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Ski-in/Ski-out vacation rentals in Olsberg

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

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Vacation rentals for every style

Get the amount of space that is right for you

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

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

Ski-in/ski-out house rentals

Guest favorite
An aerial view of BergZauber showcases its two-story architecture, featuring traditional elements and a welcoming facade. Surrounding greenery enhances the natural setting, while outdoor seating areas with umbrellas invite relaxation. The logo is prominently displayed at the top, representing the essence of the location.
Home in Winterberg
5 out of 5 average rating, 7 reviews

Berg · See · Sauna · Creative-Offsite

Superhost
An open dining area features a large wooden table surrounded by four chairs in varying colors. A modern pendant light hangs above the table, and a television is mounted on a textured stone wall. Light wood flooring adds warmth to the inviting space.
Home in Brilon
4.66 out of 5 average rating, 32 reviews

New | Comfort Chalet | Sauna | 5 people | Skiing

Guest favorite
A cozy living area is presented with a grey sectional sofa featuring plush cushions. A wooden coffee table with a star design sits at the center, next to a decorative candle. Natural light enters through glass doors, highlighting warm wood accents and a rustic dining area.
Home in Allendorf (Eder)
5 out of 5 average rating, 7 reviews

House with forest view in Bromskirchen

Guest favorite
The exterior of a classic detached house is surrounded by lush greenery, featuring a spacious garden area. Patio furniture is visible, offering an inviting spot for relaxation. The two-story structure displays a wooden roof and windows, blending harmoniously with the natural landscape.
Home in Olsberg
4.91 out of 5 average rating, 11 reviews

House with sauna 15 min. from Winterberg and Willingen

Superhost
Home in Winterberg
4.86 out of 5 average rating, 29 reviews

Villa SKYLO, complete prime location in Winterberg!

Superhost
A spacious holiday home stands amidst lush greenery, featuring a dark roof and contrasting white walls. Tall trees provide shade, while two cyclists ride along the road in the foreground, highlighting the peaceful surroundings. A clear blue sky completes the serene outdoor setting.
Home in Medebach
4.84 out of 5 average rating, 38 reviews

Spacious, vintage holiday home with a view.

Superhost
A charming exterior of a renovated house is visible, featuring a sloped roof and a combination of wooden and dark materials. Surrounding greenery includes tall plants and pink flowering accents, creating a natural, inviting environment. A window is situated atop the wooden structure.
Home in Winterberg
4.69 out of 5 average rating, 13 reviews

Haus Ludwiges (Winterberg)

A private terrace is presented with wooden furniture, including a round table and four chairs, set amidst lush greenery. Surrounding landscape features trees and shrubs, creating a serene outdoor environment. Clear blue skies provide a bright backdrop.
Home in Winterberg
4.89 out of 5 average rating, 9 reviews

Child-friendly vacation home | Garden & trampoline

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

Guest favorite
A spacious living area is presented featuring a comfortable sectional sofa with neutral upholstery and a soft throw blanket draped casually. A wooden coffee table sits in front of the sofa, and three framed art prints are displayed on the wall above.
Apartment in Winterberg
4.95 out of 5 average rating, 20 reviews

Pistenblume Apartment - ski slope, city center

Guest favorite
A bright and modern living space features a comfortable gray sofa and a wooden coffee table adorned with a decorative plant. A dining table for six is positioned nearby, with a view of a scenic wall art piece. Large windows let in ample natural light.
Apartment in Winterberg
4.91 out of 5 average rating, 46 reviews

Winterberg Centrum apartment privet bike cellar

Guest favorite
A snow-covered path is flanked by tall evergreen trees, their branches heavy with white snow. The clear blue sky above contrasts with the tranquil winter landscape, creating a serene atmosphere. A hint of moon is visible, adding a touch of wonder to the scene.
Apartment in Willingen
5 out of 5 average rating, 22 reviews

Apartment with fantastic views

Superhost
A balcony space is furnished with a wooden dining table surrounded by four wicker chairs. A scenic view of the greenery-covered hills and nearby houses is visible, along with a pleasant blue sky and scattered clouds.
Apartment in Willingen
4.78 out of 5 average rating, 50 reviews

Quiet apartment near a forest

Guest favorite
An outdoor terrace area is visible, featuring a round table and two black chairs. A sun umbrella stands to one side, and a trellis is situated nearby. The entrance door to the holiday apartment is also visible in the background, framed by a small garden area.
Apartment in Willingen
4.72 out of 5 average rating, 109 reviews

Apartment (bedroom, living room, bath room)

Superhost
A cozy sleeping area is highlighted by a modern design featuring wood paneling and soft lighting. A spacious bed with white linens and neatly arranged towels is complemented by large windows that allow natural light to illuminate the room.
Apartment in Winterberg
4.8 out of 5 average rating, 15 reviews

Alpenflair Apartment | 100m zum Ski & Bikepark

Superhost
A dining area features a large wooden table surrounded by six dark chairs. Natural light enters through large windows dressed with striped curtains. The open layout connects to the living space, and a comfortable ambiance is created by warm lighting.
Apartment in Winterberg
5 out of 5 average rating, 6 reviews

Villa Nordhang - Apartment 3

Guest favorite
The living area features a dining table set for six, accompanied by contemporary chairs. A modern kitchen unit is positioned in the background, showcasing an oven and stylish decor. A comfortable sofa invites relaxation, and large windows offer views of the surrounding greenery.
Apartment in Winterberg
5 out of 5 average rating, 14 reviews

Deluxe Apartment for 5| Sauna & Pool |Free Parking

Ski-in/ski-out condo rentals

A well-lit room features a spacious bed with a soft throw, complemented by a television mounted on the wall. Two chairs are positioned next to a small table, with natural light flowing through large windows overlooking a balcony adorned with greenery.
Condo in Medebach
4.83 out of 5 average rating, 58 reviews

Beautiful ski and hiking domicile with south balcony

Guest favorite
A modern kitchen features a spacious countertop with a sink and kettle, surrounded by sleek cabinetry. Sunlight filters through large windows dressed in sheer curtains, illuminating the room. Kitchen appliances such as a coffee maker and microwave are neatly arranged on the shelves.
Condo in Schmallenberg
4.86 out of 5 average rating, 28 reviews

Gierse Vacation Rental

Guest favorite
A comfortable living area is shown, featuring a gray sectional sofa adorned with teal cushions. A small white coffee table is positioned in front, with decorative items placed on it. Natural light enters through a nearby window, and a tall indoor plant adds a touch of greenery to the space.
Condo in Winterberg
4.95 out of 5 average rating, 19 reviews

vacation apartment Bergpanorama - TV, parking lot

Superhost
A modern living area features a dark blue sofa with decorative cushions, accompanied by an ottoman. A round white coffee table sits on a woven rug, with tranquil artwork depicting outdoor scenes displayed on the wall. Natural light filters in through the window, accented by a soft roller blind.
Condo in Willingen
4.79 out of 5 average rating, 33 reviews

Your dream apartment in Willingen

A modern living space features a comfortable leather sofa and an upholstered armchair. A wooden coffee table sits in the center. A wall-mounted flat-screen TV displays the Netflix logo, and a collection of framed photographs decorates one wall. Natural light enters through large windows.
Condo in Winterberg
4.7 out of 5 average rating, 151 reviews

Super cozy and in the middle of nature with pool

Guest favorite
A bedroom is featured with a spacious bed dressed in white linens, complemented by neutral-toned cushions. A large mural of leaf patterns decorates the wall behind the bed. A minimalistic side table with an elegant lamp is positioned next to the bed.
Condo in Willingen
4.98 out of 5 average rating, 49 reviews

"The Nest" | Modern apartment with a view

The living and sleeping area features a light-colored sofa with blue accent pillows and a wooden table. A soft rug adds comfort to the space. In the background, a warm lamp illuminates the room beside a cozy bunk bed. Two windows allow natural light to enter.
Condo in Winterberg
4.81 out of 5 average rating, 53 reviews

The BUDE'55

Guest favorite
The living area features a spacious seating arrangement with orange accent pillows, a large rug, and a dining table. Floor-to-ceiling windows provide natural light and scenic views of the surrounding landscape. Warm lighting fixtures add a cozy touch to the atmosphere.
Condo in Schmallenberg
4.8 out of 5 average rating, 10 reviews

Apartment with a view + 50 sqm + covered balcony

Quick stats about vacation rentals that are ski-in ski-out in Olsberg

  • Total rentals

    30 properties

  • Nightly prices starting at

    R1,230 ZAR before taxes and fees

  • Total number of reviews

    900 reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

Destinations to explore