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Compare 35 B&B in Old Chatham with updated reviews, rates, and availability.

The Cornell Inn, Lenox
Exterior
The Cornell Inn, Lenox
3.0 star property
8.8 out of 10, Excellent, (1005)
"What a joy this BnB is. Everything is so lovely, from the staff to the overall facilities. It was a true pleasure to stay here. We will be back for sure. "
The price is AED 455
AED 534 total
includes taxes & fees
29 Sep - 30 Sep
The Cornell Inn, Lenox
Lakehouse Inn
Lake
Lakehouse Inn
4.0 star property
9.8 out of 10, Exceptional, (202)
"Came here for an anniversary getaway and had a great time. Property was beautiful room was fantastic staff were great and caring. We checked in and received a bottle of Prosecco from the Inn. Will definitely come back again."
The price is AED 551
AED 646 total
includes taxes & fees
29 Sep - 30 Sep
Lakehouse Inn
The Morgan State House
Outdoor dining
The Morgan State House
3.5 star property
9.2 out of 10, Wonderful, (473)
"Great place to stay the host were very friendly and helpful. Rooms were clean great location."
The price is AED 540
AED 583 total
includes taxes & fees
23 Oct - 24 Oct
The Morgan State House
Whistler's Inn Bed & Breakfast
Interior
Whistler's Inn Bed & Breakfast
3.5 star property
7.8 out of 10, Good, (456)
"Old fashioned gilded age charm and elegance. Personal attention"
The price is AED 545
AED 679 total
includes taxes & fees
24 Sep - 25 Sep
Whistler's Inn Bed & Breakfast
Brook Farm Inn
Front of property
Brook Farm Inn
3.5 star property
9.4 out of 10, Exceptional, (146)
"Very charming inn. The staff was very friendly and helpful."
The price is AED 966
AED 1,079 total
includes taxes & fees
24 Sep - 25 Sep
Brook Farm Inn
Gardner Farm Inn
Room
Gardner Farm Inn
3.5 star property
10.0 out of 10, Exceptional, (162)
"Our first stay at a B&B far exceeded our expectations with John at the Gardner Farm Inn. Breakfast was excellent, the house and decor felt very homey. I would stay here again if we're ever back in Troy!"
The price is AED 630
AED 696 total
includes taxes & fees
7 Oct - 8 Oct
Gardner Farm Inn
Inn at Silver Maple Farm
Front of property
Inn at Silver Maple Farm
3.0 star property
9.8 out of 10, Exceptional, (73)
"Host was welcoming and check in process was seamless"
The price is AED 731
AED 789 total
includes taxes & fees
30 Sep - 1 Oct
Inn at Silver Maple Farm
Shaker Mill Inn
Garden
Shaker Mill Inn
2.5 star property
9.6 out of 10, Exceptional, (396)
"Very nice place. Clean and extreme attention to detail which is unusual in a place like this. Will definitely come back. We don't come to the Berkshires to watch TV but we did want to watch the college football game late Sat night. The TV in the room is very small but adequate. "
The price is AED 878
AED 963 total
includes taxes & fees
24 Sep - 25 Sep
Shaker Mill Inn
Devonfield Inn B&B
Room
Devonfield Inn B&B
4.0 star property
10.0 out of 10, Exceptional, (113)
"Wonderful place for a quiet getaway for a couple of nights. Scenic setting. Delicious breakfasts, helpful owners and staff on site. We'd book again!"
The price is AED 1,429
AED 1,596 total
includes taxes & fees
29 Sep - 30 Sep
Devonfield Inn B&B
Granville House
Room
Granville House
3.0 star property
10.0 out of 10, Exceptional, (75)
"The surroundings were quiet and peaceful. The hosts were welcoming and friendly. Wonderful people "
The price is AED 826
AED 923 total
includes taxes & fees
25 Sep - 26 Sep
Granville House
The Barrington
View from room
The Barrington
4.0 star property
9.8 out of 10, Exceptional, (106)
"Wonderful stay. Beautifully appointed rooms, comfortable bed, hot shower, quiet and restful. Lovely touches, but the best part of all is the incredible breakfasts prepared by French chef and manager William. Having these to look forward to each morning was a joy. Highly recommend this excellent property!"
The price is AED 1,194
AED 1,333 total
includes taxes & fees
27 Sep - 28 Sep
The Barrington
Chambery Inn
Front of property
Chambery Inn
3.0 star property
9.6 out of 10, Exceptional, (357)
"Nice place to stay in the Berkshires. The house is very quint and the room very comfortable (especially the bed and pillows). While I did not meet Bob until I checked out, they were always available to help via text. I would go back or recommend friends to stay there."
The price is AED 1,102
AED 1,231 total
includes taxes & fees
24 Sep - 25 Sep
Chambery Inn
33 Main
Room
33 Main
4.0 star property
10.0 out of 10, Exceptional, (67)
"33 Main is the best of everything. We have stayed at the location twice and loved each experience. The breakfast is delicious, accommodations are beautifully curated, and it’s perfectly located in Lenox. Highly recommend and we will be back! "
The price is AED 1,759
AED 1,965 total
includes taxes & fees
9 Oct - 10 Oct
33 Main
The Inn at Stockbridge
Exterior
The Inn at Stockbridge
4.0 star property
9.6 out of 10, Exceptional, (95)
"Well-run and elegant property. "
The Inn at Stockbridge
Inn at Kenmore Hall
Front of property
Inn at Kenmore Hall
3.0 star property
10.0 out of 10, Exceptional, (26)
"This is a beautiful property straight out of a magazine. Service was impeccable"
Inn at Kenmore Hall
Private Guest Area in Plant Based Bed and Breakfast
The main guest area with queen size bed and bathroom.
Private Guest Area in Plant Based Bed and Breakfast
10.0 out of 10, Exceptional, (7)
"I booked for (2) members of my team who were working an even in the area. The Host was amazing, answered questions promptly, was accommodating and made booking a breeze! "
Private Guest Area in Plant Based Bed and Breakfast
Tanglewood Suites
Property grounds
Tanglewood Suites
2.5 star property
8.0 out of 10, Very Good, (15)
"The property is so lovely and peaceful. I love the classic mid-century modern aesthetic. For visitors to the National Shrine of Divine Mercy, the Inn’s location couldn’t be more perfect with only a 5-minute walk to the Shrine. "
Tanglewood Suites
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
View from room
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
9.2 out of 10, Wonderful, (103)
"The breakfast was one of the best I have ever had. They were fast and lots of choices. It had lots of baked goods. I got the chesdar omeltte and bacon and toast plus fruits in season lime melon etc. Its a lovely place it takes you back in time. The owner is very easy going and nuce and can answer most questions"
The price is AED 1,685
AED 2,039 total
includes taxes & fees
24 Sep - 25 Sep
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
1735 Stone Farmhouse
Exterior
1735 Stone Farmhouse
4.5 star property
10.0 out of 10, Exceptional, (3)
"1735 is an excellent little get-a-way, I booked it for my girlfriend’s birthday as a bed and breakfast and it did not disappoint. It’s nestled in a quiet area that disconnects you from the world yet is less than 20 minutes from Albany. The design, upkeep, and architecture is quite remarkable. All the finishing touches were well thought of and placed well. Seven, our host is excellent at his craft and exudes hospitality. From the moment we arrived we were welcomed with open arms. Seven was very...
1735 Stone Farmhouse
Romantic Boutique Hotel / Bed and Breakfast - Standard Queen Handicap Accessible
Room
Romantic Boutique Hotel / Bed and Breakfast - Standard Queen Handicap Accessible
9.8 out of 10, Exceptional, (10)
"We would return to the inn again. Bob was wonderful and very, very accommodating:-)"
The price is AED 1,098
AED 1,403 total
includes taxes & fees
24 Sep - 25 Sep
Romantic Boutique Hotel / Bed and Breakfast - Standard Queen Handicap Accessible
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Other property types in Old Chatham

Beautiful Private Estate! Pool, Pond, Gym, Arcade, Barn, Trails, Library & More!
Beautiful Bellavista Country Estate! Create Timeless Memories w/ Family/ Friends
Beautiful Private Estate! Pool, Pond, Gym, Arcade, Barn, Trails, Library & More!
9.6 out of 10, Exceptional, (84)
"This large home has many comfortable bedrooms, some very large suites. The kitchen is very well stocked. Our family had a wonderful stay. The pool was great, and a center of our enjoyment. Kids also enjoyed the game room."
Beautiful Private Estate! Pool, Pond, Gym, Arcade, Barn, Trails, Library & More!
Vacation Village in the Berkshires
Lobby
Vacation Village in the Berkshires
3.0 star property
8.6 out of 10, Excellent, (1714)
"Nice place. Pleasantly surprised how big the suite was. The whole place was very clean from the suite itself, the huge indoor pool and hot tub. The clerk that checked us in was very knowledgeable of the area and just a pleasant person. She is an older lady, I forget her name but she is a definite asset to this property! On the down side the path to the main office was not well lit but we used our flashlights. Also there isn't restaurants on site or groceries available. We had to travel 25...
The price is AED 620
AED 717 total
includes taxes & fees
24 Sep - 25 Sep
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Property entrance
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, (898)
"Was good everything "
The price is AED 537
AED 589 total
includes taxes & fees
26 Sep - 27 Sep
Jiminy Peak Mountain Resort
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.

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.
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 April, 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 The Mac-Haydn Theatre or Martin Van Buren National Historic Site 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.