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Chalet vacation rentals in Willingen (Upland)

Find and book unique chalets on Airbnb

Top-rated chalet rentals in Willingen (Upland)

Guests agree: these chalets are highly rated for location, cleanliness, and more.

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Top guest favorite
Chalet
4.92 out of 5 average rating, 207 reviews

Your feel-good place - Log cabin Villa Milan

Your haven of well-being by the forest. A paradise for nature lovers, hikers, mountain bikers and winter sports enthusiasts. Relaxation at an altitude of about 600 m (1,968 ft), surrounded by nature. Experience pure peace and relaxation, where fox and rabbit say good night. The adventure begins right outside your front door. Explore wonderful hiking trails and return to a vacation home that feels like a home away from home, or use it as a base for all kinds of outings and activities. Recommendations and tips are available in the house.

Guest favorite
A modern chalet is nestled in a snowy landscape, featuring large glass windows that offer expansive views of the surrounding area. The exterior showcases a combination of wood and stone, with a simple red chair positioned on a snow-covered porch.
Chalet
4.96 out of 5 average rating, 51 reviews

Panorama Chalet 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

Top guest favorite
Chalet
4.97 out of 5 average rating, 157 reviews

Waldliebe - your retreat in the countryside

Welcome to Waldliebe 🌲❤️ – your natural refuge in Sauerland A cozy vacation home with fireplace, winter garden and large fenced garden – perfect for those seeking tranquility, nature and relaxation. Your vacation starts right outside the front door: hiking, relaxing, skiing, walking with the dog through the forest or simply sitting in the conservatory and looking into the fire. Everything you need for a relaxing break away from the hustle and bustle of everyday life can be found here.

Guest favorite
Chalet
4.89 out of 5 average rating, 197 reviews

Haus Frei Wald near Winterberg, ski resort.

Haus Frei Wald is close to Winterberg, located on the edge of the forest with a fantastic view and equipped with every comfort. You can relax 100%. At the entrance of the Feriendorf, there is a brown billboard. At the back are 3 beautiful routes. Haus Frei Wald is suitable for anyone who loves (winter) sports, nature and tranquility with facilities such as supermarkets etc. in the vicinity. Family, relatives or with the two of you? There is room for 6 people, max 4 adults. Welcome!

Guest favorite
Chalet
4.93 out of 5 average rating, 14 reviews

Vacation home 1000 mountains Winterberg fireplace & jacuzzi

Inmitten der Hügel und Wälder des Sauerlands erwartet dich ein besonderer Ort: unser Ferienhaus 1000 Berge – ein Platz zum Wohlfühlen, Loslassen und Kraft tanken. Ob mit Familie, Freunden oder auf vier Pfoten – hier beginnt deine Auszeit. Starte den Tag mit einer Wanderung durch die Natur, entspanne am Abend im holzbefeuerten Whirlpool unter freiem Himmel oder genieße auf der Terrasse ein kühles Sauerländer Bier. 1000 Berge ist mehr als ein Ferienhaus – es ist dein Zuhause auf Zeit.

Top guest favorite
Chalet
4.95 out of 5 average rating, 100 reviews

Beautiful chalet for 9 guests with two bathrooms

The chalet is very cozy and conveys a warm sense of well-being. It is a beautiful wooden house in the Alpine style with stunning views of the forests, valleys and the romantic town of Hatzfeld. It offers 110 square meters with a sun balcony, terrace and garden. Here is the ideal place to switch off and relax in the immediate vicinity of nature. Book today and draw new strength and vitality in the immediate vicinity of nature below the forest overlooking Hatzfeld Castle.

Superhost
A blue wooden house with a red roof is set against a backdrop of rolling green hills and a clear blue sky. Surrounding trees and foliage add to the serene atmosphere, creating a sense of privacy and connection to nature.
Chalet
4.88 out of 5 average rating, 91 reviews

Swedish chalet on Lake Edersee with lake view

Our vacation home is located about 100 m from Lake Edersee on a hill, so that from here, depending on the water level, you have a wonderful lake or Edersee Atlantis view. In autumn and winter you can enjoy the wonderful view through our large panoramic windows. Enjoy the absolute tranquility and watch deer, foxes and hares right at your doorstep. Our house is ideal for people who want to escape the hustle and bustle of everyday life and who want a time of relaxation.

Superhost
Chalet
4.81 out of 5 average rating, 58 reviews

Luxury chalet in a dream location in Willingen.

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

Top guest favorite
Chalet
5 out of 5 average rating, 29 reviews

Martalein - Four Seasons Chalet mit Sauna & Kamin

A beautiful & elegant retreat for those who appreciate real tranquility & timeless luxury. A new address directly on the Uplandsteig, where silence, nature & coziness merge. The finely renovated chalet with *secluded garden, *outdoor sauna, *Netflix, *Wi-Fi & *outdoor home office room is a place where sunlight dances through panoramic windows, the forest reaches up to the terrace, the owls say good night & every moment means a little bit of freedom.

Top guest favorite
A wooden chalet features a sloped roof and large glass doors leading to a balcony. Two wooden chairs and a small table are placed on the balcony, providing an outdoor seating area surrounded by trees. Soft natural light illuminates the space.
Chalet
4.98 out of 5 average rating, 52 reviews

stylish and comfortable Chalet with a wide view

Sit back and relax - in this quiet, stylish accommodation in the Hessian mountains. The stylishly furnished chalet, above the small village of Hatzfeld/Eder, offers over 50 square metres of space to relax. Situated directly on the edge of the forest, it is the ideal starting point for extended hikes; or simply enjoy the sunset from the balcony with a glass of wine or end a snowy day in front of the warm fire of the stove.

Superhost
An inviting seating area features a plush gray chair and a sofa with a streamlined design. A rustic wood coffee table is accompanied by a tall vase containing decorative branches. Soft lighting accentuates the wood-paneled walls, creating a cozy atmosphere.
Chalet
4.94 out of 5 average rating, 36 reviews

Chalet in Sauerland❤ exclusive log cabin_New 2020

Own exclusive chalet hut (for 2 people) directly on the pond with unique views of the countryside. Enjoy the tranquility in this exclusively furnished house located on the edge of the forest. We have furnished our accommodation with a lot of love for detail, with high-quality natural materials. In 2015/2016, this log cabin, unique in the Sauerland, was newly renovated and we now welcome you to a relaxing holiday ❤.

Top guest favorite
A modern A-frame vacation home is set amidst lush greenery. Large windows provide ample natural light and showcase views of the surrounding landscape. A spacious balcony, equipped with outdoor seating and an umbrella, offers a comfortable outdoor space beneath the clear blue sky.
Chalet
4.92 out of 5 average rating, 53 reviews

Chalet with magnificent distant views

Kick back and relax in this modern and cozy vacation home. The wonderful view of the hills and forests of the Sauerland are balm for the soul in every season. Whether in spring when everything shines in bright green, in summer when the sunsets accompany our evening, in autumn when the mists hang between the trees or in winter when everything is powdered white. There are many varied activities in the area

Popular amenities for Willingen (Upland) chalet rentals

Quick stats about chalet rentals in Willingen (Upland)

  • Nightly prices starting at

    Willingen (Upland) vacation rentals start at €191 per night before taxes and fees

  • Verified guest reviews

    Over 100 verified reviews to help you choose

  • Popular amenities for guests

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

  • 4.9 Average rating

    Willingen (Upland) stays are highly rated by guests—averaging 4.9 out of 5!

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