Middletown Cottages

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Cottages in Middletown

Fabulous 2-bedroom cottage in Wurtsboro

Wurtsboro NY

Located in Wurtsboro, this cottage is within a 15-minute drive of Masten Lake and Lake Louise Marie.

Kitchen

Pet friendly

Charming 2-bedroom cottage near Bethel Woods with WiFi

Eldred NY

With a stay at this cottage in Highland Lake, you'll be within a 15-minute drive of Sidwell Lake and Brook House Gallery Incorporated.

Pool

Kitchen

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Fort Montgomery NY

$271 nightly

$307 total

Jan 29 - Jan 30

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

Lazy River Cottage on the Delaware River

Matamoras PA

A stay at this cottage places you in the heart of Matamoras, within a 5-minute drive of Westfall Township Municipal Building and West End Beach.

Kitchen

Free WiFi

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

Hike & Fish: Outdoor Retreat Near Trails

Westbrookville NY

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.

Kitchen

Parking included

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

Tiny House on Spectacular Riverfront Property - Private Access to Delaware River

Barryville NY

With a stay at this cottage in Barryville, you'll be on the waterfront, just steps from Upper Delaware River and a 1-minute drive from Brook House Gallery Incorporated.

Kitchen

Dryer

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

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

Cozy Cottage with Woodstock Scavenger Hunt

Mongaup Valley NY

With a stay at this cottage in Mongaup Valley, you'll be within a 15-minute drive of Bethel Woods Center For The Arts and Resorts World Catskills.

Kitchen

Free WiFi

Hello Small Stone

Middletown NY

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

Air conditioning

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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.