Destination guide

Travel to historical Pawling

Enjoy the history and other features of Pawling. This city has something for everyone. Many of our holiday 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 holiday home and experience everything that makes Pawling a one-of-a-kind holiday spot. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • 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 holiday in Pawling. Here are some of the area’s noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • 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

Transport 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 centre. 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.

How many holiday rentals are available around Pawling?

Our 2020 accommodation listings offer a large selection of 108 holiday lettings around Pawling. From 81 houses to 10 cottages, find unique self catering accommodation for you to enjoy a memorable stay with your family and friends for a long holiday or a weekend break.

What are the most popular points of interest and landmarks to stay near when travelling to Pawling? offers a large selection of holiday accommodations near great places in Pawling. From travellers, the most popular points of interest to stay near are:

  • John Kane House: 198 holiday lettings
  • Bardavon 1869 Opera House: 318 holiday lettings
  • West Cornwall Covered Bridge: 237 holiday lettings
  • Hudson Highlands State Park: 180 holiday lettings
  • Frances Lehman Loeb Art Center: 315 holiday lettings

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

Can I rent Houses in Pawling?

Yes, of course. offers 81 Houses in Pawling. Our other popular types of Pawling holiday rentals include:

  • Cottages: 10 self catering accommodations
  • Cabins: 10 self catering accommodations
  • Flats: 3 self catering accommodations

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

Can I find a holiday accommodation with pool in Pawling?

Yes, you can select your preferred holiday accommodation with pool among our 29 holiday homes with pool available in Pawling. Please use our search bar to access the selection of holiday rentals available.