A snow-covered forest with a narrow stream running through it.

Find a Bed and Breakfast in Chester from CA $165

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Sep 11 - Sep 13
In two weeks
Sep 18 - Sep 20
In one month
Oct 2 - Oct 4
In two months
Oct 30 - Nov 1

Our top choices for Chester bed & breakfast

A snow-covered outdoor area with a patio, seating, and a covered dining area.

1. 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)
"The entire staff was amazing and the inn was beautiful, we will definitely be back"
United States
Edward
The price is CA $228
CA $261 total
includes taxes & fees
Sep 7 - Sep 8
The Cornell Inn, Lenox & The Berkshires
A two-story building with a sign reading "Chambéry Inn".

2. Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (387 reviews)
"An absolutely perfect getaway spot! Beautiful rooms, great service, and an ideal location. Highly recommend and we will be going back."
United States
Alexandra
The price is CA $374
CA $417 total
includes taxes & fees
Sep 7 - Sep 8
Chambery Inn
A large, two-story house with a well-maintained lawn and a fence.

3. Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (140 reviews)
"Excellent food and helpful staff"
United States
Richard
The price is CA $552
CA $617 total
includes taxes & fees
Sep 8 - Sep 9
Devonfield Inn B&B
A garden with a white gazebo, a brick pathway, and various plants and flowers.

4. Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very good, (517 reviews)
"Whistler's Inn is a Gilded Era mansion, passed down in the family (modernised "
United States
Mary Anna
The price is CA $245
CA $274 total
includes taxes & fees
Sep 7 - Sep 8
Whistler's Inn Bed & Breakfast

5. The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.8 out of 10, Exceptional, (106 reviews)
"Lovely grounds, property.. room was lovely. Delicious breakfast friendly helpful owners and staff great location"
United States
Jodi
The price is CA $522
CA $612 total
includes taxes & fees
Sep 13 - Sep 14
The Inn at Stockbridge
A bedroom with a bed, a nightstand, a lamp, and a window with curtains.

6. Naomi's Inn Bed & Breakfast

Naomi's Inn Bed & Breakfast
3.5 star property
Liberty Heights
9.0 out of 10, Wonderful, (452 reviews)
"Good stay"
United States
Susan
The price is CA $145
CA $165 total
includes taxes & fees
Oct 1 - Oct 2
Naomi's Inn Bed & Breakfast
A two-story white house with a green door, white picket fence, and white flowering bushes.

7. Daniel Stebbins House

Daniel Stebbins House
3.0 star property
South Hadley
10.0 out of 10, Exceptional, (55 reviews)
"Great set up and perfect for visiting Mt Holyoke"
United States
David
The price is CA $374
CA $418 total
includes taxes & fees
Sep 7 - Sep 8
Daniel Stebbins House
A two-story house with a brick entrance and a white facade.

8. 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, (116 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."
United States
Philippe
The price is CA $457
CA $553 total
includes taxes & fees
Sep 28 - Sep 29
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
A neatly made bed with a headboard, a bedside lamp, a framed painting, and a small bedside table with a tissue box.

9. Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
The price is CA $364
CA $477 total
includes taxes & fees
Sep 7 - Sep 8
Experience Timeless Elegance in The Edith Wharton Room!
A porch with a white railing, a potted plant, and a view of a garden.

10. 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 $409
CA $534 total
includes taxes & fees
Sep 7 - Sep 8
Cozy Carriage House room with a double bed and private balcony
A view of a red building by a waterway through a window.

11. Old Mill Inn

Old Mill Inn
3.0 star property
Hatfield
9.4 out of 10, Exceptional, (536 reviews)
"Great stay from beginning to end!"
United States
Sarah
The price is CA $257
CA $287 total
includes taxes & fees
Sep 20 - Sep 21
Old Mill Inn
A wooden deck with Adirondack chairs and a small table, leading to a garden area with a swing set.

12. Historic Susan B. Anthony Room - Cozy & Charming Stay

Historic Susan B. Anthony Room - Cozy & Charming Stay
Lenox
The price is CA $431
CA $564 total
includes taxes & fees
Sep 7 - Sep 8
Historic Susan B. Anthony Room - Cozy & Charming Stay
A room with a dark green sofa, a small table with a vase of flowers, a desk with a lamp, and a window with curtains.

13. 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 $464
CA $600 total
includes taxes & fees
Sep 8 - Sep 9
Elegant Carriage House room with a queen bed and private patio.
A well-appointed bedroom with a large bed, a bedside table, a chair, and a bathroom visible through an open door.

14. 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 $364
CA $477 total
includes taxes & fees
Sep 7 - Sep 8
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
A bedroom with a bed, a fireplace, a ceiling fan, and a door.

15. 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 $608
CA $787 total
includes taxes & fees
Sep 8 - Sep 9
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
A modern living room with a sloped ceiling, a sofa, a coffee table, and a unique chandelier.

16. 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 $719
CA $928 total
includes taxes & fees
Sep 8 - Sep 9
Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
A modern living room with a sofa, a coffee table, and a fireplace.

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

Elegant suite with a king bed, fireplace, and kitchenette.
Lenox
The price is CA $719
CA $928 total
includes taxes & fees
Sep 8 - Sep 9
Elegant suite with a king bed, fireplace, and kitchenette.
A bedroom with a bed, a television, a fireplace, and a window.

18. "Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Lenox
The price is CA $652
CA $832 total
includes taxes & fees
Sep 13 - Sep 14
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.

19. Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (173 reviews)
"Breakfast was not only delicious, the room was sweet and bright and staff very attentive."
United States
Carrie
The price is CA $348
CA $400 total
includes taxes & fees
Sep 17 - Sep 18
Brook Farm Inn
A large, two-story building with a symmetrical facade, multiple windows, and a central entrance with a covered porch.

20. Harbour House Inn

Harbour House Inn
3.5 star property
Cheshire
9.4 out of 10, Exceptional, (56 reviews)
"Nice place for a weekend away."
United States
Gregory
The price is CA $319
CA $338 total
includes taxes & fees
Sep 8 - Sep 9
Harbour House 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chester Hotel Reviews

Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield

10/10 Excellent
"Great stay, breakfast was ok, busy week loud neighbor. But great place"
Shirlie 3-night trip
Posted 1 hour ago
Tru by Hilton Chicopee Springfield

Find out more about Chester

Chester B&B information

Number of reviews
2,538
Accommodation
29 B&B
Lowest Price
CA $165
Highest Price
CA $928

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. Whistler's Inn Bed & Breakfast: 14 rooms. 16.6 mi (26.7 km) from the heart of downtown. Enjoy the private yard and unique décor.
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. Becket Land Trust Historic Quarry and Jacob's Pillow 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.

Explore a world of travel with Expedia