20 Best B&B in Chatham, NY - Bed and Breakfast from $173

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

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Our top choices for Chatham bed & breakfast

1. Inn at Silver Maple Farm

East Chatham

"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."

Jody

$179 nightly

Sep 17 - Sep 18

Total with taxes and fees

2. Shaker Mill Inn

West Stockbridge

Mervin

$163 nightly

Sep 21 - Sep 22

Total with taxes and fees

Suite, Private Bathroom (RedBird Suite) | View from room

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

Stockbridge

Philippe

$391 nightly

Oct 1 - Oct 2

Total with taxes and fees

Desk, laptop workspace, iron/ironing board (on request), WiFi (free)

4. Granville House

Housatonic

Nicole

$224 nightly

Sep 17 - Sep 18

Total with taxes and fees

5. The Cornell Inn, Lenox & The Berkshires

Lenox

Rosann

$212 nightly

Sep 17 - Sep 18

Total with taxes and fees

6. Whistler's Inn Bed & Breakfast

Lenox

Mary Anna

$155 nightly

Sep 22 - Sep 23

Total with taxes and fees

7. The Inn at Stockbridge

Stockbridge

Jodi

$409 nightly

Sep 17 - Sep 18

Total with taxes and fees

Deluxe Room, 1 King Bed, Ensuite (2nd Floor) | Premium bedding, desk, laptop workspace, blackout drapes

8. Changing Times Boutique Country Lodging

Craryville

Thomas

$200 nightly

Sep 21 - Sep 22

Total with taxes and fees

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Top Chatham Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"Beautiful view. Clean and comfortable. Great breakfast choices"

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

10/10 Excellent

"Everything was so smooth, from the detailed map and heads up of possible cell service interruptions, to the check in and check out process, housekeeping request, and the ease of communication via text. It was a perfect getaway, minimal interruptions, yet easy to reach with quick responses. Although I could tell there were other guests in cabins nearby because I would see parked cars, it was so quiet that I felt like I was truly there alone! They thought of everything as far as cookware, plates, cups for cold and hot drinks, and utensils. S’mores, snacks, water, coffee, tea, and use of firepit/firewood were all complimentary. There’s a fridge but no microwave which I was not expecting but useful to know. Bring seasoning if you plan to cook. Bring mosquito repellant. It was weird not having a sink in the bathroom but it wasn’t a big deal for me. Would definitely book again!"

The Red Lion Inn

8/10 Good

"Bedding and bed were lovely. excellent to have good lighting at sink as well as a magnified mirror! Often lacking in places we have stayed. AC had trouble cooling the room down until we turned it on full blast. too much ambient light from floodlight on property next door and from hall (I finally turned off hallway light which helped. ) Common areas and halls need some brightening up with fresh, lighter paint--seemed dingy. Was terribly frustrating trying to make the Nespresso machine work. We do not own one and there were NO INSTRUCTIONS. You should assume people do not know how to operate any appliances like that and should have a card with directions. We gave up and went to the Tavern where we had lovely coffee and breakfast. Also had a great dinner in Tavern after our arrival. The patch burrata salad was superb. As was our waitress."

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

10/10 Excellent

"I really love staying here. It’s no nonsense clean and i feel safe traveling as a woman alone… However they really need to step up their morning breakfast. I eat gluten free and they never have any. I’ve asked for ivermectin a month now and they just tell me they will mention it…."

Find out more about Chatham

Chatham B&B information

Number of reviews	1,570
Accommodation	40 B&B
Lowest Price	$173
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 $173 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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Room 1

Check prices for these dates

Our top choices for Chatham bed & breakfast

1. Inn at Silver Maple Farm

2. Shaker Mill Inn

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

4. Granville House

5. The Cornell Inn, Lenox & The Berkshires

6. Whistler's Inn Bed & Breakfast

7. The Inn at Stockbridge

8. Changing Times Boutique Country Lodging

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

10. Devonfield Inn B&B

11. Experience Timeless Elegance in The Edith Wharton Room!

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

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

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

15. Brook Farm Inn

16. Chambery Inn

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

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

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

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

Top Chatham Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Country Inn & Suites by Radisson, Downtown Albany New York

The Red Lion Inn

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Quality Inn Great Barrington

Hotel On North

The Whitlock

St. Charles Hotel

Find out more about Chatham

Chatham B&B information

Frequently asked questions

Explore a world of travel with Expedia

Book Chatham Bed & Breakfast

Check prices for these dates

Our top choices for Chatham bed & breakfast

1. Inn at Silver Maple Farm

2. Shaker Mill Inn

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

4. Granville House

5. The Cornell Inn, Lenox & The Berkshires

6. Whistler's Inn Bed & Breakfast

7. The Inn at Stockbridge

8. Changing Times Boutique Country Lodging

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

10. Devonfield Inn B&B

11. Experience Timeless Elegance in The Edith Wharton Room!

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

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

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

15. Brook Farm Inn

16. Chambery Inn

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

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

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

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

Top Chatham Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Find out more about Chatham

Chatham B&B information

Frequently asked questions

Explore a world of travel with Expedia