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

Middletown Holiday Rentals

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Middletown holiday rentals

A modern hotel room with a large bed, a desk, a chair, a TV, and a view of the outside.

1. Columbus Suites

Columbus Suites
3.0 star property
Middletown
6.4 out of 10, (21 reviews)
"My worst experience ever staying at the hotel no communication locked out at the sleep in my car. I would never recommend anybody to stay there. The bed is horrible no curtains window basically nothing nice to say about that property. Sorry."
United States
Edwin
The price is S$187
includes taxes & fees
6 Nov - 7 Nov
Columbus Suites
A two-story house with a porch, a table, and chairs outside.

2. Historic Horse Barn Apartment in Goshen

Historic Horse Barn Apartment in Goshen
4.0 star property
Goshen
Historic Horse Barn Apartment in Goshen
A spacious living room with a fireplace, a ceiling fan, and a large window.

3. 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, (4 reviews)
"The house was very quiet and exactly as advertised. Would stay again!"
United States
Scott
The price is S$691
includes taxes & fees
8 Nov - 9 Nov
Hudson Valley Retreat w/ Pool Near Greenwood Lake
A modern outdoor hot tub area with stone walls and a wooden deck.

4. 2 Lake Cabins Pool+hottub Game Room 23acs

2 Lake Cabins Pool+hottub Game Room 23acs
2.0 star property
Highland Lake
The price is S$1,290
includes taxes & fees
11 Nov - 12 Nov
2 Lake Cabins Pool+hottub Game Room 23acs
A spacious living room with a high ceiling, large windows, a flat-screen TV, a grey sofa, a small round table, and a wooden deck visible through the glass door.

5. Hike & Fish: Outdoor Retreat Near Trails

Hike & Fish: Outdoor Retreat Near Trails
3.0 star property
Westbrookville
The price is S$439
includes taxes & fees
6 Nov - 7 Nov
Hike & Fish: Outdoor Retreat Near Trails
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
"I stayed here twice. I thought the hotel was amazing. The price was reasonable; it was very clean, and there was plenty of parking. I really liked my king-size bed; the staff was very friendly. The breakfast was awesome. I was expecting it to be some form of continental breakfast, but it was actually a little bit better than that, including warm food, like eggs and sausage. I really liked it and I definitely recommend this hotel."
Fabian 1-night trip
Posted 6 hours ago
Sleep Inn & Suites Middletown - Goshen

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.