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Check prices for these dates

Next weekend
5 Sept - 7 Sept
In two weeks
12 Sept - 14 Sept
In one month
26 Sept - 28 Sept
In two months
24 Oct - 26 Oct

Featured B&B in Chester

Our top choices for Chester bed & breakfast

The Ellery
Lobby

The Ellery

3.5 star property
9.2 out of 10, Wonderful, (797)
"An absolutely lovely, quiet, comfortable, adorable hotel, complete with good breakfast!"
The price is AU$269
includes taxes & fees
16 Sept - 17 Sept
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, (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 AU$280
includes taxes & fees
1 Sept - 2 Sept
The Cornell Inn, Lenox & The Berkshires
Naomi's Inn Bed & Breakfast
Room (Louis XIV)

Naomi's Inn Bed & Breakfast

3.5 star property
9.0 out of 10, Wonderful, (409)
"We had a great stay and breakfast was delicious!"
The price is AU$248
includes taxes & fees
28 Aug - 29 Aug
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, (482)
"Nice quaint out of the ordinary vacation experience. "
The price is AU$298
includes taxes & fees
8 Sept - 9 Sept
Whistler's Inn Bed & Breakfast
Old Mill Inn
Room, River View (The Williamsburg Suite) | Private kitchen

Old Mill Inn

3.0 star property
9.4 out of 10, Exceptional, (492)
"Very comfortable with excellent service from the staff and owners. Quiet and out of the way yet not far from Amherst and Northampton. Would definitely recommend it and would stay there again."
The price is AU$816
includes taxes & fees
12 Sept - 13 Sept
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 AU$465
includes taxes & fees
7 Sept - 8 Sept
Daniel Stebbins House
Brook Farm Inn
Loft, Private Bathroom (Skylight Loft)

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (159)
"Inn was gorgeous and staff exceptional!"
Brook Farm Inn
Tanglewood Suites
2 Bedrooms 1 Bath

Tanglewood Suites

2.5 star property
7.2 out of 10, Good, (19)
"The owner did not honor our confirmed Expedia reservation, so we had to find a hotel at the last minute. She made up various excuses and was very rude."
The price is AU$414
includes taxes & fees
28 Aug - 29 Aug
Tanglewood Suites
Lakehouse Inn
Porch

Lakehouse Inn

4.0 star property
9.6 out of 10, Exceptional, (277)
"Great Views & Hospitality"
Lakehouse Inn
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
Harbour House Inn
Exterior

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 AU$384
includes taxes & fees
11 Sept - 12 Sept
Harbour House Inn
33 Main
Luxury Room, 1 King Bed, Bathtub

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! "
The price is AU$970
includes taxes & fees
2 Sept - 3 Sept
33 Main
Devonfield Inn B&B
Front of property - evening/night

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (128)
"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 AU$576
includes taxes & fees
10 Sept - 11 Sept
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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 AU$474
includes taxes & fees
1 Sept - 2 Sept
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
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 AU$806
includes taxes & fees
1 Sept - 2 Sept
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
Elegant suite with a king bed, fireplace, and kitchenette.
Living area

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

The price is AU$860
includes taxes & fees
1 Sept - 2 Sept
Elegant suite with a king bed, fireplace, and kitchenette.
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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Top Chester Hotel Reviews

The Ellery

The Ellery

10/10 Excellent
"The check in woman was very pleasant and nice and helpful "
Joel 1-night trip
Posted 1 day ago
The Ellery

Find out more about Chester

Find out more about Chester

Chester B&B information

Number of reviews
3,796
Accommodation
18 B&B
Lowest Price
AU$248
Highest Price
AU$970

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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. Chambery Inn: 9 rooms. Situated 14.1 mi (22.7 km) from the heart of Chester. Enjoy the private garden and snack bar/deli. Tanglewood Suites: 2 rooms. 17.5 mi (28.2 km) from the city centre. Whistler's Inn Bed & Breakfast: 14 rooms. Located 16.6 mi (26.7 km) from the core of Chester. Enjoy the private garden and unique decor.
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 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?
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.