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Our top choices for Middletown villas

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.
The price is AU$1,820
includes taxes & fees
17 Nov - 18 Nov
Luxury School House Retreat With Pool & Sauna - 1HR from NYC

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.
The price is AU$3,632
includes taxes & fees
16 Nov - 17 Nov
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.

Learn more about Middletown

Just an hour from NYC, this historic Hudson Valley town offers scenic hikes along the Heritage Trail and apple picking at local orchards. Explore the interactive exhibits at the National Soaring Museum, then catch a performance at the beautifully restored Paramount Theatre built in 1930.

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

Frequently Asked Questions

What is there to do near my villa in Middletown?

There are plenty of fabulous things to do in Middletown. Don't miss major attractions like Paramount Theatre, Castle Fun Centre and Harness Racing Museum and Hall of Fame. Highland Lakes State Park, Orange County Fair Speedway and Thomas Bull Memorial Park also appeal to many visitors.