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

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

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

Exterior

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)
"Lovely people and place. Breakfast was great and so was the room. Highly recommend."
United States
FRED
$172 nightly
The price is $191
Sep 7 - Sep 8
Total with taxes and fees
The Cornell Inn, Lenox & The Berkshires
Front of property

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
$300 nightly
The price is $335
Sep 7 - Sep 8
Total with taxes and fees
Chambery Inn
Front of property - evening/night

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
$399 nightly
The price is $446
Sep 8 - Sep 9
Total with taxes and fees
Devonfield Inn B&B
Property grounds

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
$177 nightly
The price is $198
Sep 7 - Sep 8
Total with taxes and fees
Whistler's Inn Bed & Breakfast
Front of property

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
$396 nightly
The price is $442
Sep 13 - Sep 14
Total with taxes and fees
The Inn at Stockbridge
Room (Louis XIV) | Iron/ironing board (on request), WiFi (free), individually decorated

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
$105 nightly
The price is $119
Oct 1 - Oct 2
Total with taxes and fees
Naomi's Inn Bed & Breakfast
Exterior

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
$270 nightly
The price is $302
Sep 7 - Sep 8
Total with taxes and fees
Daniel Stebbins House
Suite, Private Bathroom (RedBird Suite) | View from room

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
$358 nightly
The price is $399
Sep 28 - Sep 29
Total with taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
1 bedroom, WiFi, bed sheets

9. Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
$301 nightly
The price is $345
Sep 7 - Sep 8
Total with taxes and fees
Experience Timeless Elegance in The Edith Wharton Room!
Interior

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

Cozy Carriage House room with a double bed and private balcony
Lenox
$336 nightly
The price is $385
Sep 7 - Sep 8
Total with taxes and fees
Cozy Carriage House room with a double bed and private balcony
Exterior

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
$165 nightly
The price is $184
Sep 8 - Sep 9
Total with taxes and fees
Old Mill Inn
Terrace/patio

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

Historic Susan B. Anthony Room - Cozy & Charming Stay
Lenox
$354 nightly
The price is $405
Sep 7 - Sep 8
Total with taxes and fees
Historic Susan B. Anthony Room - Cozy & Charming Stay
Interior

13. Elegant Carriage House room with a queen bed and private patio.

Elegant Carriage House room with a queen bed and private patio.
Lenox
$381 nightly
The price is $436
Sep 8 - Sep 9
Total with taxes and fees
Elegant Carriage House room with a queen bed and private patio.
3 bedrooms, bed sheets

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

Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Lenox
$301 nightly
The price is $345
Sep 7 - Sep 8
Total with taxes and fees
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
1 bedroom, bed sheets

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
$499 nightly
The price is $571
Sep 8 - Sep 9
Total with taxes and fees
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
Fireplace

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
$589 nightly
The price is $674
Sep 8 - Sep 9
Total with taxes and fees
Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
Living area

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

Elegant suite with a king bed, fireplace, and kitchenette.
Lenox
$589 nightly
The price is $674
Sep 8 - Sep 9
Total with taxes and fees
Elegant suite with a king bed, fireplace, and kitchenette.
1 bedroom, bed sheets

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

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Lenox
$536 nightly
The price is $599
Sep 13 - Sep 14
Total with taxes and fees
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Front of property

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
$265 nightly
The price is $299
Sep 17 - Sep 18
Total with taxes and fees
Brook Farm Inn
Exterior

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
$226 nightly
The price is $239
Oct 7 - Oct 8
Total with taxes and fees
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.
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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 2 hours ago
Tru by Hilton Chicopee Springfield

Find out more about Chester

Chester B&B information

Number of reviews
2,538
Accommodation
30 B&B
Lowest Price
$119
Highest Price
$674

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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