Ski-in/Ski-out holiday rentals in Winterberg

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, 124 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.

4.96 out of 5 average rating, 25 reviews

Luxe kidsproof vakantiehuis Winterberg + uitzicht

Goldilocks Chalet is een warm familiechalet, rustig gelegen in het Heidedorf vlak bij Winterberg 🌿. Je hebt er veel privacy en vrij uitzicht, terwijl je in ongeveer 10 autominuten bij de skiliften, restaurants en het centrum bent. Wij hebben het chalet ingericht met gezinnen in gedachten: de bedden zijn opgemaakt en speelgoed, trampoline, tafelvoetbal, babybed en kinderstoel staan al klaar 🧸. Binnen vind je een complete keuken met Bora-inductie, een houtkachel en een fijne Wintergarten.

5.0 out of 5 average rating, 66 reviews

A spacious living area is furnished with a large sectional sofa and a comfortable armchair. Natural light filters through the sheer curtains, highlighting artwork on the walls. A rustic coffee table sits in the center, complemented by a soft area rug beneath.

Cottage in Winterberg

"Leo´s Cottage" Erholung im Natur- und Skigebiet

Unser gemütliches Cottage befindet sich mitten im Natur- und Skigebiet Postwiese in Winterberg. Wir haben unserem kleinen Haus, mit viel Liebe, neues Leben eingehaucht. Ein Familienprojekt zwischen Mutter und Sohn, welches wir gerne mit Euch teilen. Das Ferienhaus lädt ein zu lauschigen Abenden vor dem Pelletofen, ein Gläschen Wein auf der Terrasse, Frühstücken im Sonnenschein u.v.m.. Aber auch Aktivitäten wie z.B. Wandern, Ski fahren, Rodeln, Mountainbiking und der Astenkick warten auf Euch.

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, 197 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

4.97 out of 5 average rating, 116 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….

4.92 out of 5 average rating, 59 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!

4.96 out of 5 average rating, 57 reviews

A spacious living area features a modern wood-burning stove with a black pipe, opposite a cozy green lounge sofa. A natural wood coffee table sits on a light rug, complemented by large windows that provide access to outdoor views. Subtle mountain-themed decor is visible on the wall.

Chalet in Winterberg

PanoramaChalet Winterberg

Panorama in the open-plan living/cooking area through large window fronts in the kitchen or by the fireplace. Everything is available, from a fully automatic coffee machine to a waffle iron. The upper floor offers three bedrooms with box-spring beds for 6 people. The bathroom has a free-standing bath and a walk-in shower. Park in the carport, store bikes, skis and boards in the lockable room and enjoy the fantastic view from the terrace with gas barbecue and garden. Cosy panoramic sauna

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.

4.97 out of 5 average rating, 31 reviews

Spacious Deluxe Apartment with Sauna H1 Winterberg

Modern Holiday Apartment H1 in Winterberg Züschen Our fully renovated holiday apartment (completed in 2024) offers 165 m² of comfort for up to 8 guests – ideal for families and friends! It is located in the picturesque district of Züschen, with unobstructed views of the Hochsauerland mountains and a charming stream nearby. Just a few minutes away, you’ll find a wide range of leisure activities, including the large Winterberg ski area, bike park, summer toboggan run, and much more.

4.97 out of 5 average rating, 63 reviews

Holiday Home for 8 · Sauna, Hot Tub, Skiing

A special setting for your special occasion – a milestone birthday or the yearly reunion of eight friends. Winterberg lies at 700 metres, and from November it turns white, with snow or frost on the trees. You go skiing or walk through the white forest. Then you come back to our wellness house, which is yours alone for these days: barrel sauna in the garden, wood-fired hot tub, salt room indoors. Outside the air is cold, the water reaches 38 degrees, and inside the fire is burning.

Cottage in Willingen (Upland)

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.

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.

4.95 out of 5 average rating, 377 reviews

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.

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

4.97 out of 5 average rating, 119 reviews

5.0 out of 5 average rating, 10 reviews

Apartment Mountain Ski & Bikepark

Welcome to your cozy retreat! Our 50 m² apartment with a balcony on Kapperundweg in Winterberg offers space for up to 4 guests – ideal for couples, families, or groups of friends. You can look forward to a comfortable home with all the amenities you need – modern furnishings and personal touches make every stay special. 🏡 Feel right at home and add our listing to your wishlist ❤️ so you can easily find it again when planning your trip!

Popular amenities for Winterberg ski-in/ski-out rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Ski-in/ski-out house rentals

4.98 out of 5 average rating, 120 reviews

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

Ferienwohnung Broche, Urlaub vom Alltag

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.

5.0 out of 5 average rating, 10 reviews

"Die Chalets Herzenssache" - Chalet Lebenskunst

5.0 out of 5 average rating, 5 reviews

Haus am Wald

A charming house is depicted with a sloped roof and large front windows. Surrounding green grass is visible, along with budding bushes. An outdoor seating area featuring an orange umbrella and multiple chairs can be seen in the background, enhancing the outdoor space.

4.77 out of 5 average rating, 61 reviews

Traumhütte zum Ausspannen

5.0 out of 5 average rating, 6 reviews

Ferienhaus Sternenblick

5.0 out of 5 average rating, 16 reviews

Home in Schmallenberg

Unser Anwesen in Bödefeld

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.

4.83 out of 5 average rating, 36 reviews

Villa SKYLO, complete toplocatie in Winterberg !

A light-filled living area features a modern fireplace and a wall-mounted television. Two comfortable chairs are positioned near a minimalist coffee table. Large glass doors allow views of the outdoors, while soft curtains frame the windows, enhancing the room's spacious feel.

4.83 out of 5 average rating, 12 reviews

Stijlvolle villa nabij Winterberg

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

4.76 out of 5 average rating, 42 reviews

Snowflake | Next to Bike Park + Ski Slopes

4.89 out of 5 average rating, 9 reviews

Osternest - mit Pool & Sauna & WLAN nahe Skilift

A charming house is set among lush greenery, featuring a well-maintained garden with colorful flowers, including pink blooms and white ground cover. Large windows provide ample natural light, and a sloped lawn enhances the landscape around the property.

4.99 out of 5 average rating, 97 reviews

FeWo Natali

A cozy sitting area is arranged with two stylish armchairs adorned with patterned cushions. A small side table holds a book and a candle. A wooden shelving unit displays decorative items, while a rustic cabinet offers additional storage. Soft lighting creates a gentle ambiance.

4.91 out of 5 average rating, 76 reviews

FeWo Gipfelglück zwischen Bikepark & Skipiste

4.93 out of 5 average rating, 29 reviews

Guesthouse in Winterberg

BergZeit Karles|bei Winterberg-Dein Lieblingsplatz

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.

4.83 out of 5 average rating, 35 reviews

Winterberg Centrum1 with private bicycle storage

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.

4.94 out of 5 average rating, 35 reviews

Pistenblume Apartment - ski slope, city center

4.95 out of 5 average rating, 39 reviews

Best View Winterberg - Kleines Studioapartment

Ski-in/ski-out condo rentals

Condo in Willingen (Upland)

A well-maintained garden is shown, featuring lush green grass and trees. A modern two-story building stands prominently against a clear blue sky. Walking paths lead through the landscape, with a stone border outlining a small area of foliage.

Willingen (Upland) - Ferienwohnung

4.91 out of 5 average rating, 178 reviews

5.0 out of 5 average rating, 24 reviews

Ferienwohnung Bergzauber Sauna Bikerpark Ski

A modern living space features a comfortable sofa and a white coffee table at the center. An open kitchen area is visible, equipped with storage and appliances. A wall-mounted TV is present, complemented by decorative art and natural light coming through a window.

4.95 out of 5 average rating, 80 reviews

Fichtenblick in Winterberg direkt am Bikepark

Condo in Willingen (Upland)

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.

"The Nest" | Moderne Wohnung mit Ausblick

4.99 out of 5 average rating, 76 reviews

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.

4.86 out of 5 average rating, 22 reviews

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

4.73 out of 5 average rating, 33 reviews

Condo in Schmallenberg

Wohnung mit Weitblick + 50qm + überdachter Balkon

A comfortable living area features a gray sofa with yellow accent pillows and a stylish mustard armchair. A small black side table holds decorative items, and a wall art piece adds character to the space. Natural light enters through a nearby window, highlighting the neutral color scheme.

4.73 out of 5 average rating, 15 reviews

Luxe studio appartement (nr. 5)

A spacious living area is depicted, featuring a comfortable sectional sofa adorned with cushions. A glass coffee table sits on a textured area rug. A flat-screen TV is mounted on the wall, and a white cabinet displays glassware, contributing to a neat and inviting environment.