New Windsor Cottages

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Cottages in New Windsor

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.

Kitchen

Washer

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Fort Montgomery NY

$269 nightly

$304 total

Jan 18 - Jan 19

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.

Kitchen

Pet friendly

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.

Air conditioning

Cozy Haven: A Romantic Retreat in our Tiny House!

Middletown NY

With a stay at this cottage in Middletown, you'll be within a 10-minute drive of Maple Hill Dog Park and Paramount Theatre.

Hot Tub

Kitchen

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.

Washer

Dryer

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.

Pool

Kitchen

Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro

Bloomingburg NY

Located in Bloomingburg, this cottage is a 3-minute drive from Wurtsboro Ridge State Forest and 7 minutes from Shawangunk Ridge State Forest.

Kitchen

Free WiFi

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.

Kitchen

Free WiFi

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.

Kitchen

Washer

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.

Kitchen

Dryer

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.

Pool

Kitchen

A romantic cottage and artist's retreat looking down over an enchanted lake

Greenwood Lake NY

When you stay at this cottage in Greenwood Lake, you'll be on a lake, within a 5-minute drive of Greenwood Lake and Lion's Field Park.

Kitchen

Washer

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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.