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Next weekend
10 Oct - 12 Oct
In two weeks
17 Oct - 19 Oct
In one month
31 Oct - 2 Nov
In two months
28 Nov - 30 Nov

B&B in Chester

The Cornell Inn, Lenox & The Berkshires
Front of property

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1002)
"We have stayed at the Cornell Inn in the past. Always a comfortable, convenient and friendly stay. The food, staff and accommodations are perfect."
The price is SAR 479
SAR 681 total
includes taxes & fees
28 Oct - 29 Oct
The Cornell Inn, Lenox & The Berkshires
Naomi's Inn Bed & Breakfast
Room (Louis XIV) | 2 bedrooms, individually decorated, individually furnished

Naomi's Inn Bed & Breakfast

3.5 star property
9.0 out of 10, Wonderful, (416)
"Great host and breakfast was excellent."
The price is SAR 431
SAR 489 total
includes taxes & fees
7 Oct - 8 Oct
Naomi's Inn Bed & Breakfast
Whistler's Inn Bed & Breakfast
Property grounds

Whistler's Inn Bed & Breakfast

3.5 star property
7.8 out of 10, Good, (493)
"This family owned Inn is absolutely charming and the owners are so nice! I will definitely stay here again when I visit the Berkshires."
The price is SAR 535
SAR 597 total
includes taxes & fees
2 Nov - 3 Nov
Whistler's Inn Bed & Breakfast
Old Mill Inn
Room, River View (The Williamsburg Suite) | Private kitchen | Coffee/tea maker, cleaning supplies, paper towels

Old Mill Inn

3.0 star property
9.4 out of 10, Exceptional, (497)
"Loved our stay! "
The price is SAR 2,010
SAR 2,246 total
includes taxes & fees
3 Oct - 4 Oct
Old Mill Inn
Daniel Stebbins House
Exterior

Daniel Stebbins House

3.0 star property
10.0 out of 10, Exceptional, (47)
"The area is lovely and this building is full of history but they have managed to fit modern air-conditioning into this 226 year old building. "
The price is SAR 1,013
SAR 1,132 total
includes taxes & fees
7 Oct - 8 Oct
Daniel Stebbins House
Tanglewood Suites
2 Bedrooms 1 Bath | 1 bedroom, premium bedding, iron/ironing board, free WiFi

Tanglewood Suites

2.5 star property
6.4 out of 10, (22)
"NOT A REAL LOCATION. There was nothing there. Neighbors said this was a scam. Expedia ended up helping us find a local hotel room though the location was not as good. DO NOT BOOK THIS LOCATION -- it needs to be taken off the website."
Tanglewood Suites
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (369)
"ease of late check in. Super comfortable room."
Chambery Inn
Brook Farm Inn
Loft, Private Bathroom (Skylight Loft) | 1 bedroom, premium bedding, iron/ironing board, rollaway beds

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (161)
"Inn was gorgeous and staff exceptional!"
Brook Farm Inn
Lakehouse Inn
Porch

Lakehouse Inn

4.0 star property
9.6 out of 10, Exceptional, (283)
"Lovely location on a lake, quiet, simple, clean rooms, great breakfast included. "
The price is SAR 576
SAR 676 total
includes taxes & fees
2 Nov - 3 Nov
Lakehouse Inn
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Business center

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 SAR 1,161
SAR 1,404 total
includes taxes & fees
27 Oct - 28 Oct
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Harbour House Inn
Exterior

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!! "
The price is SAR 905
SAR 957 total
includes taxes & fees
29 Oct - 30 Oct
Harbour House Inn
Devonfield Inn B&B
Front of property - evening/night

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (129)
"The inn has an excellent location and amenities."
Devonfield Inn B&B
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
3 bedrooms, bed sheets

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

The price is SAR 778
SAR 1,120 total
includes taxes & fees
28 Oct - 29 Oct
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
33 Main
Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi

33 Main

4.0 star property
10.0 out of 10, Exceptional, (71)
"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 1,650
SAR 1,843 total
includes taxes & fees
2 Nov - 3 Nov
33 Main
Eastgate Inn B&B
Porch

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 Inn at Stockbridge
Exterior

The Inn at Stockbridge

4.0 star property
9.8 out of 10, Exceptional, (98)
"Well-run and elegant property. "
The price is SAR 1,387
SAR 1,627 total
includes taxes & fees
2 Nov - 3 Nov
The Inn at Stockbridge
The Red Door B&B
Interior

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
Historic Susan B. Anthony Room - Cozy & Charming Stay
Terrace/patio

Historic Susan B. Anthony Room - Cozy & Charming Stay

The price is SAR 958
SAR 1,342 total
includes taxes & fees
28 Oct - 29 Oct
Historic Susan B. Anthony Room - Cozy & Charming Stay
Cozy Carriage House room with a double bed and private balcony
1 bedroom, bed sheets

Cozy Carriage House room with a double bed and private balcony

The price is SAR 898
SAR 1,267 total
includes taxes & fees
28 Oct - 29 Oct
Cozy Carriage House room with a double bed and private balcony
Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
Fireplace

Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn

The price is SAR 1,528
SAR 2,096 total
includes taxes & fees
9 Oct - 10 Oct
Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
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

La Quinta Inn & Suites by Wyndham Springfield MA

La Quinta Inn & Suites by Wyndham Springfield MA

10/10 Excellent
"All that was needed is a Hot tub for these elderly bones and raise the temperature in the pool "
Frederick 1-night trip
Posted 1 day ago
La Quinta Inn & Suites by Wyndham Springfield MA

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 Cornell Inn, Lenox & The Berkshires: 16.6 mi (26.7 km) from the heart of Chester. Enjoy the free full breakfast and unique décor. Lakehouse Inn: 14 rooms. 14.8 mi (23.9 km) from the downtown core. Enjoy the free full breakfast and deli. Chambery Inn: 9 rooms. Situated 14.1 mi (22.7 km) from the heart of Chester. Enjoy the private yard and deli. Brook Farm Inn: 15 rooms. Located 16.7 mi (26.8 km) from the core of Chester. Enjoy the free cooked breakfast and outdoor pool.
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. Glendale Falls and Pyramid Lake 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.