Search B&B in Chatham

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Compare 34 B&B in Chatham with updated reviews, rates, and availability.

The Cornell Inn, Lenox
3.0 star property
8.8 out of 10, Excellent, (1001)
"Pleasant staff. Complimentary wine in the room and sangria at the bar are a nice touch. Very glad we found this gem "
The price is SAR 473
SAR 550 total
includes taxes & fees
24 Jun - 25 Jun
The Cornell Inn, Lenox
Lakehouse Inn
4.0 star property
9.6 out of 10, Exceptional, (164)
"The Inn's location has a million dollar lakeview, free breakfasts and free kayaking. This setting is great for mental health. The staff was welcoming, friendly and helpful."
The price is SAR 563
SAR 654 total
includes taxes & fees
23 Jun - 24 Jun
Lakehouse Inn
Shaker Mill Inn
2.5 star property
9.6 out of 10, Exceptional, (386)
"Wonderful place to stay in western Massachusetts."
The price is SAR 847
SAR 929 total
includes taxes & fees
25 Jun - 26 Jun
Shaker Mill Inn
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Brook Farm Inn
3.5 star property
9.4 out of 10, Exceptional, (138)
"Breakfast was nice but our room was crooked. We kept listing into a dip in the room. I guess character counts with an old inn but in a word, it was ‘meh’."
The price is SAR 754
SAR 842 total
includes taxes & fees
23 Jun - 24 Jun
Brook Farm Inn
Inn at Silver Maple Farm
3.0 star property
9.8 out of 10, Exceptional, (69)
"The room and common areas were very pleasant and clean. "
The price is SAR 709
SAR 766 total
includes taxes & fees
27 Jun - 28 Jun
Inn at Silver Maple Farm
Whistler's Inn Bed & Breakfast
3.5 star property
7.8 out of 10, Good, (435)
"My room was tiny but the Inn hostess was very accommodating/hospitable. The house was reminiscent of an English country BnB. Lots of stories have clearly played out in this old estate house. Right across street from lovely church and cemetery filled with pre-revolutionary war souls and a short walk up the hill from Lenox Main Street. "
The price is SAR 645
SAR 720 total
includes taxes & fees
23 Jun - 24 Jun
Whistler's Inn Bed & Breakfast
33 Main
4.0 star property
10.0 out of 10, Exceptional, (63)
"I love the fact that it only had eight rooms they had happy hour from 5 to 6 PM so we are able to meet other people at the hotel. I love the rooms and the cleanliness and especially the breakfast they were amazing and delicious!! I would recommend this hotel highly!"
The price is SAR 1,759
SAR 1,965 total
includes taxes & fees
24 Jun - 25 Jun
33 Main
Chambery Inn
3.0 star property
9.6 out of 10, Exceptional, (356)
"Amazing place.."
The price is SAR 1,125
SAR 1,257 total
includes taxes & fees
23 Jun - 24 Jun
Chambery Inn
The Barrington
4.0 star property
9.6 out of 10, Exceptional, (99)
"The Barrington is a wonderful bed and breakfast right in the heart of Great Barrington. The service was excellent and very friendly."
The price is SAR 1,219
SAR 1,362 total
includes taxes & fees
23 Jun - 24 Jun
The Barrington
Changing Times Boutique Country Lodging
3.5 star property
10.0 out of 10, Exceptional, (84)
"It was comfortable"
The price is SAR 563
SAR 608 total
includes taxes & fees
24 Jun - 25 Jun
Changing Times Boutique Country Lodging
Devonfield Inn B&B
4.0 star property
10.0 out of 10, Exceptional, (106)
"The classic character of the Inn is so beautiful and adds to the whole experience!"
The price is SAR 1,497
SAR 1,672 total
includes taxes & fees
27 Jun - 28 Jun
Devonfield Inn B&B
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
9.2 out of 10, Wonderful, (101)
"The b&b was so beautiful and unique! The area was serene. The host was very sweet and accommodating."
The price is SAR 1,796
SAR 2,173 total
includes taxes & fees
27 Jun - 28 Jun
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Granville House
3.0 star property
10.0 out of 10, Exceptional, (71)
"Loved it. "
The price is SAR 1,032
SAR 1,152 total
includes taxes & fees
1 Jul - 2 Jul
Granville House
The Inn at Stockbridge
4.0 star property
9.6 out of 10, Exceptional, (94)
"Fantastic!"
The Inn at Stockbridge
Inn at Kenmore Hall
3.0 star property
10.0 out of 10, Exceptional, (25)
"Gorgeous grounds, welcoming home atmosphere. wonderful breakfast and staff that made it feel like home - only better! "
Inn at Kenmore Hall
Private Guest Area in Plant Based Bed and Breakfast
10.0 out of 10, Exceptional, (5)
"Adorable, beautifully decorated, super clean house. Friendly, attentive owner., sweet dog and a delicious breakfast - what more could you ask. Our room was lovely and exactly as pictured. Would definitely return! Thanks Emily!"
Private Guest Area in Plant Based Bed and Breakfast
Berkshire Mountain House
3.0 star property
9.4 out of 10, Exceptional, (22)
"GORGEOUS Scenery and NICE place to stay !"
Berkshire Mountain House
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
1735 Stone Farmhouse
4.0 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
9.8 out of 10, Exceptional, (10)
"We would return to the inn again. Bob was wonderful and very, very accommodating:-)"
Romantic Boutique Hotel / Bed and Breakfast - Standard Queen Handicap Accessible
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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.

Other property types in Chatham

Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, (860)
"This is a sweet property. I visited in the summer. The dining options were great. The country store is awesome. I love how the rooms are suites. They feel like small apartments. I like that they have kitchens. The bed was comfortable. The ac is loud but at least it works well and it drowns out other noises. I needed a late check out and they were very cool about it. They let me hang out at the pool and then shower at the spa because I was like of stuck there several hours after check out time....
The price is SAR 596
SAR 654 total
includes taxes & fees
23 Jun - 24 Jun
Jiminy Peak Mountain Resort
Micosta Leisure Inn
3.0 star property
9.0 out of 10, Wonderful, (74)
"Only stayed one night, but would have loved to stay for one week! Beautiful grounds and our host, Steven, was super welcoming and greeted us once we arrived to check us in. Local cat also greeted us once we arrived (if you’re driving, check under your car before backing out!)"
The price is SAR 470
SAR 528 total
includes taxes & fees
23 Jun - 24 Jun
Micosta Leisure Inn
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, (29)
"We had a great time at The Freeman! The little touches like fresh fruit and a welcome basket made it even more special for our family getaway."
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
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.
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. Art Omi International Arts Center - Fields Sculpture Park and Martin Van Buren National Historic Site 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.

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