Book Luxury Vacation Rentals in Pawling

Award-winning homes from £98

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Home spotlights in Pawling

Hamlet

Hamlet

  • 8 guests

  • 5 bedrooms

Miller Place, Brookhaven

An understated colonial-style home is the perfect setting for a Northeastern getaway. It's reminiscent of a family heirloom, with history seeping through the walls.

Long Island Iced Tea

Long Island Iced Tea

  • 8 guests

  • 3 bedrooms

Remsenburg, Remsenburg-Speonk

Not too far from the bright lights of New York City, this striking and stylish home sits near the beaches of Westhampton and among the protected marshlands of Long Island. The house itself is a modern twist on the traditional clapboard homes the area is famous for, with wraparound decks looking into the treetops to the rear and plenty of sliding doors allowing the indoors to seamlessly slip into the outdoor space.

The Captain's House

The Captain's House

  • 10 guests

  • 4 bedrooms

Jamesport, North Fork

Mere steps from the beach, this four-bedroom farmhouse sleeps ten and is ideal for a large family getaway. Rustic it may be, but the interiors don’t skimp on style – white walls and pops of colour lend it a modern Scandinavian vibe.

Building Bridges

Building Bridges

  • 4 guests

  • 2 bedrooms

Astoria, Queens

This calming home-from-home is close enough to nip into the city on the subway, yet sits in a quiet and friendly neighbourhood in Astoria, Queens. Surrounded by leafy green parks, independent coffee shops, and a host of world cuisine eateries, it's the perfect spot for those looking to see the sights of NYC with a comforting place to call home outside of the concrete jungle.


We selected the top 3% holiday homes in Pawling Vacation Rentals

Explore the 932 most perfect homes in our collection

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Most popular homes in Pawling

Mystic Countryside Farm

Mystic Countryside Farm

  • 4 guests

  • 2 bedrooms

North Stonington, New London County

The Great Frontier

The Great Frontier

  • 4 guests

  • 1 bedrooms

Chatham, New York

Sea Aster

Sea Aster

  • 6 guests

  • 3 bedrooms

Sag Harbor, Southampton

Borne Back

Borne Back

  • 6 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

Wander Inn

Wander Inn

  • 6 guests

  • 2 bedrooms

Southold, New York

Crop And Saddle

Crop And Saddle

  • 6 guests

  • 4 bedrooms

Washington, Litchfield

The Edge

The Edge

  • 6 guests

  • 3 bedrooms

Ulster County, Rochester

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Frequently asked questions

Take a look at our collection of luxury Vacation Rentals in Pawling. All of the homes you'll find on Plum Guide come fully furnished with all linen, the best-equipped kitchens, and essential bathroom toiletries included. Each home is systematically reviewed before becoming part of our collection, so you can book your stay with total confidence. And if you require any assistance in finding the perfect Pawling Vacation Rentals for you, get in touch with our team of friendly experts, on hand to help with whatever you need.

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