Middletown Cottages

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Cottages in Middletown

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Fort Montgomery NY

$271 nightly

$271 total

Apr 25 - Apr 26

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

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

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

2 Lake Cabins | Pool+HotTub | Game Room & Courts

Highland Lake NY

Located in Highland Lake, this cottage is on the waterfront, a 5-minute drive from Sidwell Lake and 7 minutes from Mohican Lake.

Pool

Hot Tub

Huge Fire Pit 5 Private Lakes Hiking Trails Fishing Mountain Creek State Parks

Highland Lakes NJ

When you stay at this cottage in Highland Lakes, you'll be on a lake, within a 10-minute walk of Highland Lake and Highland Lakes Beach 1.

Kitchen

Washer

Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks

Kerhonkson NY

$166 nightly

$169 total

Apr 28 - Apr 29

Total with taxes and fees

Located in Kerhonkson, this cottage is in the mountains, within a 5-minute drive of Minnewaska State Park and Lake Minnewaska Beach.

Kitchen

Washer

Charming lake community cottage with hot tub PET FRIENDLY

Glen Spey NY

Located in Glen Spey, this cottage is on a lake, within a 15-minute drive of Mohican Lake and Sidwell Lake.

Kitchen

Pet friendly

Charming Cottage with Jacuzzi, Fire Pit and Access to Nearby Lakes!

Monticello NY

Located in Smallwood, this cottage is within a 15-minute drive of Woodstock Monument and Bethel Woods Center For The Arts.

Hot Tub

Kitchen

Charming Cottage in the Heart of the Shawangunks

Wallkill NY

Located in Wallkill, this cottage is on a river, a 1-minute drive from Minnewaska State Park and 10 minutes from Whitecliff Vineyard.

Kitchen

Washer

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Goshen NY

$281 nightly

$293 total

Apr 26 - Apr 27

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.

Kitchen

Free WiFi

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

Barryville NY

When you stay at this cottage in Barryville, you'll be on the waterfront, just steps from Upper Delaware River and Delaware River.

Kitchen

Dryer

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 Orange County Community College.

Hot Tub

Kitchen

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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.