A city street with buildings, parked cars, and solar panels.

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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 Chatham bed & breakfast

Aerial view

1. Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (115 reviews)
"Very nice hotel."
United States
Erdem
$189 nightly
The price is $212
Sep 3 - Sep 4
Total with taxes and fees
Inn at Silver Maple Farm
Garden

2. Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (471 reviews)
"Wonderful place to stay!"
United States
Mervin
$157 nightly
The price is $172
Sep 8 - Sep 9
Total with taxes and fees
Shaker Mill Inn
Suite, Private Bathroom (RedBird Suite) | View from room

3. 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
Desk, laptop workspace, iron/ironing board (on request), WiFi (free)

4. Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (105 reviews)
"Beautiful home with warm and friendly hosts. The rooms were tastefully designed, the bed was very comfortable and the large bathroom was luxurious. The breakfast was absolutely delicious. We will definitely stay again next time we are in Great Barrington. "
United States
Nicole
$275 nightly
The price is $307
Sep 3 - Sep 4
Total with taxes and fees
Granville House
Exterior

5. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,005 reviews)
"Lovely people and place. Breakfast was great and so was the room. Highly recommend."
United States
FRED
$212 nightly
The price is $236
Sep 3 - Sep 4
Total with taxes and fees
The Cornell Inn, Lenox & The Berkshires
Property grounds

6. 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
$159 nightly
The price is $178
Sep 13 - Sep 14
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
9.8 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
Deluxe Room, 1 King Bed, Ensuite (2nd Floor) | Premium bedding, desk, laptop workspace, blackout drapes

8. Changing Times Boutique Country Lodging

Changing Times Boutique Country Lodging
3.5 star property
Craryville
10.0 out of 10, Exceptional, (123 reviews)
"A great place to stay!"
United States
Thomas
$200 nightly
The price is $224
Sep 2 - Sep 3
Total with taxes and fees
Changing Times Boutique Country Lodging
1 bedroom, WiFi, bed sheets

9. Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
$363 nightly
The price is $416
Sep 8 - Sep 9
Total with taxes and fees
Experience Timeless Elegance in The Edith Wharton Room!
Interior

10. 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.
Front of property - evening/night

11. 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
$389 nightly
The price is $435
Sep 3 - Sep 4
Total with taxes and fees
Devonfield Inn B&B
Interior

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

Cozy Carriage House room with a double bed and private balcony
Lenox
$401 nightly
The price is $459
Sep 3 - Sep 4
Total with taxes and fees
Cozy Carriage House room with a double bed and private balcony
Terrace/patio

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

Historic Susan B. Anthony Room - Cozy & Charming Stay
Lenox
$417 nightly
The price is $477
Sep 8 - Sep 9
Total with taxes and fees
Historic Susan B. Anthony Room - Cozy & Charming Stay
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
$365 nightly
The price is $418
Sep 3 - Sep 4
Total with taxes and fees
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Front of property

15. 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
$284 nightly
The price is $320
Sep 17 - Sep 18
Total with taxes and fees
Brook Farm Inn
1 bedroom, bed sheets

16. 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
$502 nightly
The price is $574
Sep 3 - Sep 4
Total with taxes and fees
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
Front of property

17. Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (387 reviews)
"The room was clean and very quiet. Breakfast was delivered to our room as requested."
United States
Richard
$300 nightly
The price is $335
Sep 3 - Sep 4
Total with taxes and fees
Chambery Inn
1 bedroom, bed sheets

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

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Lenox
$538 nightly
The price is $601
Sep 3 - Sep 4
Total with taxes and fees
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Fireplace

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
$593 nightly
The price is $678
Sep 3 - Sep 4
Total with taxes and fees
Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
Living area

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

Elegant suite with a king bed, fireplace, and kitchenette.
Lenox
$593 nightly
The price is $678
Sep 3 - Sep 4
Total with taxes and fees
Elegant suite with a king bed, fireplace, and kitchenette.
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 Chatham Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Great value, great stay, friendly, couldn’t be happier!"
Michael 6-night trip
Posted 2 hours ago
Berkshire Mountain Lodge

Find out more about Chatham

Chatham B&B information

Number of reviews
3,258
Accommodation
40 B&B
Lowest Price
$172
Highest Price
$678

Frequently asked questions

What is the nightly rate for a B&B in Chatham?
Prices for B&Bs in Chatham often vary, but you can find a great deal from $172 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Chatham 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 Bed & Breakfast in Chatham?
The best time to book a B&B in Chatham is during the summer months, particularly from June to August, when the town comes alive with visitors eager to experience its charming coastal beauty. This peak season offers warm weather, with temperatures typically ranging from the mid-60s to the low 80s Fahrenheit, making it ideal for outdoor activities such as beach days, biking, and exploring the picturesque streets lined with historic homes.

July stands out as the most popular month for travelers seeking a vibrant atmosphere filled with local events, festivals, and outdoor concerts. You'll find families enjoying the sandy beaches, while couples can take romantic strolls along the shore at sunset, creating unforgettable memories.

If you're looking for a more budget-friendly experience, consider visiting in late September or early October. During this time, the summer crowds have thinned, and you can still enjoy mild weather, particularly for enjoying scenic walks along the coastline or visiting local shops and galleries without the hustle and bustle.
What is the difference between a Chatham Bed & Breakfast and a hotel?
Every Chatham 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 Chatham B&Bs.

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