Book Holiday Homes in Hagerstown

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 Hagerstown

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

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

Bluemont
Stay at this vacation home in Bluemont. Enjoy private pools, a fitness center, and a garden. Our guests praise the pool and the helpful staff in our reviews. ...
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
Stay at this vacation home in Fairfield. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Liberty Mountain Ski Resort and First Class ...
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 NZ$551 per night from 6 Jan to 7 Jan
NZ$551
includes taxes & fees
6 Jan - 7 Jan 2025
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
Save an average of 15% on thousands of hotels when you're signed in
Gettysburg Getaway! Battlefields/Wineries/Ski!

Gettysburg Getaway! Battlefields/Wineries/Ski!

Orrtanna
Stay at this vacation home in Orrtanna. Enjoy free WiFi, a pool table, and patios. Popular attractions Liberty Mountain Ski Resort and Adams County Winery are ...
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 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
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!
The Peaceful Nest

The Peaceful Nest

Fairfield
The price is NZ$592 per night from 7 Jan to 8 Jan
NZ$592
includes taxes & fees
7 Jan - 8 Jan 2025
Stay at this vacation home in Fairfield. Enjoy an in-room coffeemaker and air conditioning. Popular attractions Liberty Mountain Ski Resort and Terrain Park ...
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 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
Don't see what you're looking for?
See all available properties in Hagerstown
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.

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
393 Holiday Homes
Lowest Price
NZ$135
Highest Price
NZ$1,133
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 NZ$181 per night from 29 Dec to 30 Dec
NZ$181
includes taxes & fees
29 Dec - 30 Dec
Stay at this 3-star business-friendly hotel in Hagerstown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
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 NZ$194 per night from 30 Dec to 31 Dec
NZ$194
includes taxes & fees
30 Dec - 31 Dec
Book a stay at this business-friendly hotel in Hagerstown. Enjoy free breakfast, a fitness center, and a 24-hour front desk. Our guests praise the breakfast ...
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 NZ$135 per night from 15 Jan to 16 Jan
NZ$135
includes taxes & fees
15 Jan - 16 Jan 2025
Book a stay at this business-friendly motel in Hagerstown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Super 8 by Wyndham Hagerstown/Halfway Area
Save an average of 15% on thousands of hotels when you're signed in
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 NZ$217 per night from 12 Jan to 13 Jan
NZ$217
includes taxes & fees
12 Jan - 13 Jan 2025
Book a stay at this golf hotel in Hagerstown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our ...
Hampton Inn Hagerstown-I-81
Don't see what you're looking for?
See all available properties in Hagerstown
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.