A lake surrounded by autumn-colored trees reflecting on the water.

Villas in Middletown

Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Middletown villas

A staircase leading to a porch with a view of a house and surrounding trees.

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

Luxury School House Retreat With Pool & Sauna - 1HR from NYC
New Hampton
10.0 out of 10, Exceptional, (23 reviews)
"House was great, conveniently located to ski mountain, Hunter was a pleasure to work with, house was clean and had so many amenities for our family! Highly recommend! "
United States
Jennifer P.
$1,086 nightly
The price is $1,283
Nov 17 - Nov 18
Total with taxes and fees
Luxury School House Retreat With Pool & Sauna - 1HR from NYC
A large, multi-story house with a prominent stone chimney, multiple windows, and a well-maintained garden.

2. Spectacular Historic Mansion w/Pool&Tennis

Spectacular Historic Mansion w/Pool&Tennis
Goshen
10.0 out of 10, Exceptional, (20 reviews)
"Truly amazing house, incredible pool, easy renting experience. Would definitely be back. "
United States
Aditya U.
$2,327 nightly
The price is $2,439
Nov 15 - Nov 16
Total with taxes and fees
Spectacular Historic Mansion w/Pool&Tennis
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.
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Top Middletown Hotel Reviews

Resorts World Catskills Casino

Resorts World Catskills Casino

10/10 Excellent
"Very Clean and Beautiful Place. Staff was Great . Highly Recommend !"
Benny 1-night trip
Posted 3 hours ago
Resorts World Catskills Casino

Find out more about Middletown

Middletown Villas information

Number of reviews
43
Accommodation
15 Villas
Lowest Price
$1,283
Highest Price
$2,439

Frequently asked questions

Why book your villa in Middletown with Expedia?
Expedia makes it a breeze to find your dream villa in Middletown. Taking the kids on vacation? Take advantage of our filters to look for stays with a pool or free WiFi. If you need to stick to a budget, choose how much you'd like to spend and the star rating of the property. We'll help you find a perfect place that matches your style and taste.
How can I find cheap villas in Middletown?
With Expedia's handy filter tool, locating cheap villas in Middletown is a piece of cake. To find accommodations that are gentle on your bank balance, tailor your search results by amenities, budget and star rating.
What is there to do near my villa in Middletown?
The best travel accessory is a well-planned schedule. Orange County Fair Speedway is a good place to kick-start your sightseeing in Middletown.

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