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Check prices for these dates

Next weekend
May 9 - May 11
In two weeks
May 16 - May 18
In one month
May 30 - Jun 1
In two months
Jun 27 - Jun 29

Compare 29 B&B in Old Chatham with updated reviews, rates, and availability.

The Cornell Inn, Lenox & The Berkshires
Front of property

The Cornell Inn, Lenox & The Berkshires

3.0 star property
9.0 out of 10, Wonderful, (1001)
"Lovely, comfortable B&B with a nice feel. We plan to return."
The price is $200
includes taxes & fees
$179 per night
May 4 - May 5
The Cornell Inn, Lenox & The Berkshires
Lakehouse Inn
Aerial view

Lakehouse Inn

4.0 star property
9.6 out of 10, Exceptional, (257)
"Wonderful Location"
Lakehouse Inn
The Morgan State House
Terrace/patio

The Morgan State House

3.5 star property
9.2 out of 10, Wonderful, (506)
"Stunning rooms, very friendly staff"
The price is $208
includes taxes & fees
$192 per night
May 26 - May 27
The Morgan State House
Shaker Mill Inn
Garden

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (410)
"Nice"
Shaker Mill Inn
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (363)
"Chamberry Inn was a nice, quiet, relaxing stay. Enjoyed every second of it. The staff were kind and helpful. Would definitely stay again if I was in the area."
The price is $212
includes taxes & fees
$190 per night
May 11 - May 12
Chambery Inn
33 Main
Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi

33 Main

4.0 star property
10.0 out of 10, Exceptional, (70)
"Beautiful place. Everything was perfect and so pretty. Great location, too. Will definitely return. "
The price is $413
includes taxes & fees
$369 per night
May 8 - May 9
33 Main
Brook Farm Inn
Front of property

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (151)
"Very homy kind of Inn. Owner was very accommodative and friendly. Very safe place with great ambience. "
The price is $227
includes taxes & fees
$203 per night
May 3 - May 4
Brook Farm Inn
Devonfield Inn B&B
Front of property - evening/night

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (124)
"Very enjoyable comfortable stay"
The price is $300
includes taxes & fees
$269 per night
May 5 - May 6
Devonfield Inn B&B
Whistler's Inn Bed & Breakfast
Property grounds

Whistler's Inn Bed & Breakfast

3.5 star property
7.8 out of 10, Good, (471)
"Great historic inn loaded with interesting common areas and furnishings."
The price is $222
includes taxes & fees
$199 per night
May 7 - May 8
Whistler's Inn Bed & Breakfast
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Business center

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 star property
9.2 out of 10, Wonderful, (105)
"Great breakfast, friendly helpful staff, pretty yard, good location "
The price is $833
includes taxes & fees
$746 per night
May 15 - May 16
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Inn at Silver Maple Farm
Aerial view

Inn at Silver Maple Farm

3.0 star property
9.8 out of 10, Exceptional, (85)
"Everything about our stay in The Loft was wonderful! The hot breakfast each morning was incredible. The entire inn was very clean and well kept. We will definitely be back! "
The price is $172
includes taxes & fees
$159 per night
May 4 - May 5
Inn at Silver Maple Farm
Gardner Farm Inn
Property grounds

Gardner Farm Inn

3.5 star property
10.0 out of 10, Exceptional, (176)
"Friendly inn keeper, great breakfast, comfortable beds. Fun place to stay!"
The price is $191
includes taxes & fees
$172 per night
May 15 - May 16
Gardner Farm Inn
The Inn at Stockbridge
Exterior

The Inn at Stockbridge

4.0 star property
9.8 out of 10, Exceptional, (98)
"We we were in the Out of Africa room, set apart in a complex of 4 suites in a unit apart from the Inn itself. The room was uniquely created to feel like an escape to Africa, and heated by a lovely gas fireplace. The breakfast both mornings, delicious. A perfect getaway!"
The Inn at Stockbridge
Granville House
Interior detail

Granville House

3.0 star property
10.0 out of 10, Exceptional, (82)
"Beautiful rooms, wonderful hosts, been here several times and plan to come again. "
The price is $250
includes taxes & fees
$224 per night
May 4 - May 5
Granville House
Tanglewood Suites
2 Bedrooms 1 Bath | Premium bedding, iron/ironing board, free WiFi, bed sheets

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. "
The price is $269
includes taxes & fees
$269 per night
May 3 - May 4
Tanglewood Suites
Inn at Kenmore Hall
Lobby

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! "
The price is $466
includes taxes & fees
$425 per night
May 3 - May 4
Inn at Kenmore Hall
Eastgate Inn B&B
Porch

Eastgate Inn B&B

2.5 star property
9.2 out of 10, Wonderful, (68)
"Great host and enjoyable stay."
Eastgate Inn B&B
The Red Door B&B
Interior

The Red Door B&B

3.0 star property
10.0 out of 10, Exceptional, (5)
"We loved staying at this b&b. The owners were very accommodating, kind and helpful. Because of the pandemic, they only took us for the weekend. The breakfasts were above and beyond our expectations, simply fantastic. We highly recommend this beautiful place and we will be back for sure. "
The Red Door B&B
Berkshire Mountain House
Comfort Apartment, 1 Bedroom, Mountain View, Garden Area | Private kitchenette | Mini-fridge, paper towels

Berkshire Mountain House

3.0 star property
9.4 out of 10, Exceptional, (24)
"GORGEOUS Scenery and NICE place to stay !"
Berkshire Mountain House
Batterby House – Adults Only
Standard Room, 1 Queen Bed, Private Bathroom | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

Batterby House – Adults Only

3.5 star property
9.8 out of 10, Exceptional, (15)
"Great place to stay. Joe the owner is fantastic. "
Batterby House – Adults Only
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

5 STAR ESTATE w/ POOL, POND, ARCADE, GYM, TRAILS! 07/13/25 - 07/20/25 REDUCED!
Fridge, microwave, oven, stovetop

5 STAR ESTATE w/ POOL, POND, ARCADE, GYM, TRAILS! 07/13/25 - 07/20/25 REDUCED!

9.6 out of 10, Exceptional, (85)
"We had fun! Game room great! Spacious and comfortable. Never got to enjoy outdoors, so maybe another trip in the future!"
5 STAR ESTATE w/ POOL, POND, ARCADE, GYM, TRAILS! 07/13/25 - 07/20/25 REDUCED!
Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1802)
"The property was clean and the staff very accommodated."
The price is $127
includes taxes & fees
$114 per night
May 18 - May 19
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, (928)
"Staff was exceptionally helpful and friendly."
The price is $140
includes taxes & fees
$125 per night
May 8 - May 9
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 & 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. Chambery Inn: 9 rooms. Situated 18.3 mi (29.4 km) from the heart of Old Chatham. Enjoy the private yard and deli. Whistler’s Inn Bed & Breakfast: 14 rooms. 15.2 mi (24.5 km) from the heart of downtown. Enjoy the private yard and unique décor. 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 The Mac-Haydn Theatre 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.