Book Holiday Homes in Middletown

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Featured Holiday Homes in Middletown

*Luxury Condo In Downtown Frederick*

*Luxury Condo In Downtown Frederick*

Frederick
The price is AU$408 per night from 1 May to 2 May
AU$408
includes taxes & fees
1 May - 2 May
A stay at this vacation home places you in the heart of Frederick, steps from Carroll Creek Linear Park and 5 minutes by foot from City of Frederick Dog ...
*Luxury Condo In Downtown Frederick*
Walk to Harpers Ferry! Dog-friendly. Beautiful Views.

Walk to Harpers Ferry! Dog-friendly. Beautiful Views.

Harpers Ferry
With a stay at this vacation home in Harpers Ferry, you'll be a 2-minute drive from Harpers Ferry National Historical Park and 10 minutes from Hollywood Casino ...
Walk to Harpers Ferry! Dog-friendly. Beautiful Views.
Riverside cottage, minutes from historic Harpers Ferry!  Private river access!

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

Harpers Ferry
With a stay at this vacation home in Harpers Ferry, you'll be within a 15-minute drive of Harpers Ferry National Historical Park and Potomac River.
Riverside cottage, minutes from historic Harpers Ferry! Private river access!
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Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!

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

Harpers Ferry
When you stay at this vacation home in Harpers Ferry, you'll be on a river, within a 15-minute drive of Harpers Ferry National Historical Park and Hollywood ...
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!

Hot Tub, Campfire Ring, Convenient Location, Large Groups!!

Harpers Ferry
When you stay at this vacation home in Harpers Ferry, you'll be on a river, within a 10-minute drive of Harpers Ferry National Historical Park and Hollywood ...
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
Modern Country House on the Shenandoah River

Modern Country House on the Shenandoah River

Charles Town
When you stay at this vacation home in Charles Town, you'll be on the waterfront and steps from Shenandoah River.
Modern Country House on the Shenandoah River
*In The Heart Of Antietam*

*In The Heart Of Antietam*

Sharpsburg
With a stay at this vacation home, you'll be centrally located in Sharpsburg, just a 4-minute walk from Tolson's Chapel and 10 minutes by foot from Antietam ...
*In The Heart Of Antietam*
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

Frederick
The price is AU$496 per night from 6 Apr to 7 Apr
AU$496
includes taxes & fees
6 Apr - 7 Apr
A stay at this vacation home places you in the heart of Frederick, steps from Carroll Creek Linear Park and 5 minutes by foot from National Museum of Civil War ...
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Cottage on King | Charming Historic Leesburg Home

Cottage on King | Charming Historic Leesburg Home

Leesburg
The price is AU$552 per night from 22 Apr to 23 Apr
AU$552
includes taxes & fees
22 Apr - 23 Apr
A stay at this vacation home places you in the heart of Leesburg, steps from Catoctin Valley and Rotary Park.
Cottage on King | Charming Historic Leesburg Home
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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
285 Holiday Homes
Lowest Price
AU$135
Highest Price
AU$552
Popular accommodation
*Luxury Condo In Downtown Frederick*, Walk to Harpers Ferry! Dog-friendly. Beautiful Views., Riverside cottage, minutes from historic Harpers Ferry! Private river access!, Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!, Hot Tub, Campfire Ring, Convenient Location, Large Groups!!, Modern Country House on the Shenandoah River , *In The Heart Of Antietam* , RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT., Cottage on King | Charming Historic Leesburg Home

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 in the mountains, within a 5-minute drive of Maryland National Golf Club and Gambrill State Park.
Countryside Cabin with Mountain Views near Surreybrooke Gardens
Serene Log Cabin Nestled Among the Battlefields

Serene Log Cabin Nestled Among the Battlefields

Middletown
Located in Middletown, this cabin is in the mountains, a 5-minute drive from South Mountain State Park and 8 minutes from Washington Monument State Park.
Serene Log Cabin Nestled Among the Battlefields
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$351 per night from 6 Apr to 7 Apr
AU$351
includes taxes & fees
6 Apr - 7 Apr
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.
Save an average of 15% on thousands of hotels when you're signed in
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$135 per night from 17 Apr to 18 Apr
AU$135
includes taxes & fees
17 Apr - 18 Apr
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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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.