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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.

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Top guest favorite
Apartment in Winterberg
5 out of 5 average rating, 15 reviews

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!

Top guest favorite
The bathroom features wooden accents on the walls, creating a warm atmosphere. A walk-in shower with a glass enclosure is present alongside a modern toilet. Natural light fills the space through a window that overlooks greenery, complemented by a small indoor plant on the sill.
Home in Hilchenbach
4.97 out of 5 average rating, 110 reviews

Apartment Broche, vacation from everyday life

Cozy apartment since September 2017 in a very quietly located former farmhouse on the edge of the forest. If you are looking for hustle and bustle, you will not find it here. However, if you want to switch off and are looking for relaxation, you have come to the right place. Certified by the DTV with 3 stars. If desired, the refrigerator (for a fee) can be filled. In the garden there is a spacious garden house, which we also make available to our guests by arrangement.

Guest favorite
A modern bathroom features a walk-in shower with a rain showerhead and stylish cabinetry. A private balcony displays a hammock, inviting relaxation amidst greenery. The cozy living area includes a gray sofa, a wooden coffee table, and artwork on a light wall. A sauna is equipped with wooden seating and complimentary towels.
Vacation home in Winterberg
4.98 out of 5 average rating, 95 reviews

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

Top guest favorite
The living area features a comfortable couch arranged facing a flat-screen TV. A dining table with dark leather chairs sits nearby. Large windows allow natural light to fill the space, showcasing views of the surrounding landscape. Decorative items and artwork add character to the room.
Condo in Neuastenberg
4.92 out of 5 average rating, 134 reviews

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!

Guest favorite
A cozy cabin with a dark exterior sits amid vibrant greenery and blooming lilacs. A wooden fence surrounds the property, and a clear blue sky adds to the serene atmosphere. The background features rolling hills and a dense forest, completing the tranquil outdoor setting.
Cabin in Willingen
4.99 out of 5 average rating, 105 reviews

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.

Guest favorite
A dining table is set with white plates and glasses, surrounded by black placemats. Soft natural light filters through large windows, illuminating the space. In the background, a cozy seating area is visible, featuring dark furniture and decorative elements.
Apartment in Winterberg
4.88 out of 5 average rating, 183 reviews

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.

Top guest favorite
A dark wooden chalet is nestled among lush greenery, with a gently sloping lawn leading towards it. Tall trees flank the property, providing a sense of privacy. The modern structure features a large glass wall, allowing natural light to illuminate the interior.
Chalet in Bromskirchen
4.97 out of 5 average rating, 294 reviews

Cozy chalet including hot tub and sauna

We offer a cozy chalet including hot tub and sauna, in the holiday village of Bromskirchen. A beautiful forest property in absolute privacy and tranquility. In winter, you can relax in the sauna and hot tub in the evening after a day in the snow. For nature lovers, summer invites you to numerous hiking trails or to chill on the new sun deck with a cool bathing barrel. Our property is open , it is only bordered by plants!

Guest favorite
Chalet in Bromskirchen
4.92 out of 5 average rating, 179 reviews

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.

Superhost
A living area features a gray sofa adorned with yellow cushions, paired with a small side table and a stylish floor lamp. A wooden dining table with black chairs accommodates gatherings. A large TV is mounted on the wall, set against a patterned accent backdrop.
Apartment in Brilon
4.79 out of 5 average rating, 38 reviews

Comfort apartment | Sauna | 4 people | 4 stars

Comfortable apartment in the immediate vicinity of the ski slope. The 51 sqm apartment is well-equipped and offers everything you need. → Box spring beds → large living/dining area → Flat screen and smart TV → Kitchen with coffee machine → Use of the 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

Superhost
A cozy studio apartment features a spacious bed with a floral patterned headboard. A small dining table is set for two, complemented by two upholstered chairs. Large windows provide views of outside greenery, enhancing the bright and open feel of the space.
Vacation home in Winterberg
4.89 out of 5 average rating, 150 reviews

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.

Guest favorite
A yurt is illuminated at dusk, showcasing a wooden door and a chimney. Surrounding the yurt, natural grass and stones create a rustic atmosphere. Wooden seating options, including benches, are positioned nearby, offering a space for relaxation amid serene natural surroundings.
Yurt in Olsberg
4.94 out of 5 average rating, 158 reviews

* 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.

Guest favorite
A cozy seating area features a woven sofa with soft cushions and a small wooden table. Decorative elements include a plant and a patterned rug, creating an inviting outdoor space. Sunlight reflects off the windows, enhancing the serene environment.
Apartment in Niedersfeld
4.95 out of 5 average rating, 97 reviews

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

When is the best time to visit Olsberg?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$27,611 GYDG$27,401 GYDG$24,264 GYDG$26,356 GYDG$25,937 GYDG$26,146 GYDG$26,356 GYDG$25,101 GYDG$25,519 GYDG$25,101 GYDG$23,846 GYDG$30,539 GYD
Avg. temp-2°C-1°C1°C6°C10°C13°C15°C15°C11°C7°C2°C-1°C

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

  • Total vacation rentals

    Explore 20 vacation rentals in Olsberg

  • Nightly prices starting at

    Olsberg vacation rentals start at G$12,550 GYD per night before taxes and fees

  • Verified guest reviews

    Over 840 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Olsberg vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Olsberg rentals

  • 4.8 Average rating

    Olsberg stays are highly rated by guests—averaging 4.8 out of 5!