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
Stay at this vacation home in Oakland. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions Deep Creek Lake and Deep Creek Lake State ...
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
Stay at this vacation home in Swanton. Enjoy patios, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Deep Creek Lake and Deep Creek ...
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
Stay at this vacation home in McHenry. Enjoy tennis courts, patios, and cable/satellite TV service. Popular attractions Deep Creek Lake and Wisp Resort are located ...
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
Stay at this vacation home in Oakland. Enjoy breakfast (surcharge), concierge services, and patios. Popular attractions Deep Creek Lake and Deep Creek Lake State ...
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
Book a stay at this ski vacation home in McHenry. Enjoy breakfast (surcharge), concierge services, and ski-in/ski-out access. Popular attractions Deep Creek ...
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
Book a stay at this ski vacation home in McHenry. Enjoy a water park, ski-in/ski-out access, and patios. Popular attractions 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
Stay at this vacation home in Oakland. Enjoy patios, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Deep Creek Lake and Deep Creek ...
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
Book a stay at this family-friendly vacation home in Oakland. Enjoy private pools, breakfast (surcharge), and concierge services. Popular attractions Deep Creek ...
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
Stay at this vacation home in Oakland. Enjoy patios, an in-room coffeemaker, and air conditioning. Popular attractions Deep Creek Lake and Deep Creek Lake State ...
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
1856 Holiday Homes
Lowest Price
NZ$152
Highest Price
NZ$239
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 NZ$239 per night from 10 Apr to 11 Apr
NZ$239
includes taxes & fees
10 Apr - 11 Apr
Stay at this 3-star spa hotel in Cumberland. Enjoy free parking, an outdoor pool, and 3 restaurants. Our guests praise the helpful staff and the clean rooms ...
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 NZ$168 per night from 13 Apr to 14 Apr
NZ$168
includes taxes & fees
13 Apr - 14 Apr
Book a stay at this business-friendly hotel in Cumberland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in ...
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 NZ$152 per night from 20 Apr to 21 Apr
NZ$152
includes taxes & fees
20 Apr - 21 Apr
Book a stay at this business-friendly hotel in Cumberland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Ramada by Wyndham Cumberland Downtown
Save an average of 15% on thousands of hotels when you're signed in
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 NZ$228 per night from 7 Apr to 8 Apr
NZ$228
includes taxes & fees
7 Apr - 8 Apr
Book a stay at this business-friendly hotel in Cumberland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Comfort Inn & Suites LaVale - Cumberland
Don't see what you're looking for?
See all available properties in Cumberland
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.