
Holiday rentals in Pawling
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Top-rated holiday rentals in Pawling
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
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Popular amenities for Pawling holiday rentals
Other great holiday rentals in Pawling
Top guest favourite

Home in Patterson
4.98 out of 5 average rating, 47 reviewsFarmhouse & private yard
Top guest favourite

Barn in Roxbury
5 out of 5 average rating, 47 reviewsFully Renovated Rural Barn
Top guest favourite

Home in Pawling
5 out of 5 average rating, 226 reviewsHobbit House of Pawling
Top guest favourite

Cabin in Holmes
5 out of 5 average rating, 80 reviewsCabin Charadora
Guest favourite

Cottage in New Fairfield
4.97 out of 5 average rating, 39 reviewsSunset Cabin Modern Home Kayak FirePit Lake Access
Guest favourite

Farm stay in Brewster
4.84 out of 5 average rating, 70 reviewsCrooked Cottage at Lobster Hill Farm
Guest favourite

Home in New Fairfield
4.97 out of 5 average rating, 76 reviewsHilltop Retreat- Lakefront with Dock
Guest favourite

Campervan/Motorhome in Wassaic
5 out of 5 average rating, 26 reviewsAirstream Forest Glamping near Metro North Train
Destinations to explore
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- Fairfield Beach
- Yale University
- Rye Beach
- Rye Playland Beach
- Minnewaska State Park Preserve
- Walnut Public Beach
- Woodmont Beach
- Jennings Beach
- Thunder Ridge Ski Area
- Taconic State Park
- Silver Sands Beach
- Bushnell Park
- Sunken Meadow State Park
- Seaside Beach
- Sherwood Island State Park
- Rye Town Beach
- Calf Pasture Beach
- Brownstone Adventure Sports Park
- Ringwood State Park
- Hudson Highlands State Park
- Glen Island Beach
- Walkway Over the Hudson State Historic Park
- Bash Bish Falls State Park
- Brotherhood, America's Oldest Winery