Middletown Villas

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Villas in Middletown

Hemlock Estate: Indoor Hot Tub, Pool, Game Room; Spacious, Ski & More!

Monticello NY

With a stay at this villa in Monticello, you'll be in the mountains, within a 15-minute drive of Resorts World Catskills and Monticello Motor Club.

Pool

Hot Tub

Serene 10BR Retreat w/Pool, Gym & Hot Tub

Chester NY

$2,168 nightly

$2,506 total

Oct 18 - Oct 19

Total with taxes and fees

Located in Chester, this villa is within a 15-minute drive of Woodbury Common Premium Outlets and LEGOLAND® New York.

Pool

Hot Tub

Magical Family Escape, Pool, HotTub, Pets, <1 Hr NYC

Harriman NY

Located in Harriman, this villa is in a rural location, within a 5-minute drive of Harriman State Park and Harriman Plaza Shopping Center.

Pool

Hot Tub

7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space

Monroe NY

With a stay at this villa in Monroe, you'll be within a 15-minute drive of Woodbury Common Premium Outlets and LEGOLAND® New York.

Pool

Hot Tub

Magnificent Villa, Private Pool, Fire Pit w/Huge Backyard

Chester NY

With a stay at this villa in Chester, you'll be within a 15-minute drive of Woodbury Common Premium Outlets and LEGOLAND® New York.

Pool

Kitchen

Pinnacle Pointe by Relaxtay | 600-Acre Private Luxury Estate with Spa, Pool, Theater & Lake

Middletown NY

With a stay at this villa, you'll be centrally located in Middletown, within a 10-minute drive of Otisville Veterans Memorial Park and Bloomingburg Village Hall.

Pool

Hot Tub

Luxe Mountain Getaway, Fire Pit,Arcade, Hot Tub, Near Lake Minnewaska

Kerhonkson NY

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

Hot Tub

Kitchen

Spacious 8BR Catskills Cabin w/ Game Room & Deck

Rock Hill NY

With a stay at this villa in Rock Hill, you'll be within a 10-minute drive of Resorts World Catskills and Lake Louise Marie.

Hot Tub

Kitchen

11BR Retreat w Pool, Hot Tub, Sauna & Game Room

Chester NY

With a stay at this villa in Chester, you'll be within a 15-minute drive of Woodbury Common Premium Outlets and LEGOLAND® New York.

Pool

Kitchen

Lakefront Paradise w/Pool, Hot Tub, Sauna & Kayaks

Woodridge NY

$4,099 nightly

$4,571 total

Oct 25 - Oct 26

Total with taxes and fees

Located in Woodridge, this villa is on the waterfront, within a 15-minute drive of East Pond and Neversink River.

Pool

Hot Tub

Luxury School House Retreat With Pool & Sauna - 1HR from NYC

New Hampton NY

$1,142 nightly

$1,349 total

Oct 20 - Oct 21

Total with taxes and fees

Located in New Hampton, this villa is on a river, within a 15-minute drive of Pine Island Town Park and Scenic Farms Golf Course.

Pool

Kitchen

Modern Villa with private pond near Legoland and Delaware River.

Port Jervis NY

Located in Port Jervis, this villa is within a 5-minute drive of Huckleberry Ridge State Forest and Stone Beach.

Kitchen

Washer

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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.