Find a Bed and Breakfast in Chester from CA $185

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Check prices for these dates

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

Our top choices for Chester bed & breakfast

Room (Louis XIV)

Naomi's Inn Bed & Breakfast

Naomi's Inn Bed & Breakfast
3.5 star property
Liberty Heights
9.0 out of 10, Wonderful, (442 reviews)
"He room was very clean, the staff was engaging and the breakfast was delicious. "
United States
John
The price is CA $163
CA $185 total
includes taxes & fees
May 31 - Jun 1
Naomi's Inn Bed & Breakfast
Exterior

Daniel Stebbins House

Daniel Stebbins House
3.0 star property
South Hadley
10.0 out of 10, Exceptional, (52 reviews)
"Daniel Stebbins House was wonderful. Beautiful rooms. Next to downtown. Enjoyable breakfast. Fabulous experience!"
United States
Holly
The price is CA $373
CA $416 total
includes taxes & fees
Jun 14 - Jun 15
Daniel Stebbins House
Exterior

Old Mill Inn

Old Mill Inn
3.0 star property
Hatfield
9.4 out of 10, Exceptional, (508 reviews)
"Nice, quiet, new furnishings, continental breakfast was very fresh, staff is friendly. "
United States
Jeffrey
The price is CA $231
CA $258 total
includes taxes & fees
May 31 - Jun 1
Old Mill Inn
Front of property

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (377 reviews)
"Yes the room was spotless and always the staff is ready to answer any questions that we might have. We have been enjoying the Chambery Inn for many years always had a great stay and again looking for our next visit. Vincent Farricielli and Roibert Modena. "
United States
robert
The price is CA $236
CA $263 total
includes taxes & fees
Jun 7 - Jun 8
Chambery Inn
Front of property - evening/night

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (138 reviews)
"Room was great, staff was awesome, amenities were cool"
United States
Francis
The price is CA $453
CA $507 total
includes taxes & fees
May 31 - Jun 1
Devonfield Inn B&B
Suite, Private Bathroom (RedBird Suite) | View from room

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, (111 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
The price is CA $455
CA $551 total
includes taxes & fees
Jun 15 - Jun 16
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Property grounds

Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very good, (501 reviews)
"This family owned Inn is absolutely charming and the owners are so nice! I will definitely stay here again when I visit the Berkshires."
United States
Stacey
The price is CA $366
CA $409 total
includes taxes & fees
May 31 - Jun 1
Whistler's Inn Bed & Breakfast
Luxury Room, 1 King Bed, Bathtub

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (74 reviews)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is CA $809
CA $903 total
includes taxes & fees
May 31 - Jun 1
33 Main
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 CA $363
CA $473 total
includes taxes & fees
Jun 15 - Jun 16
Experience Timeless Elegance in The Edith Wharton Room!
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 CA $341
CA $443 total
includes taxes & fees
Jun 7 - Jun 8
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Interior

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 CA $430
CA $559 total
includes taxes & fees
Jun 14 - Jun 15
Elegant Carriage House room with a queen bed and private patio.
Interior

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 CA $407
CA $530 total
includes taxes & fees
May 31 - Jun 1
Cozy Carriage House room with a double bed and private balcony
Exterior

Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is CA $322
CA $340 total
includes taxes & fees
Jun 2 - Jun 3
Harbour House Inn
Terrace/patio

Historic Susan B. Anthony Room - Cozy & Charming Stay

Historic Susan B. Anthony Room - Cozy & Charming Stay
Lenox
The price is CA $429
CA $559 total
includes taxes & fees
May 31 - Jun 1
Historic Susan B. Anthony Room - Cozy & Charming Stay
1 bedroom, bed sheets

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Lenox
The price is CA $617
CA $784 total
includes taxes & fees
Jun 1 - Jun 2
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
1 bedroom, bed sheets

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
The price is CA $528
CA $688 total
includes taxes & fees
May 31 - Jun 1
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
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
The price is CA $639
CA $831 total
includes taxes & fees
May 31 - Jun 1
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
The price is CA $639
CA $831 total
includes taxes & fees
May 31 - Jun 1
Elegant suite with a king bed, fireplace, and kitchenette.
Exterior

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,001 reviews)
"Great place, nice amenities and convenient location, highly recommended."
United States
Arthur
The price is CA $223
CA $257 total
includes taxes & fees
Jun 11 - Jun 12
The Cornell Inn, Lenox & The Berkshires
Front of property

Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (164 reviews)
"Everything was perfect - location and accommodation."
United States
Christopher
The price is CA $253
CA $293 total
includes taxes & fees
Jun 2 - Jun 3
Brook Farm 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

Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield

8/10 Good
"Night bangs outside room"
Tamara 2-night trip
Posted 1 hour ago
Tru by Hilton Chicopee Springfield

Find out more about Chester

Chester B&B information

Number of reviews
2,809
Accommodation
30 B&B
Lowest Price
CA $185
Highest Price
CA $903

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?
Here are some well-liked B&Bs in the surrounding 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 heart of downtown. 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.

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