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 $95 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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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 2020 property listings offer a large selection of 571 vacation rentals around Chatham. From 413 house rentals to 47 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What are the popular point of interests near where I can stay when traveling to Chatham?

Vrbo offers a large selection of vacation rentals near lovely places in Chatham. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • The Mac-Haydn Theatre: 467 vacation rentals
  • Jiminy Peak Mountain Resort: 268 vacation rentals
  • Dutchman’s Landing: 730 vacation rentals
  • New York State Executive Mansion: 124 vacation rentals
  • Ski Butternut: 419 vacation rentals

But there are many other points of interest around Chatham listed on Vrbo where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Chatham?

Yes, of course. Vrbo has 413 Houses in Chatham. Our other popular types of vacation rentals in Chatham include:

  • Cottages: 47 rentals available
  • Cabins: 47 rentals available
  • Condos/Apartments: 77 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 140 vacation rentals with pool available in Chatham. Please use our search bar to access the selection of vacation rentals available.

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