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

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Check prices for these dates

Next weekend
Jul 24 - Jul 26
In two weeks
Jul 31 - Aug 2
In one month
Aug 14 - Aug 16
In two months
Sep 11 - Sep 13

Our top choices for Chatham bed & breakfast

Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (464 reviews)
"Wonderful place to stay!"
United States
Mervin
$165 nightly
The price is $181
Jul 22 - Jul 23
Total with taxes and fees
Shaker Mill Inn
Aerial view

Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (112 reviews)
"Very nice hotel."
United States
Erdem
$189 nightly
The price is $212
Jul 22 - Jul 23
Total with taxes and fees
Inn at Silver Maple Farm
Exterior

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,002 reviews)
"The staff were super friendly"
United States
John
$172 nightly
The price is $192
Jul 22 - Jul 23
Total with taxes and fees
The Cornell Inn, Lenox & The Berkshires
Property grounds

Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very Good, (505 reviews)
"Beautiful inn with the most interesting treasures and decorations."
United States
Mary
$191 nightly
The price is $213
Jul 20 - Jul 21
Total with taxes and fees
Whistler's Inn Bed & Breakfast
Interior detail

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (58 reviews)
"Great stay and the breakfast was fantastic"
United States
Jennifer
$207 nightly
The price is $231
Jul 27 - Jul 28
Total with taxes and fees
Wilder House Berkshires
Front of property

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (381 reviews)
"Location is convenient to walk through downtown Lee and to get to a show at Tanglewood."
United States
Joseph
$293 nightly
The price is $328
Jul 27 - Jul 28
Total with taxes and fees
Chambery Inn
Desk, laptop workspace, iron/ironing board (on request), WiFi (free)

Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (102 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
$225 nightly
The price is $251
Jul 27 - Jul 28
Total with taxes and fees
Granville House
Front of property

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.8 out of 10, Exceptional, (99 reviews)
"Great spot close to town. Cozy, tasteful, comfortable room. Nice breakfasts and pleasant interaction with the staff. We love the Berkshires and we’ll definitely stay here again."
United States
Stephen
$389 nightly
The price is $435
Jul 27 - Jul 28
Total with taxes and fees
The Inn at Stockbridge
Exterior

The Berkshire Mountain Inn

The Berkshire Mountain Inn
3.0 star property
Great Barrington
9.0 out of 10, Wonderful, (14 reviews)
"The staff and the cleaness of the facility"
United States
MICHAEL
$265 nightly
The price is $295
Jul 21 - Jul 22
Total with taxes and fees
The Berkshire Mountain Inn
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, (113 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."
United States
Philippe
$358 nightly
The price is $399
Aug 3 - Aug 4
Total with taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Front of property - evening/night

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (139 reviews)
"Room was great, staff was awesome, amenities were cool"
United States
Francis
$439 nightly
The price is $490
Jul 21 - Jul 22
Total with taxes and fees
Devonfield Inn B&B
1 bedroom, WiFi, bed sheets

Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
$301 nightly
The price is $345
Jul 22 - Jul 23
Total with taxes and fees
Experience Timeless Elegance in The Edith Wharton Room!
Front of property

Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (168 reviews)
"Lovely stay!"
United States
Jiacheng
$209 nightly
The price is $237
Jul 20 - Jul 21
Total with taxes and fees
Brook Farm Inn
Luxury Room, 1 King Bed, Bathtub | Premium bedding, iron/ironing board, WiFi (free), individually decorated

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
$696 nightly
The price is $777
Aug 16 - Aug 17
Total with taxes and fees
33 Main
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
$301 nightly
The price is $345
Jul 22 - Jul 23
Total with taxes and fees
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Interior

Cozy Carriage House room with a double bed and private balcony

Cozy Carriage House room with a double bed and private balcony
Lenox
$337 nightly
The price is $386
Jul 26 - Jul 27
Total with taxes and fees
Cozy Carriage House room with a double bed and private balcony
Terrace/patio

Historic Susan B. Anthony Room - Cozy & Charming Stay

Historic Susan B. Anthony Room - Cozy & Charming Stay
Lenox
$356 nightly
The price is $407
Jul 27 - Jul 28
Total with taxes and fees
Historic Susan B. Anthony Room - Cozy & Charming Stay
Interior

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

Elegant Carriage House room with a queen bed and private patio.
Lenox
$408 nightly
The price is $467
Jul 29 - Jul 30
Total with taxes and fees
Elegant Carriage House room with a queen bed and private patio.
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
$438 nightly
The price is $501
Jul 23 - Jul 24
Total with taxes and fees
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
$529 nightly
The price is $605
Jul 22 - Jul 23
Total with taxes and fees
Experience Luxury in The Lady Cicely Grand Suite at The Cornell 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 Chatham Hotel Reviews

St. Charles Hotel

St. Charles Hotel

8/10 Good
"The room was good. The internet and TV did not function consistently. The common areas needed sprucing up"
Sara 1-night trip
Posted less than an hour ago
St. Charles Hotel

Find out more about Chatham

Chatham B&B information

Number of reviews
2,903
Accommodation
40 B&B
Lowest Price
$181
Highest Price
$777

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 $181 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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