Photo by Stephanie Sutton

Middletown holiday rentals

We found 89 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in Middletown to find one that's perfect for your trip. Whether you’re staying in a holiday home with friends, family or even just your pets, you'll find the best amenities for hanging out with the people that matter most, which might include parking and a hot tub. At the end of the day, you'll be sure to find a property to rent that has what everyone needs, including a place that is accessible or non-smoking.

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Why people love visiting captivating Middletown

Enjoy the area's entertainment, churches and theatre scene with a rental holiday home in Middletown. This city's riverfront, hockey games and bars draw many visitors. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in Middletown

Are you hoping to find things to do in the city? Venture out of your cosy holiday rental and check out everything that Middletown has to offer. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Dinosaur Land (7.9 mi / 12.7 km)
  • Rock Harbor Golf Course (11.3 mi / 18.1 km)
  • Linden Vineyards (15.2 mi / 24.5 km)
  • Naked Mountain Winery & Vineyards (16.7 mi / 26.8 km)
  • Delaplane Cellars (19.2 mi / 30.9 km)
  • Valerie Hill Winery (4.5 mi / 7.2 km)

Exploring the natural landscape of Middletown

Whether you're an active traveller or just want to appreciate the scenery, Middletown is a great place to get outside. Here are some of the area’s most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • Lake Frederick Boat Launch (6.7 mi / 10.8 km)
  • Shenandoah River (7.6 mi / 12.2 km)
  • Skyline Caverns (9.4 mi / 15.2 km)
  • Front Royal Entrance Shenandoah National Park (9.8 mi / 15.8 km)
  • Dickey Ridge Visitor Center (11.6 mi / 18.7 km)
  • Lost River (28.6 mi / 46.1 km)

How to get to and around Middletown

The nearest airport is in Martinsburg, WV (MRB-Eastern West Virginia Regional), located 30.4 mi (48.9 km) from the city centre.

Frequently asked questions

What is the best area to stay in Middletown when booking a holiday rental?
When considering the best area to stay in Middletown, Virginia, for a holiday rental, the town itself offers a charming blend of history and natural beauty. One of the most appealing neighbourhoods is the historic centre, which is rich in heritage, featuring quaint streets and beautifully preserved buildings. Here, you can easily explore local attractions, such as the stunning Cedar Creek and Belle Grove National Historical Park, where you can delve into Civil War history while enjoying scenic views of the surrounding landscape.Another fantastic option is the area near the Shenandoah River, which provides opportunities for outdoor activities like kayaking and fishing. This neighbourhood is ideal for those who appreciate nature and want to take advantage of the lovely river trails. With a variety of holiday rentals available, you can find accommodations that suit your preferences, whether you're looking for a cosy cabin or a spacious family home.
When is the best time to visit Middletown for a holiday rental?
The best time to visit Middletown for a holiday rental is during the peak season, which runs from July to September. This vibrant period attracts families and outdoor enthusiasts eager to explore the scenic beauty of the Virginia countryside. July, in particular, stands out as the most popular month, when the warm temperatures (averaging between 20 and 30 degrees Celsius) encourage a host of outdoor activities, including hiking, biking, and exploring local vineyards.Visitors during these months can enjoy a lively option filled with various events, including summer festivals that showcase local culture and cuisine. The natural landscapes around Middletown provide ample opportunities for sightseeing, with lush greenery and stunning views that enhance any outdoor adventure.For those looking for a more budget-friendly option, December presents a charming alternative. While this is considered the low season, the winter months offer a serene atmosphere great for a peaceful retreat. You can experience the beauty of the area in a different light, perhaps indulging in cosy evenings by the fire or exploring local holiday festivities without the crowds.Ultimately, your choice of when to visit Middletown will hinge on whether you prefer the energetic vibe of summer or the tranquil charm of winter.
What are the top attractions in Middletown?
In Middletown, Virginia, visitors can enjoy a range of attractions that highlight the area's rich history and natural beauty. The historic downtown showcases charming architecture and local shops, providing a quaint atmosphere for leisurely strolls. Nearby, the Cedar Creek and Belle Grove National Historical Park offers insights into Civil War history and features picturesque landscapes for hiking and exploration.For those interested in outdoor activities, the surrounding Shenandoah Valley provides stunning scenery, with opportunities for hiking, biking, and enjoying the local flora and fauna. The nearby Skyline Drive, located in Shenandoah National Park, offers breathtaking views and access to numerous trails.Additionally, the local wineries and breweries in the region make for delightful excursions, where visitors can sample local produce and enjoy the serene countryside.
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.