Book Holiday Homes in Western Maryland

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Featured Holiday Homes in Western Maryland

Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit

Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit

Oakland
With a stay at this vacation home in Oakland, you'll be on the waterfront, within a 10-minute drive of Deep Creek Lake and Youghiogheny River.
Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit
Deep Creek Lake and Wisp just minutes away,  includes pass to CARC (pool/gym)

Deep Creek Lake and Wisp just minutes away, includes pass to CARC (pool/gym)

Accident
Located in Accident, this vacation home is in a rural location, within a 10-minute drive of Garrett County Dog Park and Deep Creek Lake.
Deep Creek Lake and Wisp just minutes away, includes pass to CARC (pool/gym)
Serene Mountain Escape: Hot Tub, Foosball, Views

Serene Mountain Escape: Hot Tub, Foosball, Views

Oakland
When you stay at this vacation home in Oakland, you'll be in the mountains, within a 15-minute drive of Deep Creek Lake and Deep Creek Lake State Park.
Serene Mountain Escape: Hot Tub, Foosball, Views
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Lakefront/Dock/Amazing views HotTub

Lakefront/Dock/Amazing views HotTub

Oakland
When you stay at this vacation home in Oakland, you'll be on the waterfront, a 1-minute drive from Deep Creek Lake and 8 minutes from Wisp Resort.
Lakefront/Dock/Amazing views HotTub
Charming "Cream of the Crop" Cape ~❤️of Middletown

Charming "Cream of the Crop" Cape ~❤️of Middletown

Middletown
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
Ski-in/out townhome with free WiFi, wood fireplace, gas grill, & deck - dogs OK

Ski-in/out townhome with free WiFi, wood fireplace, gas grill, & deck - dogs OK

McHenry
With a stay at this vacation home in McHenry, you'll be in the mountains, steps from Wisp Resort and a 2-minute drive from Deep Creek Lake.
Ski-in/out townhome with free WiFi, wood fireplace, gas grill, & deck - dogs OK
Lakefront, dog friendly, dock slip, hot tub, and fire pit

Lakefront, dog friendly, dock slip, hot tub, and fire pit

Oakland
With a stay at this vacation home in Oakland, you'll be on the waterfront, within a 10-minute drive of Deep Creek Lake and Youghiogheny River.
Lakefront, dog friendly, dock slip, hot tub, and fire pit
Beautiful Cabin in the Woods with Private Hot Tub & Game Room, Close to Skiing

Beautiful Cabin in the Woods with Private Hot Tub & Game Room, Close to Skiing

McHenry
With a stay at this vacation home in McHenry, you'll be within a 5-minute drive of Deep Creek Lake and Wisp Resort.
Beautiful Cabin in the Woods with Private Hot Tub & Game Room, Close to Skiing
Level lakefront, family-friendly, hot tub, low fees, private dock

Level lakefront, family-friendly, hot tub, low fees, private dock

Oakland
With a stay at this vacation home in Oakland (Paradise Point), you'll be a 1-minute drive from Deep Creek Lake and 9 minutes from Deep Creek Lake State ...
Level lakefront, family-friendly, hot tub, low fees, private dock
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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.

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

Holiday houses in Western Maryland 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 Western Maryland 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 Western Maryland adventures, obvs.

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

Western Maryland Holiday Homes essential information

Accommodation
871 Holiday Homes
Lowest Price
AU$148
Highest Price
AU$197
Popular accommodation
Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit, Deep Creek Lake and Wisp just minutes away, includes pass to CARC (pool/gym), Serene Mountain Escape: Hot Tub, Foosball, Views, Lakefront/Dock/Amazing views HotTub, Charming "Cream of the Crop" Cape ~❤️of Middletown, Ski-in/out townhome with free WiFi, wood fireplace, gas grill, & deck - dogs OK, Lakefront, dog friendly, dock slip, hot tub, and fire pit, Beautiful Cabin in the Woods with Private Hot Tub & Game Room, Close to Skiing, Level lakefront, family-friendly, hot tub, low fees, private dock

Top trending hotels in Western Maryland

Rocky Gap Casino & Resort

Rocky Gap Casino & Resort

3 out of 5
16701 Lakeview Road NE, Cumberland, MD
Fully refundableReserve now, pay when you stay
The price is AU$197 per night from 23 Dec to 24 Dec
AU$197
includes taxes & fees
23 Dec - 24 Dec
When you a stay at Rocky Gap Casino & Resort in Cumberland, you'll be next to a golf course, just steps from Rocky Gap State Park and Rocky Gap Casino and Golf ...
Rocky Gap Casino & Resort
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$148 per night from 5 Jan to 6 Jan
AU$148
includes taxes & fees
5 Jan - 6 Jan 2025
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
Hampton Inn & Suites Frederick-Fort Detrick

Hampton Inn & Suites Frederick-Fort Detrick

2.5 out of 5
1565 Opossumtown Pike, Frederick, MD
Fully refundableReserve now, pay when you stay
The price is AU$180 per night from 4 Jan to 5 Jan
AU$180
includes taxes & fees
4 Jan - 5 Jan 2025
Located in Frederick, Hampton Inn & Suites Frederick-Fort Detrick is within a 5-minute drive of Hood College and Frederick Memorial Hospital.
Hampton Inn & Suites Frederick-Fort Detrick
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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
Don't see what you're looking for?
See all available properties in Western Maryland
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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.