Book Chatham Bed & Breakfast

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Check prices for these dates

Next weekend
Nov 14 - Nov 16
In two weeks
Nov 21 - Nov 23
In one month
Dec 5 - Dec 7
In two months
Jan 2 - Jan 4

B&B in Chatham

Front of property
Chambery Inn

Chambery Inn

3.0 star property
Lee
9.6 out of 10, Exceptional, (372)
"We LOVED our mini getaway at the Chambery Inn. The room was gorgeous, spacious, and very comfortable. The fireplace couldn't have been easier to operate. The jetted tubs were divine with plenty of hot water the towel warmer was a nice bonus. The room was fully stocked with glassware and a corkscrew which was appreciated. We look forward to coming back"
United States
Samuel
$190 nightly
The price is $212
Nov 9 - Nov 10
Total with taxes and fees
Chambery Inn
Porch
Lakehouse Inn

Lakehouse Inn

4.0 star property
Lee
9.6 out of 10, Exceptional, (287)
"Great Views & Hospitality"
United States
Gerald
$179 nightly
The price is $200
Nov 13 - Nov 14
Total with taxes and fees
Lakehouse Inn
Wilder House Berkshires Room 3 | 1 bedroom, premium bedding, individually decorated
Wilder House Berkshires

Wilder House Berkshires

2.0 star property
Sheffield
9.8 out of 10, Exceptional, (37)
"Highly recommend this beautiful bed & breakfast! The room was wonderful and overlooked the property, the breakfast was delicious, and the hospitality was amazing. I had a fantastic stay, and will definitely stay at The Wilder House again when I'm in the area."
United States
Marina
$155 nightly
The price is $174
Nov 17 - Nov 18
Total with taxes and fees
Wilder House Berkshires
Front of property
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 star property
Lenox
9.0 out of 10, Wonderful, (1000)
"Honestly I just enjoyed being able to relax Play some games in the cute pub and the breakfast was yummy and stuff was inviting and so helpful "
United States
Sandra
$164 nightly
The price is $183
Nov 9 - Nov 10
Total with taxes and fees
The Cornell Inn, Lenox & The Berkshires
Exterior
The Inn at Stockbridge

The Inn at Stockbridge

4.0 star property
Lee
9.8 out of 10, Exceptional, (98)
"A first class little inn"
United States
Philip
$289 nightly
The price is $322
Nov 9 - Nov 10
Total with taxes and fees
The Inn at Stockbridge
Garden
Shaker Mill Inn

Shaker Mill Inn

2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (433)
"Nice place, easy check in"
United States
Robert
$102 nightly
The price is $112
Nov 12 - Nov 13
Total with taxes and fees
Shaker Mill Inn
Front of property - evening/night
Devonfield Inn B&B

Devonfield Inn B&B

4.0 star property
Lee
10.0 out of 10, Exceptional, (133)
"The inn has an excellent location and amenities."
United States
Christopher
$369 nightly
The price is $412
Nov 21 - Nov 22
Total with taxes and fees
Devonfield Inn B&B
Luxury Room, 1 King Bed, Bathtub | Premium bedding, individually decorated, iron/ironing board, free WiFi
33 Main

33 Main

4.0 star property
Lenox
10.0 out of 10, Exceptional, (74)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
$445 nightly
The price is $498
Dec 7 - Dec 8
Total with taxes and fees
33 Main
Property grounds
Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast

3.5 star property
Lenox
7.8 out of 10, Good, (500)
"We had a wonderful stay. We are so glad we chose this inn. The location is superb…a five-minute walk to the center of Lenox! It is a beautiful inn with a lot of charm, and the staff is warm and friendly. We loved our large room too! Definitely plan on staying here again when we come back to the area! "
United States
Itzhak
$239 nightly
The price is $267
Nov 9 - Nov 10
Total with taxes and fees
Whistler's Inn Bed & Breakfast
3 bedrooms, bed sheets
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen

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

Lenox
$239 nightly
The price is $306
Nov 9 - Nov 10
Total with taxes and fees
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Individually decorated, individually furnished, desk, laptop workspace
Granville House

Granville House

3.0 star property
Housatonic
10.0 out of 10, Exceptional, (86)
"Wonderful! Will stay again!"
Canada
Rebecca
$225 nightly
The price is $251
Nov 10 - Nov 11
Total with taxes and fees
Granville House
2 Bedrooms 1 Bath | 1 bedroom, premium bedding, iron/ironing board, free WiFi
Tanglewood Suites

Tanglewood Suites

2.5 star property
Stockbridge
6.4 out of 10, (22)
"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...
United States
Amanda
$219 nightly
The price is $219
Dec 1 - Dec 2
Total with taxes and fees
Tanglewood Suites
Business center
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, (109)
"Wonderful! Owner/host Diane was friendly, helpful, knowledgeable. Breakfasts awesome with great choices daily. Place was spotless, cozy and classic. So glad we stayed there. "
United States
Robert
$414 nightly
The price is $462
Nov 27 - Nov 28
Total with taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Loft, Private Bathroom (Skylight Loft) | 1 bedroom, premium bedding, iron/ironing board, rollaway beds
Brook Farm Inn

Brook Farm Inn

3.5 star property
Lenox
9.4 out of 10, Exceptional, (162)
"This is our second stay at the Brook Farm Inn and we enjoyed it just as much as our first stay! Maureen and Joe are fantastic inn keepers. They are polite, full of knowledge and provide a wonderful experience. Our room was cozy and comfortable. The breakfast was delicious. We couldn’t ask for a better weekend away! "
United States
John
$165 nightly
The price is $184
Nov 12 - Nov 13
Total with taxes and fees
Brook Farm Inn
1 bedroom, WiFi, bed sheets, wheelchair access
Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!

Lenox
$239 nightly
The price is $306
Nov 9 - Nov 10
Total with taxes and fees
Experience Timeless Elegance in The Edith Wharton Room!
1 bedroom, WiFi, bed sheets
Elegant Carriage House room with a queen bed and private patio.

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

Lenox
$257 nightly
The price is $326
Nov 10 - Nov 11
Total with taxes and fees
Elegant Carriage House room with a queen bed and private patio.
1 bedroom, bed sheets
Cozy Carriage House room with a double bed and private balcony

Cozy Carriage House room with a double bed and private balcony

Lenox
$276 nightly
The price is $347
Nov 9 - Nov 10
Total with taxes and fees
Cozy Carriage House room with a double bed and private balcony
Terrace/patio
Historic Susan B. Anthony Room - Cozy & Charming Stay

Historic Susan B. Anthony Room - Cozy & Charming Stay

Lenox
$294 nightly
The price is $368
Nov 9 - Nov 10
Total with taxes and fees
Historic Susan B. Anthony Room - Cozy & Charming Stay
Fireplace
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
$376 nightly
The price is $459
Nov 11 - Nov 12
Total with taxes and fees
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn
1 bedroom, bed sheets
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

Lenox
$413 nightly
The price is $500
Nov 9 - Nov 10
Total with taxes and fees
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace
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

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent
"Solid location, great room, good breakfast. Fair Price. Been 3 different times and look forward to returning again "
Jamie 2-night trip
Posted 15 hours ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Find out more about Chatham

Chatham B&B information

Number of reviews
2,667
Accommodation
40 B&B
Lowest Price
$112
Highest Price
$500

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 $112 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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