Book Holiday Homes in Middletown

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Featured Holiday Homes in Middletown

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

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

Harpers Ferry WV
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.
Opens in a new windowRiverside cottage, minutes from historic Harpers Ferry! Private river access!
Terra Alta - Incredible River Views and Hot Tub!

Terra Alta - Incredible River Views and Hot Tub!

Charles Town WV
The price is AU$616 per night from 8 Jan to 9 Jan
AU$616
8 Jan - 9 Jan 2026
includes taxes & fees
Located in Charles Town, this vacation home is on a river, within a 15-minute drive of Shenandoah River and Shannondale Springs Wildlife Management Area.
Opens in a new windowTerra Alta - Incredible River Views and Hot Tub!
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

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

Frederick MD
The price is AU$477 per night from 11 Jan to 12 Jan
AU$477
11 Jan - 12 Jan 2026
includes taxes & fees
A stay at this vacation home places you in the heart of Frederick, steps from Carroll Creek Linear Park and 4 minutes by foot from The Delaplaine Arts ...
Opens in a new windowRETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
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Cozy Cabin w/ Hot Tub & Fire Pit perfect for up to 8 people

Cozy Cabin w/ Hot Tub & Fire Pit perfect for up to 8 people

Harpers Ferry WV
With a stay at this vacation home in Harpers Ferry, you'll be a 3-minute walk from Shannondale Springs Wildlife Management Area and within a 5-minute drive of ...
Opens in a new windowCozy Cabin w/ Hot Tub & Fire Pit perfect for up to 8 people
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex

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

Harpers Ferry WV
Located in Harpers Ferry, this vacation home is in the mountains, within a 5-minute drive of Shenandoah River and Bolivar Community Park.
Opens in a new windowLarge Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex
Hot Tub, Campfire Ring, Convenient Location, Large Groups!!

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

Harpers Ferry WV
The price is AU$948 per night from 26 Dec to 27 Dec
AU$948
26 Dec - 27 Dec
includes taxes & fees
Located in Harpers Ferry, this vacation home is on a river, within a 5-minute drive of Bolivar Community Park and Shenandoah River.
Opens in a new windowHot Tub, Campfire Ring, Convenient Location, Large Groups!!
Sprawling 9‑BR Mountaintop Oasis- BlueRidge Views

Sprawling 9‑BR Mountaintop Oasis- BlueRidge Views

Waynesboro PA
With a stay at this vacation home in Waynesboro, you'll be within a 15-minute drive of Liberty Mountain Ski Resort and Monterey Pass Battlefield Museum.
Opens in a new windowSprawling 9‑BR Mountaintop Oasis- BlueRidge Views
Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry

Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry

Harpers Ferry WV
The price is AU$767 per night from 22 Dec to 23 Dec
AU$767
22 Dec - 23 Dec
includes taxes & fees
Located in Harpers Ferry, this vacation home is in the mountains, within a 5-minute drive of Shenandoah River and Shannondale Springs Wildlife Management ...
Opens in a new windowCharming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry
Historic Queen Anne Family Home w Modern Comforts

Historic Queen Anne Family Home w Modern Comforts

Harpers Ferry WV
The price is AU$587 per night from 4 Jan to 5 Jan
AU$587
4 Jan - 5 Jan 2026
includes taxes & fees
With a stay at this vacation home in Harpers Ferry, you'll be within a 5-minute walk of Harpers Ferry Children's Park and Storer College Campus.
Opens in a new windowHistoric Queen Anne Family Home w Modern Comforts
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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
259 Holiday Homes
Lowest Price
AU$116
Highest Price
AU$948
Popular accommodation
Riverside cottage, minutes from historic Harpers Ferry! Private river access!, Terra Alta - Incredible River Views and Hot Tub!, RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT., Cozy Cabin w/ Hot Tub & Fire Pit perfect for up to 8 people, Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex, Hot Tub, Campfire Ring, Convenient Location, Large Groups!!, Sprawling 9‑BR Mountaintop Oasis- BlueRidge Views, Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry, Historic Queen Anne Family Home w Modern Comforts

Top trending hotels in Middletown

Hilton Garden Inn Frederick

Hilton Garden Inn Frederick

3 out of 5
7226 Corporate Ct Frederick MD
Fully refundableReserve now, pay when you stay
The price is AU$147 per night from 24 Dec to 25 Dec
AU$147
24 Dec - 25 Dec
includes taxes & fees
When you stay at Hilton Garden Inn Frederick in Frederick, you'll be in a shopping district, within a 15-minute walk of Westview Promenade and Regal ...
Opens in a new windowHilton Garden Inn Frederick
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$116 per night from 16 Jan to 17 Jan
AU$116
16 Jan - 17 Jan 2026
includes taxes & fees
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 ...
Opens in a new windowCountry Inn & Suites by Radisson, Frederick, MD
Clarion Inn Harpers Ferry - Charles Town

Clarion Inn Harpers Ferry - Charles Town

2.5 out of 5
4328 William L Wilson Fwy Harpers Ferry WV
Fully refundableReserve now, pay when you stay
The price is AU$151 per night from 30 Dec to 31 Dec
AU$151
30 Dec - 31 Dec
includes taxes & fees
A stay at Clarion Inn Harpers Ferry - Charles Town places you in the heart of Harpers Ferry, within a 5-minute drive of Appalachian Trail Conservancy Headquarters ...
Opens in a new windowClarion Inn Harpers Ferry - Charles Town
Save an average of 15% on thousands of hotels when you're signed in
Hampton Inn & Suites Charles Town

Hampton Inn & Suites Charles Town

2.5 out of 5
157 Pimlico Dr Charles Town WV
Fully refundableReserve now, pay when you stay
The price is AU$175 per night from 4 Jan to 5 Jan
AU$175
4 Jan - 5 Jan 2026
includes taxes & fees
A stay at Hampton Inn & Suites Charles Town places you in the heart of Charles Town, within a 5-minute drive of Hollywood Casino at Charles Town Races and Old ...
Opens in a new windowHampton Inn & Suites Charles Town
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.

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^Subject to availability and chosen travel dates.