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.

0 of 0 items showing

1 of 3 pages

Guest favorite

Home in Fishing Creek

5 out of 5 average rating, 38 reviews

Fishing Creek waterfront cottage

Waterfront cottage featuring a wall of floor to ceiling windows overlooking the Chesapeake Bay! Catch your own crabs, fish on our dock, relax on the deck, & watch the BEST sunsets of your life- followed by a night sky with countless stars. Hoopers Island was recently named the Best Little Town in MD. This is a laid back watermen community where the closest stoplight is 28 miles away, with NO activities for young children. (The island doesn't have the typical boardwalk, mini golf, shops etc )

Guest favorite

Farm stay in Ellerslie

5 out of 5 average rating, 40 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.

Guest favorite

Cabin in McHenry

4.96 out of 5 average rating, 24 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.

Guest favorite

Home in McHenry

4.9 out of 5 average rating, 127 reviews

Ski/in Ski/out Luxury Home Voted #1

For Summer or Winter---The Best House and LOCATION in Deep Creek Lake- Large level lawn with a sandy beach. Private dock slip. Views on both sides- across street from chairlift. Watch your family and friends ski and ride down the mountain from the glass enclosed 45' x25' open great room at the party lodge located at base of chair 5. Luxury with gourmet kitchen.- lots of room for parties. 70" flat screen, two wet bars, pool table, three indoor Jacuzzis, hot tub, fire pit--- many extras!

Guest favorite

Home in Swanton

4.97 out of 5 average rating, 150 reviews

Log Cabin at the Lake, 5300+ sq ft of fun!

Pristine log cabin lake home located in the heart of Deep Creek Lake with over 5500 sq ft. A four seasons rental with activities year around. Enjoy summer on the lake, winter skiing at the wisp or a round of golf! Not to mention the close proximity to lake and many attractions. Our home is private and serene. Perfect for couples, families and large groups; Fire pit, hot tub, pool table, arcade system, pinball, shuffleboard, wood burning fireplaces, ping pong, kids toys and board games!

Guest favorite

Townhouse in McHenry

5 out of 5 average rating, 24 reviews

4 Seasons Wisp -Ski-in-Ski-out, HotTub,Lake Access

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.

Guest favorite

Home in McHenry

4.95 out of 5 average rating, 58 reviews

Pet Friendly 5BR Chalet Ski-in-out w/ New Hot Tub

Serendipity by the slopes! Enjoy this stylish 5BR pet friendly mountain top cabin. Spacious ski in/ski out cabin is less than 100 yards from WISP chair rail 4! +EV charging for your car. In summer walk next door to ASCI adventure center with whitewater rafting and the best summer sunsets. Lake is < 5 min drive. In fall enjoy the beauty of the majestic trees and in spring enjoy the quiet serenity and peaceful views from the large windows or while relaxing in the hot tub on the patio.

Guest favorite

Cabin in McHenry

4.99 out of 5 average rating, 112 reviews

#1 Ski Cabin~Walk to Wisp~Firepit~Game RM~Hot Tub!

The perfect, five star mountain log cabin, awaits! Slippery Slope is in desirable McHenry Cove walkable to Wisp Resort. This home is near marinas, skiing, golf, restaurants & everything you'll need in McHenry. ✔TWO King suites ✔Queen suite (2 beds) ✔+2 Queen sofa beds ✔3 Bath ✔Sleeps 10 ✔Dogs OK ✔Hot Tub ✔Fire-pit ✔FAST WiFi ✔Game room- arcades & pool table ✔Coffee/tea bar ✔Stocked kitchen ✔Roku Smart TVs ✔Propane grill ✔Central heat & AC ✔Washer & dryer ✔Lake access ✔Dock (to rent)

Superhost

Home in McHenry

4.84 out of 5 average rating, 88 reviews

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 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.

Superhost

Home in McHenry

5 out of 5 average rating, 4 reviews

Luxury! Stunning Mountaintop Home with Hot Tub

Wisp Me Away is a stunning mountaintop home. The popular Eyeopener and Main Street slopes surrounding the home on either side. but if you are looking for easier slopes to get you started, you are within walking/skiing distance of chair lift 4, which will put you on several green and blue trails. You'll find jaw-dropping views of Deep Creek Lake and our rolling mountains from the back deck, main level master balcony, from the lower level patio, from the abundant windows of the home!

Guest favorite

Cottage in McHenry

4.96 out of 5 average rating, 26 reviews

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!

Guest favorite

Home in McHenry

4.94 out of 5 average rating, 290 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!