Poughkeepsie Villas

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Villas in Poughkeepsie

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.

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.

Lakefront Paradise w/Pool, Hot Tub, Sauna & Kayaks

Woodridge NY

With a stay at this villa in Woodridge, you'll be within a 15-minute drive of Neversink River and Sullivan County Dramatic Workshop - Rivoli Theatre.

Luxury 10BR Escape w/ Pool, Hot Tub & Game Lounge

Stony Point NY

Located in Stony Point, this villa is a 2-minute drive from Harriman State Park and 6 minutes from Patriot Hills Golf Club.

Warm Escape, Wood Stove, HotTub, Pets, <1 Hr NYC

Harriman NY

With a stay at this villa in Harriman, you'll be within a 10-minute drive of Woodbury Common Premium Outlets and Harriman State Park.

Dome House Retreat

116 canaan rd New Paltz NY

When you stay at Dome House Retreat in New Paltz, you'll be near the airport and 9 minutes by car from Nyquist-Harcourt Wildlife Sanctuary.

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.

Spacious Retreat w/ Pool, Hot Tub & Game Room

Stony Point NY

Located in Stony Point, this villa is within a 5-minute drive of Harriman State Park and Patriot Hills Golf Club.

New Luxury 5BR3BTh Woodstock Secret Retreat Near all Ski MT Heated Pool& Hot Tub

Woodstock NY

A stay at this villa places you in the heart of Woodstock, steps from Catskill State Park and a 4-minute drive from Woodstock Golf Club.

Rhinebrook Estate - 8 Bed/8Bath (Sleeps 20)

Hyde Park NY

With a stay at this villa in Hyde Park, you'll be within a 15-minute drive of Culinary Institute of America and Hyde Park Railroad Station.

Family Retreat with Autumn Views and Game Room

Stony Point NY

Located in Stony Point, this villa is in a rural location, within a 5-minute drive of Harriman State Park and Penguin Rep Theatre.

Country home with rock climbing gym, pond & creek.

New Paltz NY

Located in New Paltz, this villa is on the waterfront, within a 10-minute drive of Nyquist-Harcourt Wildlife Sanctuary and G. Steve Jordan Gallery.

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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.