Book Holiday Homes in Middletown

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Featured Holiday Homes in Middletown

Charming "Cream of the Crop" Cape ~❤️of Middletown

Charming "Cream of the Crop" Cape ~❤️of Middletown

Middletown
The price is AU$564 per night from 30 Dec to 31 Dec
AU$564
includes taxes & fees
30 Dec - 31 Dec
When you stay at this vacation home in Middletown, you'll be within a 10-minute drive of Orchid Cellar Winery and Willow Oaks Craft Cider and Wine.
Charming "Cream of the Crop" Cape ~❤️of Middletown
Terra Alta - Incredible River Views and Hot Tub!

Terra Alta - Incredible River Views and Hot Tub!

Charles Town
The price is AU$1,049 per night from 26 Dec to 27 Dec
AU$1,049
includes taxes & fees
26 Dec - 27 Dec
With a stay at this vacation home in Charles Town, you'll be on a river, within a 15-minute drive of Hollywood Casino at Charles Town Races and Shenandoah ...
Terra Alta - Incredible River Views and Hot Tub!
Charles Town Home w/ Private Pool & Hot Tub

Charles Town Home w/ Private Pool & Hot Tub

Charles Town
With a stay at this vacation home in Charles Town, you'll be within a 10-minute drive of Hollywood Casino at Charles Town Races and Locust Hill Golf Course.
Charles Town Home w/ Private Pool & Hot Tub
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Charming 3-Bedroom Home in Harpers Ferry Historic District: Walk to Attractions!

Charming 3-Bedroom Home in Harpers Ferry Historic District: Walk to Attractions!

Harpers Ferry
With a stay at this vacation home in Harpers Ferry, you'll be within a 15-minute drive of Hollywood Casino at Charles Town Races and Appalachian Trail Conservancy ...
Charming 3-Bedroom Home in Harpers Ferry Historic District: Walk to Attractions!
Private, Relaxing, quite, 3 Bedroom  Unit, sleeps 6 to 8 people

Private, Relaxing, quite, 3 Bedroom Unit, sleeps 6 to 8 people

Hagerstown
The price is AU$328 per night from 31 Dec to 1 Jan
AU$328
includes taxes & fees
31 Dec - 1 Jan 2025
Located in Hagerstown, this vacation home is within a 5-minute drive of Hagerstown Suns Municipal Stadium and Maryland Theater.
Private, Relaxing, quite, 3 Bedroom Unit, sleeps 6 to 8 people
Riverside cottage, minutes from historic Harpers Ferry!  Private river access!

Riverside cottage, minutes from historic Harpers Ferry! Private river access!

Harpers Ferry
The price is AU$356 per night from 26 Dec to 27 Dec
AU$356
includes taxes & fees
26 Dec - 27 Dec
With a stay at this vacation home in Harpers Ferry, you'll be a 3-minute walk from Potomac River and within a 5-minute drive of Chesapeake and Ohio Canal.
Riverside cottage, minutes from historic Harpers Ferry! Private river access!
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!

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

Harpers Ferry
With a stay at this vacation home in Harpers Ferry, you'll be on a river, within a 15-minute drive of Hollywood Casino at Charles Town Races and John Brown Wax ...
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
Walk to Potomac River and downtown Harpers Ferry

Walk to Potomac River and downtown Harpers Ferry

Knoxville
With a stay at this vacation home in Knoxville, you'll be within a 15-minute drive of Hollywood Casino at Charles Town Races and Chesapeake and Ohio Canal.
Walk to Potomac River and downtown Harpers Ferry
The PINK PEARL in Historic Leesburg

The PINK PEARL in Historic Leesburg

Leesburg
A stay at this vacation home places you in the heart of Leesburg, steps from Catoctin Valley and 7 minutes by foot from Raflo Park.
The PINK PEARL in Historic Leesburg
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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 Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Middletown vacation homes are the perfect way for you to wing it.

Holiday houses in Middletown let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Middletown in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Middletown adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Middletown with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Middletown vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Middletown Holiday Homes essential information

Accommodation
214 Holiday Homes
Lowest Price
AU$148
Highest Price
AU$1,049
Popular accommodation
Charming "Cream of the Crop" Cape ~❤️of Middletown, Terra Alta - Incredible River Views and Hot Tub!, Charles Town Home w/ Private Pool & Hot Tub, Charming 3-Bedroom Home in Harpers Ferry Historic District: Walk to Attractions!, Private, Relaxing, quite, 3 Bedroom Unit, sleeps 6 to 8 people, Riverside cottage, minutes from historic Harpers Ferry! Private river access!, Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!, Walk to Potomac River and downtown Harpers Ferry, The PINK PEARL in Historic Leesburg

Top trending hotels in Middletown

Countryside Cabin with Mountain Views near Surreybrooke Gardens

Countryside Cabin with Mountain Views near Surreybrooke Gardens

Middletown
When you stay at this cabin in Middletown, you'll be on a lake, within a 5-minute drive of Maryland National Golf Club and Gambrill State Park.
Countryside Cabin with Mountain Views near Surreybrooke Gardens
Vintage cabin in the ❤️ of Middletown , MD.  Pet friendly and prime location.

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

Middletown
The price is AU$412 per night from 29 Dec to 30 Dec
AU$412
includes taxes & fees
29 Dec - 30 Dec
With a stay at this cabin in Middletown, you'll be within a 10-minute drive of Orchid Cellar Winery and Willow Oaks Craft Cider and Wine.
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Country Inn & Suites by Radisson, Frederick, MD

Country Inn & Suites by Radisson, Frederick, MD

3 out of 5
5579 Spectrum Dr, Frederick, MD
Fully refundable
The price is AU$148 per night from 2 Jan to 3 Jan
AU$148
includes taxes & fees
2 Jan - 3 Jan 2025
A stay at Country Inn & Suites by Radisson, Frederick, MD places you in the heart of Frederick, just a 5-minute walk from Francis Scott Key Mall and within a ...
Country Inn & Suites by Radisson, Frederick, MD
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Hampton Inn & Suites Frederick-Fort Detrick

Hampton Inn & Suites Frederick-Fort Detrick

2.5 out of 5
1565 Opossumtown Pike, Frederick, MD
Fully refundableReserve now, pay when you stay
The price is AU$180 per night from 4 Jan to 5 Jan
AU$180
includes taxes & fees
4 Jan - 5 Jan 2025
Located in Frederick, Hampton Inn & Suites Frederick-Fort Detrick is within a 5-minute drive of Hood College and Frederick Memorial Hospital.
Hampton Inn & Suites Frederick-Fort Detrick
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See all available properties in Middletown
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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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^Subject to availability and chosen travel dates.