Search B&B in Old Chatham

Plan, book, stay with confidence

Be picky

Search almost a million properties worldwide

Treat yourself

Change your mind

Book hotels with free cancellation

Compare 32 B&B in Old Chatham with updated reviews, rates, and availability.

"Loved every minute of our stay. The room was a bit small but the lovely staff, beautiful atmosphere, great location, yummy breakfast… more than compensated for this detail! "

SAR 617 total

includes taxes & fees

10 Jan - 11 Jan

"Great place "

SAR 537 total

includes taxes & fees

13 Jan - 14 Jan

"Great property in prime location. Highly recommend"

SAR 630 total

includes taxes & fees

6 Jan - 7 Jan

"Everything was amazing. It was truly an experience. "

SAR 797 total

includes taxes & fees

6 Jan - 7 Jan

"Beautiful rooms, wonderful hosts, been here several times and plan to come again. "

SAR 944 total

includes taxes & fees

26 Jan - 27 Jan

"Quaint "

SAR 433 total

includes taxes & fees

7 Jan - 8 Jan

"Great location "

SAR 1,086 total

includes taxes & fees

8 Jan - 9 Jan

"John, the host of the Inn, was in contact with us earlier in the day, to provide helpful information prior to our arrival. The property, inside and out, is very eclectic in its furnishings and decor. It was quite interesting seeing what was displayed throughout this spacious home! Many of the displayed items brought back memories :) which made for enjoyable conversation with the John along with the other guests. The May West room was spacious, clean, comfy, quiet and warm ; as was the...

SAR 729 total

includes taxes & fees

20 Jan - 21 Jan

"33 Main is the best of everything. We have stayed at the location twice and loved each experience. The breakfast is delicious, accommodations are beautifully curated, and it’s perfectly located in Lenox. Highly recommend and we will be back! "

SAR 1,527 total

includes taxes & fees

20 Jan - 21 Jan

"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...

SAR 822 total

includes taxes & fees

6 Jan - 7 Jan

"Loves that they had en EV charger for me to charge while we were “home”. Beautiful location and house. Welcoming hospitality that was very refreshing. Thank you. "

SAR 961 total

includes taxes & fees

7 Jan - 8 Jan

"Everything "

SAR 564 total

includes taxes & fees

6 Jan - 7 Jan

"Very enjoyable stat."

"I liked that it is an older style bed and breakfast place. You could say "classy" or "vintage". It reminded me of places where I would visit with family when I was a child. I received a personal welcome and orientation to the property. Breakfast was nice and cooked options were available for me to choose. Another guest in the dining room at breakfast was also enjoying the visit and it was natural to strike up a conversation and get to know each other. It was a more personal kind of stay than...

"The breakfast was one of the best I have ever had. They were fast and lots of choices. It had lots of baked goods. I got the chesdar omeltte and bacon and toast plus fruits in season lime melon etc. Its a lovely place it takes you back in time. The owner is very easy going and nuce and can answer most questions"

SAR 1,928 total

includes taxes & fees

6 Jan - 7 Jan

"1735 is an excellent little get-a-way, I booked it for my girlfriend’s birthday as a bed and breakfast and it did not disappoint. It’s nestled in a quiet area that disconnects you from the world yet is less than 20 minutes from Albany. The design, upkeep, and architecture is quite remarkable. All the finishing touches were well thought of and placed well. Seven, our host is excellent at his craft and exudes hospitality. From the moment we arrived we were welcomed with open arms. Seven was very...

"We would return to the inn again. Bob was wonderful and very, very accommodating:-)"

SAR 4,790 total

includes taxes & fees

6 Jan - 7 Jan

"Never even met the inn keepers...no one is in sight...WiFi wouldn’t work...a/c in room would not stay on.....1 item only for breakfast- delivered to room- that has no table or chair- stood in the bathroom to eat!!!! Very expensive for what u get "

SAR 4,790 total

includes taxes & fees

6 Jan - 7 Jan

"A wonderful experience……….breakfast overlooking the property, the beautiful flowers grown by the innkeepers, decorated to perfection, with owners there to make your stay as comfortable as possible! "

SAR 1,751 total

includes taxes & fees

6 Jan - 7 Jan

"The property was a converted parochial school The rooms were old class rooms. Very spacious and extremely comfortable. Lots to do in the area or like we did just relax . We would recommend the inn for a great summer getaway . Community theater is a big attraction although not open yet Enjoy"

SAR 4,769 total

includes taxes & fees

7 Jan - 8 Jan

Save an average of 15% on thousands of hotels when you're signed in

Other property types in Old Chatham

Beautiful Bellavista Country Estate!
Create Timeless Memories w/ Family/ Friends

"We had fun! Game room great! Spacious and comfortable. Never got to enjoy outdoors, so maybe another trip in the future!"

"So enjoyed this property and all the staff was always there to help in anyway!"

SAR 810 total

includes taxes & fees

6 Jan - 7 Jan

"It’s challenging to read the reviews and know what to expect for this hotel. One main reason for that is because each unit is owned by different owners. Some units may have been renovated more recently than other units. I booked 3 rooms. One unit had an old electric stove with coils while the other had a newer electric stove. 1 had a toaster oven while the others did not. We brought food to cook, but kept it simple because we didn’t know what cooking pots and utensils would be available. One...

SAR 779 total

includes taxes & fees

6 Jan - 7 Jan

Recent reviews of Old Chatham hotels

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel

5/5 Excellent

"I don't have 1 negative thing to say about this place. The staff was friendly, the room and public spaces were clean. Fun place to brings kids, lots to do. "

A verified traveler stayed at Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel

Posted 1 day ago

5/5 Excellent

"Check in and check out was very easy. The location was quiet and peaceful for a weekend getaway like we needed after the holidays. The location was perfect for visiting Great Barrington and within walking distance of downtown. When we got there, my husband opened the door saying it was the nicest Quality Inn he's ever been to (and that's saying a lot since he's picky). Would definitely stay there again and recommend it as well!"

A verified traveler stayed at Quality Inn

Posted 1 day ago

5/5 Excellent

"We love this property! We’ve stayed there two times so far and have had an great experience each time. The rooms are clean. The vibe is very sophisticated, and the food at the restaurant is out of this world. The staff is friendly and helpful. What more could you ask for in the Berkshires?!"

A verified traveler stayed at Life House Berkshires

Posted 4 days ago

The Yankee, Trademark Collection by Wyndham

5/5 Excellent

Very clean, comfortable and friendly!

"Very welcoming from the time we entered the front door. Everyone is sweet and willing to help you. The room was spotlessly clean. Housekeeping very detail oriented - even made a bow of the top tissue in the box (so cute i didn't want to use it! :-)Bed very comfortable. Spacious room. Nice little porch. Hot tub on site next to pool. Could have been better organized/tidied with the towels but water was clean. Parking was convenient. Location near a grocery store and restaurants. Really enjoyed our stay. Only the vending machine wasn't working. "

A verified traveler stayed at The Yankee, Trademark Collection by Wyndham

Posted 4 days ago

Explore a world of travel with Expedia

Frequently asked questions

Searching for B&Bs in Old Chatham?

Whether you’re on a romantic trip and want to stay somewhere quiet and intimate, or you’re a solo traveler hoping to get some local recommendations, B&Bs can be a great choice for many travelers. When you want to venture out to explore Old Chatham, consider browsing the exhibits at Shaker Museum and Library.

Why consider a B&B versus a traditional hotel?

With attentive service, opportunities to meet guests from other places, and top-rated breakfasts, B&Bs provide a one-of-a-kind setting.

What are the best B&Bs in Old Chatham?

Here are some B&Bs in the surrounding area: The Cornell Inn, Lenox: 15.2 mi (24.5 km) from the heart of Old Chatham. Enjoy the free full breakfast and unique décor. Lakehouse Inn: 14 rooms. 17.3 mi (27.8 km) from the downtown core. Enjoy the free full breakfast and deli. The Morgan State House: 16 rooms. Situated 18.2 mi (29.2 km) from the heart of Old Chatham. Chambery Inn: 9 rooms. 18.3 mi (29.4 km) from the heart of downtown. Enjoy the private yard and deli. Shaker Mill Inn: 9 rooms. Located 12.2 mi (19.7 km) from the core of Old Chatham.

When should I book my B&B in Old Chatham?

When you’re planning your stay in Old Chatham, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 67°F, while the coldest months are January and February with an average of 29°F. The snowiest months in Old Chatham are January, March, December, and November, with each month seeing an average of 7 inches of snowfall.

What is there to do in Old Chatham?

If you want to check out some popular attractions in Old Chatham, you might enjoy a visit to Shaker Museum and Library. You might also consider a trip to sites like Kinderhook Lake or Queechy Lake if you have time to see more of the area.

How can I get to and around Old Chatham?

Mapping out your trip in and around Old Chatham is easy with these transportation options. Fly into Hudson, NY (HCC-Columbia County), which is located 12.7 mi (20.4 km) away from the heart of the city. Otherwise, look for flights into Pittsfield, MA (PSF-Pittsfield Municipal), which is 13.9 mi (22.3 km) away. If you’d like to venture out around the area, consider renting a car to take in more sights.

Search B&B in Old Chatham

Plan, book, stay with confidence

Check availability on B&B in Old Chatham

Compare 32 B&B in Old Chatham with updated reviews, rates, and availability.

Lakehouse Inn

Lakehouse Inn

The Cornell Inn, Lenox

The Cornell Inn, Lenox

The Morgan State House

The Morgan State House

Chambery Inn

Chambery Inn

Granville House

Granville House

Shaker Mill Inn

Shaker Mill Inn

Devonfield Inn B&B

Devonfield Inn B&B

Gardner Farm Inn

Gardner Farm Inn

33 Main

33 Main

Tanglewood Suites

Tanglewood Suites

Brook Farm Inn

Brook Farm Inn

Inn at Silver Maple Farm

Inn at Silver Maple Farm

The Inn at Stockbridge

The Inn at Stockbridge

Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast

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

1735 Stone Farmhouse

1735 Stone Farmhouse

Romantic Boutique Hotel / Bed and Breakfast - Standard Queen Handicap Accessible

Romantic Boutique Hotel / Bed and Breakfast - Standard Queen Handicap Accessible

Romantic Boutique Hotel / Bed and Breakfast - Smallest Room in The Berkshires

Romantic Boutique Hotel / Bed and Breakfast - Smallest Room in The Berkshires

Inn at Kenmore Hall

Inn at Kenmore Hall

Romantic Boutique Hotel / B&B - Deluxe Firespa Suite

Romantic Boutique Hotel / B&B - Deluxe Firespa Suite

Other property types in Old Chatham

Beautiful 5-Star Private Estate! Inquire about our Early Booking Reduced Rates!

Beautiful 5-Star Private Estate! Inquire about our Early Booking Reduced Rates!

Vacation Village in the Berkshires

Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

Recent reviews of Old Chatham hotels

Recent reviews of Old Chatham hotels

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Popular Destinations

Top B&B in Other Destinations

More Accommodation Types in Old Chatham

Frequently asked questions