Where to stay around Chatham, NY?

Our 2018 property listings offer a large selection of 743 vacation rentals near Chatham. From 392 Houses to 145 Condos/Apartments, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Chatham for a holiday or a weekend are on VRBO.

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: 579 vacation rentals
  • Ski Butternut: 554 vacation rentals
  • Catamount Ski Area: 513 vacation rentals
  • Tanglewood Music Center: 621 vacation rentals
  • Dutchman’s Landing: 794 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 392 Houses in Chatham. Our other popular types of vacation rentals in Chatham include:

  • Condos/Apartments: 145 rentals available
  • Cabins: 74 rentals available
  • Cottages: 74 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 prefered vacation rental with pool among our 205 vacation rentals with pool available in Chatham. Please use our search bar to access the selection of vacation rentals available.

    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.

    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)

    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)