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Check prices for these dates

Next weekend
12 Sept - 14 Sept
In two weeks
19 Sept - 21 Sept
In one month
3 Oct - 5 Oct
In two months
31 Oct - 2 Nov

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, (1003)
"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
2 Sept - 3 Sept
The Cornell Inn, Lenox & The Berkshires
Shaker Mill Inn
Garden

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (424)
"Very casual and easy check in and out; lovely and substantial breakfast"
The price is AU$280
includes taxes & fees
4 Sept - 5 Sept
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, (93)
"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
2 Sept - 3 Sept
Inn at Silver Maple Farm
Harbour House Inn
Exterior

Harbour House Inn

3.5 star property
9.4 out of 10, Exceptional, (51)
"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
9 Sept - 10 Sept
Harbour House Inn
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, (135)
"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$307
includes taxes & fees
9 Sept - 10 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
Devonfield Inn B&B
Front of property - evening/night

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (128)
"Very enjoyable comfortable stay"
Devonfield Inn B&B
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$801
includes taxes & fees
7 Sept - 8 Sept
The Inn at Stockbridge
Whistler's Inn Bed & Breakfast
Property grounds

Whistler's Inn Bed & Breakfast

3.5 star property
7.8 out of 10, Good, (484)
"Nice quaint out of the ordinary vacation experience. "
The price is AU$275
includes taxes & fees
2 Sept - 3 Sept
Whistler's Inn Bed & Breakfast
Brook Farm Inn
Loft, Private Bathroom (Skylight Loft)

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (159)
"Inn was gorgeous and staff exceptional!"
Brook Farm Inn
33 Main
Luxury Room, 1 King Bed, Bathtub

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 AU$962
includes taxes & fees
18 Sept - 19 Sept
33 Main
Experience Timeless Elegance in The Edith Wharton Room!
1 bedroom, bed sheets, wheelchair access

Experience Timeless Elegance in The Edith Wharton Room!

The price is AU$470
includes taxes & fees
2 Sept - 3 Sept
Experience Timeless Elegance in The Edith Wharton Room!
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$470
includes taxes & fees
2 Sept - 3 Sept
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Cozy Carriage House room with a double bed and private balcony
1 bedroom, bed sheets

Cozy Carriage House room with a double bed and private balcony

The price is AU$521
includes taxes & fees
22 Sept - 23 Sept
Cozy Carriage House room with a double bed and private balcony
Elegant Carriage House room with a queen bed and private patio.
1 bedroom, WiFi, bed sheets

Elegant Carriage House room with a queen bed and private patio.

The price is AU$497
includes taxes & fees
10 Sept - 11 Sept
Elegant Carriage House room with a queen bed and private patio.
Tanglewood Suites
2 Bedrooms 1 Bath

Tanglewood Suites

2.5 star property
6.8 out of 10, (20)
"The owner did not honor our confirmed Expedia reservation, so we had to find a hotel at the last minute. She made up various excuses and was very rude."
The price is AU$411
includes taxes & fees
2 Sept - 3 Sept
Tanglewood Suites
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
1 bedroom, bed sheets

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

The price is AU$759
includes taxes & fees
7 Sept - 8 Sept
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
Fireplace

Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn

The price is AU$706
includes taxes & fees
9 Sept - 10 Sept
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
Historic Susan B. Anthony Room - Cozy & Charming Stay
Terrace/patio

Historic Susan B. Anthony Room - Cozy & Charming Stay

The price is AU$565
includes taxes & fees
2 Sept - 3 Sept
Historic Susan B. Anthony Room - Cozy & Charming Stay
Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
Fireplace

Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn

The price is AU$851
includes taxes & fees
2 Sept - 3 Sept
Experience Luxury in The Lady Cicely Grand Suite at The Cornell 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

Find out more about Cheshire

Find out more about Cheshire

Cheshire B&B information

Number of reviews
Accommodation
34 B&B
Lowest Price
AU$275
Highest Price
AU$962

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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.