Photo by Vincent Ramundo

Middletown vacation rentals

We found 2,240 vacation rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
Discover a selection of 18 homes, 12 apartments, and other vacation rentals in Middletown that are perfect for your trip. Whether you're traveling with your kids or with friends, vacation homes have the amenities you need and want for your stay, which might include parking and a washer and dryer. No matter what you're looking for, you'll be sure to find a rental 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
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, yards and more
  • More for less
    More space, more privacy, more amenities — more value
  • A place for everyone
    We stand for diversity, inclusion and families everywhere.
    Learn more

Head to the friendly city of Middletown

Enjoy the area's churches, architecture and festivals and make a vacation rental your home during your stay in Middletown. This welcoming city allures visitors with its shopping and restaurants. Are you looking for specific amenities for your getaway? Many of our vacation rentals feature full kitchens and laundry facilities.

Activities and attractions in and around Middletown

Are you looking for attractions to see while you're in the area? Venture out of your vacation home and experience everything that makes Middletown a fun place to get away. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • LEGOLAND® New York (7.5 mi / 12 km)
  • Castle Fun Center (9.2 mi / 14.8 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 looking for fun outdoor activities or just want to spend some time taking in the scenery, Middletown is a great place to get outside. Here are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city center:

  • The Rock Sports Complex (10.3 mi / 16.5 km)
  • Sam's Point Preserve (15.7 mi / 25.3 km)
  • High Point State Park (16.1 mi / 25.8 km)
  • Lake Minnewaska Beach (21.7 mi / 34.9 km)
  • Minnewaska State Park (22.1 mi / 35.6 km)
  • Harriman State Park (22.2 mi / 35.7 km)

Traveling to and around Middletown

The nearest airport is in Stewart Intl. Airport (SWF), located 17.8 mi (28.7 km) from the city center.

Frequently asked questions

What is the best area to stay in Middletown when booking a vacation rental?

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 vacation rental accommodation in Middletown?

The most desirable types of vacation rentals in Middletown are houses. Searching for something different? Vrbo offers a variety of options to match our guests' unique needs, so you'll see vacation 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 vacation rental in Middletown?

The average price for a vacation 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 cozy 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 vacation 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 Vrbo 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 vacation rentals in Middletown?

Pack a travel bag and a bone for your canine companion because Middletown has eight vacation rentals that roll out the welcome mat to pets. Let your furriest pal join in with the family fun at one of our pet-friendly vacation rentals on Vrbo. Simply enter your dates then check the "Pets allowed" filter box.

What are popular rental amenities in Middletown?

Some of the most popular rental 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, Vrbo vacation homes provide the best amenities for beginning new traditions with the people who matter most.

Are there vacation rentals in Middletown that welcome kids?

Middletown has eight family-friendly vacation rentals. 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 Center
  • Harness Racing Museum and Hall of Fame
  • Thomas Bull Memorial Park

Are there one-bedroom vacation rentals in Middletown?

Yes, you'll find two one-bedroom properties in Middletown to pick from. A one-bedroom vacation 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 vacation rentals in Middletown?

Gather your besties and enjoy a relaxing escape in one of the three two-bedroom vacation homes Middletown has to offer.

Are there vacation rentals with WiFi in Middletown?

Middletown has three vacation rentals with WiFi, so you'll be able to stay connected during your vacation. 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 Vrbo homes make it a breeze to get online.

How can I find vacation rentals with air conditioning in Middletown?

Work out your travel dates and then use the filter tool to look for vacation rentals with ac in Middletown on Vrbo. With seven air-conditioned properties available, you can look forward to a comfortable and cool stay.

More Vacation Rentals ideas

People also search for

Vacation Rental options in Middletown