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Middletown vacation rentals

We found 853 vacation rentals — enter your dates for availability

Discover a selection of 13 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.

Vacation rentals with weekly discounts - Middletown

Showing deals for:Nov 14 - Nov 21
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Find out more about Middletown

Find out more about Middletown

Why visit Middletown

  1. Rich Cultural Heritage: Explore historic colleges and universities that reflect Middletown's vibrant educational environment.
  2. Scenic Outdoor Activities: Enjoy national and state parks that offer a variety of outdoor adventures for nature lovers.
  3. Charming Downtown Atmosphere: Stroll through downtown Middletown, filled with friendly locals and family-friendly spots.
  4. Romantic Getaways: Experience intimate settings perfect for couples, making it ideal for a romantic retreat.
  5. Diverse Accommodation Options: Choose from private homes, cozy cottages, and comfortable apartments tailored to your needs.

Popular types of accommodation in Middletown

If you're exploring vacation rentals in Middletown, you're in for a treat! Our most popular options include houses, charming cottages, and comfortable apartments. Whether you're searching for a cozy apartment in Middletown or an array of monthly rentals, we have the perfect option to suit your needs. Enjoy transparency, savings, and reassurance as you plan your getaway in this delightful destination.

  • Houses: The top choice among visitors to Middletown, these homes offer spacious and comfortable accommodations ideal for families or groups.
  • Cottages: A charming option, cottages provide a quaint and cozy atmosphere perfect for a relaxing getaway.
  • Apartments: A practical selection, apartments offer convenience and a homely feel for those seeking longer stays.
  • Cabins: For a rustic experience, cabins blend comfort with nature, making them a popular retreat.
  • Condos: These modern spaces provide amenities and easy access to local attractions, appealing to many travellers.**

Top attractions in Middletown

Middletown, Connecticut, offers a delightful blend of culture, outdoor adventures, and romantic experiences, making it perfect for various types of vacations. Visitors can explore national and state parks, historic colleges and universities, and urban parks. With attractions catering to outdoor enthusiasts, culture seekers, and families alike, Middletown promises a memorable getaway for all types of travellers.

  1. Wesleyan University: A historic college with a vibrant cultural atmosphere, offering beautiful architecture and engaging arts programs. Stroll through the picturesque campus and explore its galleries and theatres.
  2. Wadsworth Mansion: An elegant venue that blends history with modern business vibes. Perfect for events, its stunning gardens and grand interiors create a memorable backdrop for any occasion.
  3. Dinosaur State Park: Located 9.7km from Middletown, this national park invites adventure seekers to explore its extensive trails and fascinating fossil tracks, surrounded by beautiful scenery.

Things to do recommended for couples

If you're seeking romance in Middletown, consider a cozy day at Arrigoni Winery, just 4.8km away, where you can enjoy outdoor tastings. For a bit of adventure, try Putter's Paradise Mini Golf, or hit the slopes at Powder Ridge Mountain Park, 9.7km from town.

Things to do recommended for families

During your family vacation in Middletown, explore the thrilling Brownstone Exploration & Discovery Park, enjoy star-gazing at the Van Vleck Observatory, and experience the excitement of karting at Checkered Flag Raceway, all perfect for creating unforgettable memories together.

Things to do recommended for groups

Experience the thrill of golfing at TPC River Highlands, just 8.0km from Middletown. Enjoy cultural performances at Artfarm in town, and shop for unique finds at Cromwell Commons Shopping Center, located 6.4km away. Perfect activities for your group getaway!

What do I need to keep in mind when booking a vacation in Middletown

If you're planning a trip with a group, family, pets, or looking for extended stays, it's important to prioritize your preferences during your search. Here are some helpful Vrbo booking tips for you.

  • Traveling to Middletown with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for all of these options and more on Vrbo.
  • Traveling to Middletown with young kids: Traveling with young children can present its own set of challenges. It’s important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, considering your closeness to family-friendly attractions can enhance your experience.
  • Taking your pets with you to Middletown: For many families, a trip wouldn’t feel complete without their furry companions. If that resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of your family feels comfortable and at home.
  • Planning for a long term stay visiting Middletown: If you're in search of vacation rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Middletown

Explore the charming city of Middletown, Connecticut, where culture and scenic beauty collide. Stroll through downtown Middletown, soaking in its vibrant atmosphere filled with friendly locals and family-friendly spots. Nearby neighborhoods offer a relaxing escape with a blend of urban settings and captivating scenery. Whether you're seeking a romantic getaway or an adventurous outing, Middletown's rich experiences and welcoming vibe promise an unforgettable vacation.

  • Cromwell: Located only 3.2km from Middletown, Cromwell is a vibrant city that attracts visitors with its rich outdoor, sports, and cultural experiences. The city is well-known for its recreational activities, including a picturesque golf course that caters to both beginners and seasoned players. Cromwell also features a historic college university and an exciting theme park, offering a variety of family-friendly attractions. Whether you're looking to engage in outdoor sports or enjoy cultural events at the local conference venues, Cromwell provides an inviting atmosphere for all types of travelers.
  • Portland: Just 1.4km from Middletown, Portland is a charming city renowned for its outdoor adventures and romantic spots, making it a perfect getaway for couples and families alike. Visitors can enjoy a range of activities, including a thrilling arcade adventure zone and a vibrant casino scene. The local landscape is dotted with beautiful lakes, ideal for leisurely strolls or picnics. With its historic college university and various event venues, Portland combines educational experiences with entertainment, offering a delightful escape from the hustle and bustle.
  • Meriden: Situated 12.9km from Middletown, Meriden is a family-friendly city that promises a blend of culture and outdoor experiences. This vibrant community is home to a variety of attractions, including theaters and casinos that cater to diverse interests. Meriden's historic college university and nearby theme park offer engaging activities for all ages. The city's welcoming atmosphere, coupled with its rich cultural heritage, makes it an ideal destination for families looking to create lasting memories while exploring the region.

Best time to go to Middletown

If you're planning a trip to Middletown, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in June to July and September, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January29.1°F (-1.6°C)Light RainMostly SunnyAverageSlightly Low
February30.6°F (-0.8°C)Light RainMostly SunnyAverageSlightly Low
March37.8°F (3.2°C)Light RainMostly SunnyAverageSlightly Low
April48.7°F (9.3°C)Light RainMostly SunnyAverageAverage
May59.2°F (15.1°C)Light RainMostly SunnyAverageAverage
June67.5°F (19.7°C)Light RainMostly SunnySlightly HighSlightly High
July74.3°F (23.5°C)Light RainMostly SunnySlightly HighSlightly High
August72.5°F (22.5°C)Light RainMostly SunnyAverageSlightly High
September65.5°F (18.6°C)Light RainMostly SunnySlightly HighAverage
October54.9°F (12.7°C)Light RainMostly SunnySlightly LowAverage
November43.3°F (6.3°C)Light RainMostly SunnySlightly LowAverage
December35.2°F (1.8°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is simple

Looking to save on your next adventure? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, extending your stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, take advantage of our filters to search by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo's Trip Board offers a helpful platform for planning your travels. You can easily create new trips, resume your previous arrangements, or organize your plans all in one place. You'll find your saved and booked properties neatly sorted into categories: Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

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)
  • 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 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:

  • 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)

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.
How old do you have to be to rent a vacation rental in Middletown?
The minimum age is typically 16, 18 or 21. It can differ from one property to another on Vrbo, so look at the rules of your preferred Middletown stay before booking your stay.
How long can I rent a vacation rental in Middletown for?
How long you can book a vacation rental in Middletown is up to the property. Just enter your desired dates to view a list of options offering extended stays. With many amenities such as kitchens and air conditioning, as well as some offering weekly or monthly discounts, you're sure to discover a terrific place to call your home away from home in Middletown.

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