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B&B in Old Chatham

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 AED 392
AED 430 total
includes taxes & fees
10 Dec - 11 Dec
Shaker Mill 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

Lakehouse Inn

4.0 star property
Lee
9.6 out of 10, Exceptional, (290)
"A charming inn in the center of the Berkshires."
United States
Danny
The price is AED 684
AED 802 total
includes taxes & fees
12 Dec - 13 Dec
Lakehouse Inn

Granville House

3.0 star property
Housatonic
10.0 out of 10, Exceptional, (88)
"Outstanding all around!"
United States
Jonathan
The price is AED 735
AED 821 total
includes taxes & fees
1 Jan - 2 January 2026
Granville House

The Cornell Inn, Lenox & The Berkshires

3.5 star property
Lenox
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 614
AED 706 total
includes taxes & fees
9 Dec - 10 Dec
The Cornell Inn, Lenox & The Berkshires

The Inn at Stockbridge

4.0 star property
Lee
9.8 out of 10, Exceptional, (99)
"Well-run and elegant property. "
United States
Steven
The price is AED 921
AED 1,080 total
includes taxes & fees
1 Jan - 2 January 2026
The Inn at Stockbridge

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 AED 1,636
AED 1,828 total
includes taxes & fees
5 Jan - 6 January 2026
33 Main

Inn at Silver Maple Farm

3.0 star property
East Chatham
9.8 out of 10, Exceptional, (98)
"Great stay, comfortable place"
United States
barry
The price is AED 474
AED 531 total
includes taxes & fees
9 Dec - 10 Dec
Inn at Silver Maple Farm

Devonfield Inn B&B

4.0 star property
Lee
10.0 out of 10, Exceptional, (134)
"The inn has an excellent location and amenities."
United States
Christopher
Devonfield Inn B&B

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 AED 804
AED 804 total
includes taxes & fees
9 Dec - 10 Dec
Tanglewood Suites

Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen

Lenox
The price is AED 995
AED 1,301 total
includes taxes & fees
9 Dec - 10 Dec
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen

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 AED 1,403
AED 1,697 total
includes taxes & fees
5 Jan - 6 January 2026
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

Experience Timeless Elegance in The Edith Wharton Room!

Lenox
The price is AED 995
AED 1,301 total
includes taxes & fees
9 Dec - 10 Dec
Experience Timeless Elegance in The Edith Wharton Room!

Inn at Kenmore Hall

3.0 star property
Richmond
10.0 out of 10, Exceptional, (27)
"Gorgeous grounds, welcoming home atmosphere. wonderful breakfast and staff that made it feel like home - only better! "
United States
Margaret
The price is AED 1,561
AED 1,712 total
includes taxes & fees
16 Dec - 17 Dec
Inn at Kenmore Hall

Brook Farm Inn

3.5 star property
Lenox
9.4 out of 10, Exceptional, (163)
"Everything was perfect - location and accommodation."
United States
Christopher
Brook Farm Inn

Cozy Carriage House room with a double bed and private balcony

Lenox
The price is AED 1,116
AED 1,461 total
includes taxes & fees
9 Dec - 10 Dec
Cozy Carriage House room with a double bed and private balcony

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

Lenox
The price is AED 1,055
AED 1,379 total
includes taxes & fees
9 Dec - 10 Dec
Elegant Carriage House room with a queen bed and private patio.

Historic Susan B. Anthony Room - Cozy & Charming Stay

Lenox
The price is AED 1,177
AED 1,538 total
includes taxes & fees
9 Dec - 10 Dec
Historic Susan B. Anthony Room - Cozy & Charming Stay

Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn

Lenox
The price is AED 1,752
AED 2,289 total
includes taxes & fees
9 Dec - 10 Dec
Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn

Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn

Lenox
The price is AED 1,449
AED 1,896 total
includes taxes & fees
10 Dec - 11 Dec
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 Old Chatham Hotel Reviews

Frequently asked questions

Searching for B&Bs in Old Chatham?
Whether you're on a romantic trip and want to stay somewhere quiet and intimate, or you're a solo traveler hoping to get some local recommendations, B&Bs can be a great choice for many travelers. When you want to venture out to explore Old Chatham, consider browsing the exhibits at Shaker Museum and Library.
Why consider a B&B versus a traditional hotel?
With attentive service, opportunities to meet guests from other places, and top-rated breakfasts, B&Bs provide a one-of-a-kind setting.
What are the best B&Bs in Old Chatham?
Here are some B&Bs in the surrounding area: The Cornell Inn, Lenox & The Berkshires: 15.2 mi (24.5 km) from the heart of Old Chatham. Enjoy the free full breakfast and unique décor. The Morgan State House: 16 rooms. 18.2 mi (29.2 km) from the downtown core. Shaker Mill Inn: 9 rooms. Situated 12.2 mi (19.7 km) from the heart of Old Chatham. Chambery Inn: 9 rooms. 18.3 mi (29.4 km) from the heart of downtown. Enjoy the private yard and deli. Lakehouse Inn: 14 rooms. Located 17.3 mi (27.8 km) from the core of Old Chatham. Enjoy the free full breakfast and deli.
When should I book my B&B in Old Chatham?
When you're planning your stay in Old 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 Old Chatham are January, March, December, and November, with each month seeing an average of 7 inches of snowfall.
What is there to do in Old Chatham?
If you want to check out some popular attractions in Old Chatham, you might enjoy a visit to Shaker Museum and Library. You might also consider a trip to sites like Kinderhook Lake or Queechy Lake if you have time to see more of the area.
How can I get to and around Old Chatham?
Mapping out your trip in and around Old Chatham is easy with these transportation options. Fly into Hudson, NY (HCC-Columbia County), which is located 12.7 mi (20.4 km) away from the heart of the city. Otherwise, look for flights into Pittsfield, MA (PSF-Pittsfield Municipal), which is 13.9 mi (22.3 km) away. If you'd like to venture out around the area, consider renting a car to take in more sights.