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Check prices for these dates

Next weekend
24 Jan - 26 Jan
In two weeks
31 Jan - 2 Feb
In one month
14 Feb - 16 Feb
In two months
14 Mar - 16 Mar

Compare 32 B&B in Chatham with updated reviews, rates, and availability.

The Cornell Inn, Lenox
Exterior

The Cornell Inn, Lenox

3.0 star property
9.0 out of 10, Wonderful, (1002)
"My room was adorable...completely charming and well appointed. I appreciated the phone call with detailed late check-in instructions and when I arrived the property manager walked me to my room. Breakfast was lovely and the staff very friendly. Town a is an easy walk."
The price is AED 448
AED 526 total
includes taxes & fees
23 Jan - 24 Jan
The Cornell Inn, Lenox
Lakehouse Inn
Lake

Lakehouse Inn

4.0 star property
9.8 out of 10, Exceptional, (239)
"Amazing breakfast!"
The price is AED 514
AED 603 total
includes taxes & fees
24 Jan - 25 Jan
Lakehouse Inn
Wilder House Berkshires
Breakfast meal

Wilder House Berkshires

2.0 star property
10.0 out of 10, Exceptional, (13)
"I had a wonderful stay here! I felt very safe and very clean, the room smelled so nice and the bed was very comfortable. The floors are a bit creaky but it just comes with the character of the house. It’s such a great vibe, beautifully decorated and the snacks and coffee are great"
The price is AED 498
AED 556 total
includes taxes & fees
23 Jan - 24 Jan
Wilder House Berkshires
Chambery Inn
Front of property

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (362)
"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 AED 698
AED 779 total
includes taxes & fees
30 Jan - 31 Jan
Chambery Inn
Granville House
Room

Granville House

3.0 star property
10.0 out of 10, Exceptional, (81)
"Lovely place with lovely hosts. The property is eclectic and wonderfully decorated with a very cool common area. Highly recommend "
The price is AED 826
AED 923 total
includes taxes & fees
26 Jan - 27 Jan
Granville House
Shaker Mill Inn
Garden

Shaker Mill Inn

2.5 star property
9.6 out of 10, Exceptional, (406)
"Beautiful inn. It was nice and quiet, exactly what I needed. "
The price is AED 386
AED 423 total
includes taxes & fees
21 Jan - 22 Jan
Shaker Mill Inn
Devonfield Inn B&B
Room

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (121)
"Great location "
The price is AED 988
AED 1,104 total
includes taxes & fees
27 Jan - 28 Jan
Devonfield Inn B&B
Brook Farm Inn
Front of property

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (149)
"Loves that they had en EV charger for me to charge while we were “home”. Beautiful location and house. Welcoming hospitality that was very refreshing. Thank you. "
The price is AED 738
AED 825 total
includes taxes & fees
23 Jan - 24 Jan
Brook Farm Inn
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 1,337
AED 1,493 total
includes taxes & fees
26 Jan - 27 Jan
33 Main
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
20 Jan - 21 Jan
Tanglewood Suites
Inn at Silver Maple Farm
Front of property

Inn at Silver Maple Farm

3.0 star property
9.8 out of 10, Exceptional, (80)
"Everything "
The price is AED 511
AED 551 total
includes taxes & fees
21 Jan - 22 Jan
Inn at Silver Maple Farm
The Inn at Stockbridge
Exterior

The Inn at Stockbridge

4.0 star property
9.8 out of 10, Exceptional, (97)
"Very enjoyable stat."
The Inn at Stockbridge
Whistler's Inn Bed & Breakfast
Interior

Whistler's Inn Bed & Breakfast

3.5 star property
7.8 out of 10, Good, (471)
"I liked that it is an older style bed and breakfast place. You could say "classy" or "vintage". It reminded me of places where I would visit with family when I was a child. I received a personal welcome and orientation to the property. Breakfast was nice and cooked options were available for me to choose. Another guest in the dining room at breakfast was also enjoying the visit and it was natural to strike up a conversation and get to know each other. It was a more personal kind of stay than...
Whistler's Inn Bed & Breakfast
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 1,559
AED 1,885 total
includes taxes & fees
20 Jan - 21 Jan
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Changing Times Boutique Country Lodging
Front of property

Changing Times Boutique Country Lodging

3.5 star property
10.0 out of 10, Exceptional, (93)
"The stay was great. The host baked delicious muffins for breakfast and everything was clean "
The price is AED 551
AED 595 total
includes taxes & fees
23 Jan - 24 Jan
Changing Times Boutique Country Lodging
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
24 Jan - 25 Jan
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
24 Jan - 25 Jan
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! "
The price is AED 1,561
AED 1,712 total
includes taxes & fees
20 Jan - 21 Jan
Inn at Kenmore Hall
Romantic Boutique Hotel / B&B - Deluxe Firespa Suite
Room

Romantic Boutique Hotel / B&B - Deluxe Firespa Suite

10.0 out of 10, Exceptional, (4)
"The property was a converted parochial school The rooms were old class rooms. Very spacious and extremely comfortable. Lots to do in the area or like we did just relax . We would recommend the inn for a great summer getaway . Community theater is a big attraction although not open yet Enjoy"
The price is AED 3,673
AED 4,685 total
includes taxes & fees
20 Jan - 21 Jan
Romantic Boutique Hotel / B&B - Deluxe Firespa Suite
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 Chatham

Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1756)
"Room was right across from the pool. Beautiful view of the mountain five min drive to the base. Beautiful pool and outdoor jacuzzi. Had an amazing stay! Cant wait to go back!"
The price is AED 689
AED 792 total
includes taxes & fees
20 Jan - 21 Jan
Vacation Village in the Berkshires
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Welcome to The Freeman Berkshires

The Freeman - Newly Renovated 14K SF Estate on 40 Acres

10.0 out of 10, Exceptional, (32)
"We had such a lovely time at this property! The space is gorgeous and the outside is perfect for walking around and exploring with the dogs. We had 18 people staying overnight and we all fit well (with the addition of some curtains for privacy) and had our own space to hide away in when needed. It was stocked with pretty much everything we needed, including firewood, glass vases for wedding decorations, tons of dishware, throw blankets, etc. Our group made wonderful memories here - thank you!"
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (234)
"Very lovely place to stay. Everything was clean and the owner made everything simple."
The price is AED 551
AED 837 total
includes taxes & fees
21 Jan - 22 Jan
Berkshire Village Carriage House - Super Private!!
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 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: 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. Chambery Inn: 9 rooms. Situated 17.9 mi (28.9 km) from the heart of Chatham. Enjoy the private yard and deli. Shaker Mill Inn: 9 rooms. 11.7 mi (18.8 km) from the heart of downtown.Brook Farm Inn: 15 rooms. Located 15.6 mi (25.1 km) from the core of Chatham. Enjoy the free cooked breakfast and outdoor pool.
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. Kinderhook Lake and Queechy Lake 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.