Cumberland Ski Chalets Rentals & Holiday Homes

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 Ski Chalet Rentals in Cumberland:

• Lakefront Cabin, Kayaks, Private Dock, Hot Tub, 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
• 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 many ski chalets available in Cumberland; however, here are the most popular ski chalets listed in Cumberland:

• Wooded Retreat w Hot Tub, Loft, Game Room & Sauna
• Updated in 2026 Barrel Sauna/Hot Tub, GameRoom
• Chalet in the Orchard;Romance, Luxury, Relaxation -Movie theater, Sauna, Hot tub
• Mountain Escape! Deep Creek Lake Maryland
• Lake Pointe Inn
• 4BR/4BA~New Hot Tub~Pet Friendly~Minutes to Wisp~Private Bath for Each BR
• Blue Moon Rising
• Lake View

Unpluggedweekend offers availability throughout the year, but you can book pre-Christmas, mid-January, or before and after the school break at Easter are the best times for renting in Cumberland.

At Unpluggedweekend most of our ski chalets are perfect for families. Check out the complete list of ski chalets in Cumberland to find what works for you.

Yes, there are 4 self-catering family ski chalet in Cumberland that have hot tubs & other amenities.