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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

Top 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 Niedersfeld
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

Neu | Komfort-Chalet | Sauna | 5-Personen | Ski

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 Assinghausen
4.91 out of 5 average rating, 11 reviews

Huis met sauna 15 min. van Winterberg en Willingen

Guest favorite
The view showcases a charming half-timbered house surrounded by lush greenery. A gravel courtyard is visible, bordered by stone and two trees. The house features a wooden facade and inviting front door, framed by climbing plants and complemented by small potted plants at its base.
Home in Balve
4.83 out of 5 average rating, 12 reviews

Altes, gemütliches Fachwerkhaus

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

Villa SKYLO, complete toplocatie 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 Küstelberg
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 Langewiese
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 Hildfeld
4.89 out of 5 average rating, 9 reviews

Kindvriendelijk vakantiehuis | Tuin & trampoline

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

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 Usseln
5 out of 5 average rating, 22 reviews

Ferienwohnung mit traumhaften Ausblick

Guest favorite
A bright sleeping area features a spacious bed with crisp linens and plush pillows. A relaxed seating option is positioned nearby. Soft lighting adds warmth to the room, while a unique angled window offers a glimpse of the outside landscape.
Apartment in Küstelberg
4.81 out of 5 average rating, 16 reviews

Apartment in Küstelberg/Nähe Winterberg

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 Stryck
4.78 out of 5 average rating, 50 reviews

Rustig appartement bij een bos

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 Eimelrod
4.72 out of 5 average rating, 109 reviews

Apartment (bedroom, living room, bath room)

Top guest favorite
A modern living space is depicted featuring a black dining table set for four, with glasses and a wine bottle. Light wood flooring contrasts with the muted wall color. A comfortable seating area, TV, and greenery are visible, framed by large windows offering scenic views.
Apartment in Siedlinghausen
4.96 out of 5 average rating, 134 reviews

Panoramawohnung mit tollem Ausblick ✨

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

Guest favorite
A cozy living area is displayed, featuring two soft chairs on a patterned rug. Exposed wooden beams highlight the ceiling, while a large television is mounted on the wall. In the background, wooden storage cabinets and a comfortable leather sofa are visible.
Apartment in Altastenberg
5 out of 5 average rating, 14 reviews

Gemütliches Ferienhaus in Winterberg Altastenberg

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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 Küstelberg
4.83 out of 5 average rating, 58 reviews

Schönes Ski- und Wanderdomizil mit Südbalkon

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 Bödefeld
4.86 out of 5 average rating, 28 reviews

Ferienwohnung Gierse

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

Deine Traumwohnung 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, 48 reviews

"The Nest" | Moderne Wohnung mit Ausblick

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

Die 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 Nordenau
4.8 out of 5 average rating, 10 reviews

Wohnung mit Weitblick + 50qm + überdachter Balkon

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

  • Total rentals

    30 properties

  • Nightly prices starting at

    R1,243 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