Photo by Doug Kerr

Middletown Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Middletown

Countryside Cabin with Mountain Views near Surreybrooke Gardens

10.0 out of 10, Exceptional, (108)
"Beautiful location with some of the most immaculately cared for grounds I’ve ever seen!"
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, (99)
"It was just wonderful. Totally charming "
The price is AU$323
includes taxes & fees
3 Aug - 4 Aug
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

Serene Log Cabin Nestled Among the Battlefields

8.2 out of 10, Very good, (27)
"The cabin was very nice"
Serene Log Cabin Nestled Among the Battlefields

Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!

10.0 out of 10, Exceptional, (125)
"The view from the porch, accessibility to food, good coffee, hikes, shops, and important history, are unmatched. Our hosts are kind and accommodating. This is our second time here and won't be our last. "
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!

Charming Cabin in the Woods with River Access

9.8 out of 10, Exceptional, (28)
"Very nice rest time…"
The price is AU$461
includes taxes & fees
31 July - 1 Aug
Charming Cabin in the Woods with River Access

RIVERKEEPER INN, Waterfront Property on the Potomac River

9.4 out of 10, Exceptional, (123)
"Riverkeeper Inn is located in a peaceful and quiet area of Harpers Ferry, equally perfect in early mornings and late nights. The check-in and check-out process were very easy, and the property itself had everything we could've asked for, and then some."
RIVERKEEPER INN, Waterfront Property on the Potomac River

Cottage on King | Charming Historic Leesburg Home

9.6 out of 10, Exceptional, (54)
"Walkable to downtown historic Leesburg. Clean and super cute little house. Would stay again! "
The price is AU$453
includes taxes & fees
30 July - 31 July
Cottage on King | Charming Historic Leesburg Home

Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.

10.0 out of 10, Exceptional, (136)
"Wonderful house for a great weekend away"
The price is AU$690
includes taxes & fees
10 Aug - 11 Aug
Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.

Blue Ridge Getaway - Sunset Views, A.T. Access

10.0 out of 10, Exceptional, (53)
"Our stay was perfect "
The price is AU$562
includes taxes & fees
31 July - 1 Aug
Blue Ridge Getaway - Sunset Views, A.T. Access

Hollow Hideaway is perfect for your holiday stay!

10.0 out of 10, Exceptional, (47)
"Very clean, well appointed home, was a great place to stay for a few days while we explored the area. Nice outdoor space to relax and the board games and arcade game were fun for the kids. "
Hollow Hideaway is perfect for your holiday stay!

❤️ Secluded 1940s Romantic Tiny House on the River

10.0 out of 10, Exceptional, (57)
"We truly loved this location and definitely will be back!"
The price is AU$212
includes taxes & fees
5 Aug - 6 Aug
❤️ Secluded 1940s Romantic Tiny House on the River

Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex

9.8 out of 10, Exceptional, (98)
"Our stay was great and really enjoyed the house. We had so much space to have our own time and then still be able to come together for meals and hanging in the hot tub. We now want to come back in the winter and go to the sledding hill right in front of the house! "
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex

Walk to Potomac River and downtown Harpers Ferry

10.0 out of 10, Exceptional, (118)
"The house was amazing, great views and a great layout that allowed for us to hang as a group or have some privacy. Very convenient to everything we wanted to do; Harper’s Ferry, Ziplining (or rafting based on time of year), and the Brewery that we went to on the last night felt like it was almost walking distance. Definitely recommend and would stay again in a heartbeat. "
Walk to Potomac River and downtown Harpers Ferry

Kalia’s Mountain Momma Getaway

10.0 out of 10, Exceptional, (9)
"Location was nice"
The price is AU$272
includes taxes & fees
31 July - 1 Aug
Kalia’s Mountain Momma Getaway

Cozy Mountain Cabin w/ Steam Shower. Family Friendly!

10.0 out of 10, Exceptional, (72)
"It's the perfect place to stay if you're going to HF but want some distance from people/a view of the mountains. Really nice property. We'd stay again! Thanks!"
The price is AU$516
includes taxes & fees
30 July - 31 July
Cozy Mountain Cabin w/ Steam Shower. Family Friendly!

Charles Town Home w/ Private Pool & Hot Tub

10.0 out of 10, Exceptional, (51)
"This is our third year staying in this house and we love it. The company accommodates our requests and is quick to respond if we need anything. The house itself is laid out perfectly for what we need with lots of rooms for both kids and adults. "
Charles Town Home w/ Private Pool & Hot Tub

Cozy cabin among the trees near Historic Gettysburg / Liberty Mountain Resort

10.0 out of 10, Exceptional, (14)
"The cabin was amazing and relaxing. I especially enjoyed the babbling brook in the morning while sipping my coffee on the deck—great for pet-friendly families."
Cozy cabin among the trees near Historic Gettysburg / Liberty Mountain Resort

Single Level, 3 Bedroom Home In Between Harper's Ferry & Casino.

7.6 out of 10, Good, (25)
"Easy check in. House is located in a cluster of homes. Photos are misleading. Cleanliness was sub par. Linens and towels from previous guests were laying on top of the washer. Wasn’t sure if the linens and towels that we did have were even clean and fresh. Home smelled of alcohol and cigarettes. Good location."
Single Level, 3 Bedroom Home In Between Harper's Ferry & Casino.

Birch Cabin at Hunting Creek Hideaway

9.4 out of 10, Exceptional, (6)
"Cabin was perfect! So cute! We loved it and will definitely stay there again! "
The price is AU$229
includes taxes & fees
1 Aug - 2 Aug
Birch Cabin at Hunting Creek Hideaway

Walk to Top-Rated Restaurants & Trails! 7BR w/HotTub Gazebo & Built-in FirePit!

10.0 out of 10, Exceptional, (13)
"Everything was wonderful!"
Walk to Top-Rated Restaurants & Trails! 7BR w/HotTub Gazebo & Built-in FirePit!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Middletown Hotel Reviews

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?

Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!: This holiday home rental outside of Middletown is located on a river, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of private gardens in this rental home to help you unwind.

How many holiday rentals will I find in Middletown?

Expedia has 4 holiday rentals for your stay in Middletown.

What can I see and do in Middletown?

While exploring the area, visit family-friendly sights like Catoctin Wildlife Preserve and Zoo, or get outside and enjoy nature at Baker Park. Other places in town to visit include Maryland National Golf Club and South Mountain State Park.

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.