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

Middletown Holiday Rentals

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Our top choices for Middletown holiday 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 S$351
includes taxes & fees
2 Jul - 3 Jul
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 S$665
includes taxes & fees
28 Jun - 29 Jun
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 S$336
includes taxes & fees
24 Jun - 25 Jun
Historic Horse Barn Apartment in Goshen

Carriage House Apartment Goshen NY

Carriage House Apartment Goshen NY
4.0 star property
Goshen
The price is S$693
includes taxes & fees
13 Jul - 14 Jul
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 S$2,150
includes taxes & fees
23 Jun - 24 Jun
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 S$442
includes taxes & fees
22 Jun - 23 Jun
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 S$531
includes taxes & fees
22 Jun - 23 Jun
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 S$942
includes taxes & fees
26 Jun - 27 Jun
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 S$901
includes taxes & fees
25 Jun - 26 Jun
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
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

Frequently asked questions

Can I find a holiday rental in Middletown?

Yes, there are holiday rentals in Middletown close to Orange County Fairgrounds, or you can select a more secluded option if you're looking for a relaxing 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.

How many holiday rentals are there in Middletown?

With 11 Expedia holiday rentals, you're guaranteed 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 holiday rental in Middletown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Middletown. Holiday rentals offer amenities such as hot tubs, fire pits and patios to help you enjoy your stay. If you're concerned about a sanitised environment, a holiday rental can provide a sense of security away from public hotel lifts and lobbies packed with people while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for family trips or small group gatherings.