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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)
"The owner Brandi was outstanding, friendly, she made us fresh homemade breakfast each morning, which the best. Will differently stay there again. Wonderful place and people."
United States
alton
$196 nightly
The price is $208
Jan 19 - Jan 20, 2026
Total with taxes and fees
Harbour House Inn

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (438)
"Nice place, easy check in"
United States
Robert
$110 nightly
The price is $121
Jan 5 - Jan 6, 2026
Total with taxes and fees
Shaker Mill Inn

UU Rowe Camp and Conference Center

UU Rowe Camp and Conference Center
2.0 star property
Rowe
$149 nightly
The price is $157
Dec 23 - Dec 24
Total with taxes and fees
UU Rowe Camp and Conference Center

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, (142)
"Staff was great, very clean, Breakfast was terrific"
United States
michael
$174 nightly
The price is $194
Dec 23 - Dec 24
Total with taxes and fees
The Trail in Adams - Berkshires’ Art Hotel

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (373)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
$190 nightly
The price is $212
Dec 23 - Dec 24
Total with taxes and fees
Chambery Inn

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (290)
"A charming inn in the center of the Berkshires."
United States
Danny
$192 nightly
The price is $214
Dec 29 - Dec 30
Total with taxes and fees
Lakehouse Inn

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (134)
"The inn has an excellent location and amenities."
United States
Christopher
$349 nightly
The price is $390
Dec 23 - Dec 24
Total with taxes and fees
Devonfield Inn B&B

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99)
"Well-run and elegant property. "
United States
Steven
$263 nightly
The price is $294
Jan 1 - Jan 2, 2026
Total with taxes and fees
The Inn at Stockbridge

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1000)
"The Inn was very nice and the staff was super friendly and attentive."
United States
Steven
$172 nightly
The price is $192
Dec 23 - Dec 24
Total with taxes and fees
The Cornell Inn, Lenox & The Berkshires

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (74)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
$364 nightly
The price is $407
Jan 19 - Jan 20, 2026
Total with taxes and fees
33 Main

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

Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Lenox
$310 nightly
The price is $354
Dec 23 - Dec 24
Total with taxes and fees
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen

Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
$310 nightly
The price is $354
Dec 23 - Dec 24
Total with taxes and fees
Experience Timeless Elegance in The Edith Wharton Room!

Cozy Carriage House room with a double bed and private balcony

Cozy Carriage House room with a double bed and private balcony
Lenox
$342 nightly
The price is $391
Dec 23 - Dec 24
Total with taxes and fees
Cozy Carriage House room with a double bed and private balcony

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)
"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. "
United States
Robert
$414 nightly
The price is $462
Jan 5 - Jan 6, 2026
Total with taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

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

Elegant Carriage House room with a queen bed and private patio.
Lenox
$336 nightly
The price is $385
Jan 1 - Jan 2, 2026
Total with taxes and fees
Elegant Carriage House room with a queen bed and private patio.

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
$450 nightly
The price is $514
Dec 23 - Dec 24
Total with taxes and fees
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn

Historic Susan B. Anthony Room - Cozy & Charming Stay

Historic Susan B. Anthony Room - Cozy & Charming Stay
Lenox
$361 nightly
The price is $413
Dec 23 - Dec 24
Total with taxes and fees
Historic Susan B. Anthony Room - Cozy & Charming Stay

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Lenox
$487 nightly
The price is $544
Dec 23 - Dec 24
Total with taxes and fees
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (164)
"Everything was perfect - location and accommodation."
United States
Christopher
$165 nightly
The price is $184
Dec 30 - Dec 31
Total with taxes and fees
Brook Farm Inn

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
$537 nightly
The price is $614
Dec 23 - Dec 24
Total with taxes and fees
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

Cheshire B&B information

Number of reviews
2,354
Accommodation
35 B&B
Lowest Price
$121
Highest Price
$614

Frequently asked questions

What are the most popular Cheshire Bed & Breakfasts?
Harbour House Inn is a great choice for travelers seeking a memorable experience in Cheshire, boasting an impressive 9.6 rating. Guests rave about the delightful full breakfast, which features homemade baked goodies that set a warm tone for the day. The friendly space and stunning mountain views create a serene backdrop, superb for couples looking to escape the hustle and bustle of everyday life.
What is the nightly rate for a Bed & Breakfast in Cheshire?
Prices for B&Bs in Cheshire often vary, but you can find a great deal from $121 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Cheshire B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a Bed & Breakfast in Cheshire?
The best time to book a B&B in Cheshire is during the late spring and summer months, particularly from May to August. This period attracts visitors eager to explore the charming countryside, picturesque villages, and lush landscapes that Cheshire is renowned for. As the weather warms up, with temperatures typically ranging from the mid-50s to the mid-70s Fahrenheit, travelers can comfortably enjoy outdoor activities, including walking, cycling, and sightseeing.

July stands out as the peak month, offering lively events and festivals that bring the community to life. Visitors can immerse themselves in local culture while exploring attractions like the historic Chester Zoo or taking leisurely strolls along the scenic canals. The vibrant atmosphere during this time makes it superb for those who appreciate a bustling environment filled with fellow adventurers.

For those looking for a more budget-friendly option, consider visiting in early September. This month often provides pleasant weather and fewer crowds, allowing for a more relaxed experience while still enjoying the stunning scenery and local attractions.
What is the difference between a Cheshire Bed & Breakfast and a hotel?
Every Cheshire B&B has its own unique feel. 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 home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Cheshire B&Bs.

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