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3 Oct - 5 Oct
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24 Oct - 26 Oct
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Featured B&B in Cheshire

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, (1005)
"We have stayed at the Cornell Inn in the past. Always a comfortable, convenient and friendly stay. The food, staff and accommodations are perfect."
The price is AU$278
includes taxes & fees
28 Oct - 29 Oct
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, (492)
"This family owned Inn is absolutely charming and the owners are so nice! I will definitely stay here again when I visit the Berkshires."
The price is AU$227
includes taxes & fees
29 Sept - 30 Sept
Whistler's Inn Bed & Breakfast
Inn at Silver Maple Farm
Aerial view

Inn at Silver Maple Farm

3.0 star property
9.8 out of 10, Exceptional, (94)
"What a wonderful one-night stay on the July 4th weekend. It’s a beautiful, comfortable inn with lovely hosts. Also in a great location, set back from a fairly busy country road with several good food options nearby, and charming villages and towns to tour. Highly recommend. "
The price is AU$358
includes taxes & fees
29 Sept - 30 Sept
Inn at Silver Maple Farm
Shaker Mill Inn
Garden

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (427)
"Very casual and easy check in and out; lovely and substantial breakfast"
The price is AU$300
includes taxes & fees
1 Oct - 2 Oct
Shaker Mill Inn
Tanglewood Suites
2 Bedrooms 1 Bath

Tanglewood Suites

2.5 star property
6.4 out of 10, (22)
"NOT A REAL LOCATION. There was nothing there. Neighbors said this was a scam. Expedia ended up helping us find a local hotel room though the location was not as good. DO NOT BOOK THIS LOCATION -- it needs to be taken off the website."
The price is AU$411
includes taxes & fees
28 Sept - 29 Sept
Tanglewood Suites
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, (136)
"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. "
The price is AU$297
includes taxes & fees
28 Sept - 29 Sept
The Trail in Adams - Berkshires’ Art Hotel
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (369)
"ease of late check in. Super comfortable room."
Chambery Inn
Brook Farm Inn
Loft, Private Bathroom (Skylight Loft)

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (160)
"Inn was gorgeous and staff exceptional!"
Brook Farm Inn
Lakehouse Inn
Porch

Lakehouse Inn

4.0 star property
9.6 out of 10, Exceptional, (282)
"Lovely location on a lake, quiet, simple, clean rooms, great breakfast included. "
The price is AU$297
includes taxes & fees
29 Sept - 30 Sept
Lakehouse Inn
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 AU$572
includes taxes & fees
20 Oct - 21 Oct
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Harbour House Inn
Exterior

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!! "
The price is AU$407
includes taxes & fees
29 Sept - 30 Sept
Harbour House Inn
Devonfield Inn B&B
Front of property – evening/night

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (129)
"The inn has an excellent location and amenities."
Devonfield Inn B&B
Inn at Kenmore Hall
Lobby

Inn at Kenmore Hall

3.0 star property
10.0 out of 10, Exceptional, (27)
"This is a beautiful property straight out of a magazine. Service was impeccable"
Inn at Kenmore Hall
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
3 bedrooms, bed sheets

Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen

The price is AU$460
includes taxes & fees
28 Oct - 29 Oct
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
33 Main
Luxury Room, 1 King Bed, Bathtub

33 Main

4.0 star property
10.0 out of 10, Exceptional, (71)
"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 AU$1,025
includes taxes & fees
22 Oct - 23 Oct
33 Main
Eastgate Inn B&B
Porch

Eastgate Inn B&B

2.5 star property
9.2 out of 10, Wonderful, (69)
"Dahlia is great. Excellent accommodation. We walked to Tanglewood "
Eastgate Inn B&B
Berkshire Mountain House
Comfort Apartment, 1 Bedroom, Mountain View, Garden Area | Private kitchenette

Berkshire Mountain House

3.0 star property
9.6 out of 10, Exceptional, (27)
"GORGEOUS Scenery and NICE place to stay !"
Berkshire Mountain House
The Inn at Stockbridge
Exterior

The Inn at Stockbridge

4.0 star property
9.8 out of 10, Exceptional, (98)
"Well-run and elegant property. "
The price is AU$709
includes taxes & fees
28 Sept - 29 Sept
The Inn at Stockbridge
The Red Door B&B
Interior

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."
The Red Door B&B
UU Rowe Camp and Conference Center
Front of property

UU Rowe Camp and Conference Center

2.0 star property
UU Rowe Camp and Conference Center
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 Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

10/10 Excellent
"Staff is friendly and accommodating "
Karol 1-night trip
Posted 2 days ago
Best Western Plus Berkshire Hills Inn & Suites

Find out more about Cheshire

Find out more about Cheshire

Cheshire B&B information

Number of reviews
2,747
Accommodation
34 B&B
Lowest Price
AU$227
Highest Price
AU$1,025

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. Inn at Silver Maple Farm: 11 rooms. Situated 18.2 mi (29.3 km) from the heart of Cheshire. Enjoy the free buffet breakfast and designer toiletries.
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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