A large steel bridge spanning a river, surrounded by trees and buildings.

Middletown Vacation Rentals

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Our top choices for Middletown vacation rentals

Cottage Suites

Cottage Suites
3.0 star property
Middletown
6.6 out of 10, (7 reviews)
"It was a great place "
United States
Jose
The price is CA $178
CA $385 total
includes taxes & fees
Jul 1 - Jul 2
Cottage Suites

Hudson Valley Retreat w/ Pool Near Greenwood Lake

Hudson Valley Retreat w/ Pool Near Greenwood Lake
3.0 star property
Monroe
10.0 out of 10, Exceptional, (3 reviews)
"fantastic accommodations"
United States
David
The price is CA $259
CA $729 total
includes taxes & fees
Jun 28 - Jun 29
Hudson Valley Retreat w/ Pool Near Greenwood Lake

Historic Horse Barn Apartment in Goshen

Historic Horse Barn Apartment in Goshen
4.0 star property
Goshen
The price is CA $338
CA $416 total
includes taxes & fees
Jun 24 - Jun 25
Historic Horse Barn Apartment in Goshen

Carriage House Apartment Goshen NY

Carriage House Apartment Goshen NY
4.0 star property
Goshen
The price is CA $554
CA $682 total
includes taxes & fees
Jun 24 - Jun 25
Carriage House Apartment Goshen NY

West Point Summer Pool Jacuzzi Events Pets OK

West Point Summer Pool Jacuzzi Events Pets OK
2.0 star property
Cornwall
The price is CA $1,344
CA $2,357 total
includes taxes & fees
Jun 24 - Jun 25
West Point Summer Pool Jacuzzi Events Pets OK

Close to Trails: Studio w/ Water Views

Close to Trails: Studio w/ Water Views
3.0 star property
Westbrookville
The price is CA $259
CA $484 total
includes taxes & fees
Jun 25 - Jun 26
Close to Trails: Studio w/ Water Views

Hike & Fish: Outdoor Retreat Near Trails

Hike & Fish: Outdoor Retreat Near Trails
3.0 star property
Westbrookville
The price is CA $303
CA $583 total
includes taxes & fees
Jun 25 - Jun 26
Hike & Fish: Outdoor Retreat Near Trails

Family Home Close to Warwick, 5 Mi to Lake!

Family Home Close to Warwick, 5 Mi to Lake!
3.0 star property
Monroe
The price is CA $398
CA $1,033 total
includes taxes & fees
Jun 26 - Jun 27
Family Home Close to Warwick, 5 Mi to Lake!

Bright Cornwall-on-hudson Vacation Rental!

Bright Cornwall-on-hudson Vacation Rental!
3.0 star property
Cornwall
10.0 out of 10, Exceptional, (1 review)
"Very nice property, very comfortable, close to multiple sightseeing location including bear mountain."
United States
Poyuk
The price is CA $485
CA $988 total
includes taxes & fees
Jun 25 - Jun 26
Bright Cornwall-on-hudson Vacation Rental!

Peaceful Mountian Oasis: Firepit, Hot Tub, Sauna!

Peaceful Mountian Oasis: Firepit, Hot Tub, Sauna!
3.0 star property
Vernon
The price is CA $2,072
CA $4,200 total
includes taxes & fees
Jun 30 - Jul 1
Peaceful Mountian Oasis: Firepit, Hot Tub, Sauna!
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

Find out more about Middletown

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Middletown. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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 Pool + Paddle Boats Sleeps 12: This vacation home rental outside of Middletown offers an outdoor pool, a balcony, and air-conditioning to help you feel perfectly comfortable in your new surroundings. You can relax into your vacation with a garden and a pool table.

How many vacation rentals are there in Middletown?

With 11 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.