Photo by Elizabeth Massa Peroulakis

Find a Bed and Breakfast in Chester from CA $155

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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Chester B&B

The Ellery
Relax in a spacious room with a large window, central seating area, and dining table.

The Ellery

3.5 star property
9.2 out of 10, Wonderful, (782)
"Wonderful breakfast and cute and cozy lobby "
The price is CA $192
CA $215 total
includes taxes & fees
Aug 17 - Aug 18
The Ellery
The Cornell Inn, Lenox & The Berkshires
Traditional two-story house with a welcoming porch and balcony, set amidst snow-covered trees.

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1001)
"Lovely place. Excellent staff, Wonderful breakfast."
The price is CA $175
CA $250 total
includes taxes & fees
Sep 1 - Sep 2
The Cornell Inn, Lenox & The Berkshires
Naomi's Inn Bed & Breakfast
Classic bedroom with a large bed, nightstands, and elegant curtains.

Naomi's Inn Bed & Breakfast

3.5 star property
9.0 out of 10, Wonderful, (406)
"We had a great stay and breakfast was delicious!"
The price is CA $155
CA $176 total
includes taxes & fees
Aug 10 - Aug 11
Naomi's Inn Bed & Breakfast
Whistler's Inn Bed & Breakfast
Stroll through the beautifully manicured lawn and discover a vibrant garden filled with lush purple flowering bushes.

Whistler's Inn Bed & Breakfast

3.5 star property
7.8 out of 10, Good, (479)
"Nice quaint out of the ordinary vacation experience. "
The price is CA $225
CA $251 total
includes taxes & fees
Aug 10 - Aug 11
Whistler's Inn Bed & Breakfast
Old Mill Inn
Enjoy cooking in this well-equipped kitchen with stainless steel appliances, white cabinetry, and a tiled backsplash.

Old Mill Inn

3.0 star property
9.4 out of 10, Exceptional, (488)
"The staff were very polite and accomodatin"
The price is CA $290
CA $324 total
includes taxes & fees
Aug 10 - Aug 11
Old Mill Inn
Lakehouse Inn
Relax on the deck with a glass of wine, taking in the serene views of the surrounding water and lush landscape.

Lakehouse Inn

4.0 star property
9.6 out of 10, Exceptional, (276)
"Great Views & Hospitality"
Lakehouse Inn
Brook Farm Inn
Relax in this inviting room with a comfortable bed, fireplace, and thoughtful amenities.

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (155)
"Maureen and her lovely staff operate a first class B&B. Thoughtful amenities and conveniences, clean and comfortable. Amazing home cooked breakfast, both plentiful and delicious. Thank you"
The price is CA $332
CA $371 total
includes taxes & fees
Sep 3 - Sep 4
Brook Farm Inn
Tanglewood Suites
Relax in this serene bedroom with a large bed, two chairs, and a small table, surrounded by lush views.

Tanglewood Suites

2.5 star property
7.8 out of 10, Good, (16)
"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. "
The price is CA $370
CA $370 total
includes taxes & fees
Aug 10 - Aug 11
Tanglewood Suites
33 Main
Features a sleek glass-enclosed shower, vanity with sink and mirror, toilet, and bidet.

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! "
33 Main
Daniel Stebbins House
A charming two-story home with a green door and picket fence, surrounded by a beautifully manicured lawn and flowering bushes.

Daniel Stebbins House

3.0 star property
10.0 out of 10, Exceptional, (46)
"Beautiful home that provided a relaxed, comfortable stay. If we are in the area again we would definitely return."
The price is CA $371
CA $415 total
includes taxes & fees
Aug 10 - Aug 11
Daniel Stebbins House
Chambery Inn
Chambery Inn features a traditional two-story building with a pitched roof and multiple windows.

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. "
The price is CA $309
CA $345 total
includes taxes & fees
Aug 11 - Aug 12
Chambery Inn
Harbour House Inn
Stunning traditional architecture with a central entrance and beautifully landscaped surroundings.

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!! "
The price is CA $324
CA $343 total
includes taxes & fees
Aug 14 - Aug 15
Harbour House Inn
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Enjoy meals in this inviting dining room with a large table, comfortable chairs, and ample natural light.

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 "
The price is CA $539
CA $652 total
includes taxes & fees
Aug 25 - Aug 26
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
The Inn at Stockbridge
Stroll through the serene park and enjoy the soothing sounds of the multi-tiered fountain surrounded by lush trees and a shaded walkway.

The Inn at Stockbridge

4.0 star property
9.8 out of 10, Exceptional, (98)
"Well-run and elegant property. "
The Inn at Stockbridge
Devonfield Inn B&B
Stunning two-story house with a central entrance and beautifully manicured lawn.

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (128)
"Very enjoyable comfortable stay"
The price is CA $382
CA $427 total
includes taxes & fees
Sep 2 - Sep 3
Devonfield Inn B&B
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Cozy retreat with a dresser, comfortable bed, and a warm throw blanket.

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

The price is CA $285
CA $410 total
includes taxes & fees
Sep 1 - Sep 2
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Eastgate Inn B&B
Relax in a cozy outdoor space with wicker chairs and a small table.

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
Enjoy a serene view of the lush garden from the comfort of your room.

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
Elegant suite with a king bed, fireplace, and kitchenette.
Relax in this stylish living room with a large coffee table, two sofas, and a fireplace.

Elegant suite with a king bed, fireplace, and kitchenette.

The price is CA $560
CA $759 total
includes taxes & fees
Sep 1 - Sep 2
Elegant suite with a king bed, fireplace, and kitchenette.
Chesapeake Inn of Lenox
Sit and enjoy conversation or dining in this serene outdoor space surrounded by lush greenery.

Chesapeake Inn of Lenox

3.0 star property
7.4 out of 10, Good, (8)
"Very convenient location to arts / outdoors events in Lenox area. Available for one night stay, last minute booking. Host very responsive"
Chesapeake Inn of Lenox
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 Chester Hotel Reviews

D. Hotel Suites & Spa

D. Hotel Suites & Spa

10/10 Excellent
"Clean, comfortable beds and fun live music at the restaurant attached"
Ashley 1-night trip
Posted 2 days ago
D. Hotel Suites & Spa