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Middletown holiday rentals

We found 115 holiday rentals — enter your dates for availability

your current months are April, 2024 and May, 2024.
April 2024
May 2024
Discover a selection of 5 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 rentals have the best amenities for hanging out with the people that matter most, such as parking and air conditioning. What you'll find is a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

Find spaces that suit your style

  • 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

Take in the riverfront 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 find top things to see and do while you're in the area? Venture out of your cosy holiday rental and check out everything that makes Middletown a one-of-a-kind holiday spot. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • 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, you'll be sure to find the perfect setting for your holiday in Middletown. These are some of the area's most stunning sights, all within 30 miles (48.2 km) of the city centre:

  • 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 centre. If you can't find a flight that works for your travel itinerary, you could 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 holiday home 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 holiday 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 holiday home in Middletown?

Property type, season and length of stay are some of the things that can affect the price of a holiday home. Simply enter your travel dates to find your dream escape. From cosy chalets to plush villas, all Vrbo holiday homes 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 holiday home. 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 home.

Are there pet-friendly holiday homes 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 holiday homes and find a holiday home that'll set tails wagging on Vrbo.

What are popular home amenities in Middletown?

A fireplace, a barbecue grill and a porch rank as the most popular home 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 holiday home that fits your tastes with a load of extras you'll love.

Are there holiday homes in Middletown that welcome kids?

Bring the entire family together for a fun-packed adventure in Middletown at one of our three family-friendly holiday 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 favourite.

What are the top attractions for families in Middletown?

If you're holidaying 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 holiday homes in Middletown?

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

How can I find holiday homes with air conditioning in Middletown?

There are three Vrbo holiday homes 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 holiday home in Middletown?

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

How long can I rent a holiday home in Middletown for?

The amount of time you can rent a Middletown holiday 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 holiday properties may also offer discounted weekly or monthly prices, so you can stick around for longer for less.

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