Photo by Michelle Gonzalez

Middletown vacation rentals

We found 63 vacation rentals — enter your dates for availability

Discover a selection of vacation rentals in Middletown that are perfect for your trip. Whether you're going on vacation with family or friends, vacation homes have the best amenities for hanging out with the people that matter most, which might include a garden and pool. No matter what you're looking for, you're sure to find a rental that has what everyone needs, including accessible or non-smoking choices.

Vacation rentals with weekly discounts - Middletown

Showing deals for:Sep 12 - Sep 19
  • Peace of mind
    Our Book with Confidence guarantee gives you 24/7 support
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, yards and more
  • More for less
    More space, more privacy, more amenities — more value
  • A place for everyone
    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Middletown

Find out more about Middletown

Why visit Middletown

  1. Outdoor Activities: Enjoy a range of outdoor pursuits in urban and state parks, perfect for families and nature lovers.
  2. Charming Neighborhoods: Explore the picturesque town of Whitehall, known for its friendly atmosphere and historical significance.
  3. Family-Friendly Attractions: Discover numerous attractions suitable for kids and adults, ensuring a fun day out for everyone.
  4. Budget-Friendly Accommodations: Stay in a variety of vacation rentals, from cozy cottages to spacious homes, catering to all budgets.
  5. Cultural Experiences: Immerse yourself in local culture through scenic views and charming architecture throughout the area.

Popular types of accommodation in Middletown

If you're exploring vacation rentals in Middletown, you'll find a variety of popular accommodations to suit your needs. From cozy houses and well-equipped apartments to charming cottages, there's something for everyone. Whether you're on a budget or seeking a place with amenities like studio apartments and attached garages, Middletown has it all. Discover the perfect house or rent a Del Mar property to make your stay unforgettable.

  • Houses: The top choice for travelers seeking comfort and space, these homes offer a home-away-from-home experience in Middletown.
  • Apartments: A popular option for those looking for convenience, offering all the essentials for a cozy stay in the heart of the area.
  • Cottages: Charming and quaint, these rentals provide a rustic atmosphere perfect for a peaceful retreat.
  • Cabins: Ideal for nature lovers, these cozy getaways immerse you in the beauty of the outdoors.
  • Condos: Modern and stylish, condos offer amenities and access to community features, perfect for a relaxing stay.**

Top attractions in Middletown

Middletown, Delaware, is an ideal destination for outdoor enthusiasts and families alike, offering a variety of attractions such as urban parks and state parks. Visitors can enjoy a blend of cultural experiences while exploring local points of interest, including scenic views and charming houses. Whether you're looking for a relaxing day in nature or a fun family outing, Middletown has something for everyone to enjoy.

  1. University of Delaware: A historic college located 16 miles from Middletown, the University of Delaware boasts a rich cultural atmosphere with beautiful architecture and vibrant student life, making it a great spot for a leisurely stroll and exploration.
  2. Frightland: Situated in Middletown, Frightland is an exciting theme park that offers family-friendly entertainment with various attractions and thrilling experiences, perfect for visitors seeking fun and adventure.
  3. Lums Pond State Park: Located 8 miles away, Lums Pond State Park is a national park ideal for outdoor enthusiasts, featuring scenic trails, water activities, and opportunities for adventure amidst nature's beauty.

Things to do recommended for couples

For a romantic getaway in Middletown, venture to Crow Farm and Vineyard, just 15 miles away, where you can enjoy wine tasting amidst charming scenery. Alternatively, visit Tilmon's Island Winery, located 19 miles from town, perfect for a cozy afternoon filled with entertainment and romance.

Things to do recommended for families

Families visiting Middletown will love the Kirkwood Soccer Complex for its wellness vibes, the adventurous Patriot Ice Center for ice skating fun, and the serene Elkton Indoor Tennis for relaxation. Each spot offers unique experiences just a short drive away, perfect for creating lasting memories together.

Things to do recommended for groups

Groups visiting Middletown can enjoy a shopping spree at Christiana Mall, play a round of golf at Back Creek Golf Club, and savor local produce at the Dutch Country Farmers Market, all while soaking in the vibrant atmosphere of this charming town.

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

If you're traveling with a group, as a family, bringing your pets, or seeking extended stays, be sure to refine your search based on your specific needs. Here are some helpful booking tips for Vrbo.

  • Traveling to Middletown with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor area for group gatherings. Luckily, you can easily filter for all of these options and more on Vrbo.
  • Traveling to Middletown with young kids: Traveling with young kids can be tough. It’s important to prioritize their comfort and safety, along with suitable amenities like a private pool. Additionally, think about how close you are to family-friendly attractions.
  • Taking your pets with you to Middletown: For many, a family vacation isn’t truly complete without their furry companion by their side. If you relate to this, explore Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with 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 that offer discounts for stays of a month or more, you've come to the right place. 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

Middletown, Delaware, offers a delightful blend of outdoor activities and family-friendly attractions for travelers. Explore the charming town of Whitehall, known for its welcoming atmosphere and rich history. Whether you're enjoying the local parks or visiting nearby towns, the area's budget-friendly options and friendly community make for an unforgettable vacation experience. Discover the best of both relaxation and adventure in this sought-after destination!

  • Newark: Located 16 miles from Middletown, Newark is a vibrant city known for its rich cultural scene and family-friendly atmosphere. With a historic university at its heart, travelers can explore educational venues, shop at bustling malls, and enjoy the local parks. The city offers a diverse range of activities, from attending sports events at the stadium to enjoying leisurely walks in its scenic green spaces. Newark’s blend of academic charm and city vibes makes it a perfect spot for those looking to immerse themselves in local culture.
  • Wilmington: About 22 miles from Middletown, Wilmington is a dynamic city that combines outdoor adventures with urban excitement. Visitors flock to Wilmington for its beautiful parks and inviting boardwalks, making it a great place for families and outdoor enthusiasts. The bustling shopping centers and esplanades provide ample opportunities for shopping and dining. With a variety of cultural attractions, including museums and theaters, Wilmington promises a rich city experience filled with both relaxation and exploration.
  • New Castle: Situated 17 miles from Middletown, New Castle is a charming city that offers a blend of outdoor activities and romantic settings. Visitors can stroll along scenic boardwalks and explore quaint shopping areas, while the nearby beach and esplanade provide beautiful views and leisure options. Ideal for families and couples alike, New Castle’s tourist precinct invites exploration of its historical sites and natural beauty, making it a delightful destination for relaxation and adventure.

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 April and June to July, 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
January33.4°F (0.8°C)Light RainMostly SunnyAverageSlightly Low
February36.0°F (2.2°C)Light RainMostly SunnyAverageSlightly Low
March43.2°F (6.2°C)Light RainMostly SunnyAverageAverage
April53.8°F (12.1°C)Light RainMostly SunnySlightly HighSlightly High
May63.3°F (17.4°C)Light RainMostly SunnyAverageSlightly High
June71.8°F (22.1°C)Light RainMostly SunnySlightly HighSlightly Low
July77.2°F (25.1°C)Light RainMostly SunnySlightly HighAverage
August75.2°F (24.0°C)Light RainMostly SunnyAverageAverage
September68.9°F (20.5°C)Light RainMostly SunnyAverageAverage
October58.3°F (14.6°C)Light RainMostly SunnySlightly LowSlightly High
November46.6°F (8.1°C)Light RainMostly SunnySlightly LowAverage
December39.4°F (4.1°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is simple

Looking to save on your upcoming trip? Consider being flexible with your travel dates, as prices can fluctuate significantly. Also, opting for a longer stay can often result in substantial savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to refine your search by price, location, and type of vacation rental.

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash™ on the full booking amount. It truly benefits you to take on the role of planner! When you join our travel rewards program, One Key, you'll gain access to exclusive discounts and earn OneKeyCash™ on eligible bookings. Sign up today and begin enjoying your savings!

Vrbo Trips: Effortless planning

Vrbo’s Trip Board feature offers you a convenient way to plan your travel. You can create new trips, pick up right where you left off, or easily view and arrange your travel plans. Your previously saved and booked properties are now neatly organized under Potential, Upcoming, or Current Trips. To explore and utilize Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties booked during 2023 and 2024.

The lush setting of Middletown is ready to explore

Enjoy the area's festivals, churches and monuments and make a vacation rental your home during your stay in Middletown. Renowned for its restaurants, cheese shops and forests, this city welcomes all visitors. A vacation rental can help make your stay complete. Many rentals come with a full kitchen and laundry facilities.

Activities and attractions in Middletown

Are you looking for attractions to see in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that Middletown has to offer. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Back Creek Golf Club (4.2 mi / 6.8 km)
  • Crow Farm and Vineyard (14.5 mi / 23.3 km)
  • Tilmon's Island Winery (19 mi / 30.5 km)
  • Brandywine Zoo (22.9 mi / 36.9 km)
  • Auburn Road Vineyard (24.3 mi / 39 km)
  • Frightland (6.5 mi / 10.5 km)

Exploring the natural features in Middletown

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, Middletown is a great place to get outside. These are some of the area's most enchanting features, all within 30 miles (48.2 km) of the city center:

  • Chespeake & Delaware Branch Canal (10.9 mi / 17.6 km)
  • Kirkwood Soccer Complex (13.6 mi / 21.9 km)
  • North East Beach Area (14.8 mi / 23.9 km)
  • Llangollen Estates Park (15.2 mi / 24.4 km)
  • Woodland Beach (15.5 mi / 24.9 km)
  • Lewis Park (15.5 mi / 24.9 km)

Traveling to and around Middletown

The nearest airport is in Millville, NJ (MIV-Millville Municipal), located 34.8 mi (56.1 km) from the city center. If you can't find a flight that's convenient for your trip, you can also fly into Philadelphia Intl. Airport (PHL), which is 38.9 mi (62.6 km) away.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Middletown?
Based on our data, apartments are the most desirable vacation rental type in Middletown. But of course, everyone’s idea of an epic trip is bound to be different. Vrbo has vacation rentals of all shapes and sizes, and we’ll help you discover your perfect match.
How much does it cost to rent a vacation rental in Middletown?
Different factors influence the price of a vacation rental in Middletown, including the time of year, length of stay and property type. Still, all Vrbo homes have something in common — unbeatable value. Simply add your travel dates to find your perfect fit.
How much does it cost to rent a beach house in Middletown?
The average price for a vacation rental close to the beach in Middletown depends on when you’ll be there and the size and type of property you’re searching for. You can find prices quickly and easily on Vrbo by entering your travel dates and destination. Then use our handy filter tool to select the number of bedrooms and amenities that you prefer, such as air conditioning, a pool and WiFi.
Are there pet-friendly vacation rentals in Middletown?
With seven vacation rentals that host pets, your furry best friend can join you on your Middletown getaway. Use our filter tool to browse our pet-friendly vacation rentals and find your pawfect digs on Vrbo.
What are popular rental amenities in Middletown?
Some of the most popular rental amenities people look for in Middletown include a nearby waterfront, a firepit and a fireplace. Whether you’re going on vacation with buddies, family or even pets, Vrbo vacation rentals come with the best amenities for chilling out with the people who matter most.
Are there large group vacation rentals in Middletown?
Take your pick of three Vrbo properties in Middletown that can host five or more guests. You’ll get all the privacy and space you need to chill out with the people you’re vacationing with — and nobody else.
Are there vacation rentals in Middletown that welcome kids?
Middletown has six family-friendly vacation homes. And securing a stay that welcomes kids is a cinch with our “Properties good for families” filter. In addition to having the entire place to yourselves, you’ll also enjoy access to conveniences and perks such as bunk beds, full kitchens and private pools.
What are the top attractions for families in Middletown?
Keeping the kids entertained during your stay in Middletown is simple with these fabulous family-friendly attractions:

  • Back Creek Golf Club
  • Frog Hollow Golf Club
  • Dutch Country Farmers Market

Are there one-bedroom vacation rentals in Middletown?
Yes, you can take your pick from three one-bedroom rentals in Middletown. Whether you’d like a cozy cottage or a condo, our one-bedroom properties are ideal if you don’t need lots of space. One of the best things about having your own place? You won’t ever have to share your trip with strangers.
Can I find two-bedroom vacation rentals in Middletown?
Take off with your besties and enjoy total privacy and comfort in one of the two two-bedroom vacation homes Middletown has to offer.
Are there vacation rentals with WiFi in Middletown?
Middletown has two vacation rentals with WiFi, so you’ll be able to stay connected while traveling. Simply check the “WiFi” box in our search filter for a list of properties with this feature. From streaming movies with the family to updating your social media, these Vrbo homes make it a breeze to go online.
How can I find vacation rentals with air conditioning in Middletown?
You can choose from five Vrbo vacation homes with air conditioning in Middletown giving you that gentle, cool breeze and extra touch of comfort. Simply enter your desired travel dates and then take advantage of our filters to help you find stays with air conditioning.
How old do you have to be to rent a vacation rental in Middletown?
The minimum age is generally 16, 18 or 21. It can differ across properties on Vrbo, so check the rules of your chosen Middletown vacation rental before booking your stay.
How long can I rent a vacation rental in Middletown for?
The length of time you can book a vacation rental in Middletown differs according to the property. Simply enter your preferred travel dates to look at a list of options offering extended stays. With tons of features such as washing machines and air conditioning, as well as some offering discounted weekly or monthly prices, you’re sure to discover somewhere just right to call your home away from home in Middletown.
Does Vrbo offer discounts for vacation homes in Middletown?
Weekend adventure or extended vacation, Vrbo has some great deals and discounted options in Middletown to match your style and budget. Take a look at our weekly and monthly discounts on vacation rentals, or see what’s recently been added with one of our newly listed homes. Whatever you’re after, you’ll find the ideal place to stay — without breaking the bank.

People also search for

More Vacation Rentals ideas