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

Chatham Vacation Rentals

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Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sep - 27 Sep
In four months
23 Oct - 25 Oct

Our top choices for Chatham vacation rentals

Outdoor dining

Gatherwild Ranch

Gatherwild Ranch
3.0 star property
Germantown
The price is SAR 661
SAR 740 total
includes taxes & fees
9 Jul - 10 Jul
Gatherwild Ranch
Lobby

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,414 reviews)
"Property is great and stay was great"
United States
Isha
The price is SAR 439
SAR 532 total
includes taxes & fees
7 Jul - 8 Jul
Vacation Village in the Berkshires
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, (253 reviews)
"Really great location and near great area."
United States
Sherwin
The price is SAR 571
SAR 779 total
includes taxes & fees
3 Aug - 4 Aug
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Exterior

Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (155 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 SAR 509
SAR 570 total
includes taxes & fees
6 Jul - 7 Jul
Micosta Leisure Inn
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 SAR 841
SAR 2,081 total
includes taxes & fees
5 Jul - 6 Jul
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
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

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

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

8/10 Good
"It was generally excellent. The only difficultly I found was using the TV and that thermostat. A little too hi- tech"
James 2-night trip
Posted 7 hours ago
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Frequently asked questions

Are there vacation rentals in Chatham?

Yes, we have vacation rentals close to top points of interest in Chatham, or you can go with a secluded option if you want a relaxing place to stay. Chatham is known for its theaters and restaurants.

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

Cozy Riverside Berkshires Retreat: This vacation home rental near Chatham is located on a river and has a fireplace, a garden, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and kitchenware, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Chatham?

With 12 Expedia vacation rentals, you're sure 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 larger area.

What are vacation rentals like in Chatham?

Vacation rentals are privately owned properties you can stay in for several days or more in Chatham. Vacation rentals feature amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about a clean environment, vacation rentals can offer a sense of security away from shared hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for a family getaway.