Some info has been automatically translated. Show original language

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.

%{current} / %{total}1 / 1
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 in Willingen
4.8 out of 5 average rating, 56 reviews

Luxury chalet in a dream location in Willingen.

Deze vrijstaande woning met onlangs gerenoveerde (2024) benedenverdieping beschikt over talrijke voorzieningen, waaronder een sauna, en drie slaapkamers met badkamer. De voorzijde heeft een veranda met panoramisch uitzicht over de dorpsvallei en de Ettelsberg. Achtertuin(1100m2) met terras, voorzien van verwarming, grenst direct aan de bosrand, alwaar diverse wandelpaden en winters aansluiting op de skicarrousel. De woning is bij uitstek geschikt voor een verblijf van vier tot zes personen.

Top guest favourite
A wooden deck is furnished with a table and two comfortable chairs, surrounded by a well-maintained garden filled with blooming plants. Sun loungers are visible on the lawn, with a clear blue sky enhancing the serene outdoor environment.
Chalet in Allendorf / Bromskirchen
4.93 out of 5 average rating, 203 reviews

Your feel-good place - Log cabin Villa Milan

Dein Wohlfühlort am Wald. Ein Paradies für Naturfreunde, Wanderer, Mountainbiker und Wintersportler. Erholung auf ca. 600m Höhe inmitten der Natur. Erlebe Ruhe und Entspannung pur, da wo Fuchs und Hase sich gute Nacht sagen. Das Abenteuer beginnt direkt an Deiner Haustür. Erkunde wundervolle Wanderwege und kehre zurück in ein Ferienhaus, das sich wie ein Zuhause anfühlt oder nutze es als Ausgangspunkt für allerlei Unternehmungen und Aktivitäten. Empfehlungen und Tipps liegen im Haus aus.

Guest favourite
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 Neuastenberg
4.98 out of 5 average rating, 47 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

Guest favourite
A wooden bungalow is surrounded by snow-covered trees and shrubs. The structure, featuring a sloped roof and multiple windows, is nestled in a winter landscape, conveying a sense of serenity and connection to nature.
Chalet in Bromskirchen
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 favourite
Chalet in Winterberg
4.92 out of 5 average rating, 12 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 favourite
Chalet in Bromskirchen
4.97 out of 5 average rating, 155 reviews

Waldliebe - Nature house with fireplace and conservatory

Willkommen in der Waldliebe 🌲❤️ – deinem Naturrefugium im Sauerland Ein gemütliches Ferienhaus mit Kamin, Wintergarten und großem eingezäunten Garten – perfekt für alle, die Ruhe, Natur und Erholung suchen. Hier beginnt dein Urlaub direkt vor der Haustür: wandern, entspannen, Ski fahren, mit dem Hund durch den Wald streifen oder einfach im Wintergarten sitzen und ins Feuer gucken. Alles, was ihr für eine erholsame Auszeit abseits vom Alltagstrubel braucht, findet ihr hier.

Top guest favourite
A charming wooden chalet is surrounded by lush greenery and tall trees. The two-story structure features a balcony adorned with railings, providing a view of the natural landscape. A ladder leans against the side, indicating accessibility for maintenance.
Chalet in Hatzfeld
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 charming blue wooden house is framed by lush greenery, featuring a white door with an arched window. A small white bench is positioned on the patio, accompanied by a potted plant, creating a welcoming entrance.
Chalet in Harbshausen
4.88 out of 5 average rating, 89 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.

Guest favourite
Chalet in Neuastenberg
4.89 out of 5 average rating, 57 reviews

Genieten Chalet Eve Neuastenberg

In the heart of Sauerland Winterberg/NeuAstenberg, this lovely detached chalet/house in nature. The ski slopes Postwiese, Loipe & De Kahler Asten are within walking distance. Winterberg City is 5 km, and the Ski lift carousel Winterberg and Bikepark is 3 km away. Wonderful to relax, idyllic villages, skiing, snowboarding, hiking, mountain biking. "The place" for enjoyment, relaxation and unwinding. It's super nice here and I would like to share that with you. Free WiFi

Top guest favourite
Chalet in Willingen
5 out of 5 average rating, 26 reviews

Martalein - Four Seasons Chalet with Sauna & Fireplace

A beautiful & elegant retreat for those who appreciate true tranquility & timeless luxury. A new address directly on the Uplandsteig, where silence, nature & cosiness merge. The finely renovated chalet with *private 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 call good night & every moment means a little bit of freedom.

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 in Bromskirchen
4.97 out of 5 average rating, 316 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!

Guest favourite
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 in Oberhundem
4.92 out of 5 average rating, 50 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 $303 CAD 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!

  1. Airbnb
  2. Germany
  3. Hesse
  4. Willingen (Upland)
  5. Chalet rentals