Chatham Holiday Rentals

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Holiday Rentals in Chatham

Spacious 5-bedroom house in charming Lee with WiFi

The price is AU$1,289
includes taxes & fees
31 July - 1 Aug
Spacious 5-bedroom house in charming Lee with WiFi

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (253)
"One of the best properties i've ever stayed at "
The price is AU$455
includes taxes & fees
31 July - 1 Aug
Berkshire Village Carriage House - Super Private!!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

2.0 star property
9.0 out of 10, Wonderful, (4)
"Very clean and spacious! We enjoyed our stay with our small pup!"
The price is AU$1,029
includes taxes & fees
4 Aug - 5 Aug
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Experience Timeless Elegance in The Edith Wharton Room!

The price is AU$610
includes taxes & fees
30 July - 31 July
Experience Timeless Elegance in The Edith Wharton Room!

Cozy Carriage House room with a double bed and private balcony

The price is AU$675
includes taxes & fees
30 July - 31 July
Cozy Carriage House room with a double bed and private balcony

"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

The price is AU$754
includes taxes & fees
21 July - 22 July
"Elegant Emily Dickinson Junior Suite with King Bed & Fireplace

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

The price is AU$659
includes taxes & fees
31 July - 1 Aug
Elegant Carriage House room with a queen bed and private patio.

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

The price is AU$850
includes taxes & fees
21 July - 22 July
Elegant suite with a king bed, fireplace, and kitchenette.

Historic Susan B. Anthony Room - Cozy & Charming Stay

The price is AU$708
includes taxes & fees
4 Aug - 5 Aug
Historic Susan B. Anthony Room - Cozy & Charming Stay

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

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

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

The price is AU$849
includes taxes & fees
4 Aug - 5 Aug
Experience Timeless Elegance in The Niles Johnson Room at The Cornell Inn

Cheerful 3-bedroom cottage with woodstove

10.0 out of 10, Exceptional, (38)
"The property was centrally located for skiing, and was a comfortable stay."
The price is AU$835
includes taxes & fees
31 July - 1 Aug
Cheerful 3-bedroom cottage with woodstove

Home in Great Barrington

9.8 out of 10, Exceptional, (21)
"Our family had a wonderful experience and stay. "
The price is AU$600
includes taxes & fees
6 Aug - 7 Aug
Home in Great Barrington

Great Barrington Get Away

9.4 out of 10, Exceptional, (23)
"Nice, cozy, clean house with character. Great location as we could walk to town. Would stay again for sure."
The price is AU$1,041
includes taxes & fees
6 Aug - 7 Aug
Great Barrington Get Away

Comfortable Berkshires retreat on mtn resort, SISO

9.6 out of 10, Exceptional, (4)
"Hosts were very responsiveHouse was clean and well maintainedExcellent locationOverall great stay"
The price is AU$759
includes taxes & fees
20 July - 21 July
Comfortable Berkshires retreat on mtn resort, SISO

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (12)
"Very kinda hosts, and wonderful house."
The price is AU$1,709
includes taxes & fees
18 Aug - 19 Aug
Hancock Village Inn at Jiminy Peak

NEW RENO Historic Creamery in Berkshires w/hot tub

10.0 out of 10, Exceptional, (1)
"We used all amenities (besides hot tub) full kitchen and only brought food which worked well."
The price is AU$743
includes taxes & fees
20 July - 21 July
NEW RENO Historic Creamery in Berkshires w/hot tub

Restored Historic 1850s Barn "Carriage House" Studio @ Hillsdale Town Center

Restored Historic 1850s Barn "Carriage House" Studio @ Hillsdale Town Center

★Private Pool★ Spacious Historic 1850s "Bell House" @ Hillsdale, NY Town Center

The price is AU$1,200
includes taxes & fees
28 July - 29 July
★Private Pool★ Spacious Historic 1850s "Bell House" @ Hillsdale, NY Town Center

Hillsdale Escape with Pool, Firepit, Hot Tub, Game Room

Hillsdale Escape with Pool, Firepit, Hot Tub, Game Room
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

Frequently asked questions

Are there holiday rentals in Chatham?

Yes, there are holiday rentals close to the most popular sights in Chatham, or you can select a more secluded option if you're looking for a relaxing stay. Chatham is known for its theatres and restaurants.

What are some of the best holiday rentals that Chatham has to offer?

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT: This holiday home rental outside of Chatham is located in a rural location, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Chatham?

With 14 Expedia holiday rentals, you're guaranteed to find just the right place for your Chatham stay.

What can I see and do in Chatham?

While exploring the area, visit family-friendly sights like Bousquet Ski Area, or get outside and enjoy nature at Kinderhook Lake. The Mac-Haydn Theatre and Martin Van Buren National Historic Site are a couple of places you'll find in the wider area.

What are holiday rentals like in Chatham?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chatham. Holiday rentals offer amenities such as laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a clean environment, a holiday rental can offer a sense of privacy away from shared hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for families.