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

Villas in Middletown

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  • Upfront pricing

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

Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

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.
$1,142 nightly
The price is $1,349
Oct 20 - Oct 21
Total with taxes and fees
Luxury School House Retreat With Pool & Sauna - 1HR from NYC
A modern house with a large deck, a swimming pool, and a forested backdrop.

2. 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.
$3,741 nightly
The price is $4,167
Oct 25 - Oct 26
Total with taxes and fees
Lakefront Paradise w/Pool, Hot Tub, Sauna & Kayaks
A traditional half-timbered building with a stone staircase and a well-maintained garden.

3. 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.
$2,528 nightly
The price is $2,640
Nov 1 - Nov 2
Total with taxes and fees
Spectacular Historic Mansion w/Pool&Tennis
A wooden deck with wicker chairs and a hot tub.

4. Spacious villa w/Pool, Hot Tub & Game Room on 7.5 private acres

Spacious villa w/Pool, Hot Tub & Game Room on 7.5 private acres
Chester
Spacious villa w/Pool, Hot Tub & Game Room on 7.5 private acres
A wooden deck with outdoor furniture, a pool, and a lush garden.

5. Serene 10BR Retreat w/Pool, Gym & Hot Tub

Serene 10BR Retreat w/Pool, Gym & Hot Tub
Chester
7.0 out of 10, Good, (2 reviews)
"We had an amazing stay! The house was even better than the pictures. There was plenty of space for our large group, and the 10 bedrooms made it comfortable for everyone. The pool and hot tub were definitely highlights, and the game room kept both the kids and adults entertained throughout the trip.One of the things we loved most was how private and secluded the property felt. It was the perfect place to relax, unwind, and spend quality time together without feeling crowded. The home was clean,...
United States
Jacob F.
Serene 10BR Retreat w/Pool, Gym & Hot Tub
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

Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen

10/10 Excellent
"Room was very clean 👌 wonderful staff highly recommended!!! Will be staying there again in the future. Pool & whirlpool A++"
Adam 1-night trip
Posted 2 hours ago
Courtyard by Marriott Middletown Goshen

Find out more about Middletown

Middletown Villas information

Number of reviews
47
Accommodation
15 Villas
Lowest Price
$1,349
Highest Price
$4,167

Frequently asked questions

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How can I find cheap villas in Middletown?
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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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