Trips to 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, Finnish Sauna, Kayaks, Dock, Hot Tub, Gardens - OWLS NEST, DCL
• 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
• Beautiful Lakefront Home with Hot Tub Near Mountain and Attractions
• Peaceful Lakefront! Private deep water dock, evening sun, quiet dead end street!
• Timroc II, FIVE STAR REVIEWS! 15 MINUTES FROM WISP! HOT TUB! PRIVATE 2 ACRES!

There are 175 vacation rentals with private pools near Cumberland. Top-rated homes that have access to a swimming pool include:

• Elegant Escape Steps from Lake & Fun
• Stone Crest
• Lakefront Chalet w/Pool, Private Dock, & Hot Tub
• Spacious Dog Friendly Retreat w/Pool & Fireplaces

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:

• Dreamers Inn | Lakefront, Private Dock + Views!
• Braeside Six-Bedroom Holiday Home
• Moonlight Ridge by Taylor Made Deep Creek

Currently, the total number of properties listed in 2026 is over 3654 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.