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

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

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 £30 per night before taxes and fees

  • Verified guest reviews

    Over 2,450 verified reviews to help you choose

  • Family-friendly holiday rentals

    40 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 40 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    20 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

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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Guest favourite
Flat in Willingen (Upland)
5.0 out of 5 average rating, 21 reviews

*| 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

Guest favourite
Flat in Willingen (Upland)
4.85 out of 5 average rating, 39 reviews

Centrally located above the rooftops of Willingen

🏡 Central holiday apartment in Willingen – everything within easy walking distance Welcome to our cosy holiday apartment in the heart of Willingen. If you are looking for accommodation in a central location close to nature, with the popular, gently sloping panoramic road, the "Sonnenweg", on the Sonnenhang above the centre, then you've come to the right place. The apartment can accommodate up to 9 people and has a spacious living and dining area with direct access to the sunny balcony.

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 in Willingen (Upland)
4.98 out of 5 average rating, 122 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 wooden chalet is visible, nestled in a serene landscape. A spacious patio with seating arrangements overlooks the lush, green garden. Surrounding trees provide natural shade, while the mountain scenery in the background complements the tranquil ambiance.
Cabin in Willingen (Upland)
4.85 out of 5 average rating, 41 reviews

Chalet with fireplace in prime location Willingen.

Wooden chalet on the edge of the forest with a unique panorama of Willingen village and valley. Winters directly from the back garden on ski slopes and other seasons connection to numerous hiking trails and mountain bike trails. Village center, toboggan run and playground and restaurants are within walking distance. Almost all day sun all around. The house is one of the highest houses in the village of Willingen. The house is characterized by its cozy appearance and "outside" feeling.

Superhost
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 in Winterberg
4.87 out of 5 average rating, 197 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
Flat in Willingen (Upland)
5.0 out of 5 average rating, 3 reviews

Prime location with a view of the slopes | 2-room flat | garage included

Modern and spacious 2-room apartment measuring 65m² in a prime central location with a magnificent view of the slopes. Shops such as Rewe and Lidl are just a minute's walk away. A garage is available to you free of charge – ideal for cars, bicycles or skis. There is also a free outdoor parking space right by the property. The perfect starting point for skiing holidays, activities in the mountains and relaxing days, with all the important facilities within easy reach.

Top 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 in Willingen (Upland)
4.95 out of 5 average rating, 373 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 in Winterberg
4.97 out of 5 average rating, 118 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
Flat in Winterberg
4.97 out of 5 average rating, 114 reviews

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

Our modern equipped apartment is 68 m² and is designed for 1-5 people. The flat has: 2 double bedrooms with box spring bed 1 living & dining room with sofa bed 1 kitchen with dishwasher, oven, stove, fridge, freezer, microwave... 1 bathroom 1 hallway 1 large terrace 2 parking spaces 1 safe Wifi Amenities for the kids: 2 travel cribs 2 high chairs 1 changing table with diaper bin 1 baby tub 1 crib bumper 1 toilet seat 1 baby monitor 1 crawling blanket Toys...

Guest favourite
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.
Flat in Winterberg
4.92 out of 5 average rating, 122 reviews

Apartment Tokio + Sauna, 100 m to Ski and Bikepark

This modern 70 m² apartment with private sauna is located directly on the ski slope and the bike park – ideal for an active vacation with relaxation. Two bedrooms with box-spring beds and a sofa bed can accommodate up to 6 people. The fully equipped kitchen, a stylish bathroom with shower and two balconies create a cozy atmosphere. Wi-Fi, Netflix and Waipu TV are included. An underground parking space is also at your disposal – for an all-round carefree stay.

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 in Willingen (Upland)
4.99 out of 5 average rating, 74 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 in Winterberg
4.88 out of 5 average rating, 194 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 Willingen (Upland) ski-in/out rentals

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