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Middletown holiday lettings

We found 858 holiday rentals — enter your dates for availability

Discover a selection of 9 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.

Holiday rentals with weekly discounts - Middletown

Showing deals for:30 Jan - 6 Feb

Image gallery for Family Friendly Lake House: Lake Pocotopaug, Fire-pit, Kayaks, Canoe. Sunsets.

Living area
10 out of 10, Exceptional, (27 reviews)
Exceptional
(27 reviews)

Family Friendly Lake House: Lake Pocotopaug, Fire-pit, Kayaks, Canoe. Sunsets.

East Hampton, CT

7% off
Price is £2,528
for 7 nights, 1 home
£361 per night
includes taxes & fees
Family Friendly Lake House: Lake Pocotopaug, Fire-pit, Kayaks, Canoe. Sunsets.

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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)
  • Putter's Paradise Mini Golf (5.9 mi / 9.6 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)

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:

  • Connecticut River State Wildlife Area (1.6 mi / 2.5 km)
  • Wadsworth Falls State Park (2.9 mi / 4.6 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)
  • Bashan Lake (13.3 mi / 21.4 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 best area to stay in Middletown when booking a holiday rental?
When considering a holiday rental in Middletown, Connecticut, a popular area to stay is the historic downtown district. This charming neighbourhood is vibrant and lively, offering an excellent selection of shops, cafes, and restaurants. Staying here places you within walking distance of attractions such as the beautiful Wadsworth Falls State Park, where you can enjoy scenic hiking trails and picturesque waterfalls. Additionally, the nearby Middlesex County Historical Society provides fascinating insights into the local heritage and history, making it a great spot for culture enthusiasts.
How much does it cost to rent a holiday home in Middletown?
Prices for holiday rentals in Middletown vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Middletown to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Middletown holiday house rentals?
You can find great discounts on house rentals in Middletown on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of holiday rental accomodation in Middletown?
In Middletown, holiday houses are the most popular type of rental accommodation, with around 12 available throughout the area. These houses typically offer spacious living environments, multiple bedrooms, fully equipped kitchens, and often private outdoor spaces for relaxation. Visitors can find these properties in various neighbourhoods, providing a cozy feel ideal for families or groups. Additionally, there are several apartments and condos available, which cater to those seeking a more compact living space.
Are there any family house rentals in Middletown?
In Middletown, Connecticut, there are numerous family-friendly house rentals available, with around 11 options to choose from. This charming town offers a variety of accommodations suited for families, often featuring spacious living areas, fully equipped kitchens for preparing meals together, and outdoor spaces where children can play.
Can I rent a holiday home with a pool or hot tub in Middletown?
In Middletown, Connecticut, there are several holiday homes available for rent that feature pools and hot tubs. This charming city offers a variety of neighbourhoods where these properties can be found, providing a mix of urban convenience and suburban tranquillity. Travellers can expect amenities like private swimming pools, relaxing hot tubs, outdoor seating areas, and fully equipped kitchens, making these rentals ideal for both relaxation and entertaining.
Can I find long-stay holiday rentals in Middletown?
A long-stay holiday rental in Middletown is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Middletown?
In Middletown, Connecticut, there are several pet-friendly house rentals available, suiting travellers looking to bring their furry companions along. Many of these rentals offer a variety of amenities, including spacious backyards, fully equipped kitchens, and comfortable living areas, ensuring a homely atmosphere during your stay.

The neighbourhoods of Middletown provide easy access to local parks, which are great for pet owners. For instance, Wadsworth Falls State Park features scenic trails and open spaces, ideal for leisurely walks with pets. Additionally, the nearby Harbor Park along the Connecticut River offers lovely views and areas for pets to roam.
Are there any remote work holiday rentals in Middletown?
In Middletown, Connecticut, there are several remote work holiday rentals available, with around 16 properties suiting the needs of those looking to work while away. Many of these rentals are equipped with essential amenities such as high-speed Wi-Fi, dedicated desks, and comfortable chair setups, ensuring a productive working environment. Some properties also offer additional features like laptop workspaces and computer monitors, making it easy for guests to stay connected and complete their tasks efficiently. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Middletown holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Middletown with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Middletown?
In Middletown, popular holiday rental amenities include kitchens equipped with essential cookware, dishware, and utensils, allowing guests to prepare their meals conveniently. Many rentals also provide free Wi-Fi, ensuring that visitors can stay connected during their stay. Additionally, most properties come with refrigerators and microwaves, enhancing the overall comfort and functionality of the accommodation.
When is the best time to visit Middletown for a holiday rental?
The best time to visit Middletown for a holiday rental is during the vibrant peak season from July to September. This summer period attracts visitors eager to explore the charming town, with a lively atmosphere complemented by a variety of outdoor activities and local events.

July stands out as the most popular month, superb for those looking to enjoy warm weather and partake in the many festivals that celebrate the community's rich heritage. With temperatures typically reaching the low 30s Celsius, it's an ideal backdrop for enjoying the scenic views along the Connecticut River or taking leisurely strolls through the picturesque downtown area.

For travellers seeking a more budget-friendly experience, October presents a fantastic option. This month offers a quieter atmosphere, allowing you to appreciate the stunning fall foliage that blankets the region in vibrant hues of orange and gold. It's a wonderful time to explore local parks and indulge in seasonal events without the larger crowds.
How early should I book a Middletown holiday rental?
Book your Middletown holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Middletown home rental booking on Vrbo?
To find Middletown holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Middletown holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

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