20 Best B&B in Chatham, NY - Bed and Breakfast from $159

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

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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

East Chatham

Linda

$154 nightly

Dec 6 - Dec 7

Total with taxes and fees

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

2. Shaker Mill Inn

West Stockbridge

Mahadeva

$145 nightly

Nov 15 - Nov 16

Total with taxes and fees

A snow-covered outdoor area with a patio, seating, and a covered dining area.

3. The Cornell Inn, Lenox & The Berkshires

Lenox

judith

$178 nightly

Nov 15 - Nov 16

Total with taxes and fees

A dining table with pastries, a coffee pot, and a vase of sunflowers.

4. Granville House

Housatonic

Cynthia

$229 nightly

Nov 20 - Nov 21

Total with taxes and fees

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

Stockbridge

Philippe

$414 nightly

Nov 28 - Nov 29

Total with taxes and fees

6. The Inn at Stockbridge

Stockbridge

Kimberly

$229 nightly

Nov 15 - Nov 16

Total with taxes and fees

7. Wilder House Berkshires

Sheffield

Liliana

$189 nightly

Nov 17 - Nov 18

Total with taxes and fees

A bedroom with a large mural of a waterfall, two bedside lamps, a bed with multiple pillows, and a nightstand with a lamp.

8. Changing Times Boutique Country Lodging

Craryville

Thomas

$200 nightly

Nov 16 - Nov 17

Total with taxes and fees

A two-story building with a sign reading "Chambéry Inn".

9. Chambery Inn

Lee

Alexandra

$194 nightly

Nov 22 - Nov 23

Total with taxes and fees

A spacious living room with a fireplace, a dining area with a table and chairs, and large windows offering a view of the outdoors.

10. Devonfield Inn B&B

Lee

Sebastien

$369 nightly

Nov 16 - Nov 17

Total with taxes and fees

A neatly made bed with a headboard, a bedside lamp, a framed painting, and a small bedside table with a tissue box.

11. Experience Timeless Elegance in The Edith Wharton Room!

Lenox

$295 nightly

Nov 15 - Nov 16

Total with taxes and fees

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.

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

Lenox

$312 nightly

Nov 15 - Nov 16

Total with taxes and fees

A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.

13. Brook Farm Inn

Lenox

Carrie

$170 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

Lenox

$295 nightly

Nov 15 - Nov 16

Total with taxes and fees

A porch with a white railing, a potted plant, and a view of a garden.

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

Lenox

$329 nightly

Nov 15 - Nov 16

Total with taxes and fees

A bedroom with a bed, a fireplace, a ceiling fan, and a door.

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

Lenox

$425 nightly

Nov 17 - Nov 18

Total with taxes and fees

A wooden deck with Adirondack chairs and a small table, leading to a garden area with a swing set.

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

Lenox

$347 nightly

Nov 15 - Nov 16

Total with taxes and fees

A bedroom with a bed, a television, a fireplace, and a window.

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

Lenox

$460 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

Lenox

$512 nightly

Nov 15 - Nov 16

Total with taxes and fees

A modern living room with a sofa, a coffee table, and a fireplace.

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

Lenox

$512 nightly

Nov 15 - Nov 16

Total with taxes and fees

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Top Chatham Hotel Reviews

Quality Inn Great Barrington

8/10 Good

"Convenient location. 24 hour front desk"

Vacation Village in the Berkshires

8/10 Good

"The staff were super kind and helpful, however there were some concerns. The indoor pool was closed because there were too many pool chemicals in it, which was tough since that was a primary reason for choosing this property. This meant that the families with children were relegated to the hot tub and pool table areas because the arcade area costs money to play. The staff were kind, but the lack of swimming pool and the abundance of bored children arouns changed the atmosphere. "Too many chemicals" in the pool seems like an avoidable problem. The room was lovely, but we had to take out our own trash and wash our own dishes which wasn't quite "vacation vibes" since this was listed as a hotel. Loved the gas fireplace, but it does run on by using a dial on the wall that makes a ticking sound constantly. The walls were super thin, so I could see where that would be a challenge during busy season. Honestly, I feel like the whole property would feel kind of feral during busy season with so many "first come, first served" elements, but the mountain views were gorgeous and the staff were very very kind and helpful. Also, the room was beautifully clean and cozy, which is always a nice feeling."

Find out more about Chatham

Chatham B&B information

Number of reviews	1,733
Accommodation	40 B&B
Lowest Price	$159
Highest Price	$586

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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Our top choices for Chatham bed & breakfast

1. Inn at Silver Maple Farm

2. Shaker Mill Inn

3. The Cornell Inn, Lenox & The Berkshires

4. Granville House

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

6. The Inn at Stockbridge

7. Wilder House Berkshires

8. Changing Times Boutique Country Lodging

9. Chambery Inn

10. Devonfield Inn B&B

11. Experience Timeless Elegance in The Edith Wharton Room!

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

13. Brook Farm Inn

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

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

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

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

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

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

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

Top Chatham Hotel Reviews

Quality Inn Great Barrington

The Yankee Inn

Vacation Village in the Berkshires

The Red Lion Inn

Hotel On North

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

The Whitlock

Find out more about Chatham

Chatham B&B information

Frequently asked questions

Explore a world of travel with Expedia

Book Chatham Bed & Breakfast

Bundle & Save

OneKeyCash

Upfront pricing

Check prices for these dates

Our top choices for Chatham bed & breakfast

1. Inn at Silver Maple Farm

2. Shaker Mill Inn

3. The Cornell Inn, Lenox & The Berkshires

4. Granville House

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

6. The Inn at Stockbridge

7. Wilder House Berkshires

8. Changing Times Boutique Country Lodging

9. Chambery Inn

10. Devonfield Inn B&B

11. Experience Timeless Elegance in The Edith Wharton Room!

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

13. Brook Farm Inn

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

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

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

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

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

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

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

Top Chatham Hotel Reviews

Quality Inn Great Barrington

Find out more about Chatham

Chatham B&B information

Frequently asked questions

Explore a world of travel with Expedia