Discover a selection of 112 vacation rentals in Pawling, 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 kitchens. Prices start at $106 per night, and houses and cottages are popular options for a stay in Pawling. Either way, you'll find a rental for everyone's needs.
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.

How many vacation rentals are available around Pawling, NY?

Our 2020 property listings offer a large selection of 112 vacation rentals around Pawling. From 80 house rentals to 14 cottage rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent a lakefront property in Pawling?

Watch as the breeze makes gentle ripples across the water and look out for the local wildlife. Lakes are one of the most glorious and peaceful places to escape to. If this is paradise to you, you're in luck. Vrbo has 32 getaway rentals near lakes ready to be booked. Of course, that might not be your style. Luckily, Vrbo has tons more options, including:

  • 28 rural vacation rentals.
  • 26 lake-view vacation rentals.
  • 22 mountain-view vacation rentals.

Can I rent a house in Pawling?

Our house vacation rentals are real properties for real travelers. With plenty of space and privacy, they're perfect for those who want to live like a local. There are 74 options listed on Vrbo. Prices start at $75 a night. Or perhaps you'd prefer one of the area's other rental types, like:

  • Hotel: 15 vacation homes. Prices start from $97 per night.
  • Cottage: 11 vacation homes. Prices start from $207 per night.
  • Cabin: 6 vacation homes. Prices start from $100 per night.

Can I stay in Pawling in a large group?

There's nothing quite like being somewhere entirely new with friends and family. The best news is Vrbo has options to suit large groups. The leading option for bigger groups here are house vacation homes, and there are 16 currently listed. Around the area, the rental options that can accommodate large groups of people include:

  • If yours is a party of 6, we've got 26 vacation homes suited to that size. Spend a night for as little as $85.
  • Require a place for 8 people? We have 16 that will be perfect. Prices start from $250 per night.
  • Seeking properties for rent to suit 10 people? You'll be glad to hear we have 16 that will fit the bill. You can secure one from just $175 a night.

You and your posse will be well looked after when you plan your Pawling vacation with us!

Where are the cheapest rentals in Pawling?

Reduce your accommodation expenses when you organize your stay with Vrbo. You'll find plenty of fabulous rentals and save heaps! Cornwall Bridge has bargain written all over it. And with 4 Vrbo rentals at an average price of $203 a night, it's not difficult to see why. New Preston is another place to consider. We have 15 rentals here, and the average price is around $310 a night.