Destination guide

Travel to historic Pawling

Enjoy the history and other features of Pawling. This city has something for everyone. Many of our vacation rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.


Sightseeing in and around Pawling

Are you looking for attractions to see while you're in town? Venture out of your vacation home and experience everything that makes Pawling a one-of-a-kind vacation spot. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Thunder Ridge Ski Resort (4.8 mi / 7.7 km)
  • Beekman Golf Course (9.8 mi / 15.8 km)
  • Richter Park Golf Course (11.8 mi / 19 km)
  • Steep Rock Preserve (13.9 mi / 22.3 km)
  • Hopkins Vineyard (14.9 mi / 24 km)
  • Putnam County Golf Course (15.9 mi / 25.6 km)
Natural features

Exploring the natural landscape of Pawling

Whether you're looking for adventure or just want to take in the scenery, you'll be sure to find the perfect setting for your vacation in Pawling. Here are some of the area’s noteworthy features, all within 30 miles (48.2 km) of the city center:

  • Emmanuel Williamson Park (7.1 mi / 11.4 km)
  • James Baird State Park (13 mi / 20.9 km)
  • Lake Waramaug State Park (13.7 mi / 22.1 km)
  • Macedonia Brook State Park (13.9 mi / 22.3 km)
  • Still River Greenway (14.3 mi / 23 km)
  • Clarence Fahnestock State Park (14.5 mi / 23.4 km)
How to get there

Transportation options to and around Pawling

Fly into Danbury, CT (DXR-Danbury Municipal), the closest airport, located 15.1 mi (24.3 km) from the city center. If you can't find a flight that works for your travel itinerary, you can also fly into Oxford, CT (OXC-Waterbury - Oxford), which is 24.2 mi (38.9 km) away.

If you'd rather travel by train, the main station is Appalachian Trail.

Where to stay around Pawling?

Our 2019 property listings offer a large selection of 127 vacation rentals near Pawling. From 77 Houses to 5 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 Pawling for a holiday or a weekend are on HomeAway.

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

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 Pawling:

  • Litchfield: 163 vacation rentals
  • Falls Village: 152 vacation rentals
  • Washington Depot: 140 vacation rentals
  • Bethel: 55 vacation rentals
  • Bantam: 104 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 Pawling?

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

  • John Kane House: 232 vacation rentals
  • Lake Waramaug State Park: 286 vacation rentals
  • Omega Institute: 595 vacation rentals
  • Eleanor Roosevelt National Historic Site: 373 vacation rentals
  • Bardavon 1869 Opera House: 349 vacation rentals

But there are many other points of interest around Pawling 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 Pawling?

Yes, of course. HomeAway has 77 Houses in Pawling. Our other popular types of vacation rentals in Pawling include:

  • Condos/Apartments: 5 rentals available
  • Cabins: 20 rentals available
  • Cottages: 20 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 Pawling?

Yes, you can select your preferred vacation rental with pool among our 33 vacation rentals with pool available in Pawling. Please use our search bar to access the selection of vacation rentals available.

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