25 minutes to WISP and Deep Creek Lake
Family-friendly Cabin Rental in Oakland, MD - perfect for large families, ski trips & group getaways
✔ Large families
✔ Multi-family vacations
✔ Ski trips to WISP Resort
✔ Remote work retreats
✔ Group getaways, weddings & celebrations
Sleeps 18+ with 7 bedrooms, 4 bathrooms, multiple living areas, a private hot tub, heated pool, game room and Starlink WiFi —everything you need for an unforgettable mountain escape. Enjoy the quiet of a private mountain retreat while staying just a short drive from the lake, slopes, and local attractions. Pet-friendly and ideal for kids and adults alike.
Oakland Bear Lair Amenities
Why Book Oakland Bear Lair Direct
Secure checkout • No platform fees • Best rate guaranteed • Direct booking = best rates, no hidden fees
✔ Save 10–15% vs Airbnb & VRBO
✔ Direct communication with host
✔ Flexible booking options
✔ No hidden platform fees
Stay Minutes from Everything
Enjoy the privacy of a quiet mountain retreat while staying just 25 minutes from Deep Creek Lake, WISP Resort, Canaan Valley, Blackwater Falls, and top local attractions.
Where family memories meet mountain magic
Welcome to Oakland Bear Lair, a spacious 7-bedroom mountain retreat designed for unforgettable group getaways. Perfect for ski trips, summer lake vacations, and fall foliage escapes, this cabin combines comfort, entertainment, and prime location.
Why Guests Choose Oakland Bear Lair
A large luxury cabin rental near Deep Creek Lake, Oakland Bear Lair offers the perfect mix of location, space, and amenities. Just minutes from WISP Resort, this 7-bedroom cabin is ideal for year-round getaways including skiing, boating, hiking, and fall foliage trips.
✔ Large Group Cabin Near Deep Creek Lake
✔ Spacious 7BR | 4BA layout for large groups
✔ Hot tub, game room, piano & multiple living spaces
✔ Heated pool April-September
✔ Close to Deep Creek Lake & WISP Resort
✔ Fully setup office with a printer and large monitors
✔ Baby and toddler supplies (high-chair, portable cribs, toys and more)
✔ Pet-friendly
✔ Fully stocked kitchen (modern appliances; new dishes and cookware; Ninja indoor grill, toaster over and blender; Insta Pot; mixer; waffle maker; Keurig)
Oakland Bear Lair - Your Home Away
Reviews
⭐ “Perfect for our ski trip—hot tub was amazing.”
⭐ “Perfect setup for our group of 14—plenty of space and great location.”
⭐ “Hot tub, game room, and layout made this the best cabin we’ve stayed in.”
⭐ “Worth every minute of the short drive from the lake.”
⭐ “Plenty of space for multiple families.”
⭐ “Best cabin we’ve stayed at near Deep Creek Lake.”
⭐ "It’s a huge beautiful house and my family truly enjoyed it. It was really worth it."
⭐ "Everything exceeded our expectations."
⭐ "Highly recommend this cabin to anyone looking for a comfortable, relaxing getaway!"
⭐ "This home was much bigger and more spacious in person. Everything we needed was there."
Meet your Host
I am a COO, a mom of 3, owner of 5 dogs, 4 cats and 1 horse. I love creating moments of joy. Oakland Bear Lair is my happy place. I have poured my heart and soul into making it the best place for a big family or group of friends to spend some time together. Every detail has been thought of with love and care. I hope people can come to Oakland Bear Lair the way I do - straight out of work, with just the clothes on my back. There is everything there waiting for me in the quiet mountain.
Frequently Asked Questions
How far is the cabin from Deep Creek Lake? The cabin is approximately 25 minutes from Deep Creek Lake and WISP Resort.
Is the cabin pet-friendly? Yes, the cabin is pet-friendly and ideal for families traveling with pets.
What amenities are included? Guests enjoy a private hot tub, heated pool (April-September), game room, multiple living areas, high-speed WiFi, fire pit, 2 gas grills (including a BlackStone), and 2 fireplaces (1 gas and 1 wood burning - wood is provided).
Check-in Guide
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