Photo by Vincent Ramundo

Middletown holiday rentals

We found holiday rentals — enter your dates for availability

Discover a selection of 13 homes and other holiday rentals in Middletown that are perfect for your trip. Whether you're going on holiday with family or friends, holiday homes have the best amenities for hanging out with the people that matter most, which might include a garden and pool. Whatever you're looking for, you'll be sure to find a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Head to the friendly city of Middletown

Enjoy the area's churches, architecture and festivals with a rental holiday home in Middletown. This welcoming city attracts visitors thanks to its shopping and restaurants. LEGOLAND® New York and Woodbury Common Premium Outlets are just a couple of the must-see attractions in the area. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Activities and attractions in and around Middletown

Are you searching for attractions to see during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that Middletown has to offer. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • LEGOLAND® New York (7.5 mi / 12 km)
  • Goshen Historic Track (6.1 mi / 9.8 km)
  • Warwick Valley Winery and Distillery (10.7 mi / 17.2 km)
  • Brotherhood Winery (13.5 mi / 21.7 km)
  • Mount Peter Ski Area (15.3 mi / 24.6 km)
  • Holiday Mountain Ski and Fun Park (15.8 mi / 25.4 km)

Exploring the natural features in Middletown

Whether you're an adventurous traveller or just want to appreciate the scenery, Middletown is a great place to get out in nature. These are some of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • Orange County Arboretum (8.1 mi / 13.1 km)
  • The Rock Sports Complex (10.3 mi / 16.5 km)
  • Neversink River (13.4 mi / 21.6 km)
  • Sam's Point Preserve (15.7 mi / 25.3 km)
  • Arrow Park Lake and Lodge (16.9 mi / 27.2 km)
  • Storm King Art Center (18.9 mi / 30.4 km)

Travelling to and around Middletown

The nearest airport is in Newburgh, NY (SWF-Stewart Intl.), located 17.8 mi (28.7 km) from the city centre.

Frequently asked questions

What is the best area to stay in Middletown when booking a holiday home?
If you’re thinking about a getaway to Middletown, Mount Hope is one of the most popular locations to stay. Whether you prefer a villa, cottage or another property type, you’ll always have the whole place to yourself.
What is the most popular type of holiday home accommodation in Middletown?
The most desirable types of holiday homes in Middletown are houses. Searching for something different? Stayz offers a variety of options to match our guests’ unique needs, so you’ll see holiday properties in all sizes and shapes. The perfect fit is ready and waiting for you — find yours today.
How much does it cost to rent a holiday home in Middletown?
The average price for a holiday home in Middletown depends on a number of factors, such as time of year, length of stay and property type. Whether you’re thinking about a sprawling villa with lots of bedrooms or a cosy cabin just for the two of you, just enter your dates of travel to view stays with exceptional value.
How much does it cost to rent a beach house in Middletown?
The average price for a holiday home near the beach in Middletown depends on when you’re going and the style and size of property you’re searching for. You can quickly and easily find prices on Stayz by entering your travel dates and destination. Then use our handy filter tool to choose the number of bedrooms and amenities important to you, such as a pool, air conditioning and WiFi.
Are there pet-friendly holiday homes in Middletown?
Pack a travel bag and a bone for your canine companion because Middletown has eight holiday homes that roll out the welcome mat to pets. Let your furriest pal join in with the family fun at one of our pet-friendly holiday homes on Stayz. Simply enter your dates then check the “Pets allowed” filter box.
What are popular home amenities in Middletown?
Some of the most popular home amenities people search for in Middletown include nearby museums, a fireplace and mountain views. Whether you’re on a trip with buddies, family or even pets, Stayz holiday homes provide the best amenities for beginning new traditions with the people who matter most.
Are there holiday homes in Middletown that welcome kids?
Middletown has eight family-friendly holiday homes. And discovering a stay that welcomes youngsters is easy with our “Properties good for families” filter. In addition to having the whole place to yourselves, you can also look forward to amenities and perks like bunk beds, kitchens and pools.
What are the top attractions for families in Middletown?
Keep the kids occupied at these awesome family-friendly attractions in Middletown:

  • Castle Fun Centre
  • Harness Racing Museum and Hall of Fame
  • Thomas Bull Memorial Park

Are there one-bedroom holiday homes in Middletown?
Yes, you’ll find two one-bedroom properties in Middletown to pick from. A one-bedroom holiday property is a great option if it’s only two of you or if you’re flying solo. Add in more privacy, space and convenience than a standard hotel, and you’re sure to have a trip to remember.
Can I find two-bedroom holiday homes in Middletown?
Gather your besties and enjoy a relaxing escape in one of the three two-bedroom holiday homes Middletown has to offer.
Are there holiday homes with WiFi in Middletown?
Middletown has three holiday homes with WiFi, so you’ll be able to stay connected during your holiday. Simply check the “WiFi” box in our handy search filter for a list of properties with this feature. From streaming TV shows with the family to writing and sending emails, these Stayz homes make it a breeze to get online.
How can I find holiday homes with air conditioning in Middletown?
Work out your travel dates and then use the filter tool to look for holiday homes with ac in Middletown on Stayz. With seven air-conditioned properties available, you can look forward to a comfortable and cool stay.
How old do you have to be to rent a holiday home in Middletown?
The minimum age requirements can differ between properties on Stayz, so check the rules of the holiday home in Middletown you’re considering. But typically, it’s 16, 18 or 21.
How long can I rent a holiday home in Middletown for?
How long you can book a holiday home in Middletown differs according to the property. Simply enter your chosen travel dates to display a list of options offering extended stays. With many creature comforts like air conditioning and kitchens, as well as some offering weekly or monthly discounted prices, you’re sure to find a terrific place to call your home away from home in Middletown.

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