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Chalet vacation rentals in Willingen (Upland)

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Top-rated chalet rentals in Willingen (Upland)

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Guest favorite
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, 46 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 in Bromskirchen
4.97 out of 5 average rating, 155 reviews

Waldliebe - Nature house with fireplace and conservatory

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
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 favorite
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.

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, 88 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.

Top guest favorite
Chalet in Allendorf / Bromskirchen
4.93 out of 5 average rating, 202 reviews

Your feel-good place - Log cabin Villa Milan

Your feel-good place right by the forest. A paradise for nature lovers, hikers, mountain bikers and winter sports enthusiasts. The cottage is located at an altitude of about 600 m, in the middle of a picturesque landscape. Experience pure peace and relaxation, where fox and rabbit say good night. Ideal as a starting point for all kinds of activities and activities. Recommendations and tips are available in the house. Various hiking trails start right by the house.

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.

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 in Willingen
5 out of 5 average rating, 25 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 in Hatzfeld
4.98 out of 5 average rating, 50 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 in Meschede
4.94 out of 5 average rating, 34 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 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 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 in Oberhundem
4.92 out of 5 average rating, 49 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 ﺩ.ﺇ808 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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