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 NZ$617 per night from 30 Dec to 31 Dec
NZ$617
includes taxes & fees
30 Dec - 31 Dec
Stay at this vacation home in Middletown. Enjoy patios, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Orchid Cellar Winery and ...
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 NZ$1,133 per night from 26 Dec to 27 Dec
NZ$1,133
includes taxes & fees
26 Dec - 27 Dec
Book a stay at this family-friendly vacation home in Charles Town. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Hollywood Casino ...
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
Book a stay at this family-friendly vacation home in Charles Town. Enjoy private pools, patios, and cable/satellite TV service. Popular attractions Hollywood ...
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
Stay at this vacation home in Harpers Ferry. Enjoy free WiFi, an in-room coffeemaker, and in-room fireplaces. Popular attractions 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 NZ$358 per night from 31 Dec to 1 Jan
NZ$358
includes taxes & fees
31 Dec - 1 Jan 2025
Stay at this vacation home in Hagerstown. Enjoy in-room fireplaces and air conditioning. Popular attractions 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 NZ$390 per night from 26 Dec to 27 Dec
NZ$390
includes taxes & fees
26 Dec - 27 Dec
Stay at this vacation home in Harpers Ferry. Enjoy free WiFi, patios, and an in-room coffeemaker. Our guests praise the helpful staff in our reviews. Popular ...
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
Stay at this vacation home in Harpers Ferry. Enjoy free WiFi, a garden, and patios. Popular attractions John Brown Wax Museum and John Brown's Fort are located ...
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
Stay at this vacation home in Knoxville. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Maryland Heights and Lockhouse 33 are located ...
Walk to Potomac River and downtown Harpers Ferry
The PINK PEARL in Historic Leesburg

The PINK PEARL in Historic Leesburg

Leesburg
Stay at this vacation home in Leesburg. Enjoy free WiFi, a garden, and patios. Popular attractions Raflo Park and Gleedsville Art Gallery are located ...
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
NZ$164
Highest Price
NZ$1,133
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
Stay at this cabin in Middletown. Enjoy free WiFi, a garden, and patios. Popular attractions Maryland National Golf Club and Orchid Cellar Winery are located ...
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 NZ$450 per night from 29 Dec to 30 Dec
NZ$450
includes taxes & fees
29 Dec - 30 Dec
Stay at this cabin in Middletown. Enjoy cable/satellite TV service, an in-room coffeemaker, and in-room fireplaces. Popular attractions Orchid Cellar Winery ...
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 NZ$164 per night from 2 Jan to 3 Jan
NZ$164
includes taxes & fees
2 Jan - 3 Jan 2025
Stay at this 3-star business-friendly hotel in Frederick. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
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 NZ$199 per night from 4 Jan to 5 Jan
NZ$199
includes taxes & fees
4 Jan - 5 Jan 2025
Stay at this hotel in Frederick. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
Hampton Inn & Suites Frederick-Fort Detrick
Don't see what you're looking for?
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.