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 MD
Stay at this holiday home in Oakland. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Deep Creek Lake and Wisp Resort are located ...
Opens in a new windowIn the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,
Dog-friendly house on the lake, central AC, & EV charger

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

Oakland MD
Stay at this holiday home in Oakland. Enjoy laundry facilities, patios and an in-room coffee maker. Popular attractions Deep Creek Lake and Wisp Resort are located ...
Opens in a new windowDog-friendly house on the lake, central AC, & EV charger
Lakefront/Dock/Amazing views HotTub

Lakefront/Dock/Amazing views HotTub

Oakland MD
Stay at this family-friendly holiday home in Oakland. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Deep Creek Lake and Wisp Resort ...
Opens in a new windowLakefront/Dock/Amazing views HotTub
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Sisters Treehouse

Sisters Treehouse

Oakland MD
Stay at this holiday home in Oakland. Enjoy laundry facilities, patios and cable/satellite TV service. Popular attractions Deep Creek Lake and Wisp Resort are ...
Opens in a new windowSisters Treehouse
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 MD
Stay at this holiday home in Swanton. Enjoy laundry facilities, patios and cable/satellite TV service. Popular attractions Deep Creek Lake and Wisp Resort are ...
Opens in a new windowLakefront Home with Dock, Firepit & Views - Dogs OK, Close to the State Park
VellaVue Luxury Estate: Private Indoor Pool, Sauna, Gym & Theater – Sleeps 20

VellaVue Luxury Estate: Private Indoor Pool, Sauna, Gym & Theater – Sleeps 20

Friendsville MD
Stay at this family-friendly holiday home in Friendsville. Enjoy free Wi-Fi, private pools and a fitness centre. Popular attractions Sang Run State Park and ...
Opens in a new windowVellaVue Luxury Estate: Private Indoor Pool, Sauna, Gym & Theater – Sleeps 20
 AMAZING LAKE FRONT 7 BR Home, Hot Tub, Fire Pit, Dock, Pool Table

AMAZING LAKE FRONT 7 BR Home, Hot Tub, Fire Pit, Dock, Pool Table

Oakland MD
Stay at this family-friendly holiday home in Oakland. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Deep Creek Lake and Wisp Resort ...
Opens in a new window AMAZING LAKE FRONT 7 BR Home, Hot Tub, Fire Pit, Dock, Pool Table
Perfect Lake Escape | Dog Friendly Hot Tub, Fire Pit, Dock Slip

Perfect Lake Escape | Dog Friendly Hot Tub, Fire Pit, Dock Slip

Oakland MD
Stay at this family-friendly holiday home in Oakland. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Deep Creek Lake and Wisp Resort are ...
Opens in a new windowPerfect Lake Escape | Dog Friendly Hot Tub, Fire Pit, Dock Slip
Private Indoor Swim Pool,Hot Tub, Free Golf & Mini Golf, Tennis, Fire Pit

Private Indoor Swim Pool,Hot Tub, Free Golf & Mini Golf, Tennis, Fire Pit

Swanton MD
Stay at this golf holiday home in Swanton. Enjoy private pools, a garden and laundry facilities. Popular attractions Deep Creek Lake and Wisp Resort are located ...
Opens in a new windowPrivate Indoor Swim Pool,Hot Tub, Free Golf & Mini Golf, Tennis, Fire Pit
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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
1349 Holiday Homes
Lowest Price
NZ$141
Highest Price
NZ$217
Popular accommodation
In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,, Dog-friendly house on the lake, central AC, & EV charger, Lakefront/Dock/Amazing views HotTub, Sisters Treehouse, Lakefront Home with Dock, Firepit & Views - Dogs OK, Close to the State Park, VellaVue Luxury Estate: Private Indoor Pool, Sauna, Gym & Theater – Sleeps 20, AMAZING LAKE FRONT 7 BR Home, Hot Tub, Fire Pit, Dock, Pool Table, Perfect Lake Escape | Dog Friendly Hot Tub, Fire Pit, Dock Slip, Private Indoor Swim Pool,Hot Tub, Free Golf & Mini Golf, Tennis, Fire Pit

Top trending hotels in Cumberland

Rocky Gap Casino & Resort

Rocky Gap Casino & Resort

4 out of 5
16701 Lakeview Road NE Cumberland MD
Fully refundableReserve now, pay when you stay
The price is NZ$217 per night from 4 May to 5 May
NZ$217
4 May - 5 May
includes taxes & fees
Stay at this spa hotel in Cumberland. Enjoy free parking, an outdoor pool and 3 restaurants. Our guests praise the helpful staff and the clean rooms in their ...
Opens in a new windowRocky 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$141 per night from 10 May to 11 May
NZ$141
10 May - 11 May
includes taxes & fees
Stay at this business-friendly hotel in Cumberland. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the pool in their ...
Opens in a new windowBest 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$162 per night from 4 May to 5 May
NZ$162
4 May - 5 May
includes taxes & fees
Stay at this business-friendly hotel in Cumberland. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms ...
Opens in a new windowRamada by Wyndham Cumberland Downtown
Save an average of 15% on thousands of hotels when you're signed in
Sleep Inn & Suites Cumberland - LaVale

Sleep Inn & Suites Cumberland - LaVale

2.5 out of 5
13320 Ali Ghan Road NE Cumberland MD
Fully refundable
The price is NZ$196 per night from 25 May to 26 May
NZ$196
25 May - 26 May
includes taxes & fees
Stay at this business-friendly hotel in Cumberland. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff ...
Opens in a new windowSleep Inn & Suites Cumberland - LaVale
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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.