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.

6 Bed 5 1/2 Bath | Private Hot Tub | Walk to Wisp

Discover Mountain Retreat in McHenry, MD conveniently located near Deep Creek Lake for amazing summer activities and WISP Ski Resort in the winter time. This family-friendly vacation rental is in excellent condition and offers the perfect home base for your adventures with spacious five bedrooms 5 1/2 bathrooms and a Private Hot Tub. Experience a warm and welcoming atmosphere, ample space. Each bedroom has it's own full bathroom and in pristine condition. Create lasting memories at Deep Creek.

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.

4 Seasons Wisp- Lake Access, Hot Tub, AirCondition

This renovated, dog-friendly spacious Ski-In/Ski Out townhome is minutes from Wisp Resort's Lodge, nearby restaurants, and shops. Deep Creek Lake activities are all within a few minutes. The home has access to the "Down Under" ski trail and comes with lake access via a private lakeside park just a short walk or drive from property. Guests also have access to the Garrett College Community Aquatic and Recreation Complex(CARC) Gym and Pool during their stay. Must have AWD/4WD in winter.

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 16: 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 $187/stay.

TikiBar|Hot Tub|Lakefront|Playset|Private Dock

Welcome to FIRECRACKER CABIN, your cozy lakefront retreat in McHenry, Maryland! This charming 2-bedroom, 2-bathroom getaway offers the perfect blend of lakeside relaxation with unobstructed views and mountain adventure. Located just steps from Deep Creek Lake and close to Wisp Resort, this home features ski-in/ski-out access, a private hot tub, private dock, and pet-friendly comfort, making it ideal for families, couples, and small groups looking for the ultimate four-season escape.

Deep Creek Cottage at Wisp!

Escape to our cozy 2-bedroom, 1-bath cottage, just a 2-minute walk from the ski slopes and a 5-minute walk to the lake. Perfect for families, friends, or couples, this retreat features a spacious living room, a bedroom that doubles as a projector movie room, and a fully equipped kitchen with a coffee/hot chocolate bar. Enjoy the hot tub, expansive yard with games, and proximity to all Deep Creek attractions. Ideal for summer water activities and winter sports. Book your stay today!

Lake Access•Dock~Hot Tub •Game Room•Dogs OK!

The perfect, 5-star log cabin, with tons of amenities! You can WALK to Wisp or the lake! This spacious, two-story home is near marinas, skiing, golf, rafting, food & everything in Deep Creek Lake. ✔ TWO King suites ✔Queen suite w/2 beds ✔TWO Queen sofa beds ✔3 Baths ✔Sleeps 10 ✔Dogs OK (fee) ✔Hot Tub ✔Fire-pit ✔FAST WiFi ✔Pool table ✔Skee Ball ✔PinBall ✔PacMan ✔Coffee/tea bar ✔Roku SmartTVs ✔Grill ✔Central heat & AC ✔Washer / Dryer ✔Lake access & dock ✔ READ House RULES

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!

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 ductless AC/Heating. Enjoy a secluded and private stay with your family or group of friends. Plenty of board games to never run out of fun activities. Community offers its guests a lakefront area with a gazebo and firepit. Book your stay now!!!

Ski 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 !!

3 Cubs Cabin - Ski In, Golf Sim, Hot Tub & Arcade

Ski in and out from the top of Wisp Resort and reconnect with loved ones in this family-friendly 4 Bedroom, 3 Bathroom townhome cabin. Whether you ski/snowboard or not, this cabin offers amenities to enjoy your stay. Hot Tub, Games, Arcade, and Golf Simulator offer entertainment year round. In the summer we are a right next to Lodestone golf course and a few minute drive down to the lake or to local wineries and restaurants.