Rent Hudson Valley Homes with Swimming Pools

We selected the 102 homes worth renting in this location

Who's coming along?

Adults

Age 13+

0

Children

Age 1 to 12

0

Infants

Under 1

0

Pets

An extra fee may apply

0

Home spotlights in Hudson Valley

Summer Fridays

Summer Fridays

  • 10 guests

  • 5 bedrooms

Northwest Harbor, East Hampton

A haven of tranquillity, this serene home is perfect for recharging your batteries. Step inside and be soothed by the classic Hamptons style – think ample-sized living spaces designed for entertaining, calm colours inspired by the coast and oodles of windows flooding each room with natural light.

Hampton Set

Hampton Set

  • 6 guests

  • 4 bedrooms

Northwest Harbor, East Hampton

Live your best East Hampton life at this light-filled, mid-century architectural gem, just a seven-minute drive from the beach. With its private pool and hot tub, grassy lawns backed by juniper trees for post-pool games (table tennis, anyone?

Straight Down the Middle

Straight Down the Middle

  • 8 guests

  • 4 bedrooms

Shelter Island Heights, Shelter Island

Escape the frenetic pace of daily life and revel in an unmissable opportunity to relax and recharge at this stunning Shelter Island getaway. Set on a quiet tree-lined street and just a ten-minute walk from the pebble-strewn seashore, the home is perfectly set up for family holidays and weekend retreats with friends.

Upstate Escape

Upstate Escape

  • 10 guests

  • 4 bedrooms

Woodstock, Ulster County

Tucked away just outside of Woodstock, this impressive home welcomes families and friends to spend a few relaxing days in the Hudson Valley. Fully renovated in 2017, your hosts have truly thought of everything to ensure anyone who stays here has a magical experience.


We selected the top 3% holiday homes in Hudson Valley Homes with Swimming Pools

Explore the 102 most perfect homes in our collection

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Most popular homes in Hudson Valley

The Archway

The Archway

  • 9 guests

  • 4 bedrooms

West Hurley, Hurley

The Little Sparrow

The Little Sparrow

  • 6 guests

  • 3 bedrooms

Shinnecock Hills, Southampton

The Old Life-Saving Station

The Old Life-Saving Station

  • 13 guests

  • 6 bedrooms

East Marion, North Fork

Through the Seasons

Through the Seasons

  • 12 guests

  • 5 bedrooms

Tobyhanna Township, Monroe County

Dappled Sunlight

Dappled Sunlight

  • 8 guests

  • 4 bedrooms

Northwest Harbor, East Hampton

Rust & Stars

Rust & Stars

  • 6 guests

  • 3 bedrooms

Mamakating, Sullivan County

Doric Detail

Doric Detail

  • 8 guests

  • 4 bedrooms

Dover, Dutchess County

Zephyr Residence

Zephyr Residence

  • 10 guests

  • 5 bedrooms

Water Mill, Southampton

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Check upcoming rates & availability for Hudson Valley Homes with Swimming Pools


Frequently asked questions

You've certainly come to the right place if you are hoping to find one of the finest Holiday Homes with Swimming Pools in Hudson Valley. Our exclusive collection consists solely of homes that have passed our thorough 150-step vetting process with flying colours, so you can book with true peace of mind, knowing that everything from decibel levels in the bedroom to a room's intangible atmosphere has been tested and approved. We don't list a huge number of homes one our site, just the right ones. Each property in our collection comes fully furnished and ready to welcome you, with a fully-equipped kitchen, essential bathroom toiletries, and all linen included. Contact our dedicated team of experts to find the perfect luxury Hudson Valley Home to Rent with a Swimming Pool today, and set up a holiday to remember.

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