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.

Location · Value · Decor

Peaceful farm getaway

Relax with the whole family at this peaceful place to stay. Our farmhouse is located just outside of Washingtgeon DC. You can go into the city for all the attractions and come back home to a country and peaceful environment. we are located close to 4 wineries. one walking distance just across the street if you love wine this is the place for you. The grocery store and shopping just 10 minutes away. our farmers are here working so you maybe able to get fresh produce as well during the season.

Cleanliness · Outdoor spaces

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.

Value · Location · Getting around

Top guest favourite

Guest favourite

4 Seasons Wisp Ski-in-Ski-out, Hottub

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.

Location · Family · Quiet

Ski-In/Out: Hot Tub EV Charger DogOK 50"TV FirePit

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.

Family · Value · Nearby

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.

Location · Family · Back garden

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 head to 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

Family · Location · Grill

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!

Family · Value · View

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.

Family · Value · Bathroom

Top guest favourite

Guest favourite

Ski Access + 2 Wisp Passes | Hot Tub + Lake Views

Escape to Castle Creek Lodge, a luxury ski-access retreat in the heart of Wisp Resort near Deep Creek Lake. 🎿 NEW FOR 2026/27 SKI SEASON: Winter stays include complimentary use of TWO transferable Wisp Platinum Season Passes for your group! Enjoy direct ski access, a hot tub overlooking the mountain, expansive entertainment spaces, whole-home audio, mountain and seasonal lake views, and cozy lodge-style charm after a day on the slopes or the water.

Location · Family · Parking

Top guest favourite

Guest favourite

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.

Value · Family · Walkability

Ski-in Ski-out 5BR Cabin with Hot Tub Pet Friendly

🏂Welcome to Serendipity by the Slopes, a spacious 5-bedroom ski-in/ski-out mountain cabin near WISP Resort, perfect for families and groups. Located less than 100 yards from Chair 4, you’ll enjoy easy access to skiing, hiking, and year-round adventure. After a day on the slopes, relax in the private hot tub while taking in peaceful mountain views!

Location · Family · Comfort