Book Holiday Homes in Cumberland

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Featured Holiday Homes in Cumberland

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

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

Oakland
Book a stay at this family-friendly vacation home in Oakland. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Wisp Resort and Deep Creek ...
Lakefront, dog friendly, dock slip, hot tub, and fire pit
Lakefront/Dock/Amazing views HotTub

Lakefront/Dock/Amazing views HotTub

Oakland
Book a stay at this family-friendly vacation home in Oakland. Enjoy free WiFi, a garden, and patios. Popular attractions Deep Creek Lake and Deep Creek Lake ...
Lakefront/Dock/Amazing views HotTub
Sunset View: Lakefront Pet-Friendly + Hot Tub + Dock

Sunset View: Lakefront Pet-Friendly + Hot Tub + Dock

Swanton
Stay at this vacation home in Swanton. Enjoy free WiFi, a garden, and patios. Popular attractions Deep Creek Lake and Thousand Acres Lakeside Golf Course are ...
Sunset View: Lakefront Pet-Friendly + Hot Tub + Dock
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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
Book a stay at this ski vacation home in McHenry. Enjoy ski-in/ski-out access, patios, and an in-room coffeemaker. Popular attractions Deep Creek Lake and Wisp ...
Ski-in/out townhome with free WiFi, wood fireplace, gas grill, & deck - dogs OK
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
Alvie House: 5 min from Wisp&DCL, Outdoor Fire Pit, Fireplaces, Country Kitchen

Alvie House: 5 min from Wisp&DCL, Outdoor Fire Pit, Fireplaces, Country Kitchen

Accident
Book a stay at this family-friendly vacation home in Accident. Enjoy free WiFi, a pool table, and patios. Popular attractions Deep Creek Lake and Wisp Resort ...
Alvie House: 5 min from Wisp&DCL, Outdoor Fire Pit, Fireplaces, Country Kitchen
Deep Creek Lake Townhome w/ Deck & Water Views

Deep Creek Lake Townhome w/ Deck & Water Views

Oakland
Stay at this vacation home in Oakland. Enjoy patios, cable/satellite TV service, and in-room washers/dryers. Popular attractions Deep Creek Lake and Deep Creek ...
Deep Creek Lake Townhome w/ Deck & Water Views
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
Book a stay at this family-friendly vacation home in Accident. Enjoy free WiFi, a garden, and patios. Our guests praise the helpful staff in our reviews. Popular ...
Deep Creek Lake and Wisp just minutes away, includes pass to CARC (pool/gym)
Ski-in/ski-out mountain-view home with hot tub, fireplace & year-round fun

Ski-in/ski-out mountain-view home with hot tub, fireplace & year-round fun

McHenry
Book a stay at this ski vacation home in McHenry. Enjoy ski-in/ski-out access, patios, and cable/satellite TV service. Popular attractions Deep Creek Lake and ...
Ski-in/ski-out mountain-view home with hot tub, fireplace & year-round fun
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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
1561 Holiday Homes
Lowest Price
NZ$152
Highest Price
NZ$251
Popular accommodation
Lakefront, dog friendly, dock slip, hot tub, and fire pit, Lakefront/Dock/Amazing views HotTub, Sunset View: Lakefront Pet-Friendly + Hot Tub + Dock, Ski-in/out townhome with free WiFi, wood fireplace, gas grill, & deck - dogs OK, Adventure retreat near ski lifts and lake - private hot tub, three balconies, Alvie House: 5 min from Wisp&DCL, Outdoor Fire Pit, Fireplaces, Country Kitchen, Deep Creek Lake Townhome w/ Deck & Water Views, Deep Creek Lake and Wisp just minutes away, includes pass to CARC (pool/gym), Ski-in/ski-out mountain-view home with hot tub, fireplace & year-round fun

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$220 per night from 4 Mar to 5 Mar
NZ$220
includes taxes & fees
4 Mar - 5 Mar
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$152 per night from 11 Mar to 12 Mar
NZ$152
includes taxes & fees
11 Mar - 12 Mar
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$158 per night from 16 Mar to 17 Mar
NZ$158
includes taxes & fees
16 Mar - 17 Mar
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
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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 NZ$251 per night from 6 Mar to 7 Mar
NZ$251
includes taxes & fees
6 Mar - 7 Mar
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.

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^Subject to availability and chosen travel dates.