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Check prices for these dates

Next weekend
31 Oct - 2 Nov
In two weeks
7 Nov - 9 Nov
In one month
21 Nov - 23 Nov
In two months
19 Dec - 21 Dec

B&B in Chatham

Interior
The Red Door B&B
The Red Door B&B
3.0 star property
10.0 out of 10, Exceptional, (5)
"Centrally located. Lovely hosts. Only three bedrooms so we got to know the other guests. The breakfasts were works of art as well as delicious."
United States
Anonymous traveler
The Red Door B&B
Front of property
Chambery Inn
Chambery Inn
3.0 star property
9.6 out of 10, Exceptional, (370)
"ease of late check in. Super comfortable room."
United States
Mary
Chambery Inn
Porch
Lakehouse Inn
Lakehouse Inn
4.0 star property
9.6 out of 10, Exceptional, (285)
"Lovely location on a lake, quiet, simple, clean rooms, great breakfast included. "
United States
Roberta
The price is AED 672
AED 788 total
includes taxes & fees
2 Nov - 3 Nov
Lakehouse Inn
Front of property - evening/night
Devonfield Inn B&B
Devonfield Inn B&B
4.0 star property
10.0 out of 10, Exceptional, (132)
"The inn has an excellent location and amenities."
United States
Christopher
Devonfield Inn B&B
Front of property
The Cornell Inn, Lenox & The Berkshires
The Cornell Inn, Lenox & The Berkshires
3.5 star property
9.0 out of 10, Wonderful, (1000)
"Overall a really fun place to stay. Rooms were good quality and the staff was welcoming and helpful."
United States
Jacob
The price is AED 469
AED 667 total
includes taxes & fees
27 Oct - 28 Oct
The Cornell Inn, Lenox & The Berkshires
Exterior
The Inn at Stockbridge
The Inn at Stockbridge
4.0 star property
9.8 out of 10, Exceptional, (98)
"Well-run and elegant property. "
United States
Steven
The price is AED 1,274
AED 1,494 total
includes taxes & fees
2 Nov - 3 Nov
The Inn at Stockbridge
Wilder House Berkshires Room 3 | 1 bedroom, premium bedding, individually decorated
Wilder House Berkshires
Wilder House Berkshires
2.0 star property
9.8 out of 10, Exceptional, (37)
"Highly recommend this beautiful bed & breakfast! The room was wonderful and overlooked the property, the breakfast was delicious, and the hospitality was amazing. I had a fantastic stay, and will definitely stay at The Wilder House again when I'm in the area."
United States
Marina
The price is AED 553
AED 618 total
includes taxes & fees
27 Oct - 28 Oct
Wilder House Berkshires
Property grounds
Whistler's Inn Bed & Breakfast
Whistler's Inn Bed & Breakfast
3.5 star property
7.8 out of 10, Good, (499)
"We had the smallest room on the property.very quaint and clean. Nicest staff great place to stay."
United States
Lisa
The price is AED 491
AED 548 total
includes taxes & fees
30 Oct - 31 Oct
Whistler's Inn Bed & Breakfast
3 bedrooms, bed sheets
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
The price is AED 762
AED 1,118 total
includes taxes & fees
26 Oct - 27 Oct
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
10.0 out of 10, Exceptional, (73)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is AED 1,689
AED 1,887 total
includes taxes & fees
24 Nov - 25 Nov
33 Main
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.
The price is AED 821
AED 1,191 total
includes taxes & fees
28 Oct - 29 Oct
Elegant Carriage House room with a queen bed and private patio.
1 bedroom, WiFi, bed sheets, wheelchair access
Experience Timeless Elegance in The Edith Wharton Room!
Experience Timeless Elegance in The Edith Wharton Room!
The price is AED 762
AED 1,118 total
includes taxes & fees
27 Oct - 28 Oct
Experience Timeless Elegance in The Edith Wharton Room!
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
The price is AED 879
AED 1,265 total
includes taxes & fees
29 Oct - 30 Oct
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
The price is AED 938
AED 1,343 total
includes taxes & fees
29 Oct - 30 Oct
Historic Susan B. Anthony Room - Cozy & Charming Stay
Loft, Private Bathroom (Skylight Loft) | 1 bedroom, premium bedding, iron/ironing board, rollaway beds
Brook Farm Inn
Brook Farm Inn
3.5 star property
9.4 out of 10, Exceptional, (161)
"Inn was gorgeous and staff exceptional!"
United States
Joyce
Brook Farm 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
The price is AED 1,203
AED 1,680 total
includes taxes & fees
27 Oct - 28 Oct
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
1 bedroom, bed sheets
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
The price is AED 1,326
AED 1,838 total
includes taxes & fees
2 Nov - 3 Nov
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
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
The price is AED 1,496
AED 2,053 total
includes taxes & fees
28 Oct - 29 Oct
Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
Living area
Elegant suite with a king bed, fireplace, and kitchenette.
Elegant suite with a king bed, fireplace, and kitchenette.
The price is AED 1,496
AED 2,053 total
includes taxes & fees
26 Oct - 27 Oct
Elegant suite with a king bed, fireplace, and kitchenette.
Individually decorated, individually furnished, desk, laptop workspace
Granville House
Granville House
3.0 star property
10.0 out of 10, Exceptional, (85)
"Beautiful place! Terri and Terry are the best!"
United States
Stephanie
The price is AED 804
AED 898 total
includes taxes & fees
25 Oct - 26 Oct
Granville House
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
"We loved this place. Quiet, very clean,attractive. Loved that it had a kitchen area. Second story, sliding glass doors overlooked the fall foliage in the back of the building. Very peaceful.."
Steven 4-night trip
Posted 2 days ago
Berkshire Mountain Lodge

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. Lakehouse Inn: 14 rooms. 17.2 mi (27.7 km) from the downtown core. Enjoy the free full breakfast and deli. 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. Inn at Silver Maple Farm: 11 rooms. Located 7.7 mi (12.4 km) from the core of Chatham. Enjoy the free buffet breakfast and designer toiletries.
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. Art Omi International Arts Center - Fields Sculpture Park and Martin Van Buren National Historic Site 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.