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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

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 Bromskirchen
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 Assinghausen
4.91 out of 5 average rating, 11 reviews

House with sauna 15 min. from Winterberg and 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
4.85 out of 5 average rating, 13 reviews

Old, cozy half-timbered house

Superhost
Home in Neuastenberg
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 Küstelberg
4.85 out of 5 average rating, 39 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
4.71 out of 5 average rating, 14 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

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, 21 reviews

Pistenblume Apartment - ski slope, city center

Superhost
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/near Winterberg

Guest favorite
The contemporary building features multiple balconies with wooden accents, overlooking a colorful array of blooming flowers. The vibrant purple lupines and other wildflowers fill the foreground, enhancing the natural appeal of the surrounding landscape under clear blue skies.
Apartment in Neuastenberg
4.87 out of 5 average rating, 86 reviews

Luxury apartment with garden and unique view!

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, 51 reviews

Quiet apartment near a forest

Superhost
A wooden chalet is visible, nestled in a serene landscape. A spacious patio with seating arrangements overlooks the lush, green garden. Surrounding trees provide natural shade, while the mountain scenery in the background complements the tranquil ambiance.
Cabin in Willingen
4.79 out of 5 average rating, 29 reviews

Chalet with fireplace in prime location Willingen.

Superhost
A winter landscape captures snow-covered rooftops of homes nestled in a valley. Rolling hills are barely visible in the distance through a soft blanket of fog under a clear blue sky.
Apartment in Winterberg
4.79 out of 5 average rating, 19 reviews

Winterberg Centrum1 with private bicycle storage

Guest favorite
A charming chalet is set against a snowy landscape, featuring a sloped roof and dark wooden accents. A clear pathway leads to the front door, flanked by snow-covered shrubs. Bright blue skies contrast with the tranquil environment, emphasizing the inviting exterior.
Chalet in Neuastenberg
4.89 out of 5 average rating, 47 reviews

GENIETEN EVE's CHALET NEUASTENBERG

Superhost
A modern living space is divided into a cozy seating area with a grey sofa and a stylish dining table set for four. Large windows provide ample natural light, and a balcony is visible in the background, creating a bright and inviting atmosphere.
Apartment in Winterberg
4.67 out of 5 average rating, 138 reviews

Erlebnisberg Winterberg vacation home / 2-4 people

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

Beautiful ski and hiking domicile with south balcony

A bright seating area features a black chair beside a warm wooden side table. Large windows allow ample natural light, offering views of the landscaped exterior. Wooden cabinetry provides storage and displays decorative items. A cozy blanket and a small lamp complete the inviting setup.
Condo in Stryck
4.5 out of 5 average rating, 36 reviews

Chic apartment for 2 people

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, 29 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, 50 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

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

  • Total rentals

    30 properties

  • Nightly prices starting at

    G$14,641 GYD 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