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Ski-in/Ski-out vacation rentals in Maryland

Find and book unique ski-in/ski-out homes on Airbnb

Top-rated ski-in/ski-out rentals in Maryland

Guests agree: these ski-in/ski-out homes are highly rated for location, cleanliness, and more.

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Top guest favorite

A cozy living area is showcased, featuring a plaid armchair beside a decorative bookshelf. The fireplace is framed by white bricks, complementing the rustic wooden accent wall. Art pieces adorn the space, while a bowl of vibrant flowers adds a touch of color to the setting.

Farm stay in Ellerslie

4.95 out of 5 average rating, 60 reviews

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.

A panoramic view of the large flat front yard is presented, leading to a serene lake. A playset stands to the left, while multiple lawn chairs are positioned by the water's edge. The setting is framed by trees, creating a peaceful atmosphere.

Cabin in McHenry

4.89 out of 5 average rating, 37 reviews

TikiBar, Hot Tub, Lakefront, Playset, Private Dock

This home has a private dock, custom tiki bar, a beautiful private unobstructed view of the lake, multiple porch swings, smart tv outside in the tiki bar and 2 inside, comfortable poly furniture on the wrap around porch and around the fire pit, gas grill, hot tub, large flat front yard, and parking for 4 vehicles. Your guests will have no problem creating memories and before you leave you will be planning your annual return stay. Enjoy it like it is yours & bring your pups if you would like.

A spacious deck features a hot tub and wooden seating, accompanied by colorful lounge chairs. The cabin exterior showcases natural wood siding, while large windows provide views of the surrounding landscape.

Cabin in McHenry

4.99 out of 5 average rating, 142 reviews

Walk to Wisp & Lake • Hot Tub • Game Room•Dogs OK!

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

A two-story building is shown, featuring multiple wooden balconies and large windows. Lush greenery surrounds the entrance, with a well-maintained walking path leading to the front door. The natural landscape provides a serene backdrop, enhancing the overall appeal of the property.

Home in McHenry

5 out of 5 average rating, 17 reviews

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

Home in McHenry

4.9 out of 5 average rating, 119 reviews

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.

A living area is showcased with a blue accent wall and light wooden flooring. Comfortable seating is provided by two armchairs and a sectional sofa. A television is mounted on the wall across from the seating, with a decorative cabinet below. Stairs are visible in the background.

Home in McHenry

4.93 out of 5 average rating, 46 reviews

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!!

A hot tub filled with bubbling water is framed by lush trees and overlooks a nearby hillside. The slopes are visible in the background, showcasing a well-maintained area suited for winter sports. A clear blue sky adds to the serene atmosphere.

Home in McHenry

4.9 out of 5 average rating, 21 reviews

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!

The living room features a cozy seating area with a sectional couch and a wooden coffee table. A stone fireplace is positioned below a wall-mounted television. Soft lighting illuminates the space, complemented by a decorative plant and wall art.

Cottage in McHenry

4.89 out of 5 average rating, 56 reviews

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!

A cozy living area features a stone fireplace with a large mirror above it. Sunlight enters through multiple windows, illuminating a comfortable couch and a dining table set for four. Decorative elements create a warm and welcoming environment.

Home in McHenry

4.72 out of 5 average rating, 61 reviews

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.

Top guest favorite

The exterior of the rental home features a contemporary design with a gabled roof and wooden accents. A landscaped area with boulders and shrubs surrounds the front, while a spacious porch is supported by sturdy columns. Clear blue skies provide a bright backdrop.

Home in McHenry

5 out of 5 average rating, 26 reviews

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 !!

A spacious living area features a large sectional sofa in a light tone, complemented by a comfortable armchair. Natural light enters through multiple windows adorned with dark shades. The wooden walls and floor enhance the rustic charm of the space.

Home in McHenry

4.94 out of 5 average rating, 339 reviews

Newly Renovated 2 Bed/2 Bath in Deep Creek

Beautiful and comfortable home located 2 minutes away from Deep Creek Lake and close walking distance away from Chair 7 at Wisp Ski Resort. There are two bedrooms and two bathrooms, with a rustic inspired yet delightfully modern interior. The front porch view is stunning, overlooking our farm with horses and the surrounding mountainside. Thank you for considering our home!

Top guest favorite

A mountaintop chalet features a spacious deck wrapping around the front. Large windows provide natural light to the interior while showcasing wood accents on the exterior. Surrounding greenery enhances the scenic setting.

Cabin in McHenry

5 out of 5 average rating, 17 reviews

SkyView @ Deep Creek

Relax in our mountaintop chalet with a cozy atmosphere, outdoor living space, and a saltwater hot tub. Located in the Highline Subdivision on Wisp Mountain this chalet is close to Deep Creek Lake amenities, Wisp Resort, and ASCI. Only steps away from the ski-access and a golf cart ride away from lodestone golf course.

Vacation rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Apartments

Convenient locations with everyday essentials

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Maryland ski-in/ski-out rentals

Free parking on premises

Air conditioning

Ski-in/ski-out house rentals

A welcoming living space is presented with a large red sectional couch facing a wall-mounted television. A wooden accent wall adds warmth, while a small dining area is visible. A patterned rug is placed on the carpeted floor, enhancing the cozy atmosphere.

Home in Oxon Hill

Landmark place

The exterior of the retreat features a spacious deck surrounded by lush greenery, with large windows allowing natural light to illuminate the interior. A combination of stone and wooden siding creates a harmonious blend with the natural surroundings.

Home in McHenry

5 out of 5 average rating, 4 reviews

One Ski Hill | Ski In/Ski Out + Hot Tub!

A brown dog with an expressive face is resting on a patterned purple and white cloth. A bright red cap with a blue brim sits atop its head, contrasting with the dog's fur. A light blue shoe can be seen in the background.

Home in McHenry

New place to stay

Brand New Lake House with dock

A charming cottage is shown from an outdoor perspective, featuring a large front porch with seating. Lush green landscaping surrounds the entrance, with a paved driveway leading to the house. Trees and colorful bushes add to the natural appeal of the outdoor space.

Home in McHenry

4.5 out of 5 average rating, 6 reviews

4BR Spacious dog-friendly house w/private hot tub

Home in McHenry

4.92 out of 5 average rating, 12 reviews

Stylish 5BR Home w/ Brand New 7-Seater Hot Tub

The exterior of a unique mountaintop home is framed by lush greenery, showcasing a slate roof and a prominent front entrance. Large windows reflect the clear blue sky, while a manicured lawn leads to the paved driveway.

Home in McHenry

5 out of 5 average rating, 8 reviews

Luxury! Stunning Mountaintop Home with Hot Tub

A well-lit bedroom features a spacious bed with a blue and white checked blanket. A modern television is mounted on a stand, positioned next to a geometric patterned rug. A door leads to an adjoining room, enhancing accessibility and flow.

Private room in Maugansville

5 out of 5 average rating, 20 reviews

Spacious & Comfy Private Room4

A two-story condo features a blue exterior with multiple balconies. A wooden pathway leads through a landscaped area with green shrubs and small plants. The front entrance is framed by large windows, providing natural light to the interior.

Home in McHenry

5 out of 5 average rating, 3 reviews

Mountain Light Lodge

Family-friendly, ski-in/ski-out home rentals

A spacious living area features a comfortable sofa adorned with a decorative green pillow, set against walls of natural wood. A coffee table sits centrally, with a flat-screen TV mounted nearby. The open layout leads to a dining area and kitchen visible in the background.

Townhouse in McHenry

4.5 out of 5 average rating, 8 reviews

3BR | Dogs OK | Fireplace | Fire Pit [junoplac]

Townhouse in McHenry

5 out of 5 average rating, 4 reviews

4BR | A/C | Fireplace | Grill | Hot Tub [changalt]

A spacious ski-in/ski-out home is set amidst lush greenery, featuring a two-story exterior with a combination of stone and wood. Large windows allow natural light to fill the interior, while a well-kept driveway leads to a garage. The surrounding landscape offers a blend of trees and manicured lawn.

Home in McHenry

New place to stay

Family, Friends and Fun Times | Ski In/Ski Out,

A private outdoor space features a hot tub surrounded by wooden decking. Two black chairs are positioned nearby, offering a place to relax. The backdrop consists of lush greenery, enhancing the peaceful setting.

Townhouse in McHenry

4.4 out of 5 average rating, 5 reviews

3BR | Fireplace | Hot Tub | Pool Table [skisand]

Home in McHenry

Alpine Adventure | Ski In/Ski Out, Private Hot Tub

The exterior of a multi-level townhouse is shown, featuring multiple balconies with wooden railings. A private hot tub is positioned on a wooden deck, and a grassy area is visible, providing a natural setting surrounded by trees.

Townhouse in McHenry

New place to stay

Dog Friendly Mountain Escape w/ Hot Tub

The exterior of a charming townhouse is showcased, featuring a well-manicured lawn with vibrant green grass. A wooden pathway leads toward the entrance, flanked by trees and shrubs. Balconies are visible on the upper level, hinting at additional outdoor seating options.

Townhouse in McHenry

5 out of 5 average rating, 3 reviews

Spacious townhome with private hot tub, deck, W/D

The living area features a cozy arrangement of sofas and an armchair around a wooden coffee table. Wood-paneled walls enhance the space, complemented by a round area rug. A ceiling fan and wall-mounted air conditioning unit provide comfort, while large windows invite natural light.

Townhouse in McHenry

New! Deep Creek Townhome Near Wisp w/ Fireplace

Ski-in/ski-out cabin rentals

A spacious deck features a hot tub and wooden seating, accompanied by colorful lounge chairs. The cabin exterior showcases natural wood siding, while large windows provide views of the surrounding landscape.

Cabin in McHenry

4.99 out of 5 average rating, 142 reviews

Walk to Wisp & Lake • Hot Tub • Game Room•Dogs OK!

A panoramic view of the large flat front yard is presented, leading to a serene lake. A playset stands to the left, while multiple lawn chairs are positioned by the water's edge. The setting is framed by trees, creating a peaceful atmosphere.

Cabin in McHenry

4.89 out of 5 average rating, 37 reviews

TikiBar, Hot Tub, Lakefront, Playset, Private Dock

Top guest favorite

A mountaintop chalet features a spacious deck wrapping around the front. Large windows provide natural light to the interior while showcasing wood accents on the exterior. Surrounding greenery enhances the scenic setting.

Cabin in McHenry

5 out of 5 average rating, 17 reviews

SkyView @ Deep Creek

A snow-covered landscape is visible, featuring rolling hills with ski slopes in the background. A hot tub is positioned under a wooden overhang, with steps leading up to it. Sunlight brightens the scene, creating a serene winter atmosphere.

Cabin in McHenry

4.96 out of 5 average rating, 208 reviews

All about the view

A charming log cabin is featured, set among trees with a covered porch overlooking the landscape. The structure showcases a steep gabled roof, wooden railings, and an American flag displayed on the side. Natural surroundings enhance the serene feel of the property.

Cabin in Oakland

4.88 out of 5 average rating, 413 reviews

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