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Ski-in/Ski-out holiday rentals in Willingen (Upland)

Find and book unique ski-in/out homes on Airbnb

Top-rated ski-in/out rentals in Willingen (Upland)

Guests agree: these ski-in/out homes are highly rated for location, cleanliness and more.

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Top guest favourite
An open-plan living area features a modern kitchen with dark cabinetry and stainless steel appliances. A natural wood dining table sits at the center, surrounded by upholstered chairs. A comfortable sofa is positioned nearby, complemented by wooden wall accents and ample natural light from the window.
Flat
5 out of 5 average rating, 45 reviews

Mellie’s Fewo Willingen 2

Herzlich willkommen in unserer frisch renovierten Ferienwohnung! Die Unterkunft befindet sich im wunderschönen Strycktal, unweit des Skywalks. Genießt eure Auszeit im stilvoll eingerichteten Wohnbereich mit Elektrokamin für gemütliche Abende oder auf dem Balkon mit traumhaftem Fernblick in die Natur. Die Wohnung bietet Platz für 4 Personen und verfügt über ein separates Schlafzimmer, eine Ausziehcouch, sowie eine vollausgestatteten Küche. Hunde auf Anfrage willkommen. Ankommen und Genießen!

Guest favourite
Flat
4.98 out of 5 average rating, 103 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….

Guest favourite
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
4.98 out of 5 average rating, 116 reviews

"Black+Beauty" the design hut with sauna

New location right on the Uplandsteig. In this cozy cabin you can enjoy the view and silence - relax by the fireplace - put on an LP… The sun shines through the large windows all day. Ideal starting point for hiking, biking and skiing. Great location on the edge of Willingen/Usseln. Restaurants, Graf Stollberghütte and the Skywalk are within walking distance. With a chic mirror sauna in the garden. Black+Beauty the place of well-being in nature - be active and recharge your batteries.

Guest favourite
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.
Home
4.87 out of 5 average rating, 187 reviews

Hüttenzauber - lovely vacation home

The vacation home is about 90 square meters and can accommodate 2-6 people, spread over 3 bedrooms. On the first floor is the modern furnished living-dining room with open kitchen, a pellet fireplace, a bedroom and the shower room. The kitchen offers all amenities with a dishwasher, oven, coffee maker and toaster. On the upper floor, there is a large bedroom with panoramic windows and an extra sofa bed. The 2 single beds in the anteroom can be built together to form a 160 bed

Superhost
A wooden vacation home is situated on a green lawn, surrounded by trees. A patio area features multiple seating options, including a table and chairs. The backdrop showcases a panoramic view of the valley and distant hills under a clear blue sky.
Chalet
4.8 out of 5 average rating, 56 reviews

Luxury chalet in a dream location in Willingen.

This detached house with a recently renovated (2024) ground floor has numerous amenities, including a sauna, and three bedrooms with bathroom. The front has a veranda with panoramic views of the village valley and the Ettelsberg. Back garden (1100m2) with terrace, equipped with heating, directly adjacent to the edge of the forest, where there are various hiking trails and winter connection to the ski carousel. The home is ideally suited for stays of four to six people.

Guest favourite
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
4.94 out of 5 average rating, 353 reviews

The little black dress

The little black one! A charming cottage on the Musenberg. A beautiful colorful cottage garden welcomes guests. The covered terrace invites you to enjoy the outdoors. For grilling and cooking, use the outdoor oven. (Spring to fall) The bright house, which is converted into the roof, is decorated 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.

Guest favourite
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.
Holiday home
4.98 out of 5 average rating, 105 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 favourite
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.
Apartment
4.92 out of 5 average rating, 142 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!

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.
Flat
4.79 out of 5 average rating, 62 reviews

Quiet apartment near a forest

Relax with the whole family in this beautiful apartment on the edge of a forest. You will find many hiking trails to enjoy in nature, the center of Willingen is close by for a snack and a drink, or for skiing. You will find a nice apartment with a studio upstairs (bedroom 3), which can be reached via the stairs. (parties, smoking and noise are prohibited. We ask all guests to keep in mind that it is quiet in the building between 10 p.m. and 8 a.m.)

Top guest favourite
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
4.99 out of 5 average rating, 68 reviews

"The Nest" | Modern apartment with a view

"The Nest" is a cozy, well-equipped apartment for a maximum of four people and a toddler. It is located in a private house with beautiful views in the heart of the Willingen ski resort and is the ideal retreat for families, winter sports enthusiasts, bikers, hikers, business travelers and all those who want a relaxing stay in the Sauerland. The town center with numerous shopping, restaurants and bars is within walking distance in about 10 minutes.

Guest favourite
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.
Flat
4.88 out of 5 average rating, 185 reviews

Holiday Appartement Winterberg - Ski slopes 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 favourite
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
4.97 out of 5 average rating, 314 reviews

Cozy chalet including hot tub and sauna

We offer a cozy chalet including a hot tub and sauna in the holiday village of Bromskirchen. A beautiful forest property in total privacy and silence. In the 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 tub. Our property is open. It is only surrounded by plants!

Popular amenities for Willingen (Upland) ski-in/out rentals

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Quick stats about holiday rentals that are ski-in/out in Willingen (Upland)

  • Total holiday rentals

    Explore 80 holiday rentals in Willingen (Upland)

  • Nightly prices starting at

    Willingen (Upland) holiday rentals start at £22 per night before taxes and fees

  • Verified guest reviews

    Over 2,310 verified reviews to help you choose

  • Family-friendly holiday rentals

    40 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 30 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    80 of Willingen (Upland) holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Willingen (Upland) rentals

  • 4.7 Average rating

    Willingen (Upland) stays receive an average rating of 4.7 out of 5 from guests