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Middletown vacation rentals

We found 937 vacation rentals — enter your dates for availability

Discover a selection of 10 homes, 10 apartments, 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:Jul 31 - Aug 7

Image gallery for PRIVATE BEACH: BEACHFRONTS & BALCONIES @ NIANTIC W/ 6 QUEENS

Beach
9.8 out of 10, Exceptional, (23 reviews)
Exceptional
(23 reviews)

PRIVATE BEACH: BEACHFRONTS & BALCONIES @ NIANTIC W/ 6 QUEENS

East Lyme

13% off
Price is $1,388
$9,716 for 7 nights
All fees included
PRIVATE BEACH: BEACHFRONTS & BALCONIES @ NIANTIC W/ 6 QUEENS

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Find out more about Middletown

Why visit Middletown

  • Charming Downtown: Explore the vibrant downtown area filled with friendly people and scenic views, perfect for leisurely strolls.
  • Outdoor Adventures: Enjoy a variety of outdoor activities in national and state parks, as well as urban green spaces.
  • Cultural Experiences: Discover rich historical neighborhoods that provide a deeper connection to Middletown's heritage.
  • Romantic Getaways: The picturesque settings make Middletown an ideal spot for couples looking for a romantic escape.
  • Diverse Accommodations: Choose from cozy vacation rentals, quaint cottages, or modern apartments tailored to your needs.

Popular types of accommodation in Middletown

Experience the charm of Middletown with our diverse selection of vacation rentals. Whether you're seeking a cozy private vacation home, a quaint cottage, or a modern apartment, we have the perfect fit for your getaway. Explore the luxurious homes and convenient Middletown Brooke apartments that cater to families and solo travelers alike. Discover your ideal vacation rental and make unforgettable memories in this beautiful destination.

  • Houses: The top choice for visitors to Middletown, offering spacious accommodations ideal for families or groups.
  • Cottages: A delightful option for a cozy and charming getaway, perfect for couples or solo travelers.
  • Apartments: A convenient choice for those seeking modern amenities and a central location during their stay.
  • Cabins: A favorite among nature enthusiasts, providing a rustic and serene experience.
  • Condos: A popular selection that combines comfort with access to community amenities.**

Top attractions in and around Middletown

Middletown, Connecticut offers a charming blend of culture, outdoor activities, and romantic spots, making it an ideal destination for various travelers. Explore national and state parks, relax in urban parks, or visit local medical centers. The area's rich attractions cater to families and those seeking cultural experiences, ensuring a memorable visit for everyone. Whether you're here for a weekend getaway or a longer stay, Middletown has something special for you.

  • Middlesex Hospital: A vital healthcare facility in Middletown, Middlesex Hospital offers a welcoming atmosphere with a focus on family and community care, making it not only a place for medical needs but also a hub of support and wellness.
  • Pratt and Whitney Headquarters: Located 13 miles from Middletown, this business center is a cornerstone of aviation innovation, representing cutting-edge technology and engineering excellence in the aerospace industry.
  • Bushnell Center for the Performing Arts: Situated 14 miles away, this cultural gem hosts a variety of performances, from concerts to theatrical productions, enriching the local arts scene and providing a vibrant experience for visitors.

Things to do recommended for couples

Embark on a romantic getaway in Middletown. Enjoy a scenic stroll along the Connecticut River, savor a candlelit dinner at a cozy bistro, and explore the charming streets filled with unique shops. Don't miss a picturesque sunset view from the nearby parks for a perfect ending to your day.

Things to do recommended for families

In Middletown, families can explore the Kidcity Children's Museum, where kids can engage in interactive exhibits. Enjoy outdoor fun at Wadsworth Falls State Park, perfect for hiking and picnicking. Don’t miss the scenic views and playgrounds along the Connecticut River at Harbor Park.

Things to do recommended for groups

Groups visiting Middletown can enjoy a tour of the historic Wadsworth Mansion, explore the scenic trails at Powder Ridge Park, and savor local flavors at the vibrant farmers' market. Don't miss the chance to relax at the beautiful Harbor Park along the Connecticut River for stunning views.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

When planning your trip, whether you're traveling with a group, family, pets, or seeking extended stays, it's important to prioritize your preferences. Here are some helpful booking tips for using Vrbo.

  • Traveling to Middletown with a group: Take into account how many bedrooms you'll require, along with features like a fully-equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and many more on Vrbo.
  • Traveling to Middletown with young kids: Traveling with young kids can present some challenges. It's important to prioritize their comfort and safety, along with amenities suitable for their age, like a private swimming pool. Additionally, thinking about how close you are to family-friendly attractions is a wise choice.
  • Taking your pets with you to Middletown: For many, a family vacation wouldn’t be the same without their furry companion. If that resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly properties come equipped with feeding bowls and beds, ensuring that both you and your pet feel 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 preferences like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Middletown

Middletown, Connecticut, offers a delightful blend of culture and outdoor adventures, making it an ideal destination for romantic getaways and family-friendly vacations. Explore the charming downtown area, where you can enjoy vibrant scenery and friendly people. Nearby neighborhoods provide a rich historical atmosphere, perfect for those seeking a deeper connection to the region. With its unique vibes and welcoming environment, Middletown promises an unforgettable travel experience.

  • Hartford: Located approximately 14 miles from Middletown, Hartford is the vibrant capital city of Connecticut, offering a rich blend of history and culture. Visitors flock to Hartford for family outings, romantic evenings, and urban adventures. The city boasts a variety of attractions, including the renowned Mark Twain House and Museum, the Wadsworth Athenaeum, and Bushnell Park. Entertainment options abound, with theaters showcasing Broadway productions and music concerts. Whether you're exploring the historic college universities or attending a major event at the convention center, Hartford ensures a memorable travel experience.
  • Cromwell: Just 2 miles from Middletown, Cromwell is a charming city perfect for outdoor enthusiasts and sports lovers. Travelers are drawn to its scenic landscapes and recreational opportunities, including several golf courses and national parks. The local culture is vibrant, with educational institutions and community events that highlight the town’s spirit. Don't miss the opportunity to explore the beautiful parks and trails, which offer a perfect backdrop for family outings or a day of sports activities. Cromwell’s proximity to Middletown makes it an easy and enjoyable day trip.
  • Portland: A mere 0.9 miles from Middletown, Portland is a delightful city offering a family-friendly atmosphere with numerous outdoor activities. Set against a picturesque backdrop, visitors can enjoy recreational areas, including lakes and parks perfect for picnicking and hiking. Portland is also known for its cultural attractions, such as local art galleries and educational institutions. With its close-knit community vibe and beautiful natural settings, Portland is ideal for families looking to explore nature while indulging in cultural experiences.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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 a breeze

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

Vrbo Trips: Planning made easy

Vrbo's unique Trip Board offers you a convenient way to plan your journeys, pick up right where you left off, and keep your travel arrangements organized. You can easily access the properties you've saved or booked by checking out your Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/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)
  • Powder Ridge Mountain Park and Resort (6.3 mi / 10.1 km)
  • Machimoodus State Park (10 mi / 16.1 km)
  • Gouveia Winery (10.5 mi / 16.9 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)
  • Lake Beseck Beach (5.4 mi / 8.7 km)
  • Dinosaur State Park (6.1 mi / 9.8 km)
  • Silver Lake State Access Area (6.3 mi / 10.2 km)
  • Hubbard Park (9.6 mi / 15.4 km)
  • Iwo Jima Survivors Memorial Park (11 mi / 17.7 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 best area to stay in Middletown, Connecticut, United States of America when booking a vacation rental?
When considering a vacation rental in Middletown, Connecticut, the downtown area is an excellent choice. This vibrant neighborhood is not only rich in history but also offers a delightful mix of dining, shopping, and cultural experiences. One of the highlights here is the stunning Wesleyan University, which features beautiful architecture and lush campus grounds. Visitors can also enjoy the nearby Connecticut River, where scenic views and outdoor activities abound.

Another great option is the South Main Street area, known for its charming residential feel and proximity to various parks. This area provides easy access to attractions such as the Kidcity Children's Museum, an engaging spot for families with young children.
How much does it cost to rent a vacation home in Middletown?
Prices for vacation 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 vacation 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.
Where are the best areas for renting a beach house in Middletown?
For renting a beach house in Middletown, Connecticut, the area around the beautiful Connecticut River and its access to Long Island Sound is ideal. The shoreline along the south of Middletown near the town of Essex offers picturesque views and a variety of vacation rentals. Many properties in this region feature amenities such as private docks for boating, outdoor decks for sunbathing, and spacious backyards, great for families or groups looking to enjoy the coastal atmosphere.

Additionally, the nearby town of Old Saybrook provides more options, where beach houses often come with direct beach access, outdoor grills for barbecuing, and comfortable living spaces. This area is also rich in local charm, with quaint shops, restaurants, and historical landmarks like the Old Saybrook Lighthouse, adding to the experience.

For those who enjoy outdoor activities, the nearby Hammonasset Beach State Park is a fantastic destination. Rentals in this vicinity often include features such as easy access to hiking trails, picnic areas, and sometimes even beach gear like chairs and umbrellas, allowing visitors to fully enjoy the sandy shores and scenic parks.
What is the most popular type of vacation rental accomodation in Middletown?
In Middletown, vacation houses are the most popular type of rental, with about 11 available throughout the area. These homes typically provide spacious layouts, multiple bedrooms, and well-equipped kitchens, making them ideal for families or groups. Additionally, there are several apartments and condos that offer a more compact living space, often featuring modern amenities like laundry facilities and communal recreational areas.
Are there any family house rentals in Middletown?
In Middletown, Connecticut, family-friendly vacation rentals are plentiful, with around 11 options available. These homes can be found in various neighborhoods, providing a comfortable base for families exploring the area. Many properties feature spacious living rooms, full kitchens for preparing family meals, and outdoor areas that are great for kids to play. Guests can also expect amenities such as Wi-Fi and air conditioning to ensure a pleasant stay.

The local area is rich in attractions, including the beautiful Wadsworth Falls State Park, ideal for hiking and picnicking, or the nearby Middletown's downtown, where vibrant shops and restaurants await. See all family-friendly rentals in Middletown.
Can I rent a vacation home with a pool or hot tub in Middletown?
In Middletown, Connecticut, there are several vacation homes available for rent that feature pools and hot tubs, offering a refreshing option for travelers. The area boasts a mix of residential neighborhoods where these properties can be found, providing a variety of settings from suburban tranquility to more vibrant locales.

Travelers can expect a range of amenities in these rentals, including private pools, relaxing hot tubs, spacious outdoor areas, and fully equipped kitchens, making them superb for family gatherings or a getaway with friends. Some properties may also feature additional comforts such as outdoor dining spaces, barbecue grills, and even game rooms, enhancing the overall experience. Find your rental in Middletown with a pool or a hot tub.
Can I find long-stay vacation rentals in Middletown?
A long-stay vacation rental in Middletown is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Middletown?
In Middletown, Connecticut, there are several pet-friendly house rentals available that cater to travelers with furry companions. Many of these vacation homes come equipped with comfortable amenities such as spacious living areas, fully stocked kitchens, and outdoor spaces where pets can roam freely.

The rentals are often located within a short distance of local parks, providing opportunities for walks and playtime. Nearby, Wadsworth Falls State Park offers scenic trails and waterfalls, making it an excellent spot for outdoor adventures with pets. Additionally, the charming downtown area features pet-friendly cafes and shops, ideal for visitors traveling with their four-legged friends. See all pet-friendly rentals in Middletown.
Are there any remote work vacation rentals in Middletown?
In Middletown, Connecticut, there are around 18 vacation rentals that cater to remote work needs. This charming city offers a blend of historical charm and modern amenities, making it a suitable destination for those looking to work remotely. Many of these properties come equipped with essential amenities such as high-speed Wi-Fi, dedicated workspaces, and comfortable desks, ensuring that travelers can stay productive during their stay.

Nearby, you can explore local parks and the Connecticut River, providing opportunities for breaks and relaxation after work hours. The city also features a variety of restaurants and cafes that can serve as alternate workspaces or spots to unwind. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Middletown vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Middletown with parking available—perfect for families or travelers 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 vacation rental amenities include fully equipped kitchens, allowing guests to prepare meals at their convenience. Onsite parking is also a common feature, making it easy for travelers to access their accommodations without the hassle of searching for street parking. Many rentals come with coffee and tea makers, providing a comforting start to the day. Additionally, properties often feature desks for those needing a workspace, and decks or patios where guests can relax and enjoy the outdoors.
When is the best time to visit Middletown for a vacation rental?
The best time to visit Middletown for a vacation rental is during the peak season from July to September. This lively period attracts travelers seeking a mix of outdoor activities and cultural experiences. July stands out as the most popular month, when warm weather and vibrant local events create an inclusive setting for exploration.

During the summer, temperatures typically range from the mid-60s to the low 80s Fahrenheit, providing ideal conditions for enjoying outdoor adventures, such as hiking in nearby parks or strolling along the Connecticut River. The energy of the summer months is palpable, with festivals and events that reflect the local culture and community spirit.

For those looking for a more budget-friendly option, visiting in October can be a wonderful choice. This month offers a chance to experience the beautiful fall foliage, along with a quieter atmosphere that encourages leisurely exploration of Middletown's charming downtown and surrounding nature trails.

Ultimately, your ideal time to book a vacation rental in Middletown will hinge on your preference for vibrant summer activities or the peaceful beauty of autumn.
How early should I book a Middletown vacation rental?
Book your Middletown vacation 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 vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Middletown, Connecticut, United States of America?
In Middletown, Connecticut, visitors can explore several attractions that highlight the city's rich history and vibrant culture. The downtown area is home to the Wadsworth Falls State Park, where guests can enjoy scenic hiking trails and picturesque waterfalls. Nearby, the Connecticut River offers opportunities for kayaking and fishing, providing a great way to experience the local scenery.

The Kidcity Children's Museum is a must-visit for families, featuring interactive exhibits designed to engage young minds. Additionally, the historic Wesleyan University campus is worth a stroll, showcasing beautiful architecture and the Davison Art Center, which hosts various art exhibitions.

For those interested in performing arts, the Middletown Arts and Culture Office often has events and performances throughout the year, adding to the local cultural scene.
Can I change or cancel my Middletown home rental booking on Vrbo?
To find Middletown vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Middletown vacation 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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