Owner Direct Vacation
Rentals in Cumberland
The Best Owner Direct Vacation Rentals in Cumberland. Explore thousands of vacation home rentals, large cabins, and villas near Cumberland
GUESTS
Explore the Best Cumberland Vacation Homes
Looking for the perfect place to stay in Cumberland? Discover a curated collection of vacation rentals offering comfort, convenience, and authentic Cumberland character. Whether you want a beachfront condo, a cozy family home, or a pet-friendly stay close to downtown, Owner Direct makes it easy to compare verified options for your next trip.
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Why Travelers Love Using
Owner Direct to
Find Cumberland Vacation Rentals
What makes our vacation homes stand out?
Verified Properties
Every vacation home shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.
Value You Can Trust
Compare a range of properties and find fair, transparent pricing—no hidden fees.
Endless Variety
From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.
More Places to Stay Near Cumberland
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Popular Neighborhoods for Cumberland Vacation Rentals
What are the best areas to stay in Cumberland
Discover the top neighborhoods in Cumberland and choose a place that suits your stay.
Monday Feb 9
Cumberland, Maryland
Common Vacation Rental Amenities Typical Vacation Rental Amenities
What sort of amenities will be available at your stay?
Our Cumberland vacation rentals are designed for comfort and convenience, with everything you need for a relaxing stay.
Indoor Amenities
Fully equipped kitchens
Spacious living areas with streaming TVs
Complimentary Wi-Fi
Air conditioning and heating
In-unit washer and dryer
Plush bedding and comfortable furniture
Outdoor Amenities
Balconies or patios with coastal views
Private or shared pools
BBQ grills and outdoor dining areas
On-site parking
Easy access to beaches and attractions
More Vacation Rentals You May Like Near Cumberland
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How to Reserve Your Cumberland Vacation Rental
Booking Made Simple
Owner Direct helps travelers find verified vacation rentals from trusted sources. Once you select a property you love, you’ll be guided to our partner’s secure booking platform to complete your reservation.
SEARCH PROPERTIES
Use filters for location, amenities, and budget.
VIEW DETAILS
Check photos, reviews, and features for your top picks.
BOOK SECURELY
Confirm your stay safely through our trusted travel partners.
Cumberland Vacation Rental FAQs
1. What are the top vacation rentals in Cumberland?
There are a lot of options in Cumberland. If you plan on staying in the Cumberland area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Cumberland:
- LAKEFRONT Cabin: Hot Tub, Kayaks, Private Dock & Gardens -OWLS NEST Deep Creek
- Deep Creek Lake and Wisp just minutes away, includes pass to CARC (pool/gym)
- Boulder Ridge Cabin -a private chalet in the woods
- Minutes from Deep Creek Lake, Located on 24-acre farm with private 1-acre lake
- Sunny Escape 2 - A new era for a well loved lake front home
- 5 STAR OWNER Managed, Lake Xcess, dock, Pool, Pickle-ball, Home Theater, firepit
- Level lakefront, family-friendly, hot tub, low fees, private dock
- Peaceful Lakefront! Private deep water dock, evening sun, quiet dead end street!
- Beautiful Lakefront Home with Hot Tub Near Mountain and Attractions
- Lakefront, Wooded, & Secluded Home - Family Dogs Welcome.
2. How many vacation rentals have private pools in Cumberland?
There are 157 vacation rentals with private pools near Cumberland. Top-rated homes that have access to a swimming pool include:
3. Which vacation homes in Cumberland are best for families?
If you are looking for a family-friendly vacation home in Cumberland, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Cumberland:
4. How many vacation rentals are available in Cumberland?
Currently, the total number of properties listed in 2026 is over 3500 in the Cumberland area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Cumberland.