Ski-in/Ski-out holiday rentals in Maryland

Historic Eden Ranch, built 1837

Built in 1837, this three bedroom, 1 1/2 bath farmhouse sitting on 110 acres along Will Creek, the start of Wills Knob with Wills Mountain to the south was first transacted in 1728 when a Shawnee Indian known as "Will" sold 1000 acres to Benjamin Tomlinson for $30 and an old Rifle. This 110 acres was part of that 1000 acres! Farmhouse is registered in the Maryland Historic Society and has been restored to original floors from 1837 and original staircase and living room walls. Antique furniture.

Ski-In Ski-Out + Walking Distance to Lake!

BRAND NEW + FULLY RENOVATED! Start your next adventure and step into this Ski-In/Ski-Out get away that's just a short walk to Deep Creek Lake! This beautiful 3bedroom/3bath property in the rolling landscape of Deep Creek Lake is the perfect outdoor getaway for hiking, water sports, and snow sports depending on the season. Enjoy the outdoors and then come back and relax in the hot tub while grilling out on the back patio! It's the perfect space for families or friends, holding up to 8 people.

Hot Tub, Pool Table, Poker, Ping Pong: Big Sky

Discover Big Sky, a luxurious ski-in/ski-out mountain retreat with a rich rental history and breathtaking panoramic views near Deep Creek Lake and the surrounding peaks. Unwind in our spacious hot tub or warm up by the grand stone fireplace. The fun never ends inside - challenge your crew to pool, poker, ping pong, or shuffleboard in our fully equipped game rooms. Whether you're hitting the slopes at Wisp Resort or by the lake, this spacious year-round resort offers the perfect adventure!

Langski's Lakeview of Wisp Mt.

Langski's is your all season destination for Deep Creek Lake and all it has to offer. Beach front lake access a short walk or drive away. Centrally located 5 minutes from all activities and amenities. Wooded balcony views on every level will Wisp your stress away. Hot tub to rejuvenate after an exciting day at the Lake or Parks. Spacious 3 levels for all to spread out or gather around the fireplace for family time. Open Kitchen area for all to enjoy! Gas Grill. Free Parking. Must be 21

Hot Tub EV Charger DogsOK 50"TV Fire Pit Gas Grill

SKI-IN/SKI-OUT 50 yards to Wisp Resort Chair 4 where you will find green, blue, and black trails. Sleeps 12: K, K, Q, Q, 2xQ bunk Dog-friendly HOT TUB Great Room with stone fireplace and cathedral ceiling Dining table for 8 + 6 at breakfast bar 3 driveway spaces + garage for your gear Bonus bedroom features secluded office space Walking distance to rafting/kayaking at Wisp whitewater course. Less than a mile from the lake and award-winning Lodestone Golf Club. Happy dog fee $150/stay.

Villages of Wisp - Bright Peak!

Gorgeous Villages of Wisp Unit. This newly remodeled home features two bedrooms upstairs with their own bathroom and another bedroom in the basement with a couch, queen bed with a full trundle. All levels enjoy the comfort of NEW DUCTLESS AC. Enjoy a secluded and private stay with your family or group of friends. Plenty of board games to never run out of fun activities. NEW WASHER AND DRYER. Community offers its guests a lakefront area with a gazebo and firepit. Book your stay now!!!

Game room| W/D| Fire pit| Full Kitchen| BBQ| Walk!

Wake up to Deep Creek Lake and Wisp at your doorstep in this spacious 3 bedroom 2.5 bath house. Come back after a day on the slopes or at the lake and relax in the cozy living room with a warm fire or keep the activities going in the game room. This is a perfect location with easy access to stores, activities, the lake, and all the great things about Deep Creek and Wisp. We are very family friendly and dog friendly! Separate $50 pet fee applies* A 3 minute walk to Wisp!

Luxury Wisp Village Townhome

Enjoy a stylish experience at this centrally-located property with both ski-in/ski-out and Deep Creek Lake access! This 4 bed/3 bath that accommodates 11, includes a large kitchen, living room, deck and fire-pit for entertaining families and groups. It's a great location with quick access to Wisp Resort, and is only minutes to great restaurants, bars, and convenience stores. WiFi speed of 800/mpbs allows for guests to work remote or stream your favorite shows.

Brand New Home,Indoor Pool, Firepit,Hot Tub

Escape to the majestic mountains in this brand-new, luxurious rental home. With five bedrooms and 4.5 baths, it’s thoughtfully designed for ultimate comfort and adventure. Perfect for families or groups, this stunning retreat offers a tranquil setting just steps from the slopes. Experience the perfect blend of relaxation and excitement in a home built for making unforgettable memories. And if you must, there is a dedicated work office space for you workaholics !!