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Middletown vacation rentals

We found 115 vacation rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
Discover a selection of 5 homes and other 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.

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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:

  • Big Cork Vineyards (6.4 mi / 10.2 km)
  • Catoctin Mountain Park (14.9 mi / 24.1 km)
  • Breaux Vineyards (17.6 mi / 28.4 km)
  • Hollywood Casino at Charles Town Races (19.3 mi / 31 km)
  • Maryland National Golf Club (2.6 mi / 4.2 km)
  • Musket Ridge Golf Course (3.6 mi / 5.9 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:

  • 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)
  • Cunningham Falls State Park (13.3 mi / 21.5 km)
  • Catoctin Mountain Park (14.9 mi / 24.1 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?

Based on our data, houses are the most sought-after property type in Middletown. But naturally, everyone's idea of the perfect trip isn't going to be the same. Vrbo has vacation homes with every size, shape and budget in mind, and we'll help you find the perfect fit for you.

How much does it cost to rent a vacation rental in Middletown?

Property type, season and length of stay are some of the things that can affect the price of a vacation home. Simply enter your travel dates to find your dream escape. From cozy chalets to plush villas, all Vrbo vacation rentals provide incredible value.

How much does it cost to rent a beach house in Middletown?

When you travel and the size and style of the property will help determine the cost of your beachside vacation rental. Enter your Middletown travel dates to see all your options on Vrbo. Can't live without a hot tub? Use the filters to pick the features and amenities you want in your rental.

Are there pet-friendly vacation rentals in Middletown?

With three properties that welcome pets, your furry companion can also come along on your Middletown getaway. Use the filter tool to search our pet-friendly vacation rentals and find a vacation home that'll set tails wagging on Vrbo.

What are popular rental amenities in Middletown?

A fireplace, a barbecue grill and a porch rank as the most popular rental amenities in Middletown. Whether you plan to go on your own, with your spouse or a group of family members, Vrbo will help you find a vacation rental that fits your tastes with a load of extras you'll love.

Are there vacation rentals in Middletown that welcome kids?

Bring the entire family together for a fun-packed adventure in Middletown at one of our three family-friendly vacation homes. A lot of these stays offer amenities that are ideally suited to getaways with the kids, such as laundries, living rooms and entertainment areas. Simply check the "Properties good for families" filter and pick your favorite.

What are the top attractions for families in Middletown?

If you're vacationing with the kids, make sure you put these family-friendly attractions in Middletown on your list of things to do:

  • Musket Ridge Golf Course
  • Maryland National Golf Club

Can I find two-bedroom vacation rentals in Middletown?

Gather your besties and relax in total privacy and comfort in one of the two two-bedroom vacation homes Middletown has to offer.

How can I find vacation rentals with air conditioning in Middletown?

There are three Vrbo vacation rentals with air conditioning in Middletown giving you that cool, cool breeze and extra level of comfort. Just enter your dates of travel and then take advantage of our filter tool to help you find stays with air conditioning.

How old do you have to be to rent a vacation rental in Middletown?

We recommend you check with the Middletown vacation home you're considering on Vrbo as age restrictions differ. However, it's typically 16, 18 or 21.

How long can I rent a vacation rental in Middletown for?

The amount of time you can rent a Middletown vacation home for is down to each property. Simply enter your dates of travel to find options offering extended stays. They come with the things you need to make your extended trip more comfortable such as air conditioning and kitchens. Some Vrbo vacation properties may also offer discounted weekly or monthly prices, so you can stick around for longer for less.

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