Photo by Ed Gaffny

Search B&B in Cheshire

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Compare 34 B&B in Cheshire with updated reviews, rates, and availability.

The Cornell Inn, Lenox

3.0 star property
9.0 out of 10, Wonderful, (1003)
"The weather played a part - our room was accessed by a set of outside stairs, and the weather was cold enough to make them a bit perilous. The staff did its best to attend to it."
The price is SAR 334
SAR 519 total
includes taxes & fees
17 Mar - 18 Mar
The Cornell Inn, Lenox

Lakehouse Inn

4.0 star property
9.8 out of 10, Exceptional, (247)
"We loved the history of the hotel and how well they preserved many features of the property. Loved the suite and view of the lake. Everyone that works there was very kind and attentive."
The price is SAR 473
SAR 554 total
includes taxes & fees
1 Mar - 2 Mar
Lakehouse Inn

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (363)
"Chamberry Inn was a nice, quiet, relaxing stay. Enjoyed every second of it. The staff were kind and helpful. Would definitely stay again if I was in the area."
The price is SAR 713
SAR 796 total
includes taxes & fees
2 Mar - 3 Mar
Chambery Inn

Tanglewood Suites

2.5 star property
8.0 out of 10, Very Good, (15)
"Portion of hosts home, separate and available for rent. Heating system not efficient and took some work to sort out how to keep all areas of the unit comfortably heated. Beds clean and comfortable. Overall cleanliness was good. Bath facilities are an addition to existing structure and sufficient, but could use some TLC. Host is eager to please and pleasant to interact with. Listing indicates free breakfast for all guests. However, upon arrival, we were advised there is no winter offering of...
The price is SAR 821
SAR 821 total
includes taxes & fees
1 Mar - 2 Mar
Tanglewood Suites

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 SAR 1,440
SAR 1,609 total
includes taxes & fees
2 Mar - 3 Mar
33 Main

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (122)
"Beautiful property, great service "
The price is SAR 934
SAR 1,043 total
includes taxes & fees
4 Mar - 5 Mar
Devonfield Inn B&B

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (150)
"Loves that they had en EV charger for me to charge while we were “home”. Beautiful location and house. Welcoming hospitality that was very refreshing. Thank you. "
The price is SAR 718
SAR 802 total
includes taxes & fees
2 Mar - 3 Mar
Brook Farm Inn

Inn at Silver Maple Farm

3.0 star property
9.8 out of 10, Exceptional, (81)
"Everything "
The price is SAR 371
SAR 401 total
includes taxes & fees
2 Mar - 3 Mar
Inn at Silver Maple Farm

The Trail in Adams - Berkshires’ Art Hotel

2.5 star property
8.8 out of 10, Excellent, (128)
"The Trail in Adams offered me exactly what I needed: a quiet and convenient place prepare for a day in the woods the next day. Very convenient walking to nearby restaurants, right in the middle of Adams. There was a snowstorm that night, and the walks were shoveled several times that evening and the next morning. "
The price is SAR 652
SAR 728 total
includes taxes & fees
1 Mar - 2 Mar
The Trail in Adams - Berkshires’ Art Hotel

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

4.5 star property
9.2 out of 10, Wonderful, (105)
"The breakfast was one of the best I have ever had. They were fast and lots of choices. It had lots of baked goods. I got the chesdar omeltte and bacon and toast plus fruits in season lime melon etc. Its a lovely place it takes you back in time. The owner is very easy going and nuce and can answer most questions"
The price is SAR 1,591
SAR 1,925 total
includes taxes & fees
4 Mar - 5 Mar
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Inn at Stockbridge

4.0 star property
9.8 out of 10, Exceptional, (97)
"We we were in the Out of Africa room, set apart in a complex of 4 suites in a unit apart from the Inn itself. The room was uniquely created to feel like an escape to Africa, and heated by a lovely gas fireplace. The breakfast both mornings, delicious. A perfect getaway!"
The Inn at Stockbridge

Inn at Kenmore Hall

3.0 star property
10.0 out of 10, Exceptional, (27)
"A wonderful experience……….breakfast overlooking the property, the beautiful flowers grown by the innkeepers, decorated to perfection, with owners there to make your stay as comfortable as possible! "
The price is SAR 1,594
SAR 1,749 total
includes taxes & fees
1 Mar - 2 Mar
Inn at Kenmore Hall

Harbour House Inn

3.5 star property
9.4 out of 10, Exceptional, (49)
"Lovely space and welcoming host."
The price is SAR 1,009
SAR 1,066 total
includes taxes & fees
31 Mar - 1 Apr
Harbour House Inn

Whistler's Inn Bed & Breakfast

3.5 star property
7.8 out of 10, Good, (471)
"I liked that it is an older style bed and breakfast place. You could say "classy" or "vintage". It reminded me of places where I would visit with family when I was a child. I received a personal welcome and orientation to the property. Breakfast was nice and cooked options were available for me to choose. Another guest in the dining room at breakfast was also enjoying the visit and it was natural to strike up a conversation and get to know each other. It was a more personal kind of stay than...
Whistler's Inn Bed & Breakfast

Eastgate Inn B&B

2.5 star property
9.2 out of 10, Wonderful, (68)
"Lovely Inn and Innkeeper. The room was clean and cozy. There was hot coffee and breakfast in the morning including homemade breads and fruit. We will be back! "
Eastgate Inn B&B

Berkshire Mountain House

3.0 star property
9.4 out of 10, Exceptional, (24)
"Mona was an excellent host. Our bed was very comfortable and the food was good, too! I'd definitely recommend staying here as there's so much to do in the area."
Berkshire Mountain House

The Red Door B&B

3.0 star property
10.0 out of 10, Exceptional, (5)
"We loved staying at this b&b. The owners were very accommodating, kind and helpful. Because of the pandemic, they only took us for the weekend. The breakfasts were above and beyond our expectations, simply fantastic. We highly recommend this beautiful place and we will be back for sure. "
The Red Door B&B

Chambery Inn / 7,000 Sqft Luxury Historic Berkshire landmark on Main Street

Chambery Inn / 7,000 Sqft Luxury Historic Berkshire landmark on Main Street

Cozy Retreat in Historic Farmhouse, Charming Bunk Bed Room,- Owl Dorm

10.0 out of 10, Exceptional, (1)
"The piano, large spaces, and fireplace were all much appreciated."
The price is SAR 563
SAR 646 total
includes taxes & fees
1 Mar - 2 Mar
Cozy Retreat in Historic Farmhouse, Charming Bunk Bed Room,- Owl Dorm

Cozy Farmhouse Retreat - Ram Dass Room

The price is SAR 338
SAR 417 total
includes taxes & fees
1 Mar - 2 Mar
Cozy Farmhouse Retreat - Ram Dass Room
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.
Don't see what you're looking for?
See all available properties in Cheshire
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Cheshire

19th c. Barn in the Berkshires

9.6 out of 10, Exceptional, (84)
"This old barn was renovated into a great place to stay. Jane and Ian paid careful attention to details, light, colors, materials. Very comfortable and relaxing. The setting is gorgeous, and the sheep are fun. (FYI: It may be helpful to understand the layout and bathrooms: the new bathroom is at the far end of the smaller bedroom. This works great for a couple to have their own bathroom. The other bathroom is within the larger bedroom with the bunk bed, but in an area close to the door,...
19th c. Barn in the Berkshires

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1772)
"Absolutely outstanding! After a day of skiing at Jiminy my son & I checked into vacation village. Quick and efficient check in at the front desk by the gentleman working. Drove around to our bldg. unloaded our gear, changed into our swim trunks, grabbed a couple of cold ones and walked across the road to the hot tub! Just what the Dr. ordered! Our unit was clean & comfortable, slept great & were up and out early in the morning."
The price is SAR 409
SAR 486 total
includes taxes & fees
3 Mar - 4 Mar
Vacation Village in the Berkshires

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The Ponds at Foxhollow
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.

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. If your ideal vacation to Cheshire includes spending lots of time outside, Mount Greylock State Reservation is a good spot to enjoy the scenery.
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: 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 check out 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 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.