Philipstown Cottages

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Cottages in Philipstown

Wappinger Cottage - Scandinavian retreat on a creek

Poughkeepsie NY

With a stay at this cottage in Poughkeepsie, you'll be on a river, within a 10-minute drive of Vassar College and Overlook Drive-In Theater.

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Fort Montgomery NY

$268 nightly

$303 total

Jan 23 - Jan 24

Total with taxes and fees

With a stay at this cottage in Fort Montgomery, you'll be on a river, a 4-minute walk from Bear Mountain State Park and a 5-minute drive from Hudson River.

Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven

Croton-on-Hudson NY

Located in Croton-on-Hudson, this cottage is a 3-minute drive from Van Cortlandt Manor and 6 minutes from Brinton Brook Sanctuary.

Scenic Hudson Valley Getaway • Farms & Vineyards

Marlboro NY

Located in Marlboro, this cottage is within a 5-minute drive of Live At The falcon and Marlboro Free Library.

Cozy Retreat w/ Pool, Cinema Room & Fire Pit

Putnam Valley NY

Located in Lake Peekskill, this cottage is within a 15-minute drive of Hudson Valley Center for Contemporary Art and Oscawana Lake.

Charming & Great Location!

Verbank NY

Located in Millbrook, this cottage is on the waterfront, within a 15-minute drive of Institute of Ecosystem Studies and James Baird State Park.

Magnificent Lake View

Holmes NY

With a stay at this cottage in Holmes, you'll be on the waterfront, just steps from Whaley Lake and a 4-minute drive from Lake Dutchess.

Mountain View escape

New Paltz NY

Located in New Paltz, this cottage is within a 10-minute drive of Jenkinstown Day Spa and Loren Campbell Memorial Field.

Luxe Family Home on Orange Lake w/ Private Dock!

Newburgh NY

Located in Newburgh, Luxe Family Home on Orange Lake w/ Private Dock! is a 4-minute drive from Ice Time Sports Complex and 6 minutes from Algonquin Park.

Hudson Valley Retreat w/ Pool Near Greenwood Lake

Monroe NY

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

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Goshen NY

$281 nightly

$293 total

Jan 23 - Jan 24

Total with taxes and fees

With a stay at this cottage in Goshen, you'll be within a 10-minute drive of LEGOLAND® New York and Harness Racing Museum and Hall of Fame.

Charming Victorian Retreat w/ Hudson River Views

Newburgh NY

With a stay at this cottage in Newburgh, you'll be within a 15-minute drive of United States Military Academy and Washington Headquarters.

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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.