Bed and Breakfast in Cheshire

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Check prices for these dates

Next weekend
13 Feb - 15 Feb
In two weeks
20 Feb - 22 Feb
In one month
6 Mar - 8 Mar
In two months
3 Apr - 5 Apr

Our top choices for Cheshire bed & breakfast

Exterior

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 NZ$376
includes taxes & fees
5 Feb - 6 Feb
Harbour House Inn
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (444 reviews)
"The large kitchen and sitting/living with gas fireplace, with adjacent separate bedroom was very clean and cozy. Thank you to Meg and Dan for providing a nice holiday stay!!!"
United States
Carin
The price is NZ$208
includes taxes & fees
5 Feb - 6 Feb
Shaker Mill Inn
Porch

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (291 reviews)
"A charming inn in the center of the Berkshires."
United States
Danny
The price is NZ$280
includes taxes & fees
7 Feb - 8 Feb
Lakehouse Inn
Lobby sitting area

Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (100 reviews)
"Great property, very comfortable, incredible staff, easy access to skiing in the area!"
United States
Dominick
The price is NZ$239
includes taxes & fees
9 Feb - 10 Feb
Inn at Silver Maple Farm
2 bedrooms, WiFi

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

Cozy Retreat in Historic Farmhouse, Charming Bunk Bed Room,- Owl Dorm
Rowe
10.0 out of 10, Exceptional, (2 reviews)
"The piano, large spaces, and fireplace were all much appreciated."
United States
Benjamin B.
The price is NZ$250
includes taxes & fees
5 Feb - 6 Feb
Cozy Retreat in Historic Farmhouse, Charming Bunk Bed Room,- Owl Dorm
Exterior

UU Rowe Camp and Conference Center

UU Rowe Camp and Conference Center
2.0 star property
Rowe
10.0 out of 10, Exceptional, (1 review)
"Yes"
United States
Stuart
The price is NZ$261
includes taxes & fees
5 Feb - 6 Feb
UU Rowe Camp and Conference Center
Terrace/patio

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, (144 reviews)
"Staff was great, very clean, Breakfast was terrific"
United States
michael
The price is NZ$321
includes taxes & fees
5 Feb - 6 Feb
The Trail in Adams - Berkshires’ Art Hotel
Front of property

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 NZ$464
includes taxes & fees
22 Feb - 23 Feb
The Inn at Stockbridge
1 bedroom, WiFi

Cozy Farmhouse Retreat - Ram Dass Room

Cozy Farmhouse Retreat - Ram Dass Room
Rowe
The price is NZ$225
includes taxes & fees
5 Feb - 6 Feb
Cozy Farmhouse Retreat - Ram Dass Room
1 bedroom, WiFi

Cozy Retreat in historic Farmhouse - Tranquility Room

Cozy Retreat in historic Farmhouse - Tranquility Room
Rowe
The price is NZ$250
includes taxes & fees
5 Feb - 6 Feb
Cozy Retreat in historic Farmhouse - Tranquility Room
Front of property

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (374 reviews)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
Chambery Inn
Exterior

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,000 reviews)
"The Inn was very nice and the staff was super friendly and attentive."
United States
Steven
The price is NZ$254
includes taxes & fees
5 Feb - 6 Feb
The Cornell Inn, Lenox & The Berkshires
Room #10 Queen's Cottage | Living room

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (135 reviews)
"The inn has an excellent location and amenities."
United States
Christopher
Devonfield Inn B&B
Exterior

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 NZ$735
includes taxes & fees
23 Feb - 24 Feb
33 Main
Suite, Private Bathroom (RedBird Suite) | View from room

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, (110 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
The price is NZ$620
includes taxes & fees
17 Feb - 18 Feb
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
3 bedrooms, bed sheets

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

Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Lenox
The price is NZ$472
includes taxes & fees
5 Feb - 6 Feb
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Lobby

Inn at Kenmore Hall

Inn at Kenmore Hall
3.0 star property
Richmond
10.0 out of 10, Exceptional, (27 reviews)
"Gorgeous grounds, welcoming home atmosphere. wonderful breakfast and staff that made it feel like home - only better! "
United States
Margaret
The price is NZ$1,044
includes taxes & fees
5 Feb - 6 Feb
Inn at Kenmore Hall
1 bedroom, WiFi, bed sheets, wheelchair access

Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
The price is NZ$472
includes taxes & fees
5 Feb - 6 Feb
Experience Timeless Elegance in The Edith Wharton Room!
Interior

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 NZ$533
includes taxes & fees
5 Feb - 6 Feb
Elegant Carriage House room with a queen bed and private patio.
Interior

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 NZ$568
includes taxes & fees
5 Feb - 6 Feb
Cozy Carriage House room with a double bed and private balcony
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

Berkshires Untold

Berkshires Untold

10/10 Excellent
"loved "
Daisha 2-night trip
Posted 2 days ago
Berkshires Untold

Find out more about Cheshire

Cheshire B&B information

Number of reviews
2,339
Accommodation
35 B&B
Lowest Price
NZ$208
Highest Price
NZ$1,044

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. Lakehouse Inn: 14 rooms. Situated 17.1 mi (27.5 km) from the heart of Cheshire. Enjoy the free full breakfast and snack bar/deli. Brook Farm Inn: 15 rooms. Located 15.8 mi (25.5 km) from the core of Cheshire. Enjoy the free cooked breakfast and outdoor pool.
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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