Middletown Villas

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Villas in Middletown

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

Monticello NY

$888 nightly

$998 total

Sep 7 - Sep 8

Total with taxes and fees

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

Monticello Family Retreat. Pool, Firepit. 7min to casino. Sleeps 15

Monticello NY

$828 nightly

$930 total

Aug 26 - Aug 27

Total with taxes and fees

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

Pool

Kitchen

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

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

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

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

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

Washer

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

Chester NY

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

Pool

Hot Tub

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

Woodridge NY

With a stay at this villa in Woodridge, you'll be within a 15-minute drive of East Pond and Neversink River.

Pool

Hot Tub

Beautiful modern villa with pool suana hot tub...

Clintondale NY

Located in Clintondale, this villa is a 4-minute drive from Apple Greens Golf Course and 7 minutes from State University of New York-New Paltz.

Pool

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.