Middletown Villas

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Villas in Middletown

Luxury 9BR Retreat w/Pool & Hot Tub

Chester NY

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

Pool

Hot Tub

Family Fun Getaway near Cascade Lake in Warwick NY

Warwick NY

Located in Warwick, this villa is within a 15-minute drive of Cascade Lake Park and Strazza Art Gallery.

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 LEGOLAND® New York and Woodbury Common Premium Outlets.

Pool

Kitchen

Pool, Fire Pit Bedroom & Alaska King – Sleeps 16

goshen NY

$644 nightly

$724 total

Dec 10 - Dec 11

Total with taxes and fees

Located in Goshen, this villa is in a rural location, within a 10-minute drive of Castle Fun Center and Museum Village.

Pool

Kitchen

Spacious + beautiful 5-bedroom Mediterranean Villa in Monroe, NY.

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

Malkita Aria: Mountainview Escape with Postcard-Perfect Scenery

Woodbury NY

With a stay at this villa in Highland Mills, you'll be on a river, within a 15-minute drive of Woodbury Common Premium Outlets and Palaia Vineyards Winery.

Hot Tub

Kitchen

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 Neversink River and Sullivan County Dramatic Workshop - Rivoli Theatre.

Pool

Hot Tub

Warm Escape, Wood Stove, HotTub, Pets, <1 Hr NYC

Harriman NY

With a stay at this villa in Harriman, you'll be within a 10-minute drive of Woodbury Common Premium Outlets and Harriman State Park.

Pool

Kitchen

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

New Hampton NY

$1,127 nightly

$1,331 total

Dec 10 - Dec 11

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 Minisink Town Hall.

Pool

Kitchen

Hemlock Estate: Indoor Hot Tub, Heated 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

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

Charming 3-bedroom villa with WiFi, AC in fabulous Monroe

Monroe NY

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

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.