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Middletown Vacation Rentals

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Check prices for these dates

In two weeks
Nov 28 - Nov 30
In two months
Jan 9 - Jan 11
In three months
Feb 6 - Feb 8
In four months
Mar 6 - Mar 8

Vacation Rentals in Middletown

House (1 Bedroom) | Interior
Hike & Fish: Outdoor Retreat Near Trails

Hike & Fish: Outdoor Retreat Near Trails

3.0 star property
Westbrookville
The price is ￥28,076
￥46,948 total
includes taxes & fees
Nov 13 - Nov 14
Hike & Fish: Outdoor Retreat Near Trails
Apartment | 6 bedrooms
2 Lake Cabins Pool+hottub Game Room 23acs

2 Lake Cabins Pool+hottub Game Room 23acs

2.0 star property
Highland Lake
2 Lake Cabins Pool+hottub Game Room 23acs
Apartment (0 Bedroom) | Interior
Close to Trails: Studio w/ Water Views

Close to Trails: Studio w/ Water Views

3.0 star property
Westbrookville
The price is ￥20,810
￥36,186 total
includes taxes & fees
Nov 12 - Nov 13
Close to Trails: Studio w/ Water Views
Apartment (1 Bedroom) | Interior
Explore & Work! Stylish Washington Heights Duplex

Explore & Work! Stylish Washington Heights Duplex

3.0 star property
Newburgh
The price is ￥24,854
￥47,190 total
includes taxes & fees
Nov 24 - Nov 25
Explore & Work! Stylish Washington Heights Duplex
House | 7 bedrooms
West Point Villa - Jacuzzi Pool BBQ Games Pets

West Point Villa - Jacuzzi Pool BBQ Games Pets

2.0 star property
Cornwall
The price is ￥90,921
￥110,883 total
includes taxes & fees
Nov 13 - Nov 14
West Point Villa - Jacuzzi Pool BBQ Games Pets
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

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

10/10 Excellent
"clean rooms "
christine 1-night trip
Posted 1 day ago
Sleep Inn & Suites Middletown - Goshen

Find out more about Middletown

Search for holiday rentals in Middletown on Expedia! You can easily find your home rentals, villas, holiday apartments in Middletown using one of the methods below:

  • View our selection of featured holiday rentals in Middletown
  • Use the map to find apartments and other holiday homes in the Middletown neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Middletown while they last

Look no further and take a look at our great range of rental properties in Middletown!

Frequently asked questions

Can I find a vacation rental in Middletown?

Yes, we offer vacation rentals in Middletown close to Orange County Fairgrounds, or you can go with a more remote option if you'd like a relaxing place to stay. Visitors like the top-notch restaurants and shops in Middletown. Make sure you have time to check out the churches and architecture during your trip.

What are some of the best vacation home rentals that Middletown has to offer?

Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!: This vacation home rental outside of Middletown is located on a lake and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals are there in Middletown?

With 13 Expedia vacation rentals, you're sure to find just the right place for your Middletown stay.

What’s there to see and do in Middletown?

Highland Lake and Thomas Bull Memorial Park are a couple of scenic spots to enjoy the outdoors, whereas Paramount Theatre is one of the cultural attractions. While in the area, you can also visit popular places like LEGOLAND® New York and Woodbury Common Premium Outlets.

What’s a vacation rental in Middletown like?

Vacation rentals are privately owned properties you can book for short or long periods in Middletown. Vacation rentals offer extras such as hot tubs, fire pits, and patios so you'll have all the conveniences of home. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from public hotel elevators and lobbies bustling with people while still allowing you to travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for a family getaway.