
Ski-in/Ski-out vacation rentals in Olsberg
Find and book unique ski-in/ski-out homes on Airbnb
Top-rated ski-in/ski-out rentals in Olsberg
Guests agree: these ski-in/ski-out homes are highly rated for location, cleanliness, and more.

NEU: Hejm Mountain Vibe & Design
Willkommen bei Hejm Apart im Herzen von Winterberg! Unsere stylische 50 m² Ferienwohnung im Sportstower bietet den perfekten Rückzugsort nach Action-Tagen auf dem Bike, beim Wandern oder Skifahren. Mit elektrischem Kamin, Balkon mit Hängesesseln, voll ausgestatteter Küche und gemütlichem Doppelbett fühlt ihr euch sofort wie zuhause. Nur wenige Meter von der Kappe, Bikepark und Skigebiet entfernt – euer Abenteuer beginnt hier! Bucht jetzt und erlebt Winterberg auf eine außergewöhnliche Art!

Design Apartment - Ski. Bike. Sauna.
Welcome to our beautiful apartment in Winterberg! This cozy and newly renovated apartment can accommodate up to 4 people and is located directly at the ski slope and bike park. The location is perfect for those looking for central accommodation near the main attractions. . private sauna . private balcony with hammock . newly renovated 2023 . 100m to the bike park/ski slope . fireplace (elect.) . King size box spring bed . free, fast WIFI . Bicycle/ski cellar

Apartment with fantastic views
Experience the perfect holiday with a breathtaking view of the valley and the slopes from our apartment. This cozy apartment is ideal for 2 people and offers a living room and bedroom with panoramic views. In summer you can reach the Kahler Asten in just 15 minutes on foot, while in winter you are right on the slopes. The apartment has a fully equipped kitchen and a bathroom with a bathtub and hairdryer. Discover the perfect retreat for your next vacation!

Sauerland Panorama Vakantiehuis in Elpe (Olsberg)
Luxury holiday home (sleeps 7) by stream. Large garden and panoramic views, near Winterberg. Child-friendly house with large living room with wood-burning stove, upstairs 3 spacious bedrooms, 2 bathrooms. Table tennis and bicycles in garage. Energy surcharge applies in October-April. From 11/2/2025, the downstairs apartment (1-4 persons) plus infrared sauna is not automatically available anymore for rental; only for previous bookings and on request.

The little black dress
The little black one! A charming vacation home on the Musenberg. A beautiful colorful farm garden welcomes the guests. The covered patio invites you to enjoy outside. For grilling and cooking, use the outdoor oven. (spring to autumn) The bright house, built into the roof, is furnished with a lot of love. Experience relaxing days surrounded by nature! Hiking and cross-country skiing right outside the door. Pets are welcome upon request. Maximum 1 dog.

Comfort apartment | Sauna | 4 people | 4 stars
Feel-good apartment with large terrace & access to the garden in the immediate vicinity of the ski slope. The 64 sqm apartment is well-equipped and offers everything you need. → Box spring bed → large lounge/dining area with sofa bed → Flat screen and smart TV → Kitchen with coffee machine → Terrace & large garden → own parking space → sauna → directly on the ski slope → quiet and picturesque, yet just 15 minutes on foot for the historic old town

Black+Beauty Design Cabin in Willingen / Sauerland
New location right on the Uplandsteig. At this cozy cabin you can enjoy the view and silence - relax by the fireplace - put on an LP…The sun shines through the large window all day. Ideal starting point for hiking, biking and skiing. Great location on the edge of Willingen/Usseln. You can walk to restaurants, Graf Stollberghütte and the Skywalk. With chic mirror sauna in the garden. Black+beauty the feel-good place in nature - be active & refuel.

Holiday Appartement Winterberg - Bike park nearby
Ferienappartement Winterberg - In ski boots directly into the ski lift carousel! By bike directly to the bike park! Cosy holiday flat that is perfect for your holiday in the immediate vicinity of the ski slope and the bike park. The vibrant centre of Winterberg-Stadt can be reached on foot in 15 minutes. Our holiday flat offers space for up to 4 people and has a bedroom, a living room with a fully equipped kitchen and a bathroom.

Your place to feel good - Villa Milan log cabin
Your feel-good place right by the forest. A true paradise for nature lovers, hikers, mountain bikers, and winter sports enthusiasts. The cottage is located at 600 m altitude, in the middle of a picturesque landscape. Pure peace and relaxation, where fox and rabbit say good night. Villa Milan is a great base for all kinds of activities. Various recommendations and tips are available in the house.

AparmentRIO🌴Netflix❤️100m to Ski⛷ PlayStation4 ✔️
Die Wohnung, ca. 35 qm ist einem dschungelartigen Stil gehalten. Die Einrichtung überzeugt durch einen trendigen Style und frischen Farben, damit die Feriengäste sich wohl fühlen. In der Wohnung ist Platz für 2 Erwachsene. Das Apartment liegt direkt an der Skipiste Kahler Asten. Zur Innenstadt von Winterberg könnt ihr in ca. 2 Minuten mit dem Auto hinfahren.

* Adventure overnight stay in one of our yurts *
Watch the starry sky from bed. Enjoy the sounds of nature when you stay in this unique place. A living space without corners and edges, to relax and experience time together. The yurts are located on a 2500 sqm nature reserve with a lake and view of the natural monument Bruchhauser Steine.

Wi-Fi, 72 m², Nature, Cozy, Lake, Glücksklee 4YOU
Unsere gemütliche Ferienwohnung liegt in Niedersfeld, einem schönen und ruhigen Vorort von Winterberg. Auf der östlich gelegenen sonnen reichen Bergseite oberhalb der Kerngemeinde Niedersfeld, wohnst du in einer modern eingerichteten Ferienwohnung auf 573 Höhenmetern.
Popular amenities for Olsberg ski-in/ski-out rentals
Ski-in/ski-out house rentals

Hüttenzauber - lovely vacation home

Berg · See · Sauna · Creative-Offsite

House with forest view in Bromskirchen

House with sauna 15 min. from Winterberg and Willingen

Villa SKYLO, complete prime location in Winterberg!

Spacious, vintage holiday home with a view.

Haus Ludwiges (Winterberg)

Child-friendly vacation home | Garden & trampoline
Family-friendly, ski-in/ski-out home rentals

Pistenblume Apartment - ski slope, city center

Apartment in Küstelberg/near Winterberg

Quiet apartment near a forest

Luxury apartment with garden and unique view!

Alpinlodge Winterberg

Old, cozy half-timbered house

Apartment (bedroom, living room, bath room)

Beautiful living on the Sauerland Höhenflug
Ski-in/ski-out condo rentals

Beautiful ski and hiking domicile with south balcony

Gierse Vacation Rental

vacation apartment Bergpanorama - TV, parking lot

Your dream apartment in Willingen

Super cozy and in the middle of nature with pool

"The Nest" | Modern apartment with a view

Ski slopes and pedals: Your XL Bude 08

The BUDE'55
Quick stats about vacation rentals that are ski-in ski-out in Olsberg
Total rentals
20 properties
Nightly prices starting at
ﺩ.ﺇ220 before taxes and fees
Total number of reviews
840 reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
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