Photo by Simmie Reagor

Middletown holiday homes

We found 770 holiday rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
Discover a selection of 7 homes and other holiday rentals in Middletown that are perfect for your trip. Whether you're travelling with your children or with friends, holiday homes have the best amenities for spending time at your holiday home, which might include a garden and Wi-Fi. No matter what you're looking for, you'll be sure to find a property to rent to meet everyone's needs, including accessible or non-smoking choices.

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

The scenic area of Middletown awaits your stay

The area's entertainment and festivals are just some of the reasons to come on holiday to Middletown. Travellers 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

Do you want to find attractions to see while you're in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Middletown a fun spot to go on holiday. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • 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 looking for fun outdoor activities or just want to take in the scenery, Middletown is a great place to get outside. These are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • 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)

Transport 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 centre. If you can't find a flight that's convenient for your trip, you could book a flight to Hartford, CT (BDL-Bradley Intl.), which is 25.5 mi (41 km) away.

Frequently asked questions

What is the most popular type of holiday home accommodation in Middletown?

The most in-demand types of holiday homes in Middletown are houses. After something a little different? Bookabach 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 holiday home in Middletown?

A range of factors can determine how much you pay for a holiday home in Middletown, such as the length of stay, type of property and season. However, all our holiday 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 holiday 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 Bookabach 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 holiday homes in Middletown?

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

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 holiday homes and enjoy a pool day every day. Simply enter your travel dates into Bookabach, then check the "pool" filter to find a place to make a splash!

What are popular home amenities in Middletown?

Some of the most popular home amenities guests are looking for in Middletown are a swimming pool, a garden and a barbecue grill. Whether you're travelling with family, your besties or even pets, Bookabach holiday homes feature the best amenities for ultimate relaxation with the people closest to you.

Are there large group holiday homes in Middletown?

Take your pick of two Bookabach 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 holidaying with — and no one else.

Are there holiday homes in Middletown that welcome kids?

Middletown has eight family-friendly holiday homes. And finding a stay that welcomes kids is a breeze with Bookabach'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 holiday 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 holiday homes in Middletown?

Yes, you can pick from four one-bedroom homes in Middletown. Whether you're on the lookout for an apartment or a cabin, Bookabach's one-bedroom homes 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 holiday homes 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 holiday homes with WiFi in Middletown. Check the "WiFi" box when searching on Bookabach and stay connected on your getaway.

How can I find holiday homes with air conditioning in Middletown?

You can pick from four holiday 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.

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