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

Villas in Middletown

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Middletown villas

A red house with a stone pathway leading to the entrance, surrounded by trees and a well-maintained lawn.

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

Hemlock Estate: Indoor Hot Tub, Pool, Game Room; Spacious, Ski & More!
Monticello
9.6 out of 10, Exceptional, (42 reviews)
"hot tub was great! rooms were comfortable and neighborhood was quiet"
United States
Lester K.
Hemlock Estate: Indoor Hot Tub, Pool, Game Room; Spacious, Ski & More!
A staircase leading to a porch with a view of a house and surrounding trees.

2. 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, (22 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.
$1,142 nightly
The price is $1,349
Sep 22 - Sep 23
Total with taxes and fees
Luxury School House Retreat With Pool & Sauna - 1HR from NYC
A building with two garage doors, a covered ATV, and a chair in the foreground.

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

Monticello Family Retreat. Pool, Firepit. 7min to casino. Sleeps 15
Monticello
8.4 out of 10, Very good, (5 reviews)
"This house was a home run for our week-long stay. It was clean, comfortable, and exactly as described in the listing. The check-in process was seamless and communication with the host was great. Five stars all around, we would definitely stay here again!"
United States
Uri J.
$627 nightly
The price is $705
Sep 18 - Sep 19
Total with taxes and fees
Monticello Family Retreat. Pool, Firepit. 7min to casino. Sleeps 15
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Middletown Hotel Reviews

La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

10/10 Excellent
"It was inviting and clean. The staff was nice."
Valerie 1-night trip
Posted 12 hours ago
La Quinta Inn & Suites by Wyndham Middletown-Goshen

Find out more about Middletown

Middletown Villas information

Number of reviews
69
Accommodation
16 Villas
Lowest Price
$705
Highest Price
$1,349

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.

Explore a world of travel with Expedia