Book Holiday Homes in Western Maryland

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Featured Holiday Homes in Western Maryland

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

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

Harpers Ferry
With a stay at this vacation home in Harpers Ferry, you'll be within a 15-minute drive of Harpers Ferry National Historical Park and Potomac River.
Riverside cottage, minutes from historic Harpers Ferry! Private river access!
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

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

Frederick
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 ...
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Adventure retreat near ski lifts and lake - private hot tub, three balconies

Adventure retreat near ski lifts and lake - private hot tub, three balconies

McHenry
When you stay at this vacation home in McHenry, you'll be on a lake, within a 10-minute walk of Deep Creek Lake and Wisp Resort.
Adventure retreat near ski lifts and lake - private hot tub, three balconies
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Bon Vivant-Pet Friendly, Lake Front, Minutes to HoniHoni, Uno, Brenda's, Wisp

Bon Vivant-Pet Friendly, Lake Front, Minutes to HoniHoni, Uno, Brenda's, Wisp

Oakland
With a stay at this vacation home in Oakland, you'll be a 3-minute drive from Deep Creek Lake and 9 minutes from Wisp Resort.
Bon Vivant-Pet Friendly, Lake Front, Minutes to HoniHoni, Uno, Brenda's, Wisp
Beautiful, Spacious Historic Victorian Near Ski Liberty

Beautiful, Spacious Historic Victorian Near Ski Liberty

Cascade
Located in Sabillasville, this vacation home is in the mountains, within a 5-minute drive of Monterey Pass Battlefield Museum and Monterey Country Club.
Beautiful, Spacious Historic Victorian Near Ski Liberty
“The Train Depot” 2nd oldest in the US

“The Train Depot” 2nd oldest in the US

Frederick
A stay at this vacation home places you in the heart of Frederick, steps from Carroll Creek Linear Park and The Delaplaine Arts Center.
“The Train Depot” 2nd oldest in the US
Elevated Potomac River Retreat - King Suite - Riverfront - Large Screened Porch

Elevated Potomac River Retreat - King Suite - Riverfront - Large Screened Porch

Sharpsburg
With a stay at this vacation home in Sharpsburg, you'll be on the waterfront, just steps from Chesapeake and Ohio Canal National Historic Park and a 1-minute ...
Elevated Potomac River Retreat - King Suite - Riverfront - Large Screened Porch
*Luxury Condo In Downtown Frederick*

*Luxury Condo In Downtown Frederick*

Frederick
A stay at this vacation home places you in the heart of Frederick, steps from Carroll Creek Linear Park and 5 minutes by foot from Weinberg Center for the ...
*Luxury Condo In Downtown Frederick*
Villa With A View- 4 bedroom townhouse with lake and ski slope views

Villa With A View- 4 bedroom townhouse with lake and ski slope views

Mchenry
When you stay at this vacation home in McHenry, you'll be on a lake, within a 5-minute drive of Deep Creek Lake and Wisp Resort.
Villa With A View- 4 bedroom townhouse with lake and ski slope views
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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
1066 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
Riverside cottage, minutes from historic Harpers Ferry! Private river access!, RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT., Adventure retreat near ski lifts and lake - private hot tub, three balconies, Bon Vivant-Pet Friendly, Lake Front, Minutes to HoniHoni, Uno, Brenda's, Wisp, Beautiful, Spacious Historic Victorian Near Ski Liberty, “The Train Depot” 2nd oldest in the US, Elevated Potomac River Retreat - King Suite - Riverfront - Large Screened Porch, *Luxury Condo In Downtown Frederick*, Villa With A View- 4 bedroom townhouse with lake and ski slope views

Top trending hotels in Western Maryland

Country Inn & Suites by Radisson, Frederick, MD

Country Inn & Suites by Radisson, Frederick, MD

3 out of 5
5579 Spectrum Dr, Frederick, MD
Fully refundableReserve now, pay when you stay
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
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
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
Ramada by Wyndham Cumberland Downtown

Ramada by Wyndham Cumberland Downtown

3 out of 5
100 South George Street, Cumberland, MD
Fully refundableReserve now, pay when you stay
A stay at Ramada by Wyndham Cumberland Downtown places you in the heart of Cumberland, steps from Downtown Cumberland Historic District and 4 minutes by foot ...
Ramada by Wyndham Cumberland Downtown
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Days Inn by Wyndham Westminster

Days Inn by Wyndham Westminster

2 out of 5
25 South Cranberry Road, Route 140 & Cranberry Road, Westminster, MD
Fully refundableReserve now, pay when you stay
With a stay at Days Inn by Wyndham Westminster in Westminster, you'll be within a 10-minute walk of Cranberry Square and TownMall of Westminster.
Days Inn by Wyndham Westminster
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.