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Middletown vacation rentals

We found 64 vacation rentals — enter your dates for availability

Discover a selection of 5 homes and other 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

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Find out more about Middletown

Find out more about Middletown

Why visit Middletown

  1. Outdoor Adventures: Enjoy the abundance of urban parks and national state parks, perfect for hiking and nature exploration.
  2. Family-Friendly Atmosphere: Experience a welcoming environment with various activities suitable for all ages.
  3. Lively Downtown: Discover local shops and eateries in the vibrant downtown area, ideal for leisurely strolls.
  4. Diverse Accommodations: Choose from a range of vacation rentals, from cozy cottages to modern apartments.
  5. Relaxing Neighborhoods: Explore charming nearby neighborhoods that enhance the tranquil vibe of Middletown.

Popular types of accommodation in Middletown

Explore a diverse selection of vacation rentals in Middletown, including houses, apartments, and charming cottages. Whether you're seeking a cozy apartment in Middletown or looking for monthly rentals, our platform offers an array of options to suit your needs. With transparency and savings at the forefront, we ensure you find the perfect getaway that meets your expectations. Start planning your ideal vacation today!

  • Houses: These are the top choice for visitors seeking a spacious and comfortable stay, perfect for families or groups.
  • Apartments: A popular option for those looking for a modern, self-contained living space with convenient amenities.
  • Cottages: Ideal for a quaint and cozy experience, these charming rentals offer a homey feel in a picturesque setting.
  • Cabins: A great option for nature lovers, these rustic retreats provide a unique getaway amidst the outdoors.
  • Condos: These stylish accommodations combine comfort and convenience, often located in vibrant areas close to attractions.**

Top attractions in Middletown

Middletown, Delaware, is an excellent destination for outdoor and family-themed vacations, offering a variety of attractions such as urban parks, marinas, and national state parks. Whether you're keen to explore nature or enjoy city life, Middletown provides diverse experiences that cater to all kinds of travellers. Make the most of your visit by discovering the local points of interest that will surely create lasting memories with your loved ones.

  1. Back Creek Golf Club: Experience a welcoming atmosphere at this well-maintained golf course, perfect for players of all skill levels. Enjoy budget-friendly rates while taking in the scenic views and friendly service.
  2. Historic Houses of Odessa: Immerse yourself in rich culture at this collection of beautifully preserved historic homes. Explore the architecture and gardens that tell the story of Delaware’s past, just 4.8km from Middletown.
  3. Appoquinimink Friends Meeting House: Discover the serene beauty and cultural significance of this historic meeting house. Located 4.8km from Middletown, it offers a glimpse into the Quaker heritage and community spirit.

Things to do recommended for couples

For a romantic getaway in Middletown, explore Crow Farm and Vineyard, just 24.1km away, offering charming entertainment and a lovely atmosphere. Alternatively, visit Tilmon's Island Winery, located 30.6km from town, where you can enjoy delightful wines and intimate vibes.

Things to do recommended for families

Families will have a delightful time at Kirkwood Soccer Complex, Elkton Indoor Tennis, and Iron Hill Park, all offering wellness and relaxation vibes. These recreational spots, located within a short drive from Middletown, promise fun and engaging activities for all ages.

Things to do recommended for groups

Your group will enjoy a visit to the Christiana Mall for shopping and entertainment, explore the Dutch Country Farmers Market for local goods, and unwind at the Frog Hollow Golf Club for a day of outdoor sports in Middletown, Delaware.

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

If you're planning a trip with a group, family, or pets, or if you're seeking extended stays, it's important to prioritize your preferences while filtering your options. Here are some helpful Vrbo booking tips for you.

  • Traveling to Middletown with a group: Think about how many bedrooms you require, along with features like a full kitchen or outdoor areas for group gatherings. Fortunately, 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 essential to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to 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 that resonates with you, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Middletown: If you're searching for vacation rentals that offer 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!

Where to stay in Middletown

Welcome to Middletown, Delaware, where family-friendly vibes meet urban charm. Explore the lively downtown area, filled with local shops and eateries, and enjoy the welcoming atmosphere of nearby neighborhoods. Perfect for outdoor adventures and relaxing strolls, Middletown offers the ideal setting for a memorable vacation. Whether you're looking to unwind or discover new experiences, this city and its surrounding regions promise a delightful getaway.

  • Port Penn: Nestled in the heart of Middletown, Port Penn is a charming village that offers a delightful blend of outdoor adventure and scenic beauty. Known for its recreational areas and parks, this destination is perfect for those looking to immerse themselves in nature. Visitors can enjoy activities such as hiking, birdwatching, and picnicking at the nearby state parks and lakes. The area's proximity to pristine beaches enhances its appeal, providing opportunities for relaxation and water sports amid stunning landscapes.
  • Odessa: Located a mere 4.8km from Middletown, Odessa is a quaint city that invites families and couples to explore its charming offerings. Known for its scenic boardwalk and engaging motor racing events, Odessa also boasts educational attractions that are perfect for a family outing. The city's proximity to beautiful beaches and historic sites makes it an ideal spot for combining leisure and learning. Stroll along the esplanade, enjoy a romantic sunset, or delve into the local history—Odessa has something for everyone.
  • Townsend: Just 6.4km from Middletown, Townsend is a vibrant city that caters to outdoor enthusiasts and families alike. Known for its exhilarating motor racing and dynamic boardwalk, Townsend offers a variety of educational experiences that are sure to engage visitors of all ages. The nearby family beach is perfect for a day of sun and sand, while the local stadium often hosts thrilling events. With its close-knit community vibe and ample recreational opportunities, Townsend promises a memorable getaway.

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 SunnyAverageSlightly Low
April53.8°F (12.1°C)Light RainMostly SunnySlightly HighAverage
May63.3°F (17.4°C)Light RainMostly SunnyAverageAverage
June71.8°F (22.1°C)Light RainMostly SunnySlightly HighSlightly High
July77.2°F (25.1°C)Light RainMostly SunnySlightly HighSlightly High
August75.2°F (24.0°C)Light RainMostly SunnyAverageSlightly High
September68.9°F (20.5°C)Light RainMostly SunnyAverageAverage
October58.3°F (14.6°C)Light RainMostly SunnySlightly LowAverage
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

Are you aiming to save on your upcoming travel plans? One effective strategy is to remain flexible with your travel dates, as prices can vary significantly. Additionally, opting for a longer stay often allows for considerable savings. To discover the perfect Vrbo property that fits your budget, feel free to use our filters to sort by price, location, and type of vacation rental. We’re here to help you find the best options for your journey!

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a dedicated area to plan exciting new trips, pick up right where you left off, or manage and arrange your existing travel plans. You can easily access properties you've saved or booked in the sections for Potential, Upcoming, or Current Trips. To explore Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

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)
  • Frightland (6.5 mi / 10.5 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)
  • Patriots Glen Golf Club (12.8 mi / 20.7 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)
  • Battery Park (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)
  • Lewden Green Park (15.3 mi / 24.6 km)
  • Woodland Beach (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 best area to stay in Middletown when booking a vacation rental?
When considering a vacation rental in Middletown, Delaware, a popular area to stay is the charming historic district. This neighbourhood offers a delightful blend of quaint architecture and local charm, making it a superb base for exploring the town. You will find a variety of rental properties here, ranging from cosy cottages to more spacious homes, providing ample options for different group sizes.

Staying in the historic district places you within easy reach of attractions such as the picturesque Middletown Village Green, where you can enjoy leisurely strolls and community events. Additionally, the nearby Odessa Historic District is just a short drive away, offering a glimpse into the region's rich history with its well-preserved buildings and museums.

Another appealing area is the residential community surrounding Silver Lake, which boasts a tranquil setting and beautiful views. This neighbourhood provides a peaceful retreat while still being close to local amenities and parks, superb for families or those seeking a quieter stay. Properties in this area often feature spacious gardens and outdoor areas, enhancing the vacation experience.
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 travelling 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.
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.
What is the most popular type of vacation rental accomodation in Middletown?
In Middletown, vacation houses and apartments are both popular choices, with several of each type available throughout the area. The vacation houses typically feature spacious layouts, multiple bedrooms, and private outdoor spaces such as gardens or patios—ideal for families or larger groups seeking comfort and relaxation. On the other hand, apartments usually provide a more compact living experience, often including fully equipped kitchens, modern amenities, and convenient access to local shops and dining options.
Are there any family house rentals in Middletown?
In Middletown, Delaware, there are several family-friendly house rentals available, making it an ideal spot for those travelling with children. The locale offers a variety of homes that typically feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where kids can play and explore. Many properties come with amenities such as Wi-Fi and air conditioning, ensuring a comfortable stay.
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. 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, Delaware, there are several pet-friendly house rentals available, offering a welcoming environment for travellers with pets. Many of these properties feature spacious backyards, great for pets to roam and enjoy the outdoors. The rentals often come equipped with modern amenities such as fully equipped kitchens, comfortable living areas, and sometimes additional features like outdoor patios or decks, providing ample space for relaxation and family gatherings.
Are there any remote work vacation rentals in Middletown?
In Middletown, Delaware, there are several remote work vacation rentals available, making it a suitable spot for those looking to combine work with a relaxing getaway. Many of these properties are equipped with essential amenities such as desks, desk chairs, and reliable Wi-Fi, ensuring a comfortable work environment. 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 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, Delaware, vacation rentals typically offer a range of popular amenities that cater to travellers' needs. Most properties come equipped with a kitchen, allowing guests to prepare their own meals during their stay. You'll also find essential appliances such as coffee makers, microwaves, and ovens, making it convenient to enjoy home-cooked meals. Additionally, cookware, dishware, and utensils are usually provided, ensuring that guests have everything they need for a comfortable and functional experience.
When is the best time to visit Middletown for a vacation rental?
April is often regarded as the best time to visit Middletown, Delaware, as the spring season breathes life into the area with blooming flowers and mild temperatures. This month marks the beginning of pleasant weather, with daytime highs reaching the low 20s Celsius, making it ideal for outdoor activities and leisurely strolls through the charming town.

The peak tourist season spans from June to August when families and vacationmakers flock to Middletown for summer fun. During these months, you can enjoy various activities, including visiting local parks, enjoying outdoor festivals, and experiencing the vibrant community spirit. The warm weather is great for picnics and exploring the area's historical sites.

For those seeking a more budget-friendly experience, November offers a quieter alternative. While the temperatures drop to around 10 degrees Celsius, you can enjoy the tranquillity of the town and the beautiful autumn scenery. This time of year provides a unique opportunity to appreciate Middletown's charm without the hustle and bustle of peak season.
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.
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 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 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.

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