Discover a selection of 351 vacation rentals in Middletown, CT that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and WiFi. Prices start at $105 per night, and houses and cabins are popular options for a stay in Middletown. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Middletown
Destination guide

Why people love visiting beautiful Middletown

The area's entertainment and festivals are just a few of the reasons to vacation in Middletown. This scenic city is known for its basketball games, university setting and riverfront. Bushnell Park and Lake Compounce are just a couple of the must-sees in the area. With a vacation rental, you get a home away from home—many rentals offer full kitchens and outdoor grills for some home cooking.


Activities and attractions in and around Middletown

Are you hoping to discover top things to see and do in the city? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Middletown a fun place to get away. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Lake Compounce (15.3 mi / 24.7 km)
  • Brownstone Exploration & Discovery Park (2 mi / 3.2 km)
  • Cromwell Meadows Wildlife Management Area (3.1 mi / 5 km)
  • Arrigoni Winery (3.5 mi / 5.6 km)
  • Indian Springs Golf Club (4.1 mi / 6.6 km)
  • Lyman Orchards (4.7 mi / 7.5 km)
Natural features

Exploring the natural features in Middletown

Whether you're an active traveler or just want to spend some time taking in the scenery, Middletown is a great place to spend some time outside. Here are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city center:

  • Bushnell Park (15.1 mi / 24.3 km)
  • Harbor Park (1 mi / 1.7 km)
  • Middletown Nature Gardens (1.3 mi / 2.1 km)
  • Dooley Pond Public Access (2.3 mi / 3.7 km)
  • Ron McCutcheon Park (2.4 mi / 3.8 km)
  • Wadsworth Falls State Park (2.6 mi / 4.2 km)
How to get there

Traveling to and around Middletown

Fly into Hartford, CT (HFD-Hartford - Brainard), the closest airport, located 13.5 mi (21.8 km) from the city center. If you can't find a flight that's convenient for your trip, you could book a flight to New Haven, CT (HVN-Tweed - New Haven Regional), which is 22.8 mi (36.6 km) away.

How many vacation rentals are available around Middletown, CT?

Our 2020 property listings offer a large selection of 351 vacation rentals around Middletown. From 308 house rentals to 90 cabin rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What is the best area to stay when traveling to Middletown?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Middletown:

  • Westbrook Center: 55 vacation rentals
  • Saybrook Manor: 34 vacation rentals
  • Madison Center: 29 vacation rentals
  • Old Saybrook Center: 16 vacation rentals
  • Momauguin: 17 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular point of interests near where I can stay when traveling to Middletown?

Vrbo offers a large selection of vacation rentals near lovely places in Middletown. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Wesleyan University: 90 vacation rentals
  • Middletown Nature Gardens: 153 vacation rentals
  • Wadsworth Mansion: 139 vacation rentals
  • Dooley Pond Public Access: 188 vacation rentals
  • Kidcity Children's Museum: 89 vacation rentals

But there are many other points of interest around Middletown listed on Vrbo where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Middletown?

Yes, of course. Vrbo has 308 Houses in Middletown. Our other popular types of vacation rentals in Middletown include:

  • Cabins: 90 rentals available
  • Cottages: 90 rentals available
  • Bungalows: 90 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Condos/Apartments and more.

Can I find a vacation rental with pool in Middletown?

Yes, you can select your preferred vacation rental with pool among our 31 vacation rentals with pool available in Middletown. Please use our search bar to access the selection of vacation rentals available.

    Explore destinations around Middletown

    Old Lyme
    307 vacation rentals
    208 vacation rentals
    254 vacation rentals
    Old Saybrook
    265 vacation rentals
    178 vacation rentals
    247 vacation rentals
    353 vacation rentals
    225 vacation rentals
    27 vacation rentals
    East Haddam
    59 vacation rentals
    New Haven
    448 vacation rentals
    32 vacation rentals
    22 vacation rentals
    34 vacation rentals
    80 vacation rentals
    28 vacation rentals
    48 vacation rentals
    New Britain
    28 vacation rentals
    24 vacation rentals
    West Haven
    294 vacation rentals