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    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Oct 9 - Oct 11
In two weeks
Oct 16 - Oct 18
In one month
Oct 30 - Nov 1
In two months
Nov 27 - Nov 29

Our top choices for Chester bed & breakfast

A wooden deck with a table and chairs, surrounded by a metal railing, overlooking a lush green landscape with trees.

1. The Red Door B&B

The Red Door B&B
3.0 star property
Lee
10.0 out of 10, Exceptional, (5 reviews)
"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."
United States
Anonymous traveler
$237 nightly
The price is $265
Oct 26 - Oct 27
Total with taxes and fees
The Red Door B&B
A snow-covered outdoor area with a patio, seating, and a covered dining area.

2. 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)
"Convenient location for Tanglewood and other Berkshire sights. Nice complimentary breakfast and arrival cocktail."
United States
Rosann
$160 nightly
The price is $179
Oct 27 - Oct 28
Total with taxes and fees
The Cornell Inn, Lenox & The Berkshires
A two-story building with a sign reading "Chambéry Inn".

3. Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (388 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
$297 nightly
The price is $332
Nov 4 - Nov 5
Total with taxes and fees
Chambery Inn
A large, two-story house with a well-maintained lawn and a fence.

4. Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (141 reviews)
"Wonderful location and hosts are amazing. Breakfast was great. Clean."
United States
Sebastien
$369 nightly
The price is $412
Nov 2 - Nov 3
Total with taxes and fees
Devonfield Inn B&B
A bedroom with a bed, a nightstand, a lamp, and a window with curtains.

5. Naomi's Inn Bed & Breakfast

Naomi's Inn Bed & Breakfast
3.5 star property
Liberty Heights
9.0 out of 10, Wonderful, (461 reviews)
"Love the spirit and enthusiasm of the owner. Breakfast was superb! Highly recommend you stay here."
United States
Peter
$105 nightly
The price is $119
Oct 5 - Oct 6
Total with taxes and fees
Naomi's Inn Bed & Breakfast
A garden with a white gazebo, a brick pathway, and various plants and flowers.

6. Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very good, (519 reviews)
"Whistler's Inn is a Gilded Era mansion, passed down in the family (modernised "
United States
Mary Anna
$160 nightly
The price is $179
Oct 5 - Oct 6
Total with taxes and fees
Whistler's Inn Bed & Breakfast
Front of property

7. The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.6 out of 10, Exceptional, (107 reviews)
"Lovely grounds, property.. room was lovely. Delicious breakfast friendly helpful owners and staff great location"
United States
Jodi
$383 nightly
The price is $428
Nov 1 - Nov 2
Total with taxes and fees
The Inn at Stockbridge
A neatly made bed with a headboard, a bedside lamp, a framed painting, and a small bedside table with a tissue box.

8. Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
$281 nightly
The price is $322
Oct 27 - Oct 28
Total with taxes and fees
Experience Timeless Elegance in The Edith Wharton Room!
A two-story house with a brick entrance and a white facade.

9. 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, (119 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."
United States
Philippe
$401 nightly
The price is $448
Nov 4 - Nov 5
Total with taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
A two-story white house with a green door, white picket fence, and white flowering bushes.

10. Daniel Stebbins House

Daniel Stebbins House
3.0 star property
South Hadley
10.0 out of 10, Exceptional, (56 reviews)
"Great set up and perfect for visiting Mt Holyoke"
United States
David
$270 nightly
The price is $302
Oct 5 - Oct 6
Total with taxes and fees
Daniel Stebbins House
A well-appointed bedroom with a large bed, a bedside table, a chair, and a bathroom visible through an open door.

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

Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Lenox
$281 nightly
The price is $322
Oct 27 - Oct 28
Total with taxes and fees
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
A view of a red building by a waterway through a window.

12. Old Mill Inn

Old Mill Inn
3.0 star property
Hatfield
9.4 out of 10, Exceptional, (539 reviews)
"Very easy check in and check out. Really quiet peaceful area. Overall great experience"
United States
John
$179 nightly
The price is $200
Oct 6 - Oct 7
Total with taxes and fees
Old Mill Inn
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
$326 nightly
The price is $373
Nov 4 - Nov 5
Total with taxes and fees
Elegant Carriage House room with a queen bed and private patio.
A porch with a white railing, a potted plant, and a view of a garden.

14. Cozy Carriage House room with a double bed and private balcony

Cozy Carriage House room with a double bed and private balcony
Lenox
$344 nightly
The price is $394
Nov 1 - Nov 2
Total with taxes and fees
Cozy Carriage House room with a double bed and private balcony
A wooden deck with Adirondack chairs and a small table, leading to a garden area with a swing set.

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

Historic Susan B. Anthony Room - Cozy & Charming Stay
Lenox
$362 nightly
The price is $414
Nov 1 - Nov 2
Total with taxes and fees
Historic Susan B. Anthony Room - Cozy & Charming Stay
A modern living room with a sofa, a coffee table, and a fireplace.

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

Elegant suite with a king bed, fireplace, and kitchenette.
Lenox
$534 nightly
The price is $611
Nov 1 - Nov 2
Total with taxes and fees
Elegant suite with a king bed, fireplace, and kitchenette.
A bedroom with a bed, a television, a fireplace, and a window.

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

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Lenox
$479 nightly
The price is $535
Nov 1 - Nov 2
Total with taxes and fees
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
A bedroom with a bed, a fireplace, a ceiling fan, and a door.

18. 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
$447 nightly
The price is $511
Nov 1 - Nov 2
Total with taxes and fees
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.

19. 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
$534 nightly
The price is $611
Nov 1 - Nov 2
Total with taxes and fees
Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.

20. Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (174 reviews)
"Breakfast was not only delicious, the room was sweet and bright and staff very attentive."
United States
Carrie
$209 nightly
The price is $237
Nov 2 - Nov 3
Total with taxes and fees
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

Quality Inn West Springfield

Quality Inn West Springfield

8/10 Good
"A great place to stay if you are going to The Big E."
Thomas 1-night trip
Posted 2 hours ago
Quality Inn West Springfield

Find out more about Chester

Chester B&B information

Number of reviews
1,871
Accommodation
30 B&B
Lowest Price
$119
Highest Price
$611

Frequently asked questions

What is the nightly rate for a B&B in Chester?
Prices for B&Bs in Chester often vary, but you can find a great deal from $119 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Chester B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a B&B in Chester?
The best time to book a B&B in Chester is during the summer months, particularly from June to August. This vibrant season attracts visitors eager to enjoy the picturesque lakes, hiking trails, and outdoor activities that Chester has to offer. With warm weather and long daylight hours, it's an ideal time for families and adventure seekers to explore the natural beauty of the area.

July stands out as the peak month, bringing a lively atmosphere filled with community events, festivals, and a bustling local scene. Travelers can partake in activities such as kayaking on Lake Almanor or hiking in the nearby Lassen National Forest, all while basking in pleasant temperatures that typically range from the mid-60s to high 80s Fahrenheit.

If you're looking for a more budget-friendly option, consider visiting in September. This transitional month allows you to enjoy milder weather and fewer crowds, making it great for a peaceful getaway. You can still experience the stunning scenery, with early fall colors beginning to emerge, creating an enchanting backdrop for outdoor adventures.
What is the difference between a Chester B&B and a hotel?
Every Chester B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Chester B&Bs.

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