Find a Bed and Breakfast in Cheshire from CA $161

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Our top choices for Cheshire bed & breakfast

Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is CA $318
CA $336 total
includes taxes & fees
May 14 - May 15
Harbour House Inn

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (453 reviews)
"Everything was excellent"
United States
Barbara
The price is CA $147
CA $161 total
includes taxes & fees
May 11 - May 12
Shaker Mill Inn

The Trail in Adams - Berkshires’ Art Hotel

The Trail in Adams - Berkshires’ Art Hotel
2.5 star property
Adams
9.0 out of 10, Wonderful, (147 reviews)
"Great little Inn with a well equipped kitchen, clean rooms, and art books. It made for a lovely base for our two day Berkshires adventure."
United States
selmin
The price is CA $237
CA $265 total
includes taxes & fees
May 25 - May 26
The Trail in Adams - Berkshires’ Art Hotel

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,001 reviews)
"Delicious breakfast and beautiful room!"
United States
Laarni
The price is CA $196
CA $225 total
includes taxes & fees
May 25 - May 26
The Cornell Inn, Lenox & The Berkshires

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (376 reviews)
"Yes the room was spotless and always the staff is ready to answer any questions that we might have. We have been enjoying the Chambery Inn for many years always had a great stay and again looking for our next visit. Vincent Farricielli and Roibert Modena. "
United States
robert
The price is CA $233
CA $260 total
includes taxes & fees
May 26 - May 27
Chambery Inn

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (137 reviews)
"The inn has an excellent location and amenities."
United States
Christopher
The price is CA $368
CA $411 total
includes taxes & fees
May 10 - May 11
Devonfield Inn B&B

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99 reviews)
"Well-run and elegant property. "
United States
Steven
The price is CA $359
CA $421 total
includes taxes & fees
May 21 - May 22
The Inn at Stockbridge

Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very good, (501 reviews)
"This family owned Inn is absolutely charming and the owners are so nice! I will definitely stay here again when I visit the Berkshires."
United States
Stacey
The price is CA $348
CA $389 total
includes taxes & fees
May 24 - May 25
Whistler's Inn Bed & Breakfast

Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
The price is CA $294
CA $383 total
includes taxes & fees
May 11 - May 12
Experience Timeless Elegance in The Edith Wharton Room!

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (74 reviews)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is CA $861
CA $961 total
includes taxes & fees
May 22 - May 23
33 Main

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

Elegant Carriage House room with a queen bed and private patio.
Lenox
The price is CA $360
CA $469 total
includes taxes & fees
May 11 - May 12
Elegant Carriage House room with a queen bed and private patio.

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

Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Lenox
The price is CA $294
CA $382 total
includes taxes & fees
May 10 - May 11
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen

Historic Susan B. Anthony Room - Cozy & Charming Stay

Historic Susan B. Anthony Room - Cozy & Charming Stay
Lenox
The price is CA $404
CA $522 total
includes taxes & fees
May 10 - May 11
Historic Susan B. Anthony Room - Cozy & Charming Stay

Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (164 reviews)
"Everything was perfect - location and accommodation."
United States
Christopher
The price is CA $250
CA $290 total
includes taxes & fees
Jun 2 - Jun 3
Brook Farm Inn

Cozy Carriage House room with a double bed and private balcony

Cozy Carriage House room with a double bed and private balcony
Lenox
The price is CA $382
CA $497 total
includes taxes & fees
May 12 - May 13
Cozy Carriage House room with a double bed and private balcony

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

Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
Lenox
The price is CA $502
CA $649 total
includes taxes & fees
May 10 - May 11
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn

Elegant suite with a king bed, fireplace, and kitchenette.

Elegant suite with a king bed, fireplace, and kitchenette.
Lenox
The price is CA $611
CA $791 total
includes taxes & fees
May 10 - May 11
Elegant suite with a king bed, fireplace, and kitchenette.

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Lenox
The price is CA $546
CA $694 total
includes taxes & fees
May 11 - May 12
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

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

Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
Lenox
The price is CA $611
CA $791 total
includes taxes & fees
May 10 - May 11
Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn

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
Stockbridge
9.2 out of 10, Wonderful, (111 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
The price is CA $423
CA $512 total
includes taxes & fees
May 25 - May 26
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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

Cheshire B&B information

Number of reviews
2,504
Accommodation
45 B&B
Lowest Price
CA $161
Highest Price
CA $961

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. Chambery Inn: 9 rooms. 18.1 mi (29.1 km) from the heart of downtown. Enjoy the private yard and deli. Lakehouse Inn: 14 rooms. Located 17.1 mi (27.5 km) from the core of Cheshire. Enjoy the free full breakfast 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 Susan B. Anthony Birthplace Museum 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.

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