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Check prices for these dates

Next weekend
4 Jul - 6 Jul
In two weeks
11 Jul - 13 Jul
In one month
25 Jul - 27 Jul
In two months
22 Aug - 24 Aug

Browse Select Chester B&B

The Ellery
Lobby

The Ellery

3.5 star property
9.0 out of 10, Wonderful, (724)
"It’s a great place to stay and we like the breakfast! "
The price is ₹12,828
₹14,328 total
includes taxes & fees
13 Jul - 14 Jul
The Ellery
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, (1001)
"Breakfast each day was phenomenal, staff were all so friendly, hotel & room were beautifully decorated. We had a wonderful time & would stay here again!"
The price is ₹11,089
₹15,752 total
includes taxes & fees
30 Jun - 1 Jul
The Cornell Inn, Lenox & The Berkshires
Tanglewood Suites
2 Bedrooms 1 Bath | 1 bedroom, premium bedding, iron/ironing board, free WiFi

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. "
The price is ₹23,127
₹23,127 total
includes taxes & fees
1 Jul - 2 Jul
Tanglewood Suites
Lakehouse Inn
Aerial view

Lakehouse Inn

4.0 star property
9.6 out of 10, Exceptional, (266)
"Really peaceful and serene property due to the lake. The house was clean and the staff were friendly. "
The price is ₹21,609
₹25,344 total
includes taxes & fees
2 Jul - 3 Jul
Lakehouse Inn
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, (394)
"Gorgeous room and decadent breakfast. I loved my stay."
The price is ₹9,715
₹11,022 total
includes taxes & fees
1 Jul - 2 Jul
Naomi'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, (483)
"Quiet and very relaxing, making it a great and enjoyable stay! "
The price is ₹34,931
₹39,018 total
includes taxes & fees
16 Jul - 17 Jul
Old Mill Inn
Whistler's Inn Bed & Breakfast
Property grounds

Whistler's Inn Bed & Breakfast

3.5 star property
7.8 out of 10, Good, (473)
"Such a beautiful and historic property - like stepping into the Gilded Age! We stayed three nights and are most grateful we did. The owners/staff are top-notch and completely accomodating. We would happily return!"
The price is ₹13,997
₹17,269 total
includes taxes & fees
29 Jun - 30 Jun
Whistler's Inn Bed & Breakfast
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (365)
"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. "
Chambery Inn
Brook Farm Inn
Front of property

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (152)
"This is a charming and very pleasant place to stay."
Brook Farm Inn
Devonfield Inn B&B
Front of property – evening/night

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (127)
"Very enjoyable comfortable stay"
Devonfield Inn B&B
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Business centre

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 ₹39,504
₹47,788 total
includes taxes & fees
14 Jul - 15 Jul
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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, (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
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 Inn at Stockbridge
Harbour House Inn
Exterior

Harbour House Inn

3.5 star property
9.4 out of 10, Exceptional, (49)
"Nice place for a weekend away."
The price is ₹20,098
₹21,244 total
includes taxes & fees
1 Jul - 2 Jul
Harbour House Inn
Daniel Stebbins House
Exterior

Daniel Stebbins House

3.0 star property
10.0 out of 10, Exceptional, (45)
"Beautiful home that provided a relaxed, comfortable stay. If we are in the area again we would definitely return."
The price is ₹23,267
₹25,989 total
includes taxes & fees
29 Jun - 30 Jun
Daniel Stebbins House
Eastgate Inn B&B
Porch

Eastgate Inn B&B

2.5 star property
9.2 out of 10, Wonderful, (68)
"Great host and enjoyable stay."
Eastgate Inn B&B
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
Chesapeake Inn of Lenox
Property grounds

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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Frequently asked questions

Searching for B&Bs in Chester?
If you're looking for something a little more offbeat than your standard hotel, a stay at a bed and breakfast could be the perfect alternative for your holiday. While you're enjoying your trip to Chester, you might want to explore the theatre scene by watching 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 beautiful breakfast room, the quaint details are what make bed and breakfasts a fun place to get away.
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 & The Berkshires: 16.6 mi (26.7 km) from the city centre. Enjoy the free full breakfast and unique decor. Tanglewood Suites: 2 rooms. Situated 17.5 mi (28.2 km) from the heart of Chester. Lakehouse Inn: 14 rooms. Located 14.8 mi (23.9 km) from the core of Chester. Enjoy the free full breakfast and snack bar/deli.
What's the best time of year to 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 temperature of 19°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Chester are January, February, November and March, with each month seeing an average of 15 cm of snowfall.
What is there to do in Chester?
If you want to see some popular attractions in Chester, you might enjoy a visit to Chester Town Hall. Glendale Falls and Iroquis Waterfront are also some sites to visit if you want to see more of the area.
How can I get to and around Chester?
Mapping out your trip in and around Chester is easy with these transportation options. Fly into Westfield, MA (BAF-Barnes Municipal), which is located 15.4 mi (24.7 km) away from the city centre. 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, you may want to rent a car for your trip.