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Middletown vacation rentals

We found 124 vacation rentals — enter your dates for availability

Discover a selection of vacation rentals in Middletown that are perfect for your trip. Whether you’re traveling with friends, family, or just with your pet, vacation rentals have the amenities you expect for your stay, which might include parking and a fireplace. You'll be able to choose a rental for everyone's needs, including places that are non-smoking or accessible.

Vacation rentals with weekly discounts - Middletown

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Find out more about Middletown

Find out more about Middletown

Why visit Middletown

  1. Rich historical sites: Explore Middletown's charming historic houses and significant landmarks that reflect its heritage.
  2. Scenic outdoor adventures: Enjoy the picturesque landscapes and outdoor activities in the beautiful surroundings of Central Maryland.
  3. Family-friendly activities: Engage in various enjoyable activities suitable for visitors of all ages.
  4. Welcoming neighborhoods: Discover friendly locals and delightful neighborhoods that add to the town's charm.
  5. Diverse accommodation options: Choose from private homes, cozy apartments, and caravan parks to suit your stay.

Popular types of accommodation in Middletown

Discover the charm of Middletown with a variety of vacation rentals to suit every traveler. From cozy houses to modern apartments and welcoming caravan parks, there's something for everyone. Whether you’re looking for budget-friendly options or spacious accommodations, you'll find the perfect place to stay. Explore our selections of Middletown apartments, homes, and cheap options to make your getaway both enjoyable and affordable.

  • Houses: The top choice for visitors, offering spacious and comfortable living, perfect for families or groups.
  • Apartments: A popular option for travelers seeking a convenient and cozy stay, ideal for couples or solo adventurers.
  • Caravan Parks: A unique experience for those who enjoy outdoor settings, providing amenities for a fun-filled stay.
  • Cabins: Perfect for a rustic getaway, these accommodations offer a charming retreat in nature.
  • Cottages: Quaint and cozy, cottages provide a delightful home away from home for a relaxing vacation.**

Top attractions in Middletown

Middletown, Maryland, offers a delightful blend of outdoor adventure and scenic beauty, making it perfect for vacations filled with cultural and family experiences. Visitors can explore historic sites, urban parks, and charming historic houses. For an enhanced experience, consider taking virtual tours of the area and viewing the unique homes that reflect the town's rich heritage. Whether you're traveling solo or with loved ones, Middletown promises memorable activities and sights.

  1. Harpers Ferry National Historical Park: Immerse yourself in rich history at this scenic park, featuring significant Civil War sites, beautiful hiking trails, and stunning views of the confluence of the Potomac and Shenandoah Rivers.
  2. Hood College: Experience the vibrant atmosphere of this modern college campus, where you can explore beautiful architecture, engage in cultural events, and enjoy the lively city vibes of Frederick nearby.
  3. Frederick Fairgrounds: Join in on the family-friendly fun at this lively venue, hosting various events, fairs, and outdoor activities perfect for all ages, fostering a sense of community and enjoyment.

Things to do recommended for couples

In Middletown, enjoy a romantic outing at Big Cork Vineyards, just 6 miles away, for wine tasting with a cozy atmosphere. Indulge in relaxation at Vivo Day Spa, 14 miles away, or experience luxury at Sleepy Hollow Country Club, 17 miles away. Perfect for a couple's getaway!

Things to do recommended for families

Your family will love a visit to Harry Grove Stadium for some exciting sports action, explore the serene trails of Catoctin Mountain Park for relaxation, and have a blast at Adventure Park USA with thrilling arcade games and attractions. It’s the perfect mix of fun and adventure!

Things to do recommended for groups

Enjoy a round of golf at Musket Ridge Golf Course, just 4 miles from Middletown, or shop and dine at the Francis Scott Key Mall, located 9 miles away. For a thrilling night out, visit the Hollywood Casino at Charles Town Races, 19 miles from town.

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

If you're traveling with a group, family, pets, or planning an extended stay, be sure to prioritize your preferences when searching. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Middletown with a group: Think about how many bedrooms you'll require and any amenities that are important to you, like a full kitchen or outdoor space for gatherings. Luckily, you can easily filter for these features and many others on Vrbo.
  • Traveling to Middletown with young kids: Traveling with young children can present its own set of challenges. 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 attractions that are family-friendly.
  • Taking your pets with you to Middletown: For many families, a vacation isn’t truly enjoyable without their furry companion by their side. If that resonates with you, be sure to explore Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that your entire family feels comfortable and at ease.
  • Planning for a long term stay visiting Middletown: If you're in search of vacation rentals with special offers for extended stays of a month or more, you've come to the right spot. With 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 criteria as well.

Where to stay in Middletown

Middletown, Maryland, offers a perfect blend of outdoor adventures and scenic beauty, making it an ideal vacation spot. Explore the charming neighborhoods and enjoy family-friendly activities, friendly locals, and rich historical sites. Just a short drive away, discover the natural wonders of Central Maryland, where picturesque landscapes and delightful excursions await. Don't miss the chance to experience the enchanting atmosphere of this beautiful town and its surroundings!

  • Frederick: Located a mere 7 miles from Middletown, Frederick is a vibrant city that offers a delightful mix of outdoor adventures and family-friendly activities. Visitors can explore the local shopping mall and recreational areas, providing ample opportunities for shopping and leisure. Nature enthusiasts will appreciate the proximity to both national and state parks, where scenic trails and picturesque landscapes await. Frederick's charming downtown area features historic architecture, unique boutiques, and inviting cafés, making it a perfect destination to experience both culture and nature.
  • Ashburn: Situated 28 miles from Middletown, Ashburn is a bustling city known for its family-oriented atmosphere and thriving business scene. The city is home to several shopping centers and recreational spots that cater to visitors of all ages. Ashburn's local attractions include serene lakes and beautiful parks, perfect for a relaxing day outdoors. Whether you're looking to enjoy a family outing or explore the city's urban offerings, Ashburn provides a perfect blend of relaxation and excitement for tourists.
  • Harpers Ferry: Just 13 miles from Middletown, Harpers Ferry is a picturesque town renowned for its stunning scenery and outdoor adventures. Nestled at the confluence of the Potomac and Shenandoah Rivers, this historical gem offers a range of recreational activities, including hiking and skiing in nearby areas. The town is closely associated with national parks, making it a great spot for nature lovers. Visitors can explore the scenic beauty of the local lakes and enjoy the rich history that Harpers Ferry has to offer, ensuring a memorable experience for all.

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, June and September, while off-peak times, like January, March and October tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January31.1°F (-0.5°C)Light RainMostly SunnySlightly LowSlightly Low
February34.2°F (1.2°C)Light RainMostly SunnyAverageAverage
March41.9°F (5.5°C)Light RainMostly SunnySlightly LowSlightly Low
April52.5°F (11.4°C)Light RainMostly SunnySlightly HighSlightly Low
May62.2°F (16.8°C)Light RainMostly SunnyAverageAverage
June70.7°F (21.5°C)Light RainMostly SunnySlightly HighAverage
July76.1°F (24.5°C)Light RainMostly SunnyAverageSlightly High
August73.9°F (23.3°C)Light RainMostly SunnyAverageSlightly High
September67.1°F (19.5°C)Light RainMostly SunnySlightly HighAverage
October55.9°F (13.3°C)Light RainMostly SunnySlightly LowSlightly High
November43.5°F (6.4°C)Light RainMostly SunnyAverageAverage
December36.7°F (2.6°C)Light RainMostly SunnyAverageAverage

Booking with Vrbo is simple

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can fluctuate. Also, extending your stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, take advantage of our filters to 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 your booking. Being the planner comes with its perks! By becoming a member of our travel rewards program, One Key, you can enjoy immediate access to member discounts and earn OneKeyCash™ on eligible reservations. Sign up today and begin your journey to savings!

Vrbo Trips: Effortless planning

Vrbo’s Trip Board provides a convenient platform for you to plan new trips, keep your travel arrangements on track, or review and organize your bookings. Your saved or booked properties are neatly categorized into Potential, Upcoming, or Current Trips. To check out your Trip Boards, simply visit: https://www.vrbo.com/trips.

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

Take in the riverside beauty of Middletown

Enjoy the entertainment and other features of Middletown. Well known for its golfing, fishing and basketball games, this walkable city won't disappoint. 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

Do you want to discover attractions to visit while you're in town? Venture out of your vacation home and check out everything that makes Middletown a fun spot to vacation. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city center:

  • Musket Ridge Golf Course (3.6 mi / 5.9 km)
  • Big Cork Vineyards (6.4 mi / 10.2 km)
  • Catoctin Wildlife Preserve and Zoo (11.8 mi / 19.1 km)
  • Whiskey Creek Golf Club (14.2 mi / 22.8 km)
  • Tarara Winery (14.8 mi / 23.8 km)
  • Adventure Park USA (14.9 mi / 24 km)

Exploring the natural landscape of Middletown

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

  • Baker Park (7.1 mi / 11.4 km)
  • Greenbrier State Park (7.7 mi / 12.3 km)
  • Carroll Creek Linear Park (8 mi / 12.9 km)
  • Crystal Grottoes Caverns (8 mi / 12.9 km)
  • Antietam Creek (9.9 mi / 15.9 km)
  • Sugarloaf Mountain Park (15.6 mi / 25 km)

How to get to and around Middletown

Fly into Hagerstown, MD (HGR-Hagerstown Regional), the closest airport, located 20.6 mi (33.2 km) from the city center. If you can't find a flight that works for your travel itinerary, you can also fly into Martinsburg, WV (MRB-Eastern West Virginia Regional), which is 24 mi (38.6 km) away.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Middletown?
The most desirable types of vacation rentals in Middletown are cabins. Want something different? Vrbo has many options to match the needs of our guests, so you'll see vacation homes in loads of shapes and sizes. The ideal home away from home is waiting for you — get yours today.
How much does it cost to rent a vacation rental in Middletown?
Different things can influence what you'll pay for a vacation rental in Middletown, including the type of property, length of stay and season. However, all Vrbo homes have one thing in common — unbeatable value. Simply add your travel dates to find your ideal 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're going and the style and size of property you're searching for. You can quickly and easily find prices on Vrbo by entering your dates of travel. Then use our handy filter tool to select the number of bedrooms and amenities important to you, like a pool, WiFi and air conditioning.
Are there pet-friendly vacation rentals in Middletown?
With eight properties that welcome pets, your furry companion can join in on your Middletown break. Use our filter tool to browse our pet-friendly vacation rentals and find your pawfect pad on Vrbo.
What are popular rental amenities in Middletown?
When it comes to rental amenities that guests search for in Middletown, a fireplace, a firepit and a garden are at the top of the list. With Vrbo vacation rentals, you'll have options to fit your taste and style, whether you're on a trip with family members, friends or even pets.
Are there large group vacation rentals in Middletown?
With four Middletown properties that can accommodate five or more people, you can invite a few extra buddies or family members along. Whether you're planning an informal get-together or a birthday party, we'll help you find the perfect space for the occasion.
Are there vacation rentals in Middletown that welcome kids?
Bring the whole family together for a fun-filled adventure in Middletown at one of our eight family-friendly vacation properties. A lot of these stays offer conveniences that are perfect for getaways with the kids, such as dining rooms, bunk beds and outdoor spaces. Just click on the "Properties good for families" filter box and choose your favorite.
What are the top attractions for families in Middletown?
If you're in search of some fun for all ages near the center of Middletown, check out Maryland National Golf Club.
Are there one-bedroom vacation rentals in Middletown?
Yes, Middletown has three one-bedroom rentals on offer. Typically situated in popular spots due to their compact size, a one-bedroom vacation rental is great if you're getting away with your partner or a friend. And with home comforts such as air conditioning and more privacy than a standard hotel, you'll be able to chill out while sightseeing around this awesome destination.
Can I find two-bedroom vacation rentals in Middletown?
Middletown has four two-bedroom properties for you to select from. Experience a vacation home with all the comfort and space you need at an attractive price on Vrbo.
Are there vacation rentals with WiFi in Middletown?
You'll have a choice of five vacation rentals with WiFi in Middletown. If you want to disconnect from the world on your vacation, but still want to be connected to the internet, these getaways have just what you need. Narrow your search by applying the WiFi filter on Vrbo.
How can I find vacation rentals with air conditioning in Middletown?
Select your travel dates and then make use of the filters to find vacation rentals with ac in Middletown on Vrbo. With eight air-conditioned properties available, you can look forward to a cool and comfy break.
How old do you have to be to rent a vacation rental in Middletown?
The minimum age requirements can vary across properties on Vrbo, so check the rules of the vacation home in Middletown you're considering. But typically, it's 16, 18 or 21.
How long can I rent a vacation rental in Middletown for?
How long you can rent a vacation rental in Middletown varies according to the property. Just enter your preferred dates to see a list of options offering extended stays. With a range of amenities like air conditioning and laundries, as well as some offering weekly or monthly discounted prices, you're sure to get somewhere perfect to call your home away from home in Middletown.
Does Vrbo offer discounts for vacation homes in Middletown?
Whether you've got your sights set on one of our newly listed homes, or one of our weekly or monthly discounts on vacation rentals, you're sure to find some fabulous bargains and discounts on Vrbo. From mini stays to extended vacations, we've got the ideal space for your next Middletown escape.