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B&B in Cheshire

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1002)
"We have stayed at the Cornell Inn in the past. Always a comfortable, convenient and friendly stay. The food, staff and accommodations are perfect."
$163 nightly
The price is $182
Oct 28 - Oct 29
Total with taxes and fees
The Cornell Inn, Lenox & The Berkshires

Whistler's Inn Bed & Breakfast

3.5 star property
7.8 out of 10, Good, (492)
"This family owned Inn is absolutely charming and the owners are so nice! I will definitely stay here again when I visit the Berkshires."
$158 nightly
The price is $177
Nov 2 - Nov 3
Total with taxes and fees
Whistler's Inn Bed & Breakfast

Inn at Silver Maple Farm

3.0 star property
9.8 out of 10, Exceptional, (94)
"What a wonderful one-night stay on the July 4th weekend. It’s a beautiful, comfortable inn with lovely hosts. Also in a great location, set back from a fairly busy country road with several good food options nearby, and charming villages and towns to tour. Highly recommend. "
$189 nightly
The price is $212
Nov 2 - Nov 3
Total with taxes and fees
Inn at Silver Maple Farm

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (427)
"Very casual and easy check in and out; lovely and substantial breakfast"
$155 nightly
The price is $170
Nov 2 - Nov 3
Total with taxes and fees
Shaker Mill Inn

Tanglewood Suites

2.5 star property
6.4 out of 10, (22)
"NOT A REAL LOCATION. There was nothing there. Neighbors said this was a scam. Expedia ended up helping us find a local hotel room though the location was not as good. DO NOT BOOK THIS LOCATION -- it needs to be taken off the website."
Tanglewood Suites

The Trail in Adams - Berkshires’ Art Hotel

2.5 star property
8.8 out of 10, Excellent, (136)
"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. "
$174 nightly
The price is $194
Nov 2 - Nov 3
Total with taxes and fees
The Trail in Adams - Berkshires’ Art Hotel

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (369)
"ease of late check in. Super comfortable room."
$250 nightly
The price is $279
Oct 6 - Oct 7
Total with taxes and fees
Chambery Inn

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (161)
"Inn was gorgeous and staff exceptional!"
$179 nightly
The price is $200
Nov 1 - Nov 2
Total with taxes and fees
Brook Farm Inn

Lakehouse Inn

4.0 star property
9.6 out of 10, Exceptional, (283)
"Lovely location on a lake, quiet, simple, clean rooms, great breakfast included. "
$175 nightly
The price is $196
Nov 2 - Nov 3
Total with taxes and fees
Lakehouse Inn

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 "
$335 nightly
The price is $374
Oct 20 - Oct 21
Total with taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

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!! "
$247 nightly
The price is $262
Oct 30 - Oct 31
Total with taxes and fees
Harbour House Inn

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (129)
"The inn has an excellent location and amenities."
$379 nightly
The price is $423
Oct 5 - Oct 6
Total with taxes and fees
Devonfield Inn B&B

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

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

$232 nightly
The price is $299
Oct 28 - Oct 29
Total with taxes and fees
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen

33 Main

4.0 star property
10.0 out of 10, Exceptional, (71)
"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! "
$449 nightly
The price is $502
Nov 2 - Nov 3
Total with taxes and fees
33 Main

Eastgate Inn B&B

2.5 star property
9.2 out of 10, Wonderful, (69)
"Dahlia is great. Excellent accommodation. We walked to Tanglewood "
Eastgate Inn B&B

Berkshire Mountain House

3.0 star property
9.6 out of 10, Exceptional, (27)
"GORGEOUS Scenery and NICE place to stay !"
Berkshire Mountain House

The Inn at Stockbridge

4.0 star property
9.8 out of 10, Exceptional, (98)
"Well-run and elegant property. "
$388 nightly
The price is $434
Nov 2 - Nov 3
Total with taxes and fees
The Inn at Stockbridge

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."
$270 nightly
The price is $302
Oct 27 - Oct 28
Total with taxes and fees
The Red Door B&B

UU Rowe Camp and Conference Center

2.0 star property
$145 nightly
The price is $154
Nov 1 - Nov 2
Total with 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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Top Cheshire Hotel Reviews

Find out more about Cheshire

Find out more about Cheshire

Cheshire B&B information

Number of reviews
2,748
Accommodation
34 B&B
Lowest Price
$154
Highest Price
$502

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 $154 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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