Book Holiday Homes in Hagerstown

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Featured Holiday Homes in Hagerstown

Breathtaking views  with an  indoor private pool, come escape with us

Breathtaking views with an indoor private pool, come escape with us

Bluemont
Located in Bluemont, this vacation home is in the mountains, a 3-minute drive from Twin Oaks Tavern Winery and 6 minutes from Hill High Country Store.
Breathtaking views with an indoor private pool, come escape with us
Gettysburg Family  Retreat -  4 BR Pet Friendly!

Gettysburg Family Retreat - 4 BR Pet Friendly!

Fairfield
With a stay at this vacation home in Fairfield, you'll be in the mountains, within a 5-minute drive of Liberty Mountain Ski Resort and First Class Ski Lift.
Gettysburg Family Retreat - 4 BR Pet Friendly!
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
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Gettysburg Getaway! Battlefields/Wineries/Ski!

Gettysburg Getaway! Battlefields/Wineries/Ski!

Orrtanna
Located in Orrtanna, this vacation home is in a rural location, within a 10-minute drive of Adams County Winery and Mountain View Golf Club.
Gettysburg Getaway! Battlefields/Wineries/Ski!
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
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!
The Peaceful Nest

The Peaceful Nest

Fairfield
The price is AU$541 per night from 7 Jan to 8 Jan
AU$541
includes taxes & fees
7 Jan - 8 Jan 2025
With a stay at this vacation home in Fairfield, you'll be within a 10-minute drive of Liberty Mountain Ski Resort and Carroll Valley Resort Golf Courses.
The Peaceful Nest
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
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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.

Hagerstown 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 Hagerstown vacation homes are the perfect way for you to wing it.

Holiday houses in Hagerstown 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 Hagerstown 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 Hagerstown adventures, obvs.

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

Hagerstown Holiday Homes essential information

Accommodation
397 Holiday Homes
Lowest Price
AU$122
Highest Price
AU$1,049
Popular accommodation
Breathtaking views with an indoor private pool, come escape with us, Gettysburg Family Retreat - 4 BR Pet Friendly!, Charming "Cream of the Crop" Cape ~❤️of Middletown, Gettysburg Getaway! Battlefields/Wineries/Ski!, 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!, The Peaceful Nest , Private, Relaxing, quite, 3 Bedroom Unit, sleeps 6 to 8 people

Top trending hotels in Hagerstown

Country Inn & Suites by Radisson, Hagerstown, MD

Country Inn & Suites by Radisson, Hagerstown, MD

3 out of 5
17612 Valley Mall Rd, Hagerstown, MD
Fully refundable
The price is AU$164 per night from 29 Dec to 30 Dec
AU$164
includes taxes & fees
29 Dec - 30 Dec
Located in Hagerstown, Country Inn & Suites by Radisson, Hagerstown, MD is connected to a shopping center, a 2-minute drive from Hagerstown Roundhouse Museum ...
Country Inn & Suites by Radisson, Hagerstown, MD
Fairfield Inn & Suites by Marriott Hagerstown

Fairfield Inn & Suites by Marriott Hagerstown

2.5 out of 5
89 ALL STAR COURT, Hagerstown, MD
Fully refundableReserve now, pay when you stay
The price is AU$176 per night from 29 Dec to 30 Dec
AU$176
includes taxes & fees
29 Dec - 30 Dec
Located in Hagerstown, Fairfield Inn & Suites by Marriott Hagerstown is a 4-minute drive from Hagerstown Premium Outlets and 7 minutes from Hagerstown Roundhouse ...
Fairfield Inn & Suites by Marriott Hagerstown
Super 8 by Wyndham Hagerstown/Halfway Area

Super 8 by Wyndham Hagerstown/Halfway Area

2 out of 5
16805 Blake Rd, I 70 & I 81, Hagerstown, MD
Fully refundableReserve now, pay when you stay
The price is AU$122 per night from 15 Jan to 16 Jan
AU$122
includes taxes & fees
15 Jan - 16 Jan 2025
Located in Hagerstown, Super 8 by Wyndham Hagerstown/Halfway Area is in a shopping district, a 4-minute drive from Hagerstown Roundhouse Museum and 6 minutes ...
Super 8 by Wyndham Hagerstown/Halfway Area
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Hampton Inn Hagerstown-I-81

Hampton Inn Hagerstown-I-81

2.5 out of 5
18300 Peak Circle, Hagerstown, MD
Fully refundableReserve now, pay when you stay
The price is AU$197 per night from 12 Jan to 13 Jan
AU$197
includes taxes & fees
12 Jan - 13 Jan 2025
Located in Hagerstown, Hampton Inn Hagerstown-I-81 is in the historical district, within a 10-minute drive of Pennsylvania Dutch Market and Maryland ...
Hampton Inn Hagerstown-I-81
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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.