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Compare 26 B&B in Chester with updated reviews, rates, and availability.

The Ellery
3.5 star property
9.0 out of 10, Wonderful, (407)
"Some pink mold in the shower grout, which was unappealing of course, and could also use a few disposable cups in the bathroom for brushing teeth. Otherwise, a nice stay and the staff was very professional and friendly. "
The price is AED 558
AED 624 total
includes taxes & fees
19 Jun - 20 Jun
The Ellery
The Cornell Inn, Lenox
3.0 star property
8.8 out of 10, Excellent, (1002)
"The staff was very friendly and the breakfast was delicious. The outdoor areas were beautiful. The room was beautifully designed"
The price is AED 463
AED 538 total
includes taxes & fees
17 Jun - 18 Jun
The Cornell Inn, Lenox
Lakehouse Inn
4.0 star property
9.6 out of 10, Exceptional, (162)
"Excellent place to stay. Convenient, clean, beautiful views, wonderful breakfast and snacks. Highly recommend!"
The price is AED 551
AED 640 total
includes taxes & fees
19 Jun - 20 Jun
Lakehouse Inn
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Brook Farm Inn
3.5 star property
9.4 out of 10, Exceptional, (137)
"This is a charming and very pleasant place to stay."
The price is AED 797
AED 890 total
includes taxes & fees
21 Jun - 22 Jun
Brook Farm Inn
Old Mill Inn
3.0 star property
9.4 out of 10, Exceptional, (441)
"I loved listening to the sound of the waterfall while I slept! So clean and comfortable. Excellent coffee, which is definitely a must! "
The price is AED 733
AED 819 total
includes taxes & fees
19 Jun - 20 Jun
Old Mill Inn
Naomi's Inn Bed & Breakfast
3.5 star property
9.0 out of 10, Wonderful, (348)
"Very elegant bedroom and the dining room was fun and funky."
The price is AED 463
AED 525 total
includes taxes & fees
17 Jun - 18 Jun
Naomi's Inn Bed & Breakfast
Chambery Inn
3.0 star property
9.6 out of 10, Exceptional, (356)
"Amazing place.."
The price is AED 1,469
AED 1,641 total
includes taxes & fees
25 Jun - 26 Jun
Chambery Inn
33 Main
4.0 star property
10.0 out of 10, Exceptional, (63)
"I love the fact that it only had eight rooms they had happy hour from 5 to 6 PM so we are able to meet other people at the hotel. I love the rooms and the cleanliness and especially the breakfast they were amazing and delicious!! I would recommend this hotel highly!"
The price is AED 1,502
AED 1,678 total
includes taxes & fees
17 Jun - 18 Jun
33 Main
The Inn at Stockbridge
4.0 star property
9.6 out of 10, Exceptional, (94)
"Fantastic!"
The Inn at Stockbridge
Whistler's Inn Bed & Breakfast
3.5 star property
7.8 out of 10, Good, (435)
"My room was tiny but the Inn hostess was very accommodating/hospitable. The house was reminiscent of an English country BnB. Lots of stories have clearly played out in this old estate house. Right across street from lovely church and cemetery filled with pre-revolutionary war souls and a short walk up the hill from Lenox Main Street. "
The price is AED 579
AED 646 total
includes taxes & fees
17 Jun - 18 Jun
Whistler's Inn Bed & Breakfast
Devonfield Inn B&B
4.0 star property
10.0 out of 10, Exceptional, (106)
"The classic character of the Inn is so beautiful and adds to the whole experience!"
The price is AED 1,355
AED 1,514 total
includes taxes & fees
27 Jun - 28 Jun
Devonfield Inn B&B
Daniel Stebbins House
3.0 star property
10.0 out of 10, Exceptional, (38)
"The loveliest hosts. "
The price is AED 993
AED 1,049 total
includes taxes & fees
17 Jun - 18 Jun
Daniel Stebbins House
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
9.2 out of 10, Wonderful, (101)
"The b&b was so beautiful and unique! The area was serene. The host was very sweet and accommodating."
The price is AED 1,685
AED 2,039 total
includes taxes & fees
17 Jun - 18 Jun
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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. "
Tanglewood Suites
Romantic Boutique Hotel / Bed and Breakfast - Standard Queen Handicap Accessible
9.8 out of 10, Exceptional, (10)
"We would return to the inn again. Bob was wonderful and very, very accommodating:-)"
The price is AED 3,673
AED 4,685 total
includes taxes & fees
17 Jul - 18 Jul
Romantic Boutique Hotel / Bed and Breakfast - Standard Queen Handicap Accessible
Romantic Boutique Hotel / Bed and Breakfast - Smallest Room in The Berkshires
2.0 out of 10, (1)
"Never even met the inn keepers...no one is in sight...WiFi wouldn’t work...a/c in room would not stay on.....1 item only for breakfast- delivered to room- that has no table or chair- stood in the bathroom to eat!!!! Very expensive for what u get "
The price is AED 1,098
AED 1,391 total
includes taxes & fees
17 Jun - 18 Jun
Romantic Boutique Hotel / Bed and Breakfast - Smallest Room in The Berkshires
Harbour House Inn
3.5 star property
9.4 out of 10, Exceptional, (48)
"Decorations were beautiful, room and bed were so comfortable, hostess and food were wonderful. Brandi was thoughtful in every way possible. Can't go wrong choosing this place over a chain. Love it!"
The price is AED 908
AED 960 total
includes taxes & fees
17 Jun - 18 Jun
Harbour House Inn
Romantic Boutique Hotel / B&B - Deluxe Firespa Suite
10.0 out of 10, Exceptional, (4)
"The property was a converted parochial school The rooms were old class rooms. Very spacious and extremely comfortable. Lots to do in the area or like we did just relax . We would recommend the inn for a great summer getaway . Community theater is a big attraction although not open yet Enjoy"
The price is AED 3,673
AED 4,685 total
includes taxes & fees
21 Jun - 22 Jun
Romantic Boutique Hotel / B&B - Deluxe Firespa Suite
Eastgate Inn B&B
2.5 star property
9.2 out of 10, Wonderful, (65)
"The rooms are lovely and immaculately clean. Homey, comfortable house. The Innkeeper is personable and helpful, flexible for our needs."
Eastgate Inn B&B
Romantic Boutique Hotel / Bed and Breakfast - Deluxe Schoolhouse Suite
10.0 out of 10, Exceptional, (6)
The price is AED 3,673
AED 4,685 total
includes taxes & fees
17 Jun - 18 Jun
Romantic Boutique Hotel / Bed and Breakfast - Deluxe Schoolhouse Suite
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See all available properties in Chester
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.

Other property types in Chester

Cozy Berkshires Vacation Rental Near Hiking!
Cozy Berkshires Vacation Rental Near Hiking!
Cozy apartment located in quiet Williamsburg
9.8 out of 10, Exceptional, (35)
"Very clean and nice apartment in a pleasant little city."
The price is AED 551
AED 955 total
includes taxes & fees
17 Jun - 18 Jun
Cozy apartment located in quiet Williamsburg
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
9.8 out of 10, Exceptional, (32)
"We loved our time, very cozy cabin"
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
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.

Frequently asked questions

Searching for B&Bs in Chester?
If you’re looking for something a little different than your standard hotel experience, a bed and breakfast could be the perfect alternative for your getaway. While you’re enjoying your trip to Chester, you might want to explore the theater scene by catching a show at Chester Town Hall.
Why would you choose B&Bs instead of traditional hotels?
Every B&B has its own unique feel. Whether it’s a garden for guests to admire or a sunlit breakfast nook, the little details are what make bed and breakfasts the perfect escape.
When should I book my B&B in Chester?
When you’re planning your escape to Chester, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Chester are January, February, November, and March, with each month seeing an average of 6 inches of snowfall.
What is there to do in Chester?
If you want to check out some popular attractions in Chester, you might enjoy a visit to Chester Town Hall. Jacob’s Pillow and Otis Reservoir are also some sites to visit if you want to see more of the area.
How can I get to and around Chester?
You can map out your trip in and around Chester ahead of time with these transportation options. Fly into Westfield, MA (BAF-Barnes Municipal), which is located 15.4 mi (24.7 km) from the city center. Otherwise, you can search for flights to Pittsfield, MA (PSF-Pittsfield Municipal), which is 18.9 mi (30.4 km) away. If you’d like to explore around the area, consider renting a car to take in more sights.

Recent reviews of Chester hotels
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