Discover a selection of 500 vacation rentals in Chatham, NY that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and WiFi. Prices start at $129 per night, and houses and cottages are popular options for a stay in Chatham. Either way, you'll find a rental for everyone's needs.
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Top rated rentals — Chatham
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Destination guide

Head to the friendly city of Chatham

Enjoy the theater scene and other features of Chatham. Travelers appreciate the restaurants in this welcoming city. With a vacation rental, you get a home away from home—many rentals offer full kitchens and outdoor grills for some home cooking.

Activities

Sightseeing in and around Chatham

Are you searching for things to do while you're in the area? Venture out of your vacation home and check out everything that makes Chatham a fun spot to vacation. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Furnace Brook Winery at Hilltop Orchards (9.8 mi / 15.7 km)
  • Catamount Ski Area (12.7 mi / 20.4 km)
  • Pleasant Valley Wilderness Sanctuary (13.7 mi / 22.1 km)
  • Kennedy Park (14.8 mi / 23.9 km)
  • Bousquet Ski Area (15.6 mi / 25 km)
  • Greenock Country Club (15.7 mi / 25.3 km)
Natural features

Exploring the natural landscape of Chatham

Whether you're an outdoor enthusiast or just want to take in the scenery, Chatham is a great place to get outside. Here are some of the area’s most enchanting features, all within 30 miles (48.2 km) of the city center:

  • Berkshire Botanical Garden (11.7 mi / 18.8 km)
  • Lake Mansfield Park (13.5 mi / 21.7 km)
  • Kennedy Park (14.8 mi / 23.9 km)
  • Taconic Trail State Park (15.1 mi / 24.3 km)
  • Pittsfield State Forest (15.7 mi / 25.2 km)
  • Wood's Pond (16.1 mi / 25.9 km)
How to get there

Transportation options to and around Chatham

Fly into Hudson, NY (HCC-Columbia County), the closest airport, located 8.3 mi (13.4 km) from the city center. If you can't find a flight that works for your travel itinerary, you could also fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is 15 mi (24.1 km) away.

How many vacation rentals are available around Chatham, NY?

Our 2021 property listings offer a large selection of 702 vacation rentals around Chatham. From 486 house rentals to 52 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent Houses in Chatham?

Yes, of course. Vrbo has 486 Houses in Chatham. Our other popular types of vacation rentals in Chatham include:

  • Cottages: 52 rentals available
  • Cabins: 61 rentals available
  • Condos/Apartments: 101 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Bungalows and more.

Can I find a vacation rental with pool in Chatham?

Yes, you can select your preferred vacation rental with pool among our 179 vacation rentals with pool available in Chatham. Please use our search bar to access the selection of vacation rentals available.