Sugar Loaf Cottages

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Cottages in Sugar Loaf

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Fort Montgomery NY

$271 nightly

$307 total

Dec 6 - Dec 7

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.

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.

Hike & Fish: Outdoor Retreat Near Trails

Westbrookville NY

$272 nightly

$308 total

Dec 7 - Dec 8

Total with taxes and fees

With a stay at this cottage in Westbrookville, you'll be within a 5-minute walk of Gobbler's Knob State Forest and Sheriff H. Frank Bigger Memorial Park.

Hello Small Stone

Middletown NY

$375 nightly

$424 total

Dec 7 - Dec 8

Total with taxes and fees

Located in Middletown, this cottage is within a 10-minute drive of Otisville Veterans Memorial Park and Otisville Village Hall.

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.

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.

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Goshen NY

$281 nightly

$293 total

Dec 7 - Dec 8

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

Located in Newburgh, this cottage is within a 15-minute walk of Washington Headquarters and Ann Street Gallery.

Bright Cornwall-on-hudson Vacation Rental!

Cornwall NY

With a stay at this cottage in Cornwall, you'll be within a 5-minute drive of New York Military Academy and Storm King State Park.

Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike

Vernon Township NJ

$423 nightly

$478 total

Dec 9 - Dec 10

Total with taxes and fees

With a stay at this cottage in Vernon, you'll be a 1-minute drive from Mountain Creek Ski Resort and 10 minutes from Crystal Springs Golf Resort.

Updated Home w/ Patio Half Mile to West Point

Highland Falls NY

With a stay at this cottage in Highland Falls, you'll be within a 10-minute walk of United States Military Academy and West Point Museum.

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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.