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Compare 35 B&B in Cheshire with updated reviews, rates, and availability.

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1001)
"Breakfast each day was phenomenal, staff were all so friendly, hotel & room were beautifully decorated. We had a wonderful time & would stay here again!"
$164 nightly
The price is $183
Jun 30 - Jul 1
Total includes taxes and fees
The Cornell Inn, Lenox & The Berkshires

Tanglewood Suites

2.5 star property
8.0 out of 10, Very Good, (15)
"The property is so lovely and peaceful. I love the classic mid-century modern aesthetic. For visitors to the National Shrine of Divine Mercy, the Inn’s location couldn’t be more perfect with only a 5-minute walk to the Shrine. "
$269 nightly
The price is $269
Jun 29 - Jun 30
Total includes taxes and fees
Tanglewood Suites

Lakehouse Inn

4.0 star property
9.6 out of 10, Exceptional, (266)
"Really peaceful and serene property due to the lake. The house was clean and the staff were friendly. "
Lakehouse Inn

Inn at Silver Maple Farm

3.0 star property
9.8 out of 10, Exceptional, (86)
"Everything about our stay in The Loft was wonderful! The hot breakfast each morning was incredible. The entire inn was very clean and well kept. We will definitely be back! "
$229 nightly
The price is $247
Jul 1 - Jul 2
Total includes taxes and fees
Inn at Silver Maple Farm

The Trail in Adams - Berkshires’ Art Hotel

2.5 star property
8.8 out of 10, Excellent, (129)
"Stayed only one night Very cosy, quiet place "
$174 nightly
The price is $194
Jun 30 - Jul 1
Total includes taxes and fees
The Trail in Adams - Berkshires’ Art Hotel

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (413)
"Nice"
$142 nightly
The price is $156
Jun 30 - Jul 1
Total includes taxes and fees
Shaker Mill Inn

Whistler's Inn Bed & Breakfast

3.5 star property
7.8 out of 10, Good, (474)
"All was just as advertised and the family/staff was friendly and helpful. "
$198 nightly
The price is $221
Jun 29 - Jun 30
Total includes taxes and fees
Whistler's Inn Bed & Breakfast

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (365)
"We returned to the Chambery Inn to celebrate my wife's birthday and the Memorial Day weekend. We were very happy with our choice. We stayed in a beautiful room (203), which included a spacious sitting area and a well-appointed bath. The breakfast were nicely prepared and presented. The Inn provided timely information prior and during our stay. We will be back in the future. "
$250 nightly
The price is $279
Jun 29 - Jun 30
Total includes taxes and fees
Chambery Inn

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (152)
"This is a charming and very pleasant place to stay."
$269 nightly
The price is $300
Jun 30 - Jul 1
Total includes taxes and fees
Brook Farm Inn

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (127)
"Very enjoyable comfortable stay"
$289 nightly
The price is $323
Jun 30 - Jul 1
Total includes taxes and fees
Devonfield Inn B&B

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 star property
9.2 out of 10, Wonderful, (105)
"Great breakfast, friendly helpful staff, pretty yard, good location "
$497 nightly
The price is $555
Jul 14 - Jul 15
Total includes taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

33 Main

4.0 star property
10.0 out of 10, Exceptional, (70)
"33 Main is the best of everything. We have stayed at the location twice and loved each experience. The breakfast is delicious, accommodations are beautifully curated, and it’s perfectly located in Lenox. Highly recommend and we will be back! "
$455 nightly
The price is $509
Jul 28 - Jul 29
Total includes taxes and fees
33 Main

The Inn at Stockbridge

4.0 star property
9.8 out of 10, Exceptional, (98)
"Well-run and elegant property. "
The Inn at Stockbridge

Inn at Kenmore Hall

3.0 star property
10.0 out of 10, Exceptional, (27)
"This is a beautiful property straight out of a magazine. Service was impeccable"
Inn at Kenmore Hall

Harbour House Inn

3.5 star property
9.4 out of 10, Exceptional, (49)
"Nice place for a weekend away."
$241 nightly
The price is $255
Jul 28 - Jul 29
Total includes taxes and fees
Harbour House Inn

Eastgate Inn B&B

2.5 star property
9.2 out of 10, Wonderful, (68)
"Great host and enjoyable stay."
Eastgate Inn B&B

Berkshire Mountain House

3.0 star property
9.4 out of 10, Exceptional, (24)
"GORGEOUS Scenery and NICE place to stay !"
Berkshire Mountain House

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."
The Red Door B&B

Unique people and pet welcoming haven

Unique people and pet welcoming haven

UU Rowe Camp and Conference Center

2.0 star property
$149 nightly
The price is $157
Jun 29 - Jun 30
Total includes taxes and fees
UU Rowe Camp and Conference Center
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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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 $156 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.