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B&B in Cheshire

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!! "
United States
Lorie
$249 nightly
The price is $264
Nov 25 - Nov 26
Total with taxes and fees
Harbour House Inn
Shaker Mill Inn
2.5 star property
9.6 out of 10, Exceptional, (433)
"Very casual and easy check in and out; lovely and substantial breakfast"
United States
Jamie
$101 nightly
The price is $111
Nov 5 - Nov 6
Total with taxes and fees
Shaker Mill Inn
Inn at Silver Maple Farm
3.0 star property
9.8 out of 10, Exceptional, (97)
"This was the perfect spot for a Tanglewood night..beautiful, charming, great staff and delicious breakfast..."
United States
Jane
$129 nightly
The price is $144
Nov 23 - Nov 24
Total with taxes and fees
Inn at Silver Maple Farm
Lakehouse Inn
4.0 star property
9.6 out of 10, Exceptional, (287)
"Great Views & Hospitality"
United States
Gerald
$178 nightly
The price is $199
Nov 16 - Nov 17
Total with taxes and fees
Lakehouse Inn
UU Rowe Camp and Conference Center
2.0 star property
$149 nightly
The price is $157
Nov 4 - Nov 5
Total with taxes and fees
UU Rowe Camp and Conference Center
The Trail in Adams - Berkshires’ Art Hotel
2.5 star property
8.8 out of 10, Excellent, (140)
"It was clean and quiet good Breakfast "
United States
William
$156 nightly
The price is $175
Nov 10 - Nov 11
Total with taxes and fees
The Trail in Adams - Berkshires’ Art Hotel
Chambery Inn
3.0 star property
9.6 out of 10, Exceptional, (371)
"Lovely, unique property with huge rooms! Such a fun place to stay. "
United States
Mary
$190 nightly
The price is $212
Nov 4 - Nov 5
Total with taxes and fees
Chambery Inn
The Cornell Inn, Lenox & The Berkshires
3.5 star property
9.0 out of 10, Wonderful, (1002)
"Honestly I just enjoyed being able to relax Play some games in the cute pub and the breakfast was yummy and stuff was inviting and so helpful "
United States
Sandra
$164 nightly
The price is $183
Nov 4 - Nov 5
Total with taxes and fees
The Cornell Inn, Lenox & The Berkshires
Devonfield Inn B&B
4.0 star property
10.0 out of 10, Exceptional, (133)
"The inn has an excellent location and amenities."
United States
Christopher
$369 nightly
The price is $412
Nov 21 - Nov 22
Total with taxes and fees
Devonfield Inn B&B
The Inn at Stockbridge
4.0 star property
9.8 out of 10, Exceptional, (98)
"A first class little inn"
United States
Philip
$289 nightly
The price is $322
Nov 9 - Nov 10
Total with taxes and fees
The Inn at Stockbridge
33 Main
4.0 star property
10.0 out of 10, Exceptional, (74)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
$441 nightly
The price is $493
Nov 23 - Nov 24
Total with taxes and fees
33 Main
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
$239 nightly
The price is $306
Nov 4 - Nov 5
Total with taxes and fees
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Whistler's Inn Bed & Breakfast
3.5 star property
7.8 out of 10, Good, (500)
"Cozy spot with very friendly propeietor"
United States
Kyle
$253 nightly
The price is $282
Nov 4 - Nov 5
Total with taxes and fees
Whistler's Inn Bed & Breakfast
Tanglewood Suites
2.5 star property
6.4 out of 10, (22)
"Portion of hosts home, separate and available for rent. Heating system not efficient and took some work to sort out how to keep all areas of the unit comfortably heated. Beds clean and comfortable. Overall cleanliness was good. Bath facilities are an addition to existing structure and sufficient, but could use some TLC. Host is eager to please and pleasant to interact with. Listing indicates free breakfast for all guests. However, upon arrival, we were advised there is no winter offering of...
United States
Amanda
$219 nightly
The price is $219
Dec 1 - Dec 2
Total with taxes and fees
Tanglewood Suites
Experience Timeless Elegance in The Edith Wharton Room!
$239 nightly
The price is $306
Nov 4 - Nov 5
Total with taxes and fees
Experience Timeless Elegance in The Edith Wharton Room!
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
9.2 out of 10, Wonderful, (109)
"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
$332 nightly
The price is $371
Nov 11 - Nov 12
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.
$257 nightly
The price is $326
Nov 4 - Nov 5
Total with taxes and fees
Elegant Carriage House room with a queen bed and private patio.
Brook Farm Inn
3.5 star property
9.4 out of 10, Exceptional, (162)
"This is our second stay at the Brook Farm Inn and we enjoyed it just as much as our first stay! Maureen and Joe are fantastic inn keepers. They are polite, full of knowledge and provide a wonderful experience. Our room was cozy and comfortable. The breakfast was delicious. We couldn’t ask for a better weekend away! "
United States
John
$165 nightly
The price is $184
Nov 12 - Nov 13
Total with taxes and fees
Brook Farm Inn
Cozy Carriage House room with a double bed and private balcony
$276 nightly
The price is $347
Nov 4 - Nov 5
Total with taxes and fees
Cozy Carriage House room with a double bed and private balcony
Historic Susan B. Anthony Room - Cozy & Charming Stay
$294 nightly
The price is $368
Nov 4 - Nov 5
Total with taxes and fees
Historic Susan B. Anthony Room - Cozy & Charming Stay
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
2,775
Accommodation
35 B&B
Lowest Price
$111
Highest Price
$493

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 $111 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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