Middletown Vacation Rentals

Name: The Highland: a Cute Private Country Estate, Pool, GameRoom 18+ beds
Address: Monticello

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Vacation Rentals in Middletown

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

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.

The Perfect up to date Private Getaway to call home for a while

Located in Bloomingburg, this vacation home is in the mountains, a 3-minute drive from Bloomingburg Village Hall and 6 minutes from Wurtsboro Ridge State Forest.

Kitchen

Washer

Greenwoods of Warwick

With a stay at this vacation home in Monroe, you'll be within a 5-minute drive of Greenwood Lake and Sterling Forest State Park.

Washer

Dryer

Elegant and spacious home with sauna and heated pool

With a stay at this vacation home in Monroe, you'll be within a 15-minute drive of Woodbury Common Premium Outlets and Schunnemunk State Park.

Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out

$327

includes taxes & fees

$289 per night

Jan 6 - Jan 7, 2025

With a stay at this vacation home in Vernon, you'll be in the mountains, within a 10-minute drive of Crystal Springs Golf Resort and Mountain Creek Ski Resort.

Pool

Hot Tub

Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!

$339

includes taxes & fees

$327 per night

Jan 12 - Jan 13, 2025

Located in Wallkill, this vacation home is on the waterfront, within a 15-minute drive of Angry Orchard and Tuthilltown Spirits.

Kitchen

Washer

Spacious 4-bedroom home on 5 acre farm near Minnewaska State Park

$555

includes taxes & fees

$546 per night

Jan 7 - Jan 8, 2025

Located in Pine Bush, this vacation home is in the mountains, within a 10-minute drive of Brimstone Hill Winery and Minnewaska State Park.

Spectacular ~10k sqft Mansion w/Pool&Tennis

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

Pool

Hot Tub

By Mtn Creek Resort: ‘The Point on Highland Lake’

With a stay at this vacation home in Highland Lakes, you'll be on the waterfront, just a 1-minute walk from Highland Lake and 11 minutes by foot from Upper East Highland Lake.

Luxury Lakeside Paradise

Located in Monticello, this vacation home is on a lake, within a 15-minute drive of Mongaup River and Monticello Casino and Raceway.

Kitchen

Washer

Pet-Friendly ‘Pond View Loft' w/ Private Pool!

Located in Pine Bush, this vacation home is on a river, within a 15-minute drive of Brimstone Hill Winery and Angry Orchard.

Pool

Kitchen

The Highland: a Cute Private Country Estate, Pool, GameRoom 18+ beds

With a stay at this vacation home in Monticello, you'll be in the mountains, within a 10-minute drive of Resorts World Catskills and Monticello Casino and Raceway.

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.