New Windsor Villas

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Villas in New Windsor

Serene 10BR Retreat w/Pool, Gym & Hot Tub

Chester NY

Located in Chester, this villa is within a 15-minute drive of Woodbury Common Premium Outlets and LEGOLAND® New York.

Pool

Hot Tub

The Scenic Mansion With Breathtaking View

Highland NY

When you stay at this villa in Highland, you'll be in the mountains, within a 15-minute drive of Vassar College and Culinary Institute of America.

Pool

Kitchen

Magical Family Escape, Pool, HotTub, Pets, <1 Hr NYC

Harriman NY

Located in Harriman, this villa is in a rural location, within a 5-minute drive of Harriman State Park and Harriman Plaza Shopping Center.

Pool

Hot Tub

7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space

Monroe NY

With a stay at this villa in Monroe, you'll be within a 15-minute drive of Woodbury Common Premium Outlets and LEGOLAND® New York.

Pool

Hot Tub

Magnificent Villa, Private Pool, Fire Pit w/Huge Backyard

Chester NY

With a stay at this villa in Chester, you'll be within a 15-minute drive of Woodbury Common Premium Outlets and LEGOLAND® New York.

Pool

Kitchen

Pinnacle Pointe by Relaxtay | 600-Acre Private Luxury Estate with Spa, Pool, Theater & Lake

Middletown NY

With a stay at this villa, you'll be centrally located in Middletown, within a 10-minute drive of Otisville Veterans Memorial Park and Bloomingburg Village Hall.

11BR Retreat w Pool, Hot Tub, Sauna & Game Room

Chester NY

With a stay at this villa in Chester, you'll be within a 15-minute drive of Woodbury Common Premium Outlets and LEGOLAND® New York.

Spacious Retreat w/ Pool, Hot Tub & Game Room

Stony Point NY

With a stay at this villa in Stony Point, you'll be within a 10-minute drive of Bear Mountain State Park and Harriman State Park.

Spacious villa w/Pool, Hot Tub & Game Room on 7.5 private acres

Chester NY

Located in Chester, this villa is within a 15-minute drive of Woodbury Common Premium Outlets and LEGOLAND® New York.

Pool

Hot Tub

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.