Search B&B in Old Chatham

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Compare 33 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, (1000)
"Perfect romantic spot for a weekend getaway. Close enough to walk into town but far enough from crowds "
The price is AED 448
AED 526 total
includes taxes & fees
17 Nov - 18 Nov
The Cornell Inn, Lenox
Lakehouse Inn
Lake
Lakehouse Inn
4.0 star property
9.8 out of 10, Exceptional, (228)
"Excellent place and location in the Berkshires."
The price is AED 547
AED 642 total
includes taxes & fees
16 Nov - 17 Nov
Lakehouse Inn
The Morgan State House
Outdoor dining
The Morgan State House
3.5 star property
9.2 out of 10, Wonderful, (488)
"Great property in prime location. Highly recommend"
The price is AED 527
AED 569 total
includes taxes & fees
30 Nov - 1 Dec
The Morgan State House
Chambery Inn
Front of property
Chambery Inn
3.0 star property
9.6 out of 10, Exceptional, (359)
"Lovely, unique property with huge rooms! Such a fun place to stay. "
The price is AED 698
AED 779 total
includes taxes & fees
17 Nov - 18 Nov
Chambery Inn
Whistler's Inn Bed & Breakfast
Interior
Whistler's Inn Bed & Breakfast
3.5 star property
7.8 out of 10, Good, (471)
"This bed and breakfast is a true gem, set in a beautifully preserved 1836 mansion. The rooms feature herringbone wood floors, diamond-pane windows, and soaring 11-inch ceilings, creating an atmosphere that feels both magical and timeless. With its charming, historic details and exceptionally friendly owners, staying here is like stepping into an enchanting, old-world retreat."
The price is AED 509
AED 638 total
includes taxes & fees
18 Nov - 19 Nov
Whistler's Inn Bed & Breakfast
Shaker Mill Inn
Garden
Shaker Mill Inn
2.5 star property
9.6 out of 10, Exceptional, (399)
"This place is so comfortable and roomy. Perfect place for a quiet getaway. "
The price is AED 533
AED 584 total
includes taxes & fees
17 Nov - 18 Nov
Shaker Mill Inn
Gardner Farm Inn
Room
Gardner Farm Inn
3.5 star property
10.0 out of 10, Exceptional, (171)
"Friendly inn keeper, great breakfast, comfortable beds. Fun place to stay!"
The price is AED 598
AED 661 total
includes taxes & fees
17 Nov - 18 Nov
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, (79)
"Everything "
The price is AED 584
AED 631 total
includes taxes & fees
26 Nov - 27 Nov
Inn at Silver Maple Farm
Granville House
Room
Granville House
3.0 star property
10.0 out of 10, Exceptional, (76)
"The surroundings were quiet and peaceful. The hosts were welcoming and friendly. Wonderful people "
The price is AED 735
AED 821 total
includes taxes & fees
18 Nov - 19 Nov
Granville House
33 Main
Room
33 Main
4.0 star property
10.0 out of 10, Exceptional, (69)
"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 1,285
AED 1,436 total
includes taxes & fees
26 Nov - 27 Nov
33 Main
Brook Farm Inn
Front of property
Brook Farm Inn
3.5 star property
9.4 out of 10, Exceptional, (147)
"Very charming inn. The staff was very friendly and helpful."
The price is AED 713
AED 796 total
includes taxes & fees
26 Nov - 27 Nov
Brook Farm Inn
Devonfield Inn B&B
Room
Devonfield Inn B&B
4.0 star property
10.0 out of 10, Exceptional, (117)
"The Inn is very nice, however the room received was too small and was very limited for comfort. Breakfasts were great and the concert on Saturday was especially special. Would stay again if another room was available . "
The price is AED 988
AED 1,104 total
includes taxes & fees
17 Nov - 18 Nov
Devonfield Inn B&B
The Inn at Stockbridge
Exterior
The Inn at Stockbridge
4.0 star property
9.8 out of 10, Exceptional, (96)
"Well-run and elegant property. "
The Inn at Stockbridge
Eastgate Inn B&B
Front of property
Eastgate Inn B&B
2.5 star property
9.2 out of 10, Wonderful, (68)
"Lovely Inn and Innkeeper. The room was clean and cozy. There was hot coffee and breakfast in the morning including homemade breads and fruit. We will be back! "
Eastgate Inn B&B
Tanglewood Suites
Property grounds
Tanglewood Suites
2.5 star property
8.0 out of 10, Very Good, (15)
"Portion of hosts home, separate and available for rent. Heating system not efficient and took some work to sort out how to keep all areas of the unit comfortably heated. Beds clean and comfortable. Overall cleanliness was good. Bath facilities are an addition to existing structure and sufficient, but could use some TLC. Host is eager to please and pleasant to interact with. Listing indicates free breakfast for all guests. However, upon arrival, we were advised there is no winter offering of...
The price is AED 804
AED 804 total
includes taxes & fees
16 Nov - 17 Nov
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, (105)
"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
17 Nov - 18 Nov
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 3,673
AED 4,685 total
includes taxes & fees
16 Nov - 17 Nov
Romantic Boutique Hotel / Bed and Breakfast - Standard Queen Handicap Accessible
Romantic Boutique Hotel / Bed and Breakfast - Smallest Room in The Berkshires
Bathroom
Romantic Boutique Hotel / Bed and Breakfast - Smallest Room in The Berkshires
2.0 out of 10, (1)
"Never even met the inn keepers...no one is in sight...WiFi wouldn’t work...a/c in room would not stay on.....1 item only for breakfast- delivered to room- that has no table or chair- stood in the bathroom to eat!!!! Very expensive for what u get "
The price is AED 3,673
AED 4,685 total
includes taxes & fees
16 Nov - 17 Nov
Romantic Boutique Hotel / Bed and Breakfast - Smallest Room in The Berkshires
Inn at Kenmore Hall
Front of property
Inn at Kenmore Hall
3.0 star property
10.0 out of 10, Exceptional, (27)
"A wonderful experience……….breakfast overlooking the property, the beautiful flowers grown by the innkeepers, decorated to perfection, with owners there to make your stay as comfortable as possible! "
Inn at Kenmore Hall
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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Other property types in Old Chatham

Beautiful One-of-a Kind Estate! Pool, Gym, Trails! 100 per person for 8+guests!
Beautiful Bellavista Country Estate! Create Timeless Memories w/ Family/ Friends
Beautiful One-of-a Kind Estate! Pool, Gym, Trails! 100 per person for 8+guests!
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 One-of-a Kind Estate! Pool, Gym, Trails! 100 per person for 8+guests!
Vacation Village in the Berkshires
Lobby
Vacation Village in the Berkshires
3.0 star property
8.6 out of 10, Excellent, (1746)
"Love staying here "
The price is AED 620
AED 717 total
includes taxes & fees
16 Nov - 17 Nov
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Exterior
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, (919)
"Staff was friendly and helpful. The facility is a little run down, but it was clean. A lot was closed (ie. on site bar/restaurants) due to it being between seasons, which was disappointing. We used the hot tub, which was not very hot. We'd stay there again though. "
The price is AED 542
AED 594 total
includes taxes & fees
17 Nov - 18 Nov
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.
What are the best B&Bs in Old Chatham?
Here are some B&Bs in the surrounding area: The Cornell Inn, Lenox: 15.2 mi (24.5 km) from the heart of Old Chatham. Enjoy the free full breakfast and unique décor. Lakehouse Inn: 14 rooms. 17.3 mi (27.8 km) from the downtown core. Enjoy the free full breakfast and deli. The Morgan State House: 16 rooms. Situated 18.2 mi (29.2 km) from the heart of Old Chatham. Shaker Mill Inn: 9 rooms. 12.2 mi (19.7 km) from the heart of downtown.Brook Farm Inn: 15 rooms. Located 15.2 mi (24.5 km) from the core of Old Chatham. Enjoy the free cooked breakfast and outdoor pool.
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 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.