Middletown Vacation Rentals

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Vacation Rentals in Middletown

Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9

Newburgh NY

When you stay at this vacation home in Newburgh, you'll be on the waterfront, within a 5-minute drive of Ice Time Sports Complex and Chadwick Lake.

Large Lake House Property Your Family And Friends Will Love Staying At!

Greenwood Lake NY

With a stay at this vacation home in Greenwood Lake, you'll be on a lake, just a 1-minute walk from Greenwood Lake and 8 minutes by foot from Lion's Field Park.

Hiking & Climbing Paradise- walking distance to Mohonk,Gunks,Minnewaska

New Paltz NY

A stay at this vacation home places you in the heart of New Paltz, a 5-minute drive from Mohonk Preserve Visitor Center and 6 minutes from Testimonial Gateway.

Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.

New Windsor NY

When you stay at this vacation home in New Windsor, you'll be on a river, within a 5-minute drive of Hudson River and Delano-Hitch Recreation Park.

Spacious 7BR Villa on 14 Acres w/ Indoor Pool

Washingtonville NY

Located in Blooming Grove, this vacation home is within a 10-minute drive of Brotherhood Winery and Schunnemunk State Park.

Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Warwick NY

$131 nightly

$148 total

Apr 22 - Apr 23

Total with taxes and fees

With a stay at this vacation home in Warwick, you'll be within a 10-minute walk of Railroad Green and Strazza Art Gallery.

Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

New Paltz NY

$367 nightly

$371 total

Apr 26 - Apr 27

Total with taxes and fees

When you stay at this vacation home in New Paltz, you'll be on the waterfront, within a 5-minute drive of Historic Huguenot Street and G. Steve Jordan Gallery.

Lakefront/Legoland/West Point Retreat Under 1 Hour From NYC! Heated pool & Spa!

Monroe NY

When you stay at this vacation home in Monroe, you'll be on the waterfront, within a 15-minute drive of LEGOLAND® New York and Woodbury Common Premium Outlets.

Beacon,Hudson Valley, 4bedroom 2bath, Sleeps 7, Pool, Hot Tub, Wifi,1.5m to town

Beacon NY

A stay at this vacation home places you in the heart of Beacon, within a 5-minute drive of Mount Gulian Historic Site and Hudson River.

Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!

Monticello NY

With a stay at this vacation home in Monticello, you'll be on the waterfront, within a 15-minute drive of Woodstock Monument and Mongaup River.

Red Barn Retreat - Shawangunk Mountains Getaway

Gardiner NY

When you stay at this vacation home in Gardiner, you'll be on the waterfront, within a 5-minute drive of Whitecliff Vineyard and DM Weil Gallery.

Riverfront stone cottage Private dock & boats Personal spa private resort

Gardiner NY

Located in Gardiner, this vacation home is on the waterfront, within a 5-minute drive of DM Weil Gallery and Tuthilltown Spirits.

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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.