Ski-in/Ski-out vacation rentals in Maryland

4.89 out of 5 average rating, 432 reviews

The log cabin is situated in a snowy landscape, showcasing a warm glow from its illuminated windows. The covered porch features a railing that extends across the front, surrounded by trees that are dusted with snow, creating a cozy and inviting scene.

Cabin in Oakland

Winter is Coming

Your mountain vacation will be filled with magical memories when you choose to stay in this spectacular 3 master suite bedroom log home. You and your guests will immediately feel at home when you step through the front door. Luxurious décor compliments the gorgeous hardwood floors giving the cabin a warm and inviting feel. Cuddle up in front of the wood fireplace after an invigorating day of snowboarding at nearby Wisp Resort or enjoy your morning coffee on the covered porch swing. Pet 50extra

4.98 out of 5 average rating, 165 reviews

An inviting outdoor deck features a hot tub beside a wooden railing. Various recreational amenities are showcased, including a skee-ball machine, an arcade game, and a pool table. A pathway leads to the lake and dock area, surrounded by scenic natural views.

Cabin in McHenry

SAVE $•Walk to Wisp!~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 - Deposit HOLD req'd

4.94 out of 5 average rating, 70 reviews

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

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.

4.94 out of 5 average rating, 66 reviews

A comfortable living room is presented with plush, reclining couches facing a large smart TV. Natural light filters through sliding glass doors that open to a patio. A decorative stone wall adds texture, complemented by a coffee table and a small indoor plant.

Townhouse in McHenry

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.

5 out of 5 average rating, 5 reviews

Cabin in McHenry

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!

5 out of 5 average rating, 40 reviews

A modern living area is highlighted by a stone fireplace and large windows offering views of the surrounding nature. Comfortable seating arrangements include a gray sofa and loveseats, while a wooden coffee table centers the space. Decorative elements feature a ceiling fan and a wall-mounted TV.

Townhouse in McHenry

4 Seasons Wisp- ski in ski out, Hot Tub

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.

A spacious lodge-style home is set against a vibrant sunset, featuring a mix of natural wood and stone elements. Large windows illuminate the structure, revealing a cozy interior. A tall tree stands prominently in the yard, enhancing the outdoor setting.

4.91 out of 5 average rating, 148 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 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.

Superhost

Cabin in McHenry

4.88 out of 5 average rating, 41 reviews

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.

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.

4.95 out of 5 average rating, 42 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!

4.9 out of 5 average rating, 73 reviews

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

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 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.

4.95 out of 5 average rating, 56 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 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!!!

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.