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Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sep - 13 Sep
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Chatham holiday rentals

Lobby

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,445 reviews)
"Great and tranquil location, good sleeps, friendly and helpful staff, would do it again."
United States
Melanie
The price is 3.318.947 ₫
3.995.281 ₫ total
includes taxes & fees
22 Jul - 23 Jul
Vacation Village in the Berkshires
Exterior

Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (156 reviews)
"The room was cozy. In a very quiet part of town. The check in process was easy. I would definitely stay again while in town."
United States
Kathleen
The price is 3.639.206 ₫
4.075.564 ₫ total
includes taxes & fees
19 Jul - 20 Jul
Micosta Leisure Inn
Exterior

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
2.5 star property
Catskill
9.6 out of 10, Exceptional, (256 reviews)
"Really great location and near great area."
United States
Sherwin
The price is 5.224.745 ₫
6.776.941 ₫ total
includes taxes & fees
21 Jul - 22 Jul
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
House (3 Bedrooms) | Interior

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
Stephentown
The price is 5.881.120 ₫
14.549.471 ₫ total
includes taxes & fees
21 Jul - 22 Jul
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
Family Bungalow

Huttopia Berkshires

Huttopia Berkshires
1.0 star property
Williamstown
9.6 out of 10, Exceptional, (11 reviews)
"Healthy food too!"
United States
GEORGINA
The price is 4.135.162 ₫
4.618.976 ₫ total
includes taxes & fees
15 Jul - 16 Jul
Huttopia Berkshires
House (3 Bedrooms) | Front of property

Sleepy Hollow Lake Home w/ Deck, Pool Access!

Sleepy Hollow Lake Home w/ Deck, Pool Access!
3.0 star property
Coxsackie
10.0 out of 10, Exceptional, (2 reviews)
"The house was convenient to our friend’s wedding venue. It was spacious, clean and comfortable! There were many great amenities that we didn’t have time use due to our schedule and rainy weather."
United States
audrey
The price is 7.955.265 ₫
15.529.307 ₫ total
includes taxes & fees
19 Jul - 20 Jul
Sleepy Hollow Lake Home w/ Deck, Pool Access!
House (4 Bedrooms) | Interior

Mtn-view Retreat in Huson Valley: Great for Groups

Mtn-view Retreat in Huson Valley: Great for Groups
3.0 star property
Hudson
The price is 6.274.945 ₫
19.438.152 ₫ total
includes taxes & fees
9 Aug - 10 Aug
Mtn-view Retreat in Huson Valley: Great for Groups
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

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

10/10 Excellent
"The experience was wonderful. Great and peaceful place."
Seung Jae 1-night trip
Posted 6 hours ago
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

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.

How many holiday rentals are there in Chatham?

With 12 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.