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Middletown vacation rentals

We found 780 vacation rentals — enter your dates for availability

your current months are April, 2024 and May, 2024.
April 2024
May 2024
Discover a selection of 7 homes and other vacation rentals in Middletown that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, vacation homes have the best amenities for spending time at your vacation home, which might include WiFi and a pool. No matter what you're looking for, you'll find a rental that has what everyone needs, including accessible or non-smoking choices.

Find spaces that suit your style

  • Peace of mind
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  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, yards and more
  • More for less
    More space, more privacy, more amenities — more value

The beautiful area of Middletown awaits your stay

The area's entertainment and festivals are just a few of the reasons to vacation in Middletown. Travelers to this scenic city praise the basketball games, university setting and riverfront. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in Middletown

Are you hoping to find attractions to see during your stay? Venture out of your cozy vacation rental and 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 center:

  • Brownstone Exploration & Discovery Park (0.9 mi / 1.5 km)
  • TPC River Highlands (4.8 mi / 7.8 km)
  • Powder Ridge Mountain Park and Resort (6.3 mi / 10.1 km)
  • Machimoodus State Park (10 mi / 16.1 km)
  • Hawks Landing Country Club (11.9 mi / 19.1 km)
  • Crystal Bees (12.8 mi / 20.6 km)

Exploring the natural landscape of Middletown

Whether you're an active traveler or just want to appreciate the scenery, Middletown is a great place to get out in nature. Here are some of the area’s most stunning natural features, all within 30 miles (48.2 km) of the city center:

  • Smith Park (3.3 mi / 5.3 km)
  • Lake Beseck Beach (5.4 mi / 8.7 km)
  • Dinosaur State Park (6.1 mi / 9.8 km)
  • Hubbard Park (9.6 mi / 15.4 km)
  • Machimoodus State Park (10 mi / 16.1 km)
  • Mortensen Riverfront Plaza (14 mi / 22.6 km)

Transportation to and around Middletown

The nearest airport is in New Haven, CT (HVN-Tweed - New Haven Regional), located 23.8 mi (38.2 km) from the city center. If you can't find a flight that's convenient for your trip, you could also fly into Bradley Intl. Airport (BDL), which is 25.5 mi (41 km) away.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Middletown?

The most in-demand types of vacation rentals in Middletown are houses. After something a little different? Vrbo has a variety of options to match our guests' unique requirements, so you'll see properties in lots of shapes and sizes. The ideal fit is ready and waiting for you — lock in yours today.

How much does it cost to rent a vacation rental in Middletown?

A range of factors can determine how much you pay for a vacation rental in Middletown, such as the length of stay, type of property and season. However, all our vacation homes have something in common — amazing value. Simply enter your travel dates to find your ideal escape.

How much does it cost to rent a beach house in Middletown?

The average price for a vacation home by the beach in Middletown will depend on when you'll be there and the style and size of property you're looking for. You can find prices quickly and easily on Vrbo by entering your preferred travel dates and destination. Then use our filter tool to select the number of bedrooms and amenities that you prefer, such as WiFi, air conditioning and a hot tub.

Are there pet-friendly vacation rentals in Middletown?

With eight vacation rentals that host pets, your happy hound can join in on your Middletown vacation. Use our filter tool to search our pet-friendly vacation rentals and find your pawfect digs on Vrbo.

Can I rent a house with a pool in Middletown?

Grab your swimwear and inflatable lounger, because there are three houses with a private pool in Middletown. Stay at one of these terrific vacation rentals and enjoy a pool day every day. Simply enter your travel dates into Vrbo, then check the "pool" filter to find a place to make a splash!

What are popular rental amenities in Middletown?

Some of the most popular rental amenities guests are looking for in Middletown are a swimming pool, a garden and a barbecue grill. Whether you're traveling with family, your besties or even pets, Vrbo vacation rentals feature the best amenities for ultimate relaxation with the people closest to you.

Are there large group vacation rentals in Middletown?

Take your pick of two Vrbo properties in Middletown that can accommodate five or more people. You'll enjoy all the space and privacy you need to chill out with the people you're vacationing with — and no one else.

Are there vacation rentals in Middletown that welcome kids?

Middletown has eight family-friendly vacation rentals. And finding a stay that welcomes kids is a breeze with Vrbo's "Properties good for families" filter. Besides having the entire place to yourselves, you'll also enjoy access to perks and conveniences such as bunk beds, full kitchens and private pools.

What are the top attractions for families in Middletown?

Keeping the kiddos entertained during your vacation in Middletown is a breeze with these top family-friendly attractions:

  • Brownstone Exploration & Discovery Park
  • Lake Beseck Beach
  • Checkered Flag Raceway

Are there one-bedroom vacation rentals in Middletown?

Yes, you can pick from four one-bedroom rentals in Middletown. Whether you're on the lookout for an apartment or a cabin, Vrbo's one-bedroom rentals are great if you don't require a huge amount of space. One of the main perks of having your own place? You won't have to share your adventure with strangers.

Are there vacation rentals with WiFi in Middletown?

Whether you'd like to keep up with the news, send some emails or update your social media, there are three vacation homes with WiFi in Middletown. Check the "WiFi" box when searching on Vrbo and stay connected on your getaway.

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

You can pick from four vacation homes with air conditioning in Middletown giving you that cooling breeze and extra level of comfort. Simply enter your preferred travel dates and then use our handy filters to search for properties with air conditioning.