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Middletown Vacation Rentals

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Check prices for these dates

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Dec 28 - Dec 29
Tomorrow
Dec 29 - Dec 30
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Jan 2 - Jan 4
In two weeks
Jan 9 - Jan 11

Our top choices for Middletown vacation rentals

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

Cottage in Westbrookville

Hike & Fish: Outdoor Retreat Near Trails
3.0 star property
The price is ￥25,834
￥48,184 total
includes taxes & fees
Dec 30 - Dec 31
Hike & Fish: Outdoor Retreat Near Trails
House | 7 bedrooms
West Point Villa - Jacuzzi Pool BBQ Games Pets

Vacation Home in Cornwall

West Point Villa - Jacuzzi Pool BBQ Games Pets
2.0 star property
The price is ￥56,038
￥68,340 total
includes taxes & fees
Jan 6 - Jan 7, 2026
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

Candlewood Suites Middletown Goshen by IHG

Candlewood Suites Middletown Goshen by IHG

10/10 Excellent
"👍"
Archil 1-night trip
Posted 2 days ago
Candlewood Suites Middletown Goshen by IHG

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 5 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. Orange County Fair Speedway and Orange County Fairgrounds are other places to visit while you're in town.

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.