Photo by Doug Kerr

Middletown Holiday Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Middletown

Countryside Cabin with Mountain Views near Surreybrooke Gardens
10.0 out of 10, Exceptional, 61 reviews
"Beautiful views from the wrap around porch. Comfortable inside including the bed. Lots of neat things to look at. Highly recommend!"
Countryside Cabin with Mountain Views near Surreybrooke Gardens
Charming "Cream of the Crop" Cape ~❤️of Middletown
10.0 out of 10, Exceptional, 102 reviews
"This is our 2nd stay at the "Cape Cod". The house is quiet, clean, and modern. Heather is very responsive. The Middletown location provided us with convenient access for our outings to Gettysburg, Emmitsburg, MD and Frederick."
The price is NZ$407
per night
9 Jun - 10 Jun
Charming "Cream of the Crop" Cape ~❤️of Middletown
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
9.6 out of 10, Exceptional, 81 reviews
"My wife LOVED it here. Yes it’s an old cabin But it was furnished wonderfully and very comfortable. We had a great stay and have already recommended this place to a few friends. Over all I give it an A and this one ranks up in the top 5 of our vrbo vacation rentals"
The price is NZ$349
per night
10 Jun - 11 Jun
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Save an average of 15% on thousands of hotels when you're signed in
Serene Log Cabin Nestled Among the Battlefields
8.0 out of 10, Very good, 22 reviews
"The cabin was very nice"
Serene Log Cabin Nestled Among the Battlefields
Antietam Toll House~ an historic waterfront cabin
9.8 out of 10, Exceptional, 52 reviews
"House was very clean and relaxing. Beautiful scenery and lots of birds."
Antietam Toll House~ an historic waterfront cabin
Cozy Mountain Cabin w/ Steam Shower. Family Friendly!
10.0 out of 10, Exceptional, 28 reviews
"This little cabin was great!! Comfortable beds. Very clean. Brigid the host was so responsive. Instructions were very clear. She even answered our questions about recommendations for a goos hiking trail! Highly recommend! I hope we will be back."
The price is NZ$531
per night
19 Jun - 20 Jun
Cozy Mountain Cabin w/ Steam Shower. Family Friendly!
❤️ Secluded 1940s Romantic Tiny House on the River
10.0 out of 10, Exceptional, 41 reviews
"The tiny house is exactly as described. Its small, clean, cozy and comfortable. The location right on the river is fantastic. Being able to have a fire right by the water each night was such a plus. In better weather would be a great put in for canoeing, kataking. Very close many historic sights, unique shops, and outdoor activities. The hosts are very thoughtful, kind and responsive. We will be staying again!!"
The price is NZ$233
per night
23 Jun - 24 Jun
❤️ Secluded 1940s Romantic Tiny House on the River
Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.
9.8 out of 10, Exceptional, 97 reviews
"The house was spotless was walking distance to everything we wanted to do. Would definitely coming back here to stay!"
Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.
Riverside cottage, minutes from historic Harpers Ferry; private river access!
9.8 out of 10, Exceptional, 58 reviews
"Nice location for visiting Harpers Ferry. Great porch for watching the sunrise if you're up early."
The price is NZ$357
per night
12 Jun - 13 Jun
Riverside cottage, minutes from historic Harpers Ferry; private river access!
RIVERKEEPER INN, Waterfront Property on the Potomac River
9.4 out of 10, Exceptional, 104 reviews
"We had a wonderful time, even in the rain! Easy river access and beautiful views of both the water and green spaces."
RIVERKEEPER INN, Waterfront Property on the Potomac River
Woodpecker Woods - Cozy Log Cabin w/ Hot Tub!
9.6 out of 10, Exceptional, 10 reviews
"We enjoyed the cabin very much. We hiked during the day and was very relaxing coming back to the hot tub and a fire. Thank you for a great stay!!"
The price is NZ$604
per night
13 Jun - 14 Jun
Woodpecker Woods - Cozy Log Cabin w/ Hot Tub!
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
10.0 out of 10, Exceptional, 93 reviews
"We enjoyed our stay at this historic home in the middle of town. We loved sitting on the porch and we slept great both nights."
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
Cozy Cottage
9.2 out of 10, Wonderful, 18 reviews
"Cottage is quaint, with modern design. Perfect for my husband and I and our pup. Very clean, with tasteful decor. Within walking distance to town. Had everything you need."
The price is NZ$348
per night
10 Jun - 11 Jun
Cozy Cottage
A newly renovated, pet-friendly Penthouse condo with private rooftop deck.
9.8 out of 10, Exceptional, 18 reviews
"Check-in was a breeze, the condo was very clean, and within walking distance to lots of restaurants and shops. My favorite perk of this place was the deck. It was perfect for enjoying coffee and wine! We will definitely be back!"
A newly renovated, pet-friendly Penthouse condo with private rooftop deck.
Rustic Log Cabin with Private Dock on the Lake!
9.6 out of 10, Exceptional, 9 reviews
"The location tucked away on the lake with a dock and kayaks and gravity lounge chairs, fireplace, large dock and gas grill were fabulous."
The price is NZ$1,134
per night
30 Jun - 1 Jul
Rustic Log Cabin with Private Dock on the Lake!
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
9.8 out of 10, Exceptional, 39 reviews
"Very clean property. We enjoyed the elevated deck and timed our trip for some great bird watching. Amazing westward views. Even got to see a thunderstorm roll in. Saw deer and fox in the backyard doing their thing. We had no trouble but the driveway is steep."
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
Antietam Creek - Quiet 2 Bedroom Cabin
9.4 out of 10, Exceptional, 71 reviews
"Perfect quiet spot to relax and spend quality time! Cabin was as listed and was just what we needed!"
The price is NZ$533
per night
9 Jun - 10 Jun
Antietam Creek - Quiet 2 Bedroom Cabin
Hot Tub, Deck/Grill, Game Room, WiFi at Cute Cabin
9.8 out of 10, Exceptional, 43 reviews
"My family and I enjoyed our weekend at this comfortable cabin in the mountains. The six of us co-habited for a few days and there was plenty of room to move around comfortably without being on top of each other. The bedrooms are good sized and the game room kept my kids occupied for hours. The hot tub was an added bonus and it was warm and ready for use upon our arrival. The bathrooms are well stocked with all the necessary toiletries and we found all the equipment we needed in the kitchen to...
The price is NZ$555
per night
9 Jun - 10 Jun
Hot Tub, Deck/Grill, Game Room, WiFi at Cute Cabin
Spacious Quiet Retreat with Hot Tub and Walk to River Minutes to Harpers Ferry
9.8 out of 10, Exceptional, 8 reviews
"perfect # of bedrooms. Loved the hot tub. Would recommend the place to anyone traveling to the area."
Spacious Quiet Retreat with Hot Tub and Walk to River Minutes to Harpers Ferry
Cozy home near Casino, Breweries, Historical attractions, National Park & more
10.0 out of 10, Exceptional, 12 reviews
"The home is beautiful! The owners did an amazing job to make us feel welcomed and at home. They provided us we unexpected amenities like coffee creamer, bottle water and even a bottle of wine. We greatly appreciated the free Netflix especially since ti rained during part of our stay. The location is ideal for our weekend adventures."
The price is NZ$464
per night
26 Jun - 27 Jun
Cozy home near Casino, Breweries, Historical attractions, National Park & more
Don't see what you're looking for?
See all available properties in Middletown
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Middletown you may be interested in

Countryside Cabin with Mountain Views near Surreybrooke Gardens
10.0 out of 10, Exceptional, 61 reviews
"Beautiful views from the wrap around porch. Comfortable inside including the bed. Lots of neat things to look at. Highly recommend!"
Countryside Cabin with Mountain Views near Surreybrooke Gardens
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
9.6 out of 10, Exceptional, 81 reviews
"My wife LOVED it here. Yes it’s an old cabin But it was furnished wonderfully and very comfortable. We had a great stay and have already recommended this place to a few friends. Over all I give it an A and this one ranks up in the top 5 of our vrbo vacation rentals"
The price is NZ$349
per night
10 Jun - 11 Jun
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Country Inn & Suites by Radisson, Frederick, MD
3.0 star property
8.6 out of 10, Excellent, 1,009 reviews
"Not fancy, but clean and convenient."
The price is NZ$143
per night
16 Jun - 17 Jun
Country Inn & Suites by Radisson, Frederick, MD
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Middletown holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Middletown. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Middletown. Seeing all the best attractions is bound to make you fall in love with Middletown. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Middletown short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Middletown?

Yes, there are holiday rentals close to the most popular sights in Middletown, or you can select a more secluded option if you're looking for a relaxing stay. Middletown is known for its golf courses and riverfront. Make sure you have time to check out the entertainment choices while you're in the area.

What are some of the best holiday rentals that Middletown has to offer?

Riverside cottage, minutes from historic Harpers Ferry; private river access!: This holiday home rental outside of Middletown offers a balcony, a selection of games and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals will I find in Middletown?

Expedia has 5 holiday rentals for your stay in Middletown.

What can I see and do in Middletown?

South Mountain State Park and Gambrill State Park are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Maryland National Golf Club and Orchid Cellar Winery.

What are holiday rentals like in Middletown?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Middletown. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll have everything you need. If you're concerned about a sanitised environment, holiday rentals can offer a sense of seclusion away from public hotel lifts and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for a family trip or a small group gathering.

Recent reviews of Middletown properties
Expedia verified reviews