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Check prices for these dates

Next weekend
28 Nov - 30 Nov
In two weeks
5 Dec - 7 Dec
In one month
19 Dec - 21 Dec
In two months
16 Jan - 18 Jan

B&B in Chatham

Porch
Lakehouse Inn

Lakehouse Inn

4.0 star property
Lee
9.6 out of 10, Exceptional, (289)
"A charming inn in the center of the Berkshires."
United States
Danny
The price is SAR 589
SAR 691 total
includes taxes & fees
18 Dec - 19 Dec
Lakehouse Inn
Front of property
Chambery Inn

Chambery Inn

3.0 star property
Lee
9.6 out of 10, Exceptional, (373)
"Amazing customer service! Location was very good to explore the area."
United States
Sophia
Chambery Inn
Loft, Private Bathroom (Skylight Loft) | 1 bedroom, premium bedding, iron/ironing board, rollaway beds
Brook Farm Inn

Brook Farm Inn

3.5 star property
Lenox
9.4 out of 10, Exceptional, (162)
"Comfortable, quiet, convenient location, very friendly staff. "
United States
Susan
Brook Farm Inn
Wilder House Berkshires Room 3 | 1 bedroom, premium bedding, individually decorated
Wilder House Berkshires

Wilder House Berkshires

2.0 star property
Sheffield
9.8 out of 10, Exceptional, (38)
"Wilder House is warm and charming. I’ve stayed many times and it always feels like home. I had a lovely breakfast and a great stay. Thank you! "
United States
Allison
The price is SAR 540
SAR 603 total
includes taxes & fees
23 Nov - 24 Nov
Wilder House Berkshires
Front of property - evening/night
Devonfield Inn B&B

Devonfield Inn B&B

4.0 star property
Lee
10.0 out of 10, Exceptional, (133)
"The inn has an excellent location and amenities."
United States
Christopher
Devonfield Inn B&B
Property grounds
Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast

3.5 star property
Lenox
7.8 out of 10, Good, (500)
"We had the smallest room on the property.very quaint and clean. Nicest staff great place to stay."
United States
Lisa
The price is SAR 456
SAR 509 total
includes taxes & fees
23 Nov - 24 Nov
Whistler's Inn Bed & Breakfast
Exterior
The Inn at Stockbridge

The Inn at Stockbridge

4.0 star property
Lee
9.8 out of 10, Exceptional, (98)
"Well-run and elegant property. "
United States
Steven
The price is SAR 941
SAR 1,103 total
includes taxes & fees
23 Nov - 24 Nov
The Inn at Stockbridge
Garden
Shaker Mill Inn

Shaker Mill Inn

2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (436)
"Nice place, easy check in"
United States
Robert
The price is SAR 424
SAR 466 total
includes taxes & fees
2 Dec - 3 Dec
Shaker Mill Inn
Individually decorated, individually furnished, desk, laptop workspace
Granville House

Granville House

3.0 star property
Housatonic
10.0 out of 10, Exceptional, (87)
"Outstanding all around!"
United States
Jonathan
The price is SAR 746
SAR 834 total
includes taxes & fees
4 Dec - 5 Dec
Granville House
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
The price is SAR 784
SAR 1,148 total
includes taxes & fees
23 Nov - 24 Nov
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi
33 Main

33 Main

4.0 star property
Lenox
10.0 out of 10, Exceptional, (74)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is SAR 1,563
SAR 1,746 total
includes taxes & fees
23 Dec - 24 Dec
33 Main
1 bedroom, WiFi, bed sheets, wheelchair access
Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!

Lenox
The price is SAR 784
SAR 1,148 total
includes taxes & fees
23 Nov - 24 Nov
Experience Timeless Elegance in The Edith Wharton Room!
Front of property
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 star property
Lenox
9.0 out of 10, Wonderful, (1001)
"Overall a really fun place to stay. Rooms were good quality and the staff was welcoming and helpful."
United States
Jacob
The price is SAR 483
SAR 686 total
includes taxes & fees
23 Nov - 24 Nov
The Cornell Inn, Lenox & The Berkshires
2 Bedrooms 1 Bath | 1 bedroom, premium bedding, iron/ironing board, free WiFi
Tanglewood Suites

Tanglewood Suites

2.5 star property
Stockbridge
6.4 out of 10, (22)
"NOT A REAL LOCATION. There was nothing there. Neighbors said this was a scam. Expedia ended up helping us find a local hotel room though the location was not as good. DO NOT BOOK THIS LOCATION -- it needs to be taken off the website."
United States
Elizabeth
The price is SAR 821
SAR 821 total
includes taxes & fees
1 Dec - 2 Dec
Tanglewood Suites
Business center
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, (110)
"Wonderful! Owner/host Diane was friendly, helpful, knowledgeable. Breakfasts awesome with great choices daily. Place was spotless, cozy and classic. So glad we stayed there. "
United States
Robert
The price is SAR 1,432
SAR 1,733 total
includes taxes & fees
7 Dec - 8 Dec
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
1 bedroom, WiFi, bed sheets
Elegant Carriage House room with a queen bed and private patio.

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

Lenox
The price is SAR 844
SAR 1,223 total
includes taxes & fees
25 Nov - 26 Nov
Elegant Carriage House room with a queen bed and private patio.
1 bedroom, bed sheets
Cozy Carriage House room with a double bed and private balcony

Cozy Carriage House room with a double bed and private balcony

Lenox
The price is SAR 904
SAR 1,303 total
includes taxes & fees
23 Nov - 24 Nov
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
The price is SAR 964
SAR 1,378 total
includes taxes & fees
23 Nov - 24 Nov
Historic Susan B. Anthony Room - Cozy & Charming Stay
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
The price is SAR 1,534
SAR 2,107 total
includes taxes & fees
23 Nov - 24 Nov
Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
Fireplace
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
The price is SAR 1,234
SAR 1,722 total
includes taxes & fees
23 Nov - 24 Nov
Experience Timeless Elegance in The Niles Johnson Room 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

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

10/10 Excellent
"Good"
Donald 1-night trip
Posted 2 days ago
Best Western Plus Berkshire Hills Inn & Suites

Frequently asked questions

Searching for B&Bs in Chatham?
Whether you're on a romantic vacation and want to stay somewhere quiet, or you're traveling solo and hoping to make some connections, a B&B can be a good choice for many different types of travelers. While you're enjoying your trip to Chatham, you might want to explore the theater scene by catching a show at The Mac-Haydn Theatre.
Are you thinking about B&Bs over traditional hotel rooms?
With attentive service, opportunities to socialize with other guests, and of course a full breakfast, B&Bs offer a truly one-of-a-kind setting.
What are the best bed and breakfasts in Chatham?
Below are some well-liked B&Bs in the surrounding area: The Cornell Inn, Lenox & The Berkshires: 16 mi (25.7 km) from the heart of Chatham. Enjoy the free full breakfast and unique décor. Chambery Inn: 9 rooms. 17.9 mi (28.9 km) from the downtown core. Enjoy the private yard and deli. Shaker Mill Inn: 9 rooms. Situated 11.7 mi (18.8 km) from the heart of Chatham. Whistler's Inn Bed & Breakfast: 14 rooms. 15.9 mi (25.6 km) from the heart of downtown. Enjoy the private yard and unique décor. Lakehouse Inn: 14 rooms. Located 17.2 mi (27.7 km) from the core of Chatham. Enjoy the free full breakfast and deli.
When should I stay at a B&B in Chatham?
When you're dreaming of a escape to Chatham, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 67°F, while the coldest months are January and February with an average of 29°F. The snowiest months in Chatham are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What is there to do in Chatham?
If you want to check out some popular attractions in Chatham, you might enjoy a visit to The Mac-Haydn Theatre. Martin Van Buren National Historic Site and Kinderhook Lake are also some sites to visit if you want to see more of the area.
How can I get to and around Chatham?
Mapping out your trip in and around Chatham is easy with these transportation options. Fly into Hudson, NY (HCC-Columbia County), which is located 7.7 mi (12.4 km) away from the heart of the city. Otherwise, look for flights into Pittsfield, MA (PSF-Pittsfield Municipal), which is 16 mi (25.8 km) away. If you'd like to venture out around the area, you may want a rental car for your journey.