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

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Check prices for these dates

Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10

Our top choices for Chatham bed & breakfast

A spacious living room with high ceilings, exposed wooden beams, a fireplace, and comfortable seating.

1. Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (118 reviews)
"Perfect location for hiking, hanging out and Tanglewood Comfortable and charming common space and cozy nicely decorated rooms Generous breakfast and snacks throughout the day We’ll be back"
United States
Linda
$164 nightly
The price is $184
Dec 3 - Dec 4
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, (483 reviews)
"Loved the location, fireplace and vibe"
United States
Mahadeva
$145 nightly
The price is $159
Nov 12 - Nov 13
Total with taxes and fees
Shaker Mill Inn
A two-story house with a brick entrance and a white facade.

3. 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
9.4 out of 10, Exceptional, (120 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."
United States
Philippe
$414 nightly
The price is $462
Nov 26 - Nov 27
Total with taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
A dining area with a round table and four chairs, a radiator, and a window with a view of greenery.

4. Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (110 reviews)
"We loved everything about Granville House, especially the innkeepers! Wonderful atmosphere and excellent food! It was definitely the highlight of our trip to New England."
United States
Cynthia
$254 nightly
The price is $284
Nov 20 - Nov 21
Total with taxes and fees
Granville House
A snow-covered outdoor area with a patio, seating, and a covered dining area.

5. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.4 out of 10, Exceptional, (1,003 reviews)
"Lovely room, comfortable bed and a nice breakfast."
United Kingdom
judith
$178 nightly
The price is $198
Nov 10 - Nov 11
Total with taxes and fees
The Cornell Inn, Lenox & The Berkshires
A natural landscape with a pond surrounded by dense forest and various vegetation.

6. Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast
3.5 star property
Lenox
8.2 out of 10, Very good, (522 reviews)
"Delightful experience in a gilded age setting."
United States
George
$188 nightly
The price is $210
Nov 10 - Nov 11
Total with taxes and fees
Whistler's Inn Bed & Breakfast
Front of property

7. The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Stockbridge
9.6 out of 10, Exceptional, (110 reviews)
"Wonderful place… clean, cosy room, comfy bed, friendly staff, great breakfast. Delightful location near Norman Rockwell museum."
United States
Kimberly
$255 nightly
The price is $285
Nov 15 - Nov 16
Total with taxes and fees
The Inn at Stockbridge
A neatly made bed with a headboard, a bedside lamp, a framed painting, and a small bedside table with a tissue box.

8. Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!
Lenox
$286 nightly
The price is $328
Nov 10 - Nov 11
Total with taxes and fees
Experience Timeless Elegance in The Edith Wharton Room!
A bedroom with a large mural of a waterfall, two bedside lamps, a bed with multiple pillows, and a nightstand with a lamp.

9. Changing Times Boutique Country Lodging

Changing Times Boutique Country Lodging
3.5 star property
Craryville
10.0 out of 10, Exceptional, (128 reviews)
"A great place to stay!"
United States
Thomas
$200 nightly
The price is $224
Nov 10 - Nov 11
Total with taxes and fees
Changing Times Boutique Country Lodging
A porch with a white railing, a potted plant, and a view of a garden.

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

Cozy Carriage House room with a double bed and private balcony
Lenox
$319 nightly
The price is $366
Nov 15 - Nov 16
Total with taxes and fees
Cozy Carriage House room with a double bed and private balcony
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.

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

Elegant Carriage House room with a queen bed and private patio.
Lenox
$302 nightly
The price is $346
Nov 15 - Nov 16
Total with taxes and fees
Elegant Carriage House room with a queen bed and private patio.
A well-appointed bedroom with a large bed, a bedside table, a chair, and a bathroom visible through an open door.

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

Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Lenox
$286 nightly
The price is $328
Nov 10 - Nov 11
Total with taxes and fees
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
A spacious living room with a fireplace, a dining area with a table and chairs, and large windows offering a view of the outdoors.

13. 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
$369 nightly
The price is $412
Nov 13 - Nov 14
Total with taxes and fees
Devonfield Inn B&B
A wooden deck with Adirondack chairs and a small table, leading to a garden area with a swing set.

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

Historic Susan B. Anthony Room - Cozy & Charming Stay
Lenox
$335 nightly
The price is $384
Nov 10 - Nov 11
Total with taxes and fees
Historic Susan B. Anthony Room - Cozy & Charming Stay
A cozy living room with a fireplace, a sofa, a coffee table, and a bookshelf.

15. Brook Farm Inn

Brook Farm Inn
3.5 star property
Lenox
9.6 out of 10, Exceptional, (178 reviews)
"Breakfast was not only delicious, the room was sweet and bright and staff very attentive."
United States
Carrie
$165 nightly
The price is $187
Nov 11 - Nov 12
Total with taxes and fees
Brook Farm Inn
A crowded outdoor event with tents and people gathered in a grassy area.

16. Chambery Inn

Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (390 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
$201 nightly
The price is $225
Nov 11 - Nov 12
Total with taxes and fees
Chambery Inn
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
$413 nightly
The price is $474
Nov 12 - Nov 13
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
$445 nightly
The price is $498
Nov 10 - Nov 11
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
$495 nightly
The price is $568
Nov 15 - Nov 16
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
$495 nightly
The price is $568
Nov 10 - Nov 11
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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Stayed here on my trip to Thunder Mountain Bike Park. The service was very good. Great communication thru out the days up to my reservation. Got here check in was quick and easy. The room was exactly as it looked in the pictures. It was clean and well taken care of. Only thing that was a bummer was the pool and hot tub are being worked on so they weren't available but they did say you could use the amenities at another resort but it's about 25-30 mins away. That's why the service is four stars nothing against the how they stayed in communication with me. They did let me know ahead of time which was nice."
Anthony 3-night trip
Posted 1 hour ago
Berkshire Mountain Lodge

Find out more about Chatham

Chatham B&B information

Number of reviews
2,062
Accommodation
40 B&B
Lowest Price
$159
Highest Price
$568

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 $159 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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