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

Villas in Middletown

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

Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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, (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 29 - Sep 30
Total with taxes and fees
Luxury School House Retreat With Pool & Sauna - 1HR from NYC
A hot tub with a wooden deck and railing, surrounded by a grassy area and a stone wall.

2. 11BR Retreat w Pool, Hot Tub, Sauna & Game Room

11BR Retreat w Pool, Hot Tub, Sauna & Game Room
Chester
10.0 out of 10, Exceptional, (2 reviews)
"5 star experience! We will definitely stay here again. The host was responsive, and the house was in perfect condition. The pool was clean. The sauna was spotless!"
United States
Benny P.
$2,777 nightly
The price is $3,235
Sep 27 - Sep 28
Total with taxes and fees
11BR Retreat w Pool, Hot Tub, Sauna & Game Room
A large house with a deck, a hot tub, and a swimming pool.

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

Lakefront Paradise w/Pool, Hot Tub, Sauna & Kayaks
Woodridge
9.0 out of 10, Wonderful, (2 reviews)
"Plenty of room for big groups"
United States
Julia K.
$3,517 nightly
The price is $3,915
Sep 27 - Sep 28
Total with taxes and fees
Lakefront Paradise w/Pool, Hot Tub, Sauna & Kayaks
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

Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown

8/10 Good
"This was a quick one-night stay. Everything was fine."
Stewart 1-night trip
Posted less than an hour ago
Hampton Inn by Hilton Middletown

Find out more about Middletown

Middletown Villas information

Number of reviews
24
Accommodation
16 Villas
Lowest Price
$1,349
Highest Price
$3,915

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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