Photo by Doug Kerr

Middletown Vacation Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    one key icon
    Treat yourself
    Save instantly and earn perks with One Key
    Learn about One Key
    today icon
    Change your mind
    Book hotels with free cancellation

Vacation Rentals in Middletown

Countryside Cabin with Mountain Views near Surreybrooke Gardens
Exterior
Countryside Cabin with Mountain Views near Surreybrooke Gardens
10.0 out of 10, Exceptional, (64)
"Property was beautifully manicured. Cabin was rustic but comfortable with all the comforts of home. I loved sitting on the huge wrap around porch in the morning listening to the birds and watching the sunrise."
Countryside Cabin with Mountain Views near Surreybrooke Gardens
Charming "Cream of the Crop" Cape ~❤️of Middletown
Property grounds
Charming "Cream of the Crop" Cape ~❤️of Middletown
10.0 out of 10, Exceptional, (102)
"Cute cottage was clean and comfy. Everything you need to make a nice dinner, relax and enjoy the quiet neighborhood."
The price is $180
$352 total
includes taxes & fees
Jul 7 - Jul 8
Charming "Cream of the Crop" Cape ~❤️of Middletown
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
TV, fireplace
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
9.6 out of 10, Exceptional, (81)
"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 $85
$206 total
includes taxes & fees
Jun 23 - Jun 24
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Serene Log Cabin Nestled Among the Battlefields
Exterior
Serene Log Cabin Nestled Among the Battlefields
8.0 out of 10, Very Good, (22)
"The cabin was very nice"
Serene Log Cabin Nestled Among the Battlefields
Antietam Toll House~ an historic waterfront cabin
Property grounds
Antietam Toll House~ an historic waterfront cabin
9.8 out of 10, Exceptional, (54)
"Cabin was just as described. Small home in a very rural setting. Loved the creek running along side the property. We traveled daily to Gettysburg and it was a pleasant ride. Owner was very responsive and accommodating. Would definitely stay here again!"
The price is $150
$304 total
includes taxes & fees
Jun 24 - Jun 25
Antietam Toll House~ an historic waterfront cabin
Cozy Mountain Cabin w/ Steam Shower. Family Friendly!
Smart TV, DVD player, books, video library
Cozy Mountain Cabin w/ Steam Shower. Family Friendly!
10.0 out of 10, Exceptional, (31)
"My sister and I booked two nights here. The hosts were very communicative, and the cabin was even better than we expected."
The price is $145
$330 total
includes taxes & fees
Jul 10 - Jul 11
Cozy Mountain Cabin w/ Steam Shower. Family Friendly!
❤️ Secluded 1940s Romantic Tiny House on the River
Beach
❤️ Secluded 1940s Romantic Tiny House on the River
10.0 out of 10, Exceptional, (41)
"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 $83
$153 total
includes taxes & fees
Jul 2 - Jul 3
❤️ Secluded 1940s Romantic Tiny House on the River
Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.
Exterior
Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.
9.8 out of 10, Exceptional, (99)
"What a find! Clean, comfortable and convenient. The house has charm, modern amenities, big flat backyard, wifi, and easy parking. We played the board games that were there, and I enjoyed the travel guides and books. It's great to be able to walk around (hilly, but that makes for great scenery) - we especially enjoyed Bolivar Bakery, Snallygasters restaurant, and whitewater rafting (Harpers Ferry Adventure Center). We'd definitely stay here again."
Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.
Riverside cottage, minutes from historic Harpers Ferry! Private river access!
Property grounds
Riverside cottage, minutes from historic Harpers Ferry! Private river access!
9.8 out of 10, Exceptional, (61)
"We loved this property. All the comforts of home -- and gorgeous views of the Potomac River from the cozy balcony. Highly recommend!!!"
The price is $145
$221 total
includes taxes & fees
Jun 30 - Jul 1
Riverside cottage, minutes from historic Harpers Ferry! Private river access!
RIVERKEEPER INN, Waterfront Property on the Potomac River
View from property
RIVERKEEPER INN, Waterfront Property on the Potomac River
9.4 out of 10, Exceptional, (104)
"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!
Property grounds
Woodpecker Woods - Cozy Log Cabin w/ Hot Tub!
9.6 out of 10, Exceptional, (10)
"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 $155
$406 total
includes taxes & fees
Jun 23 - Jun 24
Woodpecker Woods - Cozy Log Cabin w/ Hot Tub!
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
Exterior
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
10.0 out of 10, Exceptional, (94)
"The house was an excellent place for my family to stay during our visit to Harper's Ferry. It is conveniently located in downtown Harper's Ferry, and we enjoyed our visit."
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
Cozy Cottage
Exterior
Cozy Cottage
9.2 out of 10, Wonderful, (19)
"Clean, quiet neighborhood, easy walk to downtown"
The price is $94
$215 total
includes taxes & fees
Jun 25 - Jun 26
Cozy Cottage
A newly renovated, pet-friendly Penthouse condo with private rooftop deck.
Interior
A newly renovated, pet-friendly Penthouse condo with private rooftop deck.
9.8 out of 10, Exceptional, (19)
"We stayed in Frederick and went to the Orioles game on Saturday. Perfect spot"
A newly renovated, pet-friendly Penthouse condo with private rooftop deck.
Rustic Log Cabin with Private Dock on the Lake!
Property grounds
Rustic Log Cabin with Private Dock on the Lake!
9.6 out of 10, Exceptional, (9)
"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 $269
$575 total
includes taxes & fees
Jun 30 - Jul 1
Rustic Log Cabin with Private Dock on the Lake!
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
Interior
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
9.8 out of 10, Exceptional, (40)
"Thoroughly enjoyed our stay at this property. The view was stunning and the communication and ease of check in was wonderful. We enjoyed the extra recommendations for wineries to visit and a weekend concert in Harper's Ferry. Very personalized and attentive service."
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
Antietam Creek - Quiet 2 Bedroom Cabin
View from property
Antietam Creek - Quiet 2 Bedroom Cabin
9.4 out of 10, Exceptional, (72)
"Perfect quiet spot to relax and spend quality time! Cabin was as listed and was just what we needed!"
The price is $200
$333 total
includes taxes & fees
Jun 23 - Jun 24
Antietam Creek - Quiet 2 Bedroom Cabin
Hot Tub, Deck/Grill, Game Room, WiFi at Cute Cabin
Exterior
Hot Tub, Deck/Grill, Game Room, WiFi at Cute Cabin
9.8 out of 10, Exceptional, (43)
"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 $145
$324 total
includes taxes & fees
Jun 24 - Jun 25
Hot Tub, Deck/Grill, Game Room, WiFi at Cute Cabin
Spacious Quiet Retreat with Hot Tub and Walk to River Minutes to Harpers Ferry
Terrace/patio
Spacious Quiet Retreat with Hot Tub and Walk to River Minutes to Harpers Ferry
9.8 out of 10, Exceptional, (8)
"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
Fridge, microwave, oven, stovetop
Cozy home near Casino, Breweries, Historical attractions, National Park & more
10.0 out of 10, Exceptional, (13)
"We were in town for the comedy show at the casino. House was within walking distance however not a walk you would want to take wearing heels. Very quiet neighborhood with plenty of restaurants close by. The house was very clean and comfortable beds. Had a really great time!! Thank you!!!"
The price is $135
$288 total
includes taxes & fees
Jun 26 - Jun 27
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.

Middletown Vacation Rental Travel Info

Number of vacation rentals
6
Popular accommodation
Middletown private vacation homes
Known landmarks
Orchid Cellar Winery, Musket Ridge Golf Course and Maryland National Golf Club
International airport
Washington, DC (IAD-Washington Dulles Intl.)

Other types of properties in Middletown you may be interested in

Countryside Cabin with Mountain Views near Surreybrooke Gardens
Exterior
Countryside Cabin with Mountain Views near Surreybrooke Gardens
10.0 out of 10, Exceptional, (64)
"Property was beautifully manicured. Cabin was rustic but comfortable with all the comforts of home. I loved sitting on the huge wrap around porch in the morning listening to the birds and watching the sunrise."
Countryside Cabin with Mountain Views near Surreybrooke Gardens
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
TV, fireplace
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
9.6 out of 10, Exceptional, (81)
"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 $85
$206 total
includes taxes & fees
Jun 23 - Jun 24
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Country Inn & Suites by Radisson, Frederick, MD
Room, 2 Queen Beds, Non Smoking | Premium bedding, down comforters, pillowtop beds, in-room safe
Country Inn & Suites by Radisson, Frederick, MD
3.0 star property
8.6 out of 10, Excellent, (1010)
"Clean hotel with nice rooms"
The price is $78
$87 total
includes taxes & fees
Jun 30 - Jul 1
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.

Everything you need to know about Middletown vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Middletown vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Middletown vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Middletown vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middletown. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Middletown in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $83 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Middletown rentals

At Expedia, we put the best Middletown vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Middletown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Middletown vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Middletown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a vacation rental in Middletown?

Yes, we offer vacation rentals near well known points of interest in Middletown, or you can select a secluded option if you're looking for relaxation. 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's the top vacation rental in Middletown?

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

How many vacation rentals will I find in Middletown?

Expedia has 5 vacation 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 vacation rentals like in Middletown?

Vacation rentals are private accommodations you can book for a couple days or more in Middletown. Vacation rentals offer extras like laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about cleanliness, a vacation rental can offer a sense of seclusion away from public hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for a small group gathering.

Recent reviews of Middletown properties
Expedia verified reviews

Comfort Inn

Comfort Inn

5/5 Excellent
"no complaints "
A verified traveler stayed at Comfort Inn
Posted 6 hours ago
Comfort Inn