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Check prices for these dates

Next weekend
4 Jul - 6 Jul
In two weeks
11 Jul - 13 Jul
In one month
25 Jul - 27 Jul
In two months
22 Aug - 24 Aug

Browse Select Cheshire B&B

Harbour House Inn
Exterior

Harbour House Inn

3.5 star property
9.4 out of 10, Exceptional, (49)
"Nice place for a weekend away."
The price is ₹19,957
₹21,095 total
includes taxes & fees
1 Jul - 2 Jul
Harbour House Inn
UU Rowe Camp and Conference Center
Front of property

UU Rowe Camp and Conference Center

2.0 star property
The price is ₹12,738
₹13,464 total
includes taxes & fees
29 Jun - 30 Jun
UU Rowe Camp and Conference Center
The Trail in Adams - Berkshires’ Art Hotel
Terrace/patio

The Trail in Adams - Berkshires’ Art Hotel

2.5 star property
8.8 out of 10, Excellent, (129)
"Stayed only one night Very cosy, quiet place "
The price is ₹14,853
₹16,591 total
includes taxes & fees
30 Jun - 1 Jul
The Trail in Adams - Berkshires’ Art Hotel
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (365)
"We returned to the Chambery Inn to celebrate my wife's birthday and the Memorial Day weekend. We were very happy with our choice. We stayed in a beautiful room (203), which included a spacious sitting area and a well-appointed bath. The breakfast were nicely prepared and presented. The Inn provided timely information prior and during our stay. We will be back in the future. "
Chambery Inn
Devonfield Inn B&B
Front of property – evening/night

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (127)
"Very enjoyable comfortable stay"
Devonfield Inn B&B
Lakehouse Inn
Porch

Lakehouse Inn

4.0 star property
9.6 out of 10, Exceptional, (266)
"Really peaceful and serene property due to the lake. The house was clean and the staff were friendly. "
The price is ₹19,064
₹22,359 total
includes taxes & fees
2 Jul - 3 Jul
Lakehouse Inn
The Cornell Inn, Lenox & The Berkshires
Front of property

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1001)
"Breakfast each day was phenomenal, staff were all so friendly, hotel & room were beautifully decorated. We had a wonderful time & would stay here again!"
The price is ₹11,011
₹15,641 total
includes taxes & fees
30 Jun - 1 Jul
The Cornell Inn, Lenox & The Berkshires
Whistler's Inn Bed & Breakfast
Property grounds

Whistler's Inn Bed & Breakfast

3.5 star property
7.8 out of 10, Good, (474)
"All was just as advertised and the family/staff was friendly and helpful. "
The price is ₹13,918
₹17,171 total
includes taxes & fees
29 Jun - 30 Jun
Whistler's Inn Bed & Breakfast
33 Main
Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi

33 Main

4.0 star property
10.0 out of 10, Exceptional, (70)
"33 Main is the best of everything. We have stayed at the location twice and loved each experience. The breakfast is delicious, accommodations are beautifully curated, and it’s perfectly located in Lenox. Highly recommend and we will be back! "
The price is ₹38,043
₹42,494 total
includes taxes & fees
28 Jul - 29 Jul
33 Main
Brook Farm Inn
Loft, Private Bathroom (Skylight Loft) | 1 bedroom, premium bedding, iron/ironing board, rollaway beds

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (152)
"This is a charming and very pleasant place to stay."
Brook Farm Inn
Tanglewood Suites
2 Bedrooms 1 Bath | 1 bedroom, premium bedding, iron/ironing board, free WiFi

Tanglewood Suites

2.5 star property
8.0 out of 10, Very good, (15)
"The property is so lovely and peaceful. I love the classic mid-century modern aesthetic. For visitors to the National Shrine of Divine Mercy, the Inn’s location couldn’t be more perfect with only a 5-minute walk to the Shrine. "
The price is ₹22,996
₹22,996 total
includes taxes & fees
29 Jun - 30 Jun
Tanglewood Suites
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Business centre

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 star property
9.2 out of 10, Wonderful, (105)
"Great breakfast, friendly helpful staff, pretty yard, good location "
The price is ₹39,226
₹47,452 total
includes taxes & fees
14 Jul - 15 Jul
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Shaker Mill Inn
Garden

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (413)
"Nice"
The price is ₹11,720
₹12,856 total
includes taxes & fees
30 Jun - 1 Jul
Shaker Mill Inn
Inn at Silver Maple Farm
Aerial view

Inn at Silver Maple Farm

3.0 star property
9.8 out of 10, Exceptional, (86)
"Everything about our stay in The Loft was wonderful! The hot breakfast each morning was incredible. The entire inn was very clean and well kept. We will definitely be back! "
The price is ₹19,577
₹21,143 total
includes taxes & fees
1 Jul - 2 Jul
Inn at Silver Maple Farm
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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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. If your ideal holiday to Cheshire includes spending lots of time outside, Mount Greylock State Reservation is a good spot to enjoy the scenery.
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. 18.1 mi (29.1 km) from the city centre. Enjoy the private garden and snack bar/deli. Lakehouse Inn: 14 rooms. Located 17.1 mi (27.5 km) from the core of Cheshire. Enjoy the free full breakfast and snack bar/deli.
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 see some attractions in town, you might consider a visit to Mount Greylock State Reservation and St Mary's of the Assumption Church. 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.