Photo by Elizabeth Massa Peroulakis

Search B&B in Chester

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Compare 25 B&B in Chester with updated reviews, rates, and availability.

The Ellery

3.5 star property
9.0 out of 10, Wonderful, (538)
"Very nice staff and small place but cozy, clean, and comfortable. The king bed room is huge and air conditioner is excellent and super silent."
The price is SAR 522
SAR 583 total
includes taxes & fees
18 Dec - 19 Dec
The Ellery

The Cornell Inn, Lenox

3.0 star property
8.8 out of 10, Excellent, (1045)
"We were greeted warmly upon arrival with hot beverages and brownies. There were bakery items available all during our stay, and the property features a quaint little bar with many offerings. The breakfast was served in a bright and very well-appointed room with a fireplace and the staff were very friendly and attentive. The food was very nicely presented and delicious. This is a wonderful bed and breakfast at a very affordable price. Will definitely return. "
The price is SAR 458
SAR 537 total
includes taxes & fees
3 Dec - 4 Dec
The Cornell Inn, Lenox

Lakehouse Inn

4.0 star property
9.8 out of 10, Exceptional, (228)
"Excellent place and location in the Berkshires."
The price is SAR 571
SAR 669 total
includes taxes & fees
20 Dec - 21 Dec
Lakehouse Inn

Old Mill Inn

3.0 star property
9.4 out of 10, Exceptional, (464)
"While we only stayed at The Old Mill for one night we enjoyed the handsome and very comfortable room (Waterfall) and the view of the waterfall and railroad bridge and would love to come back and stay longer - and try the breakfast choices (base on the aromas coming from the tavern in the morning). The staff was pleasant and helpful. "
The price is SAR 712
SAR 795 total
includes taxes & fees
3 Dec - 4 Dec
Old Mill Inn

Naomi's Inn Bed & Breakfast

3.5 star property
9.0 out of 10, Wonderful, (373)
"My daughter and I had a great stay at Naomi's Inn B&B! From the ease of checking in, to the unique decor, to our lovely room with a big comfy bed, to the amazing breakfast, we enjoyed it all and would highly recommend staying here. "
The price is SAR 526
SAR 596 total
includes taxes & fees
28 Nov - 29 Nov
Naomi's Inn Bed & Breakfast

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (147)
"Very charming inn. The staff was very friendly and helpful."
The price is SAR 642
SAR 718 total
includes taxes & fees
8 Dec - 9 Dec
Brook Farm Inn

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (359)
"Lovely, unique property with huge rooms! Such a fun place to stay. "
The price is SAR 713
SAR 797 total
includes taxes & fees
3 Dec - 4 Dec
Chambery Inn

33 Main

4.0 star property
10.0 out of 10, Exceptional, (69)
"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! "
The price is SAR 1,314
SAR 1,468 total
includes taxes & fees
3 Dec - 4 Dec
33 Main

Whistler's Inn Bed & Breakfast

3.5 star property
7.8 out of 10, Good, (471)
"I liked that it is an older style bed and breakfast place. You could say "classy" or "vintage". It reminded me of places where I would visit with family when I was a child. I received a personal welcome and orientation to the property. Breakfast was nice and cooked options were available for me to choose. Another guest in the dining room at breakfast was also enjoying the visit and it was natural to strike up a conversation and get to know each other. It was a more personal kind of stay than...
The price is SAR 683
SAR 834 total
includes taxes & fees
8 Dec - 9 Dec
Whistler's Inn Bed & Breakfast

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (117)
"Arrived Friday to see a Tanglewood concert. Inn provided lovely afternoon cocktails and appetizers with piano music. Saturday hosts sponsored garden concert with local artists - really nice after morning hike to water fall and early afternoon golf. Yummy Morning breakfast each day. Central to Stonebridge and Lenox. Hosts very knowledgeable "
The price is SAR 1,085
SAR 1,212 total
includes taxes & fees
3 Dec - 4 Dec
Devonfield Inn B&B

Tanglewood Suites

2.5 star property
8.0 out of 10, Very Good, (15)
"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...
The price is SAR 822
SAR 822 total
includes taxes & fees
28 Nov - 29 Nov
Tanglewood Suites

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

4.5 star property
9.2 out of 10, Wonderful, (105)
"The breakfast was one of the best I have ever had. They were fast and lots of choices. It had lots of baked goods. I got the chesdar omeltte and bacon and toast plus fruits in season lime melon etc. Its a lovely place it takes you back in time. The owner is very easy going and nuce and can answer most questions"
The price is SAR 1,723
SAR 2,084 total
includes taxes & fees
3 Dec - 4 Dec
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

Daniel Stebbins House

3.0 star property
10.0 out of 10, Exceptional, (45)
"What is not to love about being welcomed into Richard and Ruth’s home. They are wonderful hosts and spent hours talking to us both during our stay. The house is an amazing building and learning about its history was wonderful. We walked into the tiny town and got some dinner, lovely options available. We can not wait to visit again and will be recommending anyone travelling around this area should certainly book a stay."
The price is SAR 1,015
SAR 1,073 total
includes taxes & fees
2 Dec - 3 Dec
Daniel Stebbins House

The Inn at Stockbridge

4.0 star property
9.8 out of 10, Exceptional, (96)
"Well-run and elegant property. "
The Inn at Stockbridge

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 SAR 3,755
SAR 4,790 total
includes taxes & fees
28 Nov - 29 Nov
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 SAR 3,755
SAR 4,790 total
includes taxes & fees
28 Nov - 29 Nov
Romantic Boutique Hotel / Bed and Breakfast - Smallest Room in The Berkshires

Harbour House Inn

3.5 star property
9.4 out of 10, Exceptional, (49)
"Lovely space and welcoming host."
The price is SAR 965
SAR 1,020 total
includes taxes & fees
5 Dec - 6 Dec
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 SAR 3,755
SAR 4,790 total
includes taxes & fees
28 Nov - 29 Nov
Romantic Boutique Hotel / B&B - Deluxe Firespa Suite

Eastgate Inn B&B

2.5 star property
9.2 out of 10, Wonderful, (68)
"Lovely Inn and Innkeeper. The room was clean and cozy. There was hot coffee and breakfast in the morning including homemade breads and fruit. We will be back! "
Eastgate Inn B&B

Romantic Boutique Hotel / Bed and Breakfast - Deluxe Schoolhouse Suite

10.0 out of 10, Exceptional, (6)
The price is SAR 3,755
SAR 4,790 total
includes taxes & fees
30 Nov - 1 Dec
Romantic Boutique Hotel / Bed and Breakfast - Deluxe Schoolhouse Suite
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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Other property types in Chester

Cozy Berkshires Vacation Rental Near Hiking!

10.0 out of 10, Exceptional, (1)
"The stay at the property was enjoyable. The space was large, spacious and very clean. Two people were able to stay quite comfortably."
Cozy Berkshires Vacation Rental Near Hiking!

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (225)
"One of the best properties i've ever stayed at "
The price is SAR 548
SAR 839 total
includes taxes & fees
2 Dec - 3 Dec
Berkshire Village Carriage House - Super Private!!

Peace and quiet on the lake

9.6 out of 10, Exceptional, (198)
"Great trip to Berkshires! Had so much fun. Great property and our dog loved the backyard. We were so happy it was fenced. "
Peace and quiet on the lake
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.
What are the best B&Bs in Chester?
Below are some well-liked B&Bs in the area: The Ellery: 17.3 mi (27.8 km) from the heart of Chester.The Cornell Inn, Lenox: 16.6 mi (26.7 km) from the downtown core. Enjoy the free full breakfast and unique décor. Lakehouse Inn: 14 rooms. 14.8 mi (23.9 km) from the heart of downtown. Enjoy the free full breakfast and deli.
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. Pyramid Lake and Jacob’s Pillow 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.