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.

Where to stay around Chatham?

Our 2019 property listings offer a large selection of 798 vacation rentals near Chatham. From 430 Houses to 73 Cottages, 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 HomeAway.

What is the best area to stay when traveling to Chatham?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Chatham:

  • Copake Lake: 31 vacation rentals
  • Lee: 618 vacation rentals
  • South Lee: 15 vacation rentals
  • Housatonic: 417 vacation rentals
  • South Egremont: 22 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular points of interest near where I can stay when traveling to Chatham?

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

  • The Mac-Haydn Theatre: 606 vacation rentals
  • Jiminy Peak Mountain Resort: 441 vacation rentals
  • Tanglewood Music Center: 641 vacation rentals
  • Dutchman’s Landing: 827 vacation rentals
  • New York State Executive Mansion: 113 vacation rentals

But there are many other points of interest around Chatham listed on HomeAway 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. HomeAway has 430 Houses in Chatham. Our other popular types of vacation rentals in Chatham include:

  • Cottages: 73 rentals available
  • Bungalows: 73 rentals available
  • Farmhouses: 25 rentals available

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

Can I find a vacation rental with pool in Chatham?

Yes, you can select your preferred vacation rental with pool among our 226 vacation rentals with pool available in Chatham. Please use our search bar to access the selection of vacation rentals available.

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