49+ Vacation Rentals & Holiday Homes in Pawling |
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Pawling Accommodations - Hotels & Rentals

About Pawling Vacation Rentals

Discover More than 49 Incredible Getaway Rentals Available in Pawling. Choose from a Wide Selection of Villas, Hotels, and Other Rental Options. Explore Luxury Amenities at Affordable Prices, Creating the Ideal Base for Your Next Vacation. Plan Your Perfect Escape with Online Reservations and Uncover Fantastic Stays in Pawling.

Online Reservations Offers Numerous Last-Minute Deals on Villas, Hotels, and Rentals, Both Near You and Across the Globe. Whether You Need Accommodation for a Group or an Event, Be it a Hotel or Vacation Rental (Including Cabins and Private Luxury Villas), We're Here to Assist. With Online Reservations in Pawling, You Can Easily Compare Options from Multiple Suppliers with a Single Click to Find the Perfect Price Point, Amenities, and Style of Stay That Suit Your Needs. Looking for Group Deals, Properties with Private Pools, Hot Tubs, Pet-Friendly Options, or Spacious Master Suite Bedrooms with Open-Air Showers? You Can Find It All in the Online Reservations Vacation Rentals, Resorts, and Airbnb-Style Properties in Pawling. The Average Size of Places to Stay Near Pawling is 1196.64 ft², with Prices Averaging US $494 per Night.

Let Online Reservations Help You Discover the Ideal Holiday Rental to Create Lifelong Travel Memories in Pawling. Our Listed Prices Are Often Discounted Compared to Rack Rates. Simply Search for Your Destination and Secure the Perfect Place to Stay Today.

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Top Hotels & Vacation Rentals in Pawling

Type Count
Vacation Homes 32
Cottages 5
Holiday Apartments 1
Villas 1

Use these Quick Filters to Find a Vacation Rental in Pawling

★ Pro Tip: Online Reservations is a vacation rental website specializing in cottages, lake houses, and exclusive summer home rentals. We curate a vast selection of incredible properties from trusted suppliers, allowing you to compare prices and locations to find the perfect fit for your getaway. Create lasting memories in Pawling with Online Reservations.

Weather in Pawling, NY

View the weather forecast for Pawling before booking your Pawling Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Activities PawlingGuest Reviews Local Attractions

A Large Selection of Hotels and Vacation Rentals from Around the World PawlingGuest Reviews Discover Exciting Activities and Must-Visit Destinations for Your Upcoming Journey


John Kane House
Marist College
Vassar College
Culinary Institute of America
Ridgefield Playhouse
Mohawk Mountain Ski Area
Dia Beacon
Danbury Fair Mall
Kent Falls State Park
SplashDown Beach
Thunder Ridge Ski Resort
Mid-Hudson Civic Center
Chance Theater
Franklin D. Roosevelt Presidential Library and Museum
Stormville Airport Antique Show & Flea Market
Candlewood Lake
Elephant's Trunk Flea Market
Lake Waramaug State Park
Millbrook Vineyards and Winery
Home of Franklin D. Roosevelt National Historic Site

Find Hotels & Vacation Rentals in these Cities and Neighborhoods


John Kane House 43 Properties

Frequently Asked Questions About Pawling?

What are the top hotels, lake houses & vacation rentals in Pawling?

We provide an array of great vacation destinations in Pawling. If you are looking to stay in or around the Pawling area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Pawling:

Which hotel, lake house, or vacation rental in Pawling is best for families?

Searching for a family-friendly getaway in Pawling? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.

How many hotels, resorts, or rentals are available in Pawling?

Online Reservations™ offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Online Reservations™ in 2025 is over 49 in the Pawling area, and that number rises every day. By combining listings from multiple websites and travel providers, Online Reservations™ can provide you with a diverse amount of choices of the best luxury stays in Pawling.


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