Ski-in/Ski-out holiday rentals in Olsberg

A bright living area features a large, light-colored sectional sofa adorned with an accent pillow. A round wooden coffee table rests on a circular area rug, and a decorative plant adds greenery. Large glass doors lead to a balcony, framed by sheer drapes.

4.92 out of 5 average rating, 104 reviews

Apartment Tokio + Sauna, 100 m to Ski and Bikepark

Diese moderne 70 m² Ferienwohnung inkl. privater Sauna liegt direkt an der Skipiste und dem Bikepark – ideal für einen Aktivurlaub mit Entspannung. Zwei Schlafzimmer mit Boxspringbetten und eine Schlafcouch bieten Platz für bis zu 6 Personen. Die voll ausgestattete Küche, ein stilvolles Bad mit Dusche und zwei Balkone schaffen eine gemütliche Atmosphäre. WLAN, Netflix und Waipu-TV sind inklusive. Ein Tiefgaragenstellplatz steht dir ebenfalls zur Verfügung – für einen rundum sorglosen Aufenthalt.

5 out of 5 average rating, 9 reviews

Flat in Willingen

*| Chalet-Suite |* by Meis I Willingen (Upland)

Welcome to the chalet suite in the heart of Willingen – pure relaxation awaits! This stylishly furnished suite combines the charm of the region with modern comforts and offers everything you need for a relaxing stay: → King-size bed for a restful sleep → Smart TV + comfortable seating areas → Free Wi-Fi → Parking included + private bicycle storage → Fully equipped kitchen with automatic coffee machine + dishwasher → Bathroom with modern shower → Washing machine + large balcony for relaxation

A modern house with a sloped roof is set in a landscaped garden. Large windows reflect the sky, while a patio area with seating is visible in front. Lush greenery surrounds the property, with additional structures on the property, contributing to a spacious outdoor environment.

4.87 out of 5 average rating, 190 reviews

Hüttenzauber - schönes Ferienhaus

Das Ferienhaus ist ca. 90qm groß und bietet Platz für 2-6 Personen, verteilt auf 3 Schlafräume. Im EG befindet sich der modern eingerichtete Wohn-Essraum mit offener Küche, einem Pelletkamin, ein Schlafzimmer und das Duschbad. Die Küche bietet mit Spülmaschine, Backofen, Kaffeemaschine und Toaster alle Annehmlichkeiten. Im OG befinden sich ein großes Schlafzimmer mit Panoramafenster und eine extra Schlafcouch. Die 2 Einzelbetten im Vorraum können zu einem 160er Bett zusammen gebaut werden

4.98 out of 5 average rating, 106 reviews

Apartment Sunlife Winterberg 4**** Sterne (NEU)

Unsere modern ausgestattete Ferienwohnung hat 68m² und ist für 1-5 Personen ausgelegt. Die Wohnung hat: 2 Doppelzimmer mit Boxspringbett 1 Wohn-& Esszimmer mit Schlafsofa 1 Küche mit Spülmaschine, Backofen, Herd, Kühlschrank, Gefrierschrank, Mikrowelle... 1 Badezimmer 1 Flur 1 große Terrasse 2 Parkplätze 1 Tresor / Safe WLAN Ausstattung für die Kids: 2 Reisebetten 2 Hochstühle 1 Wickeltisch mit Windeltonne 1 Babywanne 1 Rausfallgitter 1 Toilettensitz 1 Babyphone 1 Krabbeldecke Spielzeug….

4.98 out of 5 average rating, 118 reviews

A warm interior of a sauna features wooden benches and a window showcasing a sunset over trees. A wood-burning stove stands prominently, providing comfort. Sunlight filters through the structure, creating a serene and inviting atmosphere.

Cabin in Willingen

„Black+Beauty“ die Design-Hütte mit Sauna

Neue Location direkt am Uplandsteig. In dieser gemütlichen Hütte kannst du die Aussicht und Stille genießen - am Kaminofen entspannen - eine LP auflegen…Die Sonne strahlt den ganzen Tag durch die großen Fenster. Idealer Ausgangspunkt zum Wandern, Biken und Skifahren. Tolle Lage am Rand von Willingen/Usseln. Restaurants, Graf Stollberghütte und den Skywalk kannst du zu Fuß erreichen. Mit schicker Spiegelsauna im Garten. Black+Beauty der Wohlfühlort in der Natur - aktiv sein u. auftanken.

4.94 out of 5 average rating, 358 reviews

The exterior of a black vacation home features a prominent chimney and large windows that allow natural light inside. Surrounding greenery includes a lush bush and a well-maintained garden, providing a serene outdoor ambiance.

Cottage in Willingen

Das kleine Schwarze

Das kleine Schwarze! Ein charmantes Ferienhaus auf dem Musenberg. Ein wunderschöner bunt angelegter Bauerngarten empfängt die Gäste. Die überdachte Terrasse ladet zum Genießen draußen ein. Zum grillen und kochen nutzen Sie den Outdoor Ofen. (Frühjahr bis Herbst) Das hell bis ins Dach ausgebaute Haus ist mit viel liebe eingerichtet. Erleben sie entspannte Tage inmitten der Natur! Wandern und Langlauf direkt vor der Tür. Haustiere sind auf Anfrage willkommen. Maximal 1 Hund.

Holiday home in Winterberg

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.

4.98 out of 5 average rating, 110 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

A balcony is shown with a small table and two lightweight chairs, overlooking a wide green valley and distant hills. A large umbrella provides shade. The scene is bright, with a clear sky and soft clouds, enhancing the sense of openness.

4.92 out of 5 average rating, 144 reviews

Wohnung mit traumhaftem Blick

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!

4.97 out of 5 average rating, 319 reviews

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

Gemütliches Chalet inclusive HotTub und Sauna

Wir bieten ein gemütliches Chalet inclusive Hottub und Sauna , im Feriendorf Bromskirchen an. Ein wunderschönes Waldgrundstück in absoluter Privatsphäre und Stille. Im Winter kannst du dich nach einem Tag im Schnee am Abend in der Sauna und im Hot Tub entspannen. . Für Naturliebhaber lädt der Sommer zu zahlreichen Wanderwege oder zum chillen auf dem neuen Sonnendeck mit kühlem Badefass ein. Unser Grundstück ist offen , es wird nur durch Pflanzen umgrenzt!

4.67 out of 5 average rating, 69 reviews

A spacious holiday home is nestled on a gently sloping green hillside, surrounded by well-maintained shrubbery and colorful flowerbeds. The structure features a mix of wood and light-colored exterior with multiple windows, allowing natural light to brighten the interiors.

Home in Olsberg

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.

4.97 out of 5 average rating, 61 reviews

Wellness & Family Retreat in a 5-Star Holiday Home

Your wellness getaway in Winterberg! Our 5-star holiday home accommodates up to 8 guests. Relax in the panoramic sauna with direct forest views or unwind in the hot tub on the large terrace. A cozy fireplace and two wellness areas guarantee ultimate relaxation. Great for families too: a garden playground and a kids' lounge keep the little ones happy. High-end, thoughtful, and perfect for your premium retreat in the Sauerland region.

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.

4.88 out of 5 average rating, 187 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.

Popular amenities for Olsberg ski-in/out rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Ski-in/out house rentals

4.91 out of 5 average rating, 226 reviews

A spacious outdoor terrace is featured, with wooden lounge chairs positioned opposite a rustic wooden dining table. The setting is framed by stone elements and lush greenery, providing a serene space for relaxation. A heart-shaped decoration adds a touch of charm.

Home in Willingen

Waldchalet in Willingen

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

4.69 out of 5 average rating, 39 reviews

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

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

4.8 out of 5 average rating, 15 reviews

Huis met sauna 15 min. van Winterberg en Willingen

The chalet exterior is illuminated against the evening sky, featuring a modern design with large windows. A gentle slope leads to the entrance, bordered by greenery. Warm lights highlight architectural details, inviting relaxation in the tranquil setting.

5 out of 5 average rating, 8 reviews

"Die Chalets Herzenssache" - Chalet Lebenskunst

5 out of 5 average rating, 6 reviews

The exterior of the house is depicted, featuring a modern design with large windows and balconies. A shaded outdoor dining area with several chairs and a table is visible, accompanied by a charcoal grill. A well-maintained lawn frames the patio space.

Home in Diemelsee

Luxus Ferienhaus am See

The exterior of the villa features a modern roof and a well-maintained facade with light-colored walls. Two windows on either side have flower boxes filled with blooming flowers, while a welcoming entrance with a porch leads into the home.

4.88 out of 5 average rating, 33 reviews

Villa SKYLO, complete toplocatie in Winterberg !

4.73 out of 5 average rating, 22 reviews

Chalet zur Postwiese

4.95 out of 5 average rating, 22 reviews

Family Home Winterberg: Ruimte, Natuur & Uitzicht

Family-friendly, ski-in/out home rentals

4.9 out of 5 average rating, 31 reviews

Sunshine Lodge

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.

4.97 out of 5 average rating, 30 reviews

Pistenblume Apartment - ski slope, city center

4.9 out of 5 average rating, 52 reviews

Winterberg Centrum apartment privet bike cellar

4.86 out of 5 average rating, 29 reviews

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.

Flat in Medebach

Apartment in Küstelberg/Nähe Winterberg

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.

4.79 out of 5 average rating, 19 reviews

Alpenflair Apartment | 100m zum Ski & Bikepark

4.94 out of 5 average rating, 16 reviews

"Aktive Auszeit" - Ski, Bike, Hike & Relax

A modern living area is showcased, featuring a spacious grey sectional sofa adorned with bright yellow cushions. Artwork is displayed on the wall, while a small plant rests on a rustic side table. Natural light filters in through the window, enhancing the cozy ambiance.

5 out of 5 average rating, 25 reviews

Hutstyle - *Direct piste access*SNES*Parking

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.

4.97 out of 5 average rating, 36 reviews

Deluxe Apartment for 5| Sauna & Pool |Free Parking

Ski-in/out apartment 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.

Apartment in Medebach

4.81 out of 5 average rating, 64 reviews

Schönes Ski- und Wanderdomizil mit Südbalkon

5 out of 5 average rating, 3 reviews

Apartment Forest Ski & Bikepark

Apartment in Schmallenberg

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.

4.88 out of 5 average rating, 48 reviews

Ferienwohnung Gierse

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.

4.9 out of 5 average rating, 21 reviews

Bergpanorama – Family & Bike | 5 min. to "Kappe"

4.99 out of 5 average rating, 70 reviews

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.

Apartment in Willingen

"The Nest" | Moderne Wohnung mit Ausblick

Apartment in Schmallenberg

4.83 out of 5 average rating, 23 reviews

Wohnung mit Weitblick + 50qm + überdachter Balkon

Apartment in Olsberg

4.6 out of 5 average rating, 10 reviews

Ferienwohnung im schönen Sauerland

A spacious sleeping area features a large bed with gray bedding and neatly arranged towels. Above, a decorative light fixture is showcased, while a freestanding bathtub is positioned nearby. Natural light filters in softly, highlighting the wooden beams and flooring.