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Check prices for these dates

Next weekend
28 Nov - 30 Nov
In two weeks
5 Dec - 7 Dec
In one month
19 Dec - 21 Dec
In two months
16 Jan - 18 Jan

B&B in Chester

Room (Louis XIV) | 2 bedrooms, individually decorated, individually furnished
Naomi's Inn Bed & Breakfast

Naomi's Inn Bed & Breakfast

3.5 star property
Liberty Heights
9.0 out of 10, Wonderful, (421)
"Simple yet delicious and well executed breakfast. Perfectly cooked eggs. "
United States
Donna
The price is SAR 420
SAR 476 total
includes taxes & fees
14 Dec - 15 Dec
Naomi's Inn Bed & Breakfast
Room, River View (The Williamsburg Suite) | Private kitchen | Coffee/tea maker, cleaning supplies, paper towels
Old Mill Inn

Old Mill Inn

3.0 star property
Hatfield
9.4 out of 10, Exceptional, (499)
"Loved our stay! "
United States
Jay
The price is SAR 1,471
SAR 1,643 total
includes taxes & fees
22 Nov - 23 Nov
Old Mill Inn
Porch
Lakehouse Inn

Lakehouse Inn

4.0 star property
Lee
9.6 out of 10, Exceptional, (289)
"A charming inn in the center of the Berkshires."
United States
Danny
The price is SAR 675
SAR 792 total
includes taxes & fees
21 Nov - 22 Nov
Lakehouse Inn
Front of property
Chambery Inn

Chambery Inn

3.0 star property
Lee
9.6 out of 10, Exceptional, (372)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
Chambery Inn
Exterior
The Inn at Stockbridge

The Inn at Stockbridge

4.0 star property
Lee
9.8 out of 10, Exceptional, (98)
"Well-run and elegant property. "
United States
Steven
The price is SAR 941
SAR 1,103 total
includes taxes & fees
23 Nov - 24 Nov
The Inn at Stockbridge
Property grounds
Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast

3.5 star property
Lenox
7.8 out of 10, Good, (500)
"We had the smallest room on the property.very quaint and clean. Nicest staff great place to stay."
United States
Lisa
The price is SAR 535
SAR 597 total
includes taxes & fees
21 Nov - 22 Nov
Whistler's Inn Bed & Breakfast
3 bedrooms, bed sheets
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen

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

Lenox
The price is SAR 784
SAR 1,148 total
includes taxes & fees
21 Nov - 22 Nov
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi
33 Main

33 Main

4.0 star property
Lenox
10.0 out of 10, Exceptional, (74)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is SAR 1,491
SAR 1,665 total
includes taxes & fees
30 Nov - 1 Dec
33 Main
Front of property - evening/night
Devonfield Inn B&B

Devonfield Inn B&B

4.0 star property
Lee
10.0 out of 10, Exceptional, (133)
"The inn has an excellent location and amenities."
United States
Christopher
Devonfield Inn B&B
2 Bedrooms 1 Bath | 1 bedroom, premium bedding, iron/ironing board, free WiFi
Tanglewood Suites

Tanglewood Suites

2.5 star property
Stockbridge
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."
United States
Elizabeth
The price is SAR 821
SAR 821 total
includes taxes & fees
2 Dec - 3 Dec
Tanglewood Suites
Business center
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

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

4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (110)
"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
The price is SAR 1,432
SAR 1,733 total
includes taxes & fees
3 Dec - 4 Dec
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Front of property
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 star property
Lenox
9.0 out of 10, Wonderful, (1001)
"Overall a really fun place to stay. Rooms were good quality and the staff was welcoming and helpful."
United States
Jacob
The price is SAR 483
SAR 686 total
includes taxes & fees
25 Nov - 26 Nov
The Cornell Inn, Lenox & The Berkshires
1 bedroom, WiFi, bed sheets, wheelchair access
Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!

Lenox
The price is SAR 784
SAR 1,148 total
includes taxes & fees
21 Nov - 22 Nov
Experience Timeless Elegance in The Edith Wharton Room!
1 bedroom, WiFi, bed sheets
Elegant Carriage House room with a queen bed and private patio.

Elegant Carriage House room with a queen bed and private patio.

Lenox
The price is SAR 844
SAR 1,223 total
includes taxes & fees
21 Nov - 22 Nov
Elegant Carriage House room with a queen bed and private patio.
1 bedroom, bed sheets
Cozy Carriage House room with a double bed and private balcony

Cozy Carriage House room with a double bed and private balcony

Lenox
The price is SAR 904
SAR 1,303 total
includes taxes & fees
21 Nov - 22 Nov
Cozy Carriage House room with a double bed and private balcony
Terrace/patio
Historic Susan B. Anthony Room - Cozy & Charming Stay

Historic Susan B. Anthony Room - Cozy & Charming Stay

Lenox
The price is SAR 964
SAR 1,378 total
includes taxes & fees
23 Nov - 24 Nov
Historic Susan B. Anthony Room - Cozy & Charming Stay
Fireplace
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn

Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn

Lenox
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
1 bedroom, bed sheets
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

Lenox
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Fireplace
Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn

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

Lenox
Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
Living area
Elegant suite with a king bed, fireplace, and kitchenette.

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

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

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

10/10 Excellent
"Clean, cozy, workers are very attentive. The bar and activity center is a lot of fun. "
Paige 2-night trip
Posted 4 days ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

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. Chambery Inn: 9 rooms. 14.1 mi (22.7 km) from the downtown core. Enjoy the private yard and deli. Whistler's Inn Bed & Breakfast: 14 rooms. Situated 16.6 mi (26.7 km) from the heart of Chester. Enjoy the private yard 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. Littleville Lake 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.