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

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Check prices for these dates

Next weekend
Jul 31 - Aug 2
In two weeks
Aug 7 - Aug 9
In one month
Aug 21 - Aug 23
In two months
Sep 18 - Sep 20

Our top choices for Chatham bed & breakfast

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
$229 nightly
The price is $256
Aug 5 - Aug 6
Total with taxes and fees
Inn at Silver Maple Farm
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
$167 nightly
The price is $183
Jul 27 - Jul 28
Total with taxes and fees
Shaker Mill Inn
Exterior

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,000 reviews)
"The cornel Inn is terrific! Great location near tanglewood, shops snd restaurants. Great breakfast"
United States
Judith
$172 nightly
The price is $192
Jul 26 - Jul 27
Total with taxes and fees
The Cornell Inn, Lenox & The Berkshires
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 29 - Jul 30
Total with taxes and fees
Granville House
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
$348 nightly
The price is $389
Aug 9 - Aug 10
Total with taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Property grounds

Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very Good, (506 reviews)
"Beautiful inn with the most interesting treasures and decorations."
United States
Mary
$191 nightly
The price is $213
Jul 26 - Jul 27
Total with taxes and fees
Whistler's Inn Bed & Breakfast
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 26 - Jul 27
Total with taxes and fees
The Inn at Stockbridge
Deluxe Room, 1 King Bed, Ensuite (2nd Floor) | Premium bedding, desk, laptop workspace, blackout drapes

Changing Times Boutique Country Lodging

Changing Times Boutique Country Lodging
3.5 star property
Craryville
10.0 out of 10, Exceptional, (119 reviews)
"Terrific host and freshly cooked to order hot breakfast, beautiful grounds, and dog friendly. Would definitely stay again!"
United States
Jamie
$200 nightly
The price is $224
Jul 28 - Jul 29
Total with taxes and fees
Changing Times Boutique Country Lodging
Exterior

The Berkshire Mountain Inn

The Berkshire Mountain Inn
3.0 star property
Great Barrington
9.0 out of 10, Wonderful, (15 reviews)
"Friendly staff and attention to detail making our stay in a charming inn special"
United States
Kristen
$288 nightly
The price is $321
Aug 5 - Aug 6
Total with taxes and fees
The Berkshire Mountain Inn
1 bedroom, WiFi, bed sheets

Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
$299 nightly
The price is $342
Jul 26 - Jul 27
Total with taxes and fees
Experience Timeless Elegance in The Edith Wharton Room!
Front of property

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (383 reviews)
"Location is convenient to walk through downtown Lee and to get to a show at Tanglewood."
United States
Joseph
$300 nightly
The price is $335
Jul 26 - Jul 27
Total with taxes and fees
Chambery Inn
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
Aug 19 - Aug 20
Total with taxes and fees
Devonfield Inn B&B
Front of property

Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (169 reviews)
"Lovely stay!"
United States
Jiacheng
$261 nightly
The price is $294
Aug 3 - Aug 4
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
$666 nightly
The price is $744
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
$299 nightly
The price is $342
Jul 26 - Jul 27
Total with taxes and fees
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
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
$411 nightly
The price is $470
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 27 - Jul 28
Total with taxes and fees
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
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
$193 nightly
The price is $216
Aug 18 - Aug 19
Total with taxes and fees
Wilder House Berkshires
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
$621 nightly
The price is $710
Jul 29 - Jul 30
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

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

10/10 Excellent
"Nice stay at this Holiday Express in Pittsfield. The staff were so polite and helpful, building looked brand new. My husband and I were happy with the gym equipment, the pool looked nice and clean as well. Excellent complimentary breakfast that went until 10:00. 😊 Definitely recommend!!!!"
Amy 1-night trip
Posted 1 hour ago
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Find out more about Chatham

Chatham B&B information

Number of reviews
2,304
Accommodation
40 B&B
Lowest Price
$183
Highest Price
$744

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 $183 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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