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Check prices for these dates

Next weekend
24 Oct - 26 Oct
In two weeks
31 Oct - 2 Nov
In one month
14 Nov - 16 Nov
In two months
12 Dec - 14 Dec

Featured B&B in Cheshire

Exterior
Harbour House Inn
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!! "
Lorie
The price is AU$410
includes taxes & fees
28 Oct - 29 Oct
Harbour House Inn
Garden
Shaker Mill Inn
Shaker Mill Inn
2.5 star property
9.6 out of 10, Exceptional, (429)
"Very casual and easy check in and out; lovely and substantial breakfast"
Jamie
The price is AU$221
includes taxes & fees
4 Nov - 5 Nov
Shaker Mill Inn
Terrace/patio
The Trail in Adams - Berkshires’ Art Hotel
The Trail in Adams - Berkshires’ Art Hotel
2.5 star property
8.8 out of 10, Excellent, (137)
"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. "
Jonathan
The price is AU$299
includes taxes & fees
22 Oct - 23 Oct
The Trail in Adams - Berkshires’ Art Hotel
Front of property
UU Rowe Camp and Conference Center
UU Rowe Camp and Conference Center
2.0 star property
The price is AU$242
includes taxes & fees
1 Nov - 2 Nov
UU Rowe Camp and Conference Center
Interior
The Red Door B&B
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."
Anonymous traveller
The Red Door B&B
Front of property
Chambery Inn
Chambery Inn
3.0 star property
9.6 out of 10, Exceptional, (369)
"ease of late check in. Super comfortable room."
Mary
Chambery Inn
Porch
Lakehouse Inn
Lakehouse Inn
4.0 star property
9.6 out of 10, Exceptional, (285)
"Lovely location on a lake, quiet, simple, clean rooms, great breakfast included. "
Roberta
The price is AU$324
includes taxes & fees
2 Nov - 3 Nov
Lakehouse Inn
Front of property – evening/night
Devonfield Inn B&B
Devonfield Inn B&B
4.0 star property
10.0 out of 10, Exceptional, (131)
"The inn has an excellent location and amenities."
Christopher
Devonfield Inn B&B
Front of property
The Cornell Inn, Lenox & The Berkshires
The Cornell Inn, Lenox & The Berkshires
3.5 star property
9.0 out of 10, Wonderful, (1007)
"Very friendly staff. "
Pamela
The price is AU$280
includes taxes & fees
26 Oct - 27 Oct
The Cornell Inn, Lenox & The Berkshires
Property grounds
Whistler's Inn Bed & Breakfast
Whistler's Inn Bed & Breakfast
3.5 star property
7.8 out of 10, Good, (496)
"We had the smallest room on the property.very quaint and clean. Nicest staff great place to stay."
Lisa
The price is AU$263
includes taxes & fees
21 Oct - 22 Oct
Whistler's Inn Bed & Breakfast
Exterior
The Inn at Stockbridge
The Inn at Stockbridge
4.0 star property
9.8 out of 10, Exceptional, (98)
"Well-run and elegant property. "
Steven
The price is AU$626
includes taxes & fees
9 Nov - 10 Nov
The Inn at Stockbridge
Loft, Private Bathroom (Skylight Loft)
Brook Farm Inn
Brook Farm Inn
3.5 star property
9.4 out of 10, Exceptional, (161)
"Inn was gorgeous and staff exceptional!"
Joyce
Brook Farm Inn
3 bedrooms, bed sheets
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
The price is AU$466
includes taxes & fees
26 Oct - 27 Oct
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Luxury Room, 1 King Bed, Bathtub
33 Main
33 Main
4.0 star property
10.0 out of 10, Exceptional, (73)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
James
The price is AU$891
includes taxes & fees
16 Nov - 17 Nov
33 Main
Business centre
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
9.2 out of 10, Wonderful, (107)
"Wonderful! Owner/host Diane was friendly, helpful, knowledgeable. Breakfasts awesome with great choices daily. Place was spotless, cozy and classic. So glad we stayed there. "
Robert
The price is AU$576
includes taxes & fees
16 Nov - 17 Nov
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
1 bedroom, WiFi, bed sheets
Elegant Carriage House room with a queen bed and private patio.
Elegant Carriage House room with a queen bed and private patio.
The price is AU$498
includes taxes & fees
29 Oct - 30 Oct
Elegant Carriage House room with a queen bed and private patio.
1 bedroom, WiFi, bed sheets, wheelchair access
Experience Timeless Elegance in The Edith Wharton Room!
Experience Timeless Elegance in The Edith Wharton Room!
The price is AU$466
includes taxes & fees
26 Oct - 27 Oct
Experience Timeless Elegance in The Edith Wharton Room!
1 bedroom, bed sheets
Cozy Carriage House room with a double bed and private balcony
Cozy Carriage House room with a double bed and private balcony
The price is AU$529
includes taxes & fees
29 Oct - 30 Oct
Cozy Carriage House room with a double bed and private balcony
Terrace/patio
Historic Susan B. Anthony Room - Cozy & Charming Stay
Historic Susan B. Anthony Room - Cozy & Charming Stay
The price is AU$560
includes taxes & fees
28 Oct - 29 Oct
Historic Susan B. Anthony Room - Cozy & Charming Stay
Fireplace
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
The price is AU$712
includes taxes & fees
27 Oct - 28 Oct
Experience Timeless Elegance in The Niles Johnson Room 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

Huttopia Berkshires

Huttopia Berkshires

10/10 Excellent
"Friendly and very accomodating staffs, They go extra mile in everything they do. Just want to mention the staffs Who helped is with our trashes even if they dont have to, They still helped us. The views in huttopia berkshire is so beautful and breath taking. Bery clean and safe surroundings with durable equipments"
Roma 2-night trip
Posted 5 days ago
Huttopia Berkshires

Find out more about Cheshire

Cheshire B&B information

Number of reviews
2,636
Accommodation
35 B&B
Lowest Price
AU$221
Highest Price
AU$891

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. Chambery Inn: 9 rooms. Located 18.1 mi (29.1 km) from the core of Cheshire. Enjoy the private garden and snack bar/deli.
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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