A lake surrounded by autumn-colored trees and hills.

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Check prices for these dates

Next weekend
6 Nov - 8 Nov
In two weeks
13 Nov - 15 Nov
In one month
27 Nov - 29 Nov
In two months
25 Dec - 27 Dec

Our top choices for Cheshire bed & breakfast

A large, two-story building with a symmetrical facade, multiple windows, and a central entrance with a covered porch.

1. Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.6 out of 10, Exceptional, (58 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is 6.557.130 ₫
6.930.886 ₫ total
includes taxes & fees
28 Oct - 29 Oct
Harbour House Inn
A wooden cabin interior with a dining area featuring two white chairs, a table with a coffee pot and a cup, and a view into the kitchen through an open doorway.

2. 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, (157 reviews)
"Fun decor, friendly staff, great complimentary breakfast, directly on bike path."
United States
Susan
The price is 4.490.743 ₫
5.016.160 ₫ total
includes taxes & fees
1 Nov - 2 Nov
The Trail in Adams - Berkshires’ Art Hotel
A snow-covered outdoor area with a patio, seating, and a covered dining area.

3. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.4 out of 10, Exceptional, (1,006 reviews)
"Lovely room, comfortable bed and a nice breakfast."
United Kingdom
judith
The price is 4.394.233 ₫
5.040.185 ₫ total
includes taxes & fees
1 Nov - 2 Nov
The Cornell Inn, Lenox & The Berkshires
A red building with a sign reading "Shaker Mill Inn."

4. Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (482 reviews)
"Loved the location, fireplace and vibe"
United States
Mahadeva
The price is 2.894.752 ₫
3.175.543 ₫ total
includes taxes & fees
2 Nov - 3 Nov
Shaker Mill Inn
A garden with a white gazebo, a brick pathway, and various plants and flowers.

5. Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very good, (521 reviews)
"Whistler's Inn is a Gilded Era mansion, passed down in the family (modernised "
United States
Mary Anna
The price is 3.558.994 ₫
3.975.373 ₫ total
includes taxes & fees
28 Oct - 29 Oct
Whistler's Inn Bed & Breakfast
An aerial view of a large estate with multiple buildings, surrounded by dense greenery and trees.

6. Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (118 reviews)
"Perfect location for hiking, hanging out and Tanglewood Comfortable and charming common space and cozy nicely decorated rooms Generous breakfast and snacks throughout the day We’ll be back"
United States
Linda
The price is 4.755.664 ₫
5.326.344 ₫ total
includes taxes & fees
22 Nov - 23 Nov
Inn at Silver Maple Farm
A house with a chimney, surrounded by trees with autumn foliage.

7. 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 3.465.278 ₫
3.662.799 ₫ total
includes taxes & fees
9 Nov - 10 Nov
UU Rowe Camp and Conference Center
A wooden deck with a table and chairs, surrounded by a metal railing, overlooking a lush green landscape with trees.

8. The Red Door B&B

The Red Door B&B
3.0 star property
Lee
10.0 out of 10, Exceptional, (5 reviews)
"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."
United States
Anonymous traveller
The Red Door B&B
Front of property

9. The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.6 out of 10, Exceptional, (108 reviews)
"Wonderful place… clean, cosy room, comfy bed, friendly staff, great breakfast. Delightful location near Norman Rockwell museum."
United States
Kimberly
The price is 9.428.104 ₫
11.057.694 ₫ total
includes taxes & fees
12 Nov - 13 Nov
The Inn at Stockbridge
A two-story building with a sign reading "Chambéry Inn".

10. Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (390 reviews)
"An absolutely perfect getaway spot! Beautiful rooms, great service, and an ideal location. Highly recommend and we will be going back."
United States
Alexandra
The price is 6.978.188 ₫
7.794.635 ₫ total
includes taxes & fees
28 Oct - 29 Oct
Chambery Inn
A large, two-story house with a well-maintained lawn and a fence.

11. Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (141 reviews)
"Wonderful location and hosts are amazing. Breakfast was great. Clean."
United States
Sebastien
The price is 9.537.174 ₫
10.652.946 ₫ total
includes taxes & fees
2 Nov - 3 Nov
Devonfield Inn B&B
A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.

12. Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (178 reviews)
"Breakfast was not only delicious, the room was sweet and bright and staff very attentive."
United States
Carrie
The price is 5.027.305 ₫
5.822.328 ₫ total
includes taxes & fees
2 Nov - 3 Nov
Brook Farm Inn
A two-story house with a brick entrance and a white facade.

13. 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, (120 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."
United States
Philippe
The price is 9.871.194 ₫
11.941.330 ₫ total
includes taxes & fees
11 Nov - 12 Nov
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

The Yankee Inn

The Yankee Inn

10/10 Excellent
"The hot tub and pool were great. Working on part of it but didn’t hinder us in the least. Loved the pool was warmer than most"
Betty 1-night trip
Posted 2 hours ago
The Yankee Inn

Find out more about Cheshire

Cheshire B&B information

Number of reviews
2,041
Accommodation
23 B&B
Lowest Price
3.175.543 ₫
Highest Price
11.941.330 ₫

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 attractions in town, Mount Greylock State Reservation and Cheshire Reservoir are worth a stop.
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.
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 spend some time in the great outdoors, Mount Greylock State Reservation and Cheshire Reservoir are some notable spots. 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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