New Windsor Villas

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Villas in New Windsor

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 LEGOLAND® New York and Woodbury Common Premium Outlets.

Pool

Kitchen

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

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.

Pool

Hot Tub

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

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

Beautiful modern villa with pool suana hot tub...

Clintondale NY

Located in Clintondale, this villa is a 4-minute drive from Apple Greens Golf Course and 7 minutes from State University of New York-New Paltz.

Pool

Kitchen

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.

Pool

Washer

Spacious + beautiful 5-bedroom Mediterranean Villa in Monroe, NY.

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

Charming 3-bedroom villa with WiFi, AC in fabulous Monroe

Monroe NY

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

Kitchen

Washer

11BR Retreat w Pool & Game Room

Chester NY

$3,964 nightly

$4,484 total

Jul 1 - Jul 2

Total with taxes and fees

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

Updated 3 to 4 bedroom Cape Cod

Washingtonville NY

With a stay at this villa in Blooming Grove, you'll be within a 15-minute drive of Woodbury Common Premium Outlets and Brotherhood Winery.

Kitchen

Washer

Marvelous 7-bedroom villa with AC in charming Cornwall

Cornwall NY

With a stay at this villa in Cornwall, you'll be within a 5-minute drive of Hudson Highlands Nature Museum and Cornwall Bark Park.

Washer

Dryer

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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.