edith Wharton Room!
The price is AED 762
AED 1,118 total
includes taxes & fees
27 Oct - 28 Oct
Experience Timeless Elegance in The Edith Wharton Room!
1 bedroom, bed sheets
Cozy Carriage House room with a double bed and private balcony
Cozy Carriage House room with a double bed and private balcony
The price is AED 879
AED 1,265 total
includes taxes & fees
29 Oct - 30 Oct
Cozy Carriage House room with a double bed and private balcony
Terrace/patio
Historic Susan B. Anthony Room - Cozy & Charming Stay
Historic Susan B. Anthony Room - Cozy & Charming Stay
The price is AED 938
AED 1,343 total
includes taxes & fees
29 Oct - 30 Oct
Historic Susan B. Anthony Room - Cozy & Charming Stay
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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"We loved this place. Quiet, very clean,attractive. Loved that it had a kitchen area. Second story, sliding glass doors overlooked the fall foliage in the back of the building. Very peaceful.."
Steven 4-night trip
Posted 2 days ago
Berkshire Mountain Lodge

Frequently asked questions

Searching for B&Bs in Cheshire?
If you want to find a place to stay with a small number of rooms and a more personalized environment, a B&B might be a great fit for your vacation to Cheshire. When you want to explore some of the destination's attractions, Mount Greylock State Reservation is worth a visit.
Why would you choose a B&B versus a traditional hotel?
B&Bs all have a unique charm. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a fun place to get away.
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 décor. The Cornell Inn, Lenox & The Berkshires: 14.8 mi (23.9 km) from the downtown core. Enjoy the free full breakfast and unique décor. Lakehouse Inn: 14 rooms. Situated 17.1 mi (27.5 km) from the heart of Cheshire. Enjoy the free full breakfast and deli. Chambery Inn: 9 rooms. 18.1 mi (29.1 km) from the heart of downtown. Enjoy the private yard and deli.
What's the best time of year 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 temp of 63°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Cheshire are January, March, February, and November, with each month seeing an average of 7 inches 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 like 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) away from the heart of the city. You can also search 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.