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
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 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)
"It was a great place "
United States
Jose
The price is AU$241
includes taxes & fees
22 Oct - 23 Oct
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
The price is AU$375
includes taxes & fees
8 Nov - 9 Nov
Historic Horse Barn Apartment in Goshen
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.

3. Hike & Fish: Outdoor Retreat Near Trails

Hike & Fish: Outdoor Retreat Near Trails
3.0 star property
Westbrookville
The price is AU$490
includes taxes & fees
1 Nov - 2 Nov
Hike & Fish: Outdoor Retreat Near Trails
An indoor water park with a large water slide, inflatable tubes, and lush greenery.

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 AU$1,451
includes taxes & fees
27 Oct - 28 Oct
2 Lake Cabins Pool+hottub Game Room 23acs
A spacious loft with a high ceiling, exposed beams, a kitchen with modern appliances, a dining area, and a living room with a large sofa.

5. Hay Loft Apartment in Barn - Goshen

Hay Loft Apartment in Barn - Goshen
2.0 star property
Goshen
10.0 out of 10, Exceptional, (3 reviews)
"This location was perfect for our yearly fall gathering. It is 15 minutes from Pure Terror Scream Park and nestled in a historic town. The unit was clean, spacious, and perfect for a group of 7-8 people. The hosts were very helpful and prompt with instructions. I would recommend this stay if you are looking to stay in Goshen, NY."
United States
Tammy
Hay Loft Apartment in Barn - Goshen
A modern kitchen with dark cabinets, a stainless steel stove, and a wooden countertop.

6. Carriage House Apartment Goshen NY

Carriage House Apartment Goshen NY
4.0 star property
Goshen
10.0 out of 10, Exceptional, (1 review)
Carriage House Apartment Goshen NY
A modern kitchen with white cabinets, a central island with stools, a stainless steel refrigerator, and a staircase leading to another level.

7. 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 AU$996
includes taxes & fees
22 Oct - 23 Oct
Bright Cornwall-on-hudson Vacation Rental!
A house with a covered porch, stone foundation, and a front door with a wreath.

8. West Point Summer Pool Jacuzzi Events Pets OK

West Point Summer Pool Jacuzzi Events Pets OK
2.0 star property
Cornwall
The price is AU$1,816
includes taxes & fees
16 Nov - 17 Nov
West Point Summer Pool Jacuzzi Events Pets OK
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

Ramada by Wyndham Newburgh/West Point

Ramada by Wyndham Newburgh/West Point

8/10 Good
"Was under construction, room was clean and comfortable."
Gary 4-night trip
Posted 22 hours ago
Ramada by Wyndham Newburgh/West Point

Find out more about Middletown

Everything you need to know about Middletown holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Middletown holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Middletown holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Middletown holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middletown. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Middletown holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Middletown holiday rentals we have selected for you start as low as AU$206 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Middletown rentals

At Expedia, we put the best Middletown holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Middletown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Middletown holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Middletown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.

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

Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!: This holiday home rental outside of Middletown is located on a lake, and has an outdoor pool, a balcony and a BBQ 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 that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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.