Book Holiday Homes in Middletown

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Middletown

*Luxury Condo In Downtown Frederick*

*Luxury Condo In Downtown Frederick*

Frederick
The price is NZ$446 per night from 17 Apr to 18 Apr
NZ$446
includes taxes & fees
17 Apr - 18 Apr
Stay at this vacation home in Frederick. Enjoy patios, an in-room coffeemaker, and air conditioning. Popular attractions National Museum of Civil War Medicine ...
*Luxury Condo In Downtown Frederick*
Walk to Harpers Ferry! Dog-friendly. Beautiful Views.

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

Harpers Ferry
Stay at this vacation home in Harpers Ferry. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Harpers Ferry National Historical Park ...
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
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!
Save an average of 15% on thousands of hotels when you're signed in
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 Harpers Ferry National Historical Park and John Brown ...
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
Book a stay at this ski vacation home in Harpers Ferry. Enjoy free WiFi, a garden, and tennis courts. Popular attractions Harpers Ferry National Historical Park ...
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!
Modern Country House on the Shenandoah River

Modern Country House on the Shenandoah River

Charles Town
Book a stay at this family-friendly vacation home in Charles Town. Enjoy free WiFi, a garden, and patios. Popular attractions Shannondale Springs Wildlife Management ...
Modern Country House on the Shenandoah River
*In The Heart Of Antietam*

*In The Heart Of Antietam*

Sharpsburg
Stay at this vacation home in Sharpsburg. Enjoy free WiFi, a garden, and balconies or patios. Popular attractions Tolson's Chapel and Antietam Creek Vineyards ...
*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 NZ$565 per night from 17 Apr to 18 Apr
NZ$565
includes taxes & fees
17 Apr - 18 Apr
Stay at this vacation home in Frederick. Enjoy a fitness center, patios, and cable/satellite TV service. Popular attractions National Museum of Civil War Medicine ...
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 NZ$603 per night from 22 Apr to 23 Apr
NZ$603
includes taxes & fees
22 Apr - 23 Apr
Book a stay at this family-friendly vacation home in Leesburg. Enjoy free WiFi, a garden, and patios. Popular attractions Rotary Park and Tally Ho Theatre are ...
Cottage on King | Charming Historic Leesburg Home
Don't see what you're looking for?
See all available properties in Middletown
View all properties
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
287 Holiday Homes
Lowest Price
NZ$148
Highest Price
NZ$603
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
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
Serene Log Cabin Nestled Among the Battlefields

Serene Log Cabin Nestled Among the Battlefields

Middletown
Stay at this cabin in Middletown. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions Orchid Cellar Winery and Washington Monument State ...
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 NZ$348 per night from 6 Apr to 7 Apr
NZ$348
includes taxes & fees
6 Apr - 7 Apr
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.
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 NZ$148 per night from 17 Apr to 18 Apr
NZ$148
includes taxes & fees
17 Apr - 18 Apr
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
Don't see what you're looking for?
See all available properties in Middletown
View all properties
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.