Middletown holiday rentals

We found 65 holiday rentals — enter your dates for availability
Discover a selection of 6 homes and other holiday rentals in Middletown that are perfect for your trip. Whether you're travelling with family, friends or just your furry companion, holiday homes have the amenities that you expect for your stay, which might include a hot tub and a washer and dryer. At the end of the day, you'll find a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

The lush setting of Middletown is ready to explore

Enjoy the area's festivals, churches and monuments with a rental holiday home in Middletown. Renowned for its restaurants, cheese shops and forests, this city welcomes all visitors. A holiday 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? Venture out of your holiday home and check out everything that makes Middletown a fun spot to go on holiday. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Frightland (6.5 mi / 10.5 km)
  • Brandywine Zoo (22.9 mi / 36.9 km)
  • Auburn Road Vineyard (24.3 mi / 39 km)
  • Frog Hollow Golf Club (1.2 mi / 1.9 km)
  • Back Creek Golf Club (4.2 mi / 6.8 km)
  • Chesapeake Bay Golf Club (14.4 mi / 23.2 km)

Exploring the natural features in Middletown

Whether you're an adventurous traveller or just want to spend some time taking in the scenery, Middletown is a great place to spend some time outside. These are some of the area's most enchanting features, all within 30 miles (48.2 km) of the city centre:

  • Dragon Run Park (10.7 mi / 17.3 km)
  • Kirkwood Soccer Complex (13.6 mi / 21.9 km)
  • North East Beach Area (14.8 mi / 23.9 km)
  • Woodland Beach (15.5 mi / 24.9 km)
  • University of Delaware Botanic Gardens (16 mi / 25.7 km)
  • Newark Reservoir (17 mi / 27.4 km)

Travelling to and around Middletown

The nearest airport is in Wilmington, DE (ILG-New Castle), located 16.8 mi (27.1 km) from the city centre. If you can't find a flight that's convenient for your trip, you can also fly into Millville, NJ (MIV-Millville Municipal), which is 34.8 mi (56.1 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, Delaware, a particularly appealing area to stay is the historic district. This charming neighbourhood is steeped in character, showcasing a delightful mix of traditional architecture and modern amenities. Here, visitors can easily explore local boutiques and cafes, creating a vibrant setting for a leisurely stroll.In terms of attractions, the nearby Silver Lake offers a serene setting for outdoor activities such as fishing and walking along picturesque trails. Additionally, the historic Olde Towne area features several lovely parks and is close to the renowned Middletown Historical Society, where one can delve into the town's rich heritage.This area boasts a variety of properties, suiting different tastes and budgets, ensuring a comfortable base for exploring the charm of Middletown while enjoying its unique local attractions.
What is the most popular type of holiday rental accomodation in Middletown?
In Middletown, holiday houses are the predominant type of holiday rental, with around 18 available throughout the area. These homes provide spacious living environments ideal for families or groups, featuring multiple bedrooms, fully equipped kitchens, and often outdoor spaces such as patios or gardens for relaxation. The rentals are typically situated in friendly neighbourhoods, offering a comfortable base for exploring local attractions and enjoying the charm of this Delaware town.
Are there any family house rentals in Middletown?
In Middletown, Delaware, there are some family-friendly house rentals available, making it an appealing choice for families seeking a comfortable getaway. The locale offers spacious properties with ample living areas, great for relaxation after a day of exploring. Many homes feature full kitchens, allowing families to prepare meals together, as well as outdoor spaces where children can play safely.Visitors will find that the nearby attractions, such as the historic downtown area with its charming shops and eateries, enhance the experience. Additionally, the proximity to parks and recreational areas provides opportunities for outdoor activities.
Can I rent a holiday home with a pool or hot tub in Middletown?
In Middletown, Delaware, there are several holiday homes available for rent that feature pools and hot tubs. This charming town offers a mix of modern amenities and a suburban atmosphere, making it a great choice for families or groups looking for a relaxing getaway. Many of these properties come equipped with private swimming pools, hot tubs, outdoor seating areas, and fully stocked kitchens, ideal for enjoying time together after a day of exploring the local area.Middletown is conveniently located near various parks and recreational areas, providing opportunities for outdoor activities.
Are there pet-friendly house rentals in Middletown?
In Middletown, Delaware, there are several pet-friendly house rentals available for those looking to enjoy a comfortable stay with their furry companions. These holiday homes often feature amenities such as spacious backyards, which are ideal for pets to roam and play, along with fully equipped kitchens and cosy living areas that provide an inviting space for families or groups.The town is conveniently located near parks, such as Silver Lake Park and the nearby Lums Pond State Park, both of which offer ample opportunities for outdoor activities with pets, including walking trails and picnic areas. The rentals in this area typically provide easy access to these local green spaces, making it a great choice for pet owners looking to explore the natural beauty of Delaware while enjoying the comforts of home.
Are there any remote work holiday rentals in Middletown?
In Middletown, Delaware, there are several holiday rentals suitable for remote work. Many of these properties come equipped with essential amenities such as high-speed Wi-Fi, dedicated workspaces with desks and chairs, and comfortable living areas that facilitate productivity. This quaint town offers a peaceful environment, superb for focusing on work while enjoying the comforts of home.Additionally, the surrounding area features local parks and recreational spots, allowing for a refreshing break during the workday. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Middletown?
In Middletown, popular rental amenities include fully equipped kitchens, which allow guests to prepare their own meals, as well as onsite parking for convenience. Many rentals feature coffee and tea makers for a warm beverage at any time of the day. Additionally, travellers can expect units with balconies, providing a lovely space to relax outdoors, and desks for those who may need to catch up on work or plan their activities.
When is the best time to visit Middletown for a holiday rental?
April is the most popular month to visit Middletown, as spring brings the region to life with blooming flowers and mild temperatures. This time of year is great for travellers seeking outdoor activities and local events, providing a fantastic opportunity to explore the charming historic district and enjoy the vibrant community atmosphere.The peak tourist season runs from June to August, when families flock to the area for summer adventures. During these months, you can enjoy a variety of activities, from visiting local parks to attending seasonal festivals. The warm weather, with temperatures typically ranging from the mid-teens to low 30s Celsius, makes it ideal for outdoor exploration and sightseeing.For those seeking a more tranquil experience, November is an excellent month to consider. This off-peak time allows for a quieter visit while still offering pleasant autumn weather, making it a great season for enjoying the beauty of fall foliage and the local culture without the crowds.Ultimately, your choice of when to visit Middletown will depend on your preferences for lively summer activities or a peaceful autumn retreat.
What are the top attractions in Middletown?
In Middletown, Delaware, visitors can explore several charming attractions that highlight the area's history and community spirit. The historic district features beautifully preserved buildings and quaint shops, providing a glimpse into the town's past. Nearby, the Middletown Village Historic District offers lovely walking paths and the opportunity to see several popular 18th and 19th-century homes.For outdoor enthusiasts, the Lums Pond State Park is just a short drive away, offering expansive green spaces, hiking trails, and opportunities for fishing and picnicking. This park is ideal for families and solo travellers looking to enjoy nature.Additionally, the nearby Odessa Historic District is worth a visit, showcasing antique shops and significant historical sites, including the historic Odessa Museum. This area enriches the experience of visitors interested in Delaware's heritage.
Are all fees included in the Middletown holiday homes prices shown on Stayz?
Stayz 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.
Are there any Middletown holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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.
Are there any discounts for Middletown holiday homes?
You can find great discounts on holiday homes in Middletown on Stayz, 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.
Can I change or cancel my Middletown holiday home booking on Stayz?
To find Middletown holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Middletown?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising 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 favourites, and build the perfect itinerary together.
How early should I book a Middletown holiday home?
Book your Middletown holiday home 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Middletown?
Prices for holiday homes 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. Stayz offers something for every taste and budget, from affordable homes in Middletown to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

More holiday ideas