A city street with buildings, parked cars, and solar panels.

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Check prices for these dates

Next weekend
Sep 18 - Sep 20
In two weeks
Sep 25 - Sep 27
In one month
Oct 9 - Oct 11
In two months
Nov 6 - Nov 8

Our top choices for Chatham bed & breakfast

A red building with a sign reading "Shaker Mill Inn."

1. Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (471 reviews)
"Wonderful place to stay!"
United States
Mervin
$146 nightly
The price is $160
Sep 14 - Sep 15
Total with taxes and fees
Shaker Mill Inn
A snow-covered outdoor area with a patio, seating, and a covered dining area.

2. 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)
"The entire staff was amazing and the inn was beautiful, we will definitely be back"
United States
Edward
$168 nightly
The price is $187
Sep 14 - Sep 15
Total with taxes and fees
The Cornell Inn, Lenox & The Berkshires

3. Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (64 reviews)
"Perfect little b&b."
United States
Mark
$191 nightly
The price is $213
Sep 16 - Sep 17
Total with taxes and fees
Wilder House Berkshires
A garden with a white gazebo, a brick pathway, and various plants and flowers.

4. Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.0 out of 10, Very Good, (518 reviews)
"Whistler's Inn is a Gilded Era mansion, passed down in the family (modernised "
United States
Mary Anna
$177 nightly
The price is $198
Oct 1 - Oct 2
Total with taxes and fees
Whistler's Inn Bed & Breakfast
An aerial view of a large estate with multiple buildings, surrounded by dense greenery and trees.

5. Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (116 reviews)
"We had a very pleasant stay at this. Eautiful country property. Check in was smooth and instructions were easy to follow. Our room, in the main building was well appointed. The bed was super comfortable and the amenities were fine. Breakfast was great! Common areas were lovely and inviting, and the s’mores kits in the lobby were just the thing for an evening around the outdoor fire pit. Highly recommend for anyone seeking a serene country setting."
United States
Jody
$179 nightly
The price is $200
Sep 14 - Sep 15
Total with taxes and fees
Inn at Silver Maple Farm
A dining table with pastries, a coffee pot, and a vase of sunflowers.

6. 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
$224 nightly
The price is $250
Sep 13 - Sep 14
Total with taxes and fees
Granville House
A two-story building with a sign reading "Chambéry Inn".

7. Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (387 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 13 - Sep 14
Total with taxes and fees
Chambery Inn

8. The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.8 out of 10, Exceptional, (106 reviews)
"Lovely grounds, property.. room was lovely. Delicious breakfast friendly helpful owners and staff great location"
United States
Jodi
$396 nightly
The price is $442
Sep 14 - Sep 15
Total with taxes and fees
The Inn at Stockbridge
A large, two-story house with a well-maintained lawn and a fence.

9. Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (140 reviews)
"Excellent food and helpful staff"
United States
Richard
$409 nightly
The price is $457
Sep 13 - Sep 14
Total with taxes and fees
Devonfield Inn B&B
A two-story house with a brick entrance and a white facade.

10. 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, (117 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."
United States
Philippe
$358 nightly
The price is $399
Sep 28 - Sep 29
Total with taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
A porch with a white railing, a potted plant, and a view of a garden.

11. Cozy Carriage House room with a double bed and private balcony

Cozy Carriage House room with a double bed and private balcony
Lenox
$334 nightly
The price is $382
Sep 13 - Sep 14
Total with taxes and fees
Cozy Carriage House room with a double bed and private balcony
A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.

12. 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
$284 nightly
The price is $320
Sep 17 - Sep 18
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.

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

Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Lenox
$285 nightly
The price is $327
Sep 14 - Sep 15
Total with taxes and fees
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
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.

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

Elegant Carriage House room with a queen bed and private patio.
Lenox
$381 nightly
The price is $436
Sep 16 - Sep 17
Total with taxes and fees
Elegant Carriage House room with a queen bed and private patio.
A neatly made bed with a headboard, a bedside lamp, a framed painting, and a small bedside table with a tissue box.

15. Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
$346 nightly
The price is $397
Sep 21 - Sep 22
Total with taxes and fees
Experience Timeless Elegance in The Edith Wharton Room!
A wooden deck with Adirondack chairs and a small table, leading to a garden area with a swing set.

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

Historic Susan B. Anthony Room - Cozy & Charming Stay
Lenox
$398 nightly
The price is $456
Sep 11 - Sep 12
Total with taxes and fees
Historic Susan B. Anthony Room - Cozy & Charming Stay
A bedroom with a bed, a fireplace, a ceiling fan, and a door.

17. 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
$438 nightly
The price is $501
Sep 13 - Sep 14
Total with taxes and fees
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
A bedroom with a bed, a television, a fireplace, and a window.

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

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
Lenox
$470 nightly
The price is $525
Sep 13 - Sep 14
Total with taxes and fees
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
A modern living room with a sloped ceiling, a sofa, a coffee table, and a unique chandelier.

19. Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn

Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
Lenox
$502 nightly
The price is $575
Sep 14 - Sep 15
Total with taxes and fees
Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn
A modern living room with a sofa, a coffee table, and a fireplace.

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

Elegant suite with a king bed, fireplace, and kitchenette.
Lenox
$524 nightly
The price is $600
Sep 13 - Sep 14
Total with taxes and fees
Elegant suite with a king bed, fireplace, and kitchenette.
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

Comfort Inn Glenmont - Albany South

Comfort Inn Glenmont - Albany South

10/10 Excellent
"Newly remodeled and excellent professional staff."
deborah 1-night trip
Posted less than an hour ago
Comfort Inn Glenmont - Albany South

Find out more about Chatham

Chatham B&B information

Number of reviews
2,093
Accommodation
40 B&B
Lowest Price
$160
Highest Price
$600

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 $160 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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