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Middletown Vacation Rentals

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Aug 12 - Aug 13
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Aug 13 - Aug 14
This weekend
Aug 15 - Aug 17
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Aug 22 - Aug 24

Vacation Rentals in Middletown

Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Interior

Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

9.6 out of 10, Exceptional, (99)
"Our weekend cabin stay was wonderful. The safe neighborhood was quite and peaceful. Its location near nature and the city was just perfect. The cozy cabin was clean and comfy. We loved Gambrill State Park and downtown Frederick didn't disappoint as well."
The price is ￥9,634
￥26,708 total
includes taxes & fees
Aug 14 - Aug 15
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Countryside Cabin with Mountain Views near Surreybrooke Gardens
Property grounds

Countryside Cabin with Mountain Views near Surreybrooke Gardens

10.0 out of 10, Exceptional, (110)
"Best place to get away from all the city CHAOS in Washington, DC!"
Countryside Cabin with Mountain Views near Surreybrooke Gardens
Serene Log Cabin Nestled Among the Battlefields
Property grounds

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
RIVERKEEPER INN, Waterfront Property on the Potomac River
Terrace/patio

RIVERKEEPER INN, Waterfront Property on the Potomac River

9.2 out of 10, Wonderful, (125)
"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
Charming Cabin in the Woods with River Access
Exterior

Charming Cabin in the Woods with River Access

9.8 out of 10, Exceptional, (29)
"Very nice rest time…"
The price is ￥24,158
￥44,691 total
includes taxes & fees
Aug 17 - Aug 18
Charming Cabin in the Woods with River Access
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
Exterior detail

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

10.0 out of 10, Exceptional, (127)
"Spectacular location. Charming and comfortable. The steps can be a challenge but are worth the effort."
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
❤️ Secluded 1940s Romantic Tiny House on the River
Property grounds

❤️ Secluded 1940s Romantic Tiny House on the River

9.8 out of 10, Exceptional, (59)
"We truly loved this location and definitely will be back!"
The price is ￥10,968
￥21,236 total
includes taxes & fees
Sep 1 - Sep 2
❤️ Secluded 1940s Romantic Tiny House on the River
Cottage on King | Charming Historic Leesburg Home
Terrace/patio

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 ￥19,427
￥44,839 total
includes taxes & fees
Aug 19 - Aug 20
Cottage on King | Charming Historic Leesburg Home
Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry
Microwave

Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry

9.6 out of 10, Exceptional, (7)
The price is ￥17,286
￥28,629 total
includes taxes & fees
Aug 18 - Aug 19
Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry
Modern Country House on the Shenandoah River
Property grounds

Modern Country House on the Shenandoah River

9.8 out of 10, Exceptional, (36)
"The views are beautiful and the house was the perfect size for a group of 7 friends. We had a great time!"
Modern Country House on the Shenandoah River
Cozy cabin among the trees near Historic Gettysburg / Liberty Mountain Resort
Smart TV

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

10.0 out of 10, Exceptional, (15)
"This is an amazing place to stay its not far away from alot of things but gives you the sense of being in the middle of no where. "
Cozy cabin among the trees near Historic Gettysburg / Liberty Mountain Resort
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (98)
"This home was absolutely fantastic! Very clean, very close to all things. We had a fantastic time."
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Exterior

Amazing dog-friendly cottage. Walk 2 Harpers Ferry

2.0 star property
9.8 out of 10, Exceptional, (15)
"Very nice property with convenient location! Within walking distance of down town. "
The price is ￥27,419
￥48,868 total
includes taxes & fees
Aug 17 - Aug 18
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Historic Boonsboro Vacation Rental w/ Grill
Outdoor dining

Historic Boonsboro Vacation Rental w/ Grill

9.2 out of 10, Wonderful, (16)
"It was perfect. Near my son’s school at Shepherd University and close to all the historic sites of Harper’s Ferry and Antietam."
Historic Boonsboro Vacation Rental w/ Grill
Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.
Exterior

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

10.0 out of 10, Exceptional, (139)
"Wonderful house for a great weekend away"
The price is ￥28,753
￥58,308 total
includes taxes & fees
Sep 8 - Sep 9
Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!
Exterior

Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!

10.0 out of 10, Exceptional, (3)
"Great and quiet location with all the amenities. Getting to the parking is a bit tricky but other than that great place to stay with family"
The price is ￥13,926
￥47,027 total
includes taxes & fees
Sep 3 - Sep 4
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!
Luxury Getaway on The Potomac
7 bedrooms, desk, travel crib, free WiFi

Luxury Getaway on The Potomac

9.6 out of 10, Exceptional, (15)
"We will be coming back to this hidden gem on the Potomac. The house is immaculate. Perfect spot for a family or a large group of friends. Even in early April, a few in our group used the docks to plunge in the river. Can’t wait to bring the family back. "
Luxury Getaway on The Potomac
Galloping Getaway on the rolling hills of GemStone Stable
Outdoor dining

Galloping Getaway on the rolling hills of GemStone Stable

10.0 out of 10, Exceptional, (8)
"We stayed here to visit family locally and loved it. The property had horses on site and a nice private patio to enjoy the views at the beginning and end of days. The owners while on site were accommodating and very friendly. Couldn’t say enough good things as the family and myself enjoyed our stay. "
The price is ￥18,468
￥27,126 total
includes taxes & fees
Aug 21 - Aug 22
Galloping Getaway on the rolling hills of GemStone Stable
Hollow Hideaway is perfect for your holiday stay!
Property grounds

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!
Terra Alta - Incredible River Views and Hot Tub!
Outdoor spa tub

Terra Alta - Incredible River Views and Hot Tub!

9.8 out of 10, Exceptional, (57)
"We had a great time! The house overlooks the river and we loved the hot tub and fire pit! "
The price is ￥14,821
￥60,345 total
includes taxes & fees
Aug 21 - Aug 22
Terra Alta - Incredible River Views and Hot Tub!
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.
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Top Middletown Hotel Reviews

Red Roof Inn Leesburg, VA

Red Roof Inn Leesburg, VA

10/10 Excellent
"The room was very clean and updated "
Teena 1-night trip
Posted 12 hours ago
Red Roof Inn Leesburg, VA

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?

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

How many vacation rentals will I find in Middletown?

Expedia has 4 vacation 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 South Mountain State Park and Maryland National Golf Club.

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.