Book Holiday Homes in Cumberland

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Featured Holiday Homes in Cumberland

In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,

In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,

Oakland
With a stay at this vacation home in Oakland, you'll be a 3-minute drive from Deep Creek Lake and 7 minutes from Wisp Resort.
In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,
Lakefront Home with Dock, Firepit & Views - Dogs OK, Close to the State Park

Lakefront Home with Dock, Firepit & Views - Dogs OK, Close to the State Park

Swanton
When you stay at this vacation home in Swanton, you'll be on the waterfront, within a 10-minute walk of Deep Creek Lake and Deep Creek Lake State Park.
Lakefront Home with Dock, Firepit & Views - Dogs OK, Close to the State Park
Deep Creek Mountain Retreat | House in McHenry with sweeping views

Deep Creek Mountain Retreat | House in McHenry with sweeping views

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.
Deep Creek Mountain Retreat | House in McHenry with sweeping views
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Hot tub, fire pit, lakefront, dock, pet friendly and more!

Hot tub, fire pit, lakefront, dock, pet friendly and more!

Oakland
With a stay at this vacation home in Oakland (Blakeslee), you'll be within a 15-minute drive of Deep Creek Lake and Deep Creek Lake State Park.
Hot tub, fire pit, lakefront, dock, pet friendly and more!
Stunning Luxury Home! Direct Ski Access and Hot Tub

Stunning Luxury Home! Direct Ski Access and Hot Tub

McHenry
When you stay at this vacation home in McHenry, you'll be in the mountains, a 1-minute drive from Wisp Resort and 6 minutes from Deep Creek Lake.
Stunning Luxury Home! Direct Ski Access and Hot Tub
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
Modern house on the lake with private dock, hot tub, air hockey & central AC

Modern house on the lake with private dock, hot tub, air hockey & central AC

Oakland
With a stay at this vacation home in Oakland (Mountainside), you'll be a 1-minute drive from Deep Creek Lake and 8 minutes from Wisp Resort.
Modern house on the lake with private dock, hot tub, air hockey & central AC
New: Lakefront Luxury Home with Private Indoor Heated Pool!

New: Lakefront Luxury Home with Private Indoor Heated Pool!

Oakland
When you stay at this vacation home in Oakland, you'll be on the waterfront, a 2-minute drive from Deep Creek Lake and 7 minutes from Deep Creek Lake State ...
New: Lakefront Luxury Home with Private Indoor Heated Pool!
Dog-friendly house on the lake, central AC, & EV charger

Dog-friendly house on the lake, central AC, & EV charger

Oakland
When you stay at this vacation home in Oakland, you'll be on the waterfront, within a 15-minute drive of Deep Creek Lake and Deep Creek Lake State Park.
Dog-friendly house on the lake, central AC, & EV charger
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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.

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

Holiday houses in Cumberland 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 Cumberland 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 Cumberland adventures, obvs.

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

Cumberland Holiday Homes essential information

Accommodation
1861 Holiday Homes
Lowest Price
AU$140
Highest Price
AU$217
Popular accommodation
In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,, Lakefront Home with Dock, Firepit & Views - Dogs OK, Close to the State Park, Deep Creek Mountain Retreat | House in McHenry with sweeping views, Hot tub, fire pit, lakefront, dock, pet friendly and more!, Stunning Luxury Home! Direct Ski Access and Hot Tub, Adventure retreat near ski lifts and lake - private hot tub, three balconies, Modern house on the lake with private dock, hot tub, air hockey & central AC, New: Lakefront Luxury Home with Private Indoor Heated Pool!, Dog-friendly house on the lake, central AC, & EV charger

Top trending hotels in Cumberland

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$217 per night from 1 Apr to 2 Apr
AU$217
includes taxes & fees
1 Apr - 2 Apr
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
Best Western Braddock Inn

Best Western Braddock Inn

2.5 out of 5
1268 National Hwy, Cumberland, MD
Fully refundableReserve now, pay when you stay
The price is AU$140 per night from 7 Apr to 8 Apr
AU$140
includes taxes & fees
7 Apr - 8 Apr
Located in Cumberland, Best Western Braddock Inn is within a 5-minute drive of La Vale Tollgate House and Country Club Mall.
Best Western Braddock Inn
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
The price is AU$140 per night from 6 Apr to 7 Apr
AU$140
includes taxes & fees
6 Apr - 7 Apr
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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Comfort Inn & Suites LaVale - Cumberland

Comfort Inn & Suites LaVale - Cumberland

2.5 out of 5
1216 National Hwy, Cumberland, MD
Fully refundableReserve now, pay when you stay
The price is AU$211 per night from 2 Apr to 3 Apr
AU$211
includes taxes & fees
2 Apr - 3 Apr
Located in Cumberland, Comfort Inn & Suites LaVale - Cumberland is within a 5-minute drive of LaVale Library and Country Club Mall.
Comfort Inn & Suites LaVale - Cumberland
Don't see what you're looking for?
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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.