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Our top choices for Chatham bed & breakfast

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (46 reviews)
"Clean, cute, private, nice location. Breakfast was wonderful. Great value as well. Would definitely go back. "
United States
Kristinna
The price is SAR 598
SAR 667 total
includes taxes & fees
30 Apr - 1 May
Wilder House Berkshires

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (448 reviews)
"Everything was great— the cleanliness, the plentiful breakfast, the character and coziness, and the proximity to Amici across the street (free dessert with your room key)."
United States
Patrick
The price is SAR 403
SAR 442 total
includes taxes & fees
4 May - 5 May
Shaker Mill Inn

Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (376 reviews)
"Yes the room was spotless and always the staff is ready to answer any questions that we might have. We have been enjoying the Chambery Inn for many years always had a great stay and again looking for our next visit. Vincent Farricielli and Roibert Modena. "
United States
robert
The price is SAR 641
SAR 716 total
includes taxes & fees
30 Apr - 1 May
Chambery Inn

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)
"Delicious breakfast and beautiful room!"
United States
Laarni
The price is SAR 485
SAR 558 total
includes taxes & fees
4 May - 5 May
The Cornell Inn, Lenox & The Berkshires

The Berkshire Mountain Inn

The Berkshire Mountain Inn
3.0 star property
Great Barrington
9.8 out of 10, Exceptional, (6 reviews)
"The new owners have done a great job. The place is immaculate, the room was very comfortable and well appointed, the common areas charming. Highly recommended."
United States
Robert
The price is SAR 647
SAR 723 total
includes taxes & fees
30 Apr - 1 May
The Berkshire Mountain Inn

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (137 reviews)
"The inn has an excellent location and amenities."
United States
Christopher
The price is SAR 971
SAR 1,085 total
includes taxes & fees
30 Apr - 1 May
Devonfield Inn B&B

Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (100 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
The price is SAR 750
SAR 838 total
includes taxes & fees
3 May - 4 May
Granville House

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99 reviews)
"Well-run and elegant property. "
United States
Steven
The price is SAR 986
SAR 1,156 total
includes taxes & fees
5 May - 6 May
The Inn at Stockbridge

Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very Good, (501 reviews)
"This family owned Inn is absolutely charming and the owners are so nice! I will definitely stay here again when I visit the Berkshires."
United States
Stacey
The price is SAR 959
SAR 1,071 total
includes taxes & fees
24 May - 25 May
Whistler's Inn Bed & Breakfast

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, (111 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
The price is SAR 1,161
SAR 1,404 total
includes taxes & fees
13 May - 14 May
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

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
The price is SAR 1,990
SAR 2,222 total
includes taxes & fees
30 Apr - 1 May
33 Main

Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (104 reviews)
"Very nice hotel."
United States
Erdem
The price is SAR 596
SAR 668 total
includes taxes & fees
17 May - 18 May
Inn at Silver Maple Farm

Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
The price is SAR 808
SAR 1,057 total
includes taxes & fees
3 May - 4 May
Experience Timeless Elegance in The Edith Wharton Room!

Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (164 reviews)
"Everything was perfect - location and accommodation."
United States
Christopher
The price is SAR 688
SAR 798 total
includes taxes & fees
3 May - 4 May
Brook Farm Inn

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 988
SAR 1,284 total
includes taxes & fees
5 May - 6 May
Elegant Carriage House room with a queen bed and private patio.

Changing Times Boutique Country Lodging

Changing Times Boutique Country Lodging
3.5 star property
Craryville
10.0 out of 10, Exceptional, (117 reviews)
"The place is so authentic and beautiful, the owner is so kind and friendly, and we had really good experience "
United States
Tamir
The price is SAR 731
SAR 819 total
includes taxes & fees
3 May - 4 May
Changing Times Boutique Country Lodging

Inn at Kenmore Hall

Inn at Kenmore Hall
3.0 star property
Richmond
10.0 out of 10, Exceptional, (28 reviews)
"Gorgeous grounds, welcoming home atmosphere. wonderful breakfast and staff that made it feel like home - only better! "
United States
Margaret
The price is SAR 1,594
SAR 1,749 total
includes taxes & fees
10 May - 11 May
Inn at Kenmore Hall

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 1,048
SAR 1,357 total
includes taxes & fees
3 May - 4 May
Cozy Carriage House room with a double bed and private balcony

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 808
SAR 1,057 total
includes taxes & fees
3 May - 4 May
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen

Historic Susan B. Anthony Room - Cozy & Charming Stay

Historic Susan B. Anthony Room - Cozy & Charming Stay
Lenox
The price is SAR 1,108
SAR 1,434 total
includes taxes & fees
3 May - 4 May
Historic Susan B. Anthony Room - Cozy & Charming Stay
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Top Chatham Hotel Reviews

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. The Berkshire Mountain Inn: 7 rooms. 17 mi (27.3 km) from the downtown core. Enjoy the unique décor and library. Shaker Mill Inn: 9 rooms. Situated 11.7 mi (18.8 km) from the heart of Chatham. Chambery Inn: 9 rooms. 17.9 mi (28.9 km) from the heart of downtown. Enjoy the private yard and deli. 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.