Middletown Cottages

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Check dates for Middletown hotels

Cottages in Middletown

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.

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Fort Montgomery NY

$280 nightly

$331 total

Sep 21 - Sep 22

Total with taxes and fees

When you stay at this cottage in Fort Montgomery, you'll be on a river, within a 15-minute drive of Bear Mountain State Park and United States Military Academy.

5 Mi to Marina & Raceways: Monticello Retreat!

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 Mongaup River.

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Goshen NY

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

Monticello NY

With a stay at this cottage in Smallwood, you'll be within a 15-minute drive of Bethel Woods Center For The Arts and Forest Reserve at Smallwood.

Lazy River Cottage on the Delaware River

Matamoras PA

A stay at this cottage places you in the heart of Matamoras, steps from Delaware River and 13 minutes by foot from Westfall Township Municipal Building.

Hello Small Stone

Middletown NY

$292 nightly

$330 total

Sep 21 - Sep 22

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.

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.

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

Kerhonkson NY

$235 nightly

$237 total

Oct 5 - Oct 6

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.

Scenic Hudson Valley Getaway • Farms & Vineyards

Marlboro NY

Located in Marlboro, this cottage is a 4-minute drive from Live At The falcon and 6 minutes from Quartz Rock Vineyard.

Historic Gem in Culver Lake. Branchville N.J.

Branchville NJ

With a stay at this cottage in Branchville, you'll be on a lake, just a 1-minute walk from Culver Lake and 10 minutes by foot from Stokes State Forest.

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.

Don't see what you're looking for?

See all available properties in Middletown

View all properties

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.