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B&B in Cheshire

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1001)
"Lovely place. Excellent staff, Wonderful breakfast."
$163 nightly
The price is $182
Sep 1 - Sep 2
Total includes taxes and fees
The Cornell Inn, Lenox & The Berkshires

Whistler's Inn Bed & Breakfast

3.5 star property
7.8 out of 10, Good, (481)
"Nice quaint out of the ordinary vacation experience. "
$193 nightly
The price is $215
Aug 17 - Aug 18
Total includes taxes and fees
Whistler's Inn Bed & Breakfast

The Trail in Adams - Berkshires’ Art Hotel

2.5 star property
8.8 out of 10, Excellent, (133)
"Nice unique design. A very nice seating area in the living room. The bedroom nicely arranged, fully stocked with all items one needs for the stay, and very clean. A beautiful warm breakfast and access 24/7 to a full kitchen. "
$188 nightly
The price is $209
Aug 20 - Aug 21
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, (420)
"Very casual and easy check in and out; lovely and substantial breakfast"
$183 nightly
The price is $201
Aug 19 - Aug 20
Total includes taxes and fees
Shaker Mill Inn

Lakehouse Inn

4.0 star property
9.6 out of 10, Exceptional, (277)
"Great Views & Hospitality"
Lakehouse Inn

Inn at Silver Maple Farm

3.0 star property
9.8 out of 10, Exceptional, (91)
"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. "
$209 nightly
The price is $234
Sep 2 - Sep 3
Total includes taxes and fees
Inn at Silver Maple Farm

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (156)
"Wonderful cozy and warm feel. Property, location and service are all excellent."
$249 nightly
The price is $278
Sep 1 - Sep 2
Total includes taxes and fees
Brook Farm Inn

Tanglewood Suites

2.5 star property
7.4 out of 10, Good, (18)
"Made a Friday night reservation for their 2BR suite in August. When we arrived at the location listed on Expedia, we found ourselves in a residential neighborhood with no "Tanglewood Suites" in sight. I had emailed in advance for clarification on the location but didn't get a reply. We called the place and the proprietor said there was no record of a reservation and that she never rents for one night only. We were left high and dry with no reasonably priced play to stay in the area. "
$269 nightly
The price is $269
Aug 17 - Aug 18
Total includes taxes and fees
Tanglewood Suites

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! "
$600 nightly
The price is $671
Aug 18 - Aug 19
Total includes taxes and fees
33 Main

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (368)
"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
Aug 17 - Aug 18
Total includes taxes and fees
Chambery Inn

Harbour House Inn

3.5 star property
9.4 out of 10, Exceptional, (51)
"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!! "
$252 nightly
The price is $267
Aug 18 - Aug 19
Total includes taxes and fees
Harbour House 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 "
$447 nightly
The price is $500
Aug 31 - Sep 1
Total includes taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Inn at Stockbridge

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

Berkshire Mountain House

3.0 star property
9.4 out of 10, Exceptional, (26)
"GORGEOUS Scenery and NICE place to stay !"
Berkshire Mountain House

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (128)
"Very enjoyable comfortable stay"
$309 nightly
The price is $345
Sep 1 - Sep 2
Total includes 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

$234 nightly
The price is $301
Sep 1 - Sep 2
Total includes taxes and fees
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen

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

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

UU Rowe Camp and Conference Center

2.0 star property
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

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 $182 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.