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Check prices for these dates

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

Our top choices for Chatham bed & breakfast

An aerial view of a large estate with multiple buildings, surrounded by dense greenery and trees.

1. Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (117 reviews)
"Very nice hotel."
United States
Erdem
$244 nightly
The price is $273
Oct 26 - Oct 27
Total with taxes and fees
Inn at Silver Maple Farm
A red building with a sign reading "Shaker Mill Inn."

2. Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (476 reviews)
"Wonderful place to stay!"
United States
Mervin
$179 nightly
The price is $196
Oct 1 - Oct 2
Total with taxes and fees
Shaker Mill Inn
A snow-covered outdoor area with a patio, seating, and a covered dining area.

3. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,001 reviews)
"Convenient location for Tanglewood and other Berkshire sights. Nice complimentary breakfast and arrival cocktail."
United States
Rosann
$160 nightly
The price is $179
Oct 27 - Oct 28
Total with taxes and fees
The Cornell Inn, Lenox & The Berkshires
A dining table with pastries, a coffee pot, and a vase of sunflowers.

4. Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (106 reviews)
"Beautiful home with warm and friendly hosts. The rooms were tastefully designed, the bed was very comfortable and the large bathroom was luxurious. The breakfast was absolutely delicious. We will definitely stay again next time we are in Great Barrington. "
United States
Nicole
$275 nightly
The price is $307
Oct 12 - Oct 13
Total with taxes and fees
Granville House
A two-story house with a brick entrance and a white facade.

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

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (119 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."
United States
Philippe
$559 nightly
The price is $625
Oct 18 - Oct 19
Total with taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
A garden with a white gazebo, a brick pathway, and various plants and flowers.

6. Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very good, (519 reviews)
"Whistler's Inn is a Gilded Era mansion, passed down in the family (modernised "
United States
Mary Anna
$168 nightly
The price is $188
Sep 30 - Oct 1
Total with taxes and fees
Whistler's Inn Bed & Breakfast
A bedroom with a large mural of a waterfall, two bedside lamps, a bed with multiple pillows, and a nightstand with a lamp.

7. Changing Times Boutique Country Lodging

Changing Times Boutique Country Lodging
3.5 star property
Craryville
10.0 out of 10, Exceptional, (127 reviews)
"A great place to stay!"
United States
Thomas
$200 nightly
The price is $224
Sep 30 - Oct 1
Total with taxes and fees
Changing Times Boutique Country Lodging
Front of property

8. The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.6 out of 10, Exceptional, (107 reviews)
"Lovely grounds, property.. room was lovely. Delicious breakfast friendly helpful owners and staff great location"
United States
Jodi
$460 nightly
The price is $514
Sep 30 - Oct 1
Total with taxes and fees
The Inn at Stockbridge
A wooden deck with a table and chairs, surrounded by a metal railing, overlooking a lush green landscape with trees.

9. The Red Door B&B

The Red Door B&B
3.0 star property
Lee
10.0 out of 10, Exceptional, (5 reviews)
"Centrally located. Lovely hosts. Only three bedrooms so we got to know the other guests. The breakfasts were works of art as well as delicious."
United States
Anonymous traveler
$237 nightly
The price is $265
Oct 26 - Oct 27
Total with taxes and fees
The Red Door B&B
A neatly made bed with a headboard, a bedside lamp, a framed painting, and a small bedside table with a tissue box.

10. Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
$281 nightly
The price is $322
Oct 27 - Oct 28
Total with taxes and fees
Experience Timeless Elegance in The Edith Wharton Room!
A two-story building with a sign reading "Chambéry Inn".

11. Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (388 reviews)
"An absolutely perfect getaway spot! Beautiful rooms, great service, and an ideal location. Highly recommend and we will be going back."
United States
Alexandra
$300 nightly
The price is $335
Sep 30 - Oct 1
Total with taxes and fees
Chambery Inn
A large, two-story house with a well-maintained lawn and a fence.

12. Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (141 reviews)
"Wonderful location and hosts are amazing. Breakfast was great. Clean."
United States
Sebastien
$409 nightly
The price is $457
Oct 25 - Oct 26
Total with taxes and fees
Devonfield Inn B&B
A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.

13. Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.4 out of 10, Exceptional, (174 reviews)
"Breakfast was not only delicious, the room was sweet and bright and staff very attentive."
United States
Carrie
$237 nightly
The price is $268
Oct 18 - Oct 19
Total with taxes and fees
Brook Farm Inn
A well-appointed bedroom with a large bed, a bedside table, a chair, and a bathroom visible through an open door.

14. Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen

Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Lenox
$281 nightly
The price is $322
Oct 27 - Oct 28
Total with taxes and fees
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
A wooden deck with Adirondack chairs and a small table, leading to a garden area with a swing set.

15. Historic Susan B. Anthony Room - Cozy & Charming Stay

Historic Susan B. Anthony Room - Cozy & Charming Stay
Lenox
$417 nightly
The price is $477
Sep 30 - Oct 1
Total with taxes and fees
Historic Susan B. Anthony Room - Cozy & Charming Stay
A room with a dark green sofa, a small table with a vase of flowers, a desk with a lamp, and a window with curtains.

16. Elegant Carriage House room with a queen bed and private patio.

Elegant Carriage House room with a queen bed and private patio.
Lenox
$436 nightly
The price is $499
Oct 20 - Oct 21
Total with taxes and fees
Elegant Carriage House room with a queen bed and private patio.
A bedroom with a bed, a television, a fireplace, and a window.

17. "Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Lenox
$535 nightly
The price is $598
Sep 30 - Oct 1
Total with taxes and fees
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
A modern living room with a sofa, a coffee table, and a fireplace.

18. Elegant suite with a king bed, fireplace, and kitchenette.

Elegant suite with a king bed, fireplace, and kitchenette.
Lenox
$593 nightly
The price is $678
Sep 30 - Oct 1
Total with taxes and fees
Elegant suite with a king bed, fireplace, and kitchenette.
Interior detail

19. Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (67 reviews)
"Perfect little b&b."
United States
Mark
$206 nightly
The price is $231
Oct 25 - Oct 26
Total with taxes and fees
Wilder House Berkshires
A bedroom with a bed, a fireplace, a ceiling fan, and a door.

20. Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn

Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
Lenox
$471 nightly
The price is $540
Sep 30 - Oct 1
Total with taxes and fees
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
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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Top Chatham Hotel Reviews

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

8/10 Good
"Overall, the cabin was nice. Especially if you're only planning on staying a few days. But for the price you pay for 2 nights, they could have better utensils, pan, a few more cooking utensils and a kettle for the hot water. These are just a few inexpensive amenities that these places should all have! Because most people are probably cooking there own food nowadays either by choice or the fact that there's nothing close by. But aside from the kitchen issues, this was a very nice, enjoyable getaway. I would definitely recommend it to anyone who loves the outdoors!"
Joy 2-night trip
Posted 8 hours ago
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Find out more about Chatham

Chatham B&B information

Number of reviews
2,476
Accommodation
40 B&B
Lowest Price
$179
Highest Price
$678

Frequently asked questions

What is the nightly rate for a B&B in Chatham?
Prices for B&Bs in Chatham often vary, but you can find a great deal from $179 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Chatham B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a Bed & Breakfast in Chatham?
The best time to book a B&B in Chatham is during the summer months, particularly from June to August, when the town comes alive with visitors eager to experience its charming coastal beauty. This peak season offers warm weather, with temperatures typically ranging from the mid-60s to the low 80s Fahrenheit, making it ideal for outdoor activities such as beach days, biking, and exploring the picturesque streets lined with historic homes.

July stands out as the most popular month for travelers seeking a vibrant atmosphere filled with local events, festivals, and outdoor concerts. You'll find families enjoying the sandy beaches, while couples can take romantic strolls along the shore at sunset, creating unforgettable memories.

If you're looking for a more budget-friendly experience, consider visiting in late September or early October. During this time, the summer crowds have thinned, and you can still enjoy mild weather, particularly for enjoying scenic walks along the coastline or visiting local shops and galleries without the hustle and bustle.
What is the difference between a Chatham Bed & Breakfast and a hotel?
Every Chatham B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Chatham B&Bs.

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