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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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Superhost
The image displays a spacious garden with a green lawn bordered by a wooden fence. A hot tub is visible on a stone patio near a cozy seating area. In the background, rolling hills and trees create a serene landscape under a clear blue sky.
Chalet in Medebach
4.86 out of 5 average rating, 63 reviews

Scandinavian lodge (2) with hot tub near Winterberg

New Scandinavian cozy (detached) lodges with hot tub for rent. The luxurious lodges are located on the outskirts of the village of Küstelberg and equipped with every comfort. From the house and veranda, you can look out over the meadows and the adjacent Hillekopf nature reserve. The lodges have a large garden, terrace and spacious veranda where you can enjoy the peace and privacy. In less than 10 minutes, you are in the cozy Winterberg and Medebach. The lodges are equipped with a heat pump (heating/cooling).

Chalet in Willingen
4.89 out of 5 average rating, 27 reviews

Chalet Papillon

Chalet Papillon - Your Time Out Step inside and enjoy a sense of relaxation and rejuvenation at Chalet Papillon in the Hochsauerland. The Chalet Papillon offers approximately 75 square meters of perfect vacation conditions for up to four people. Reclaimed wood and elegant interiors are perfectly and harmoniously coordinated. Nothing stands in the way of a rustic cabin vacation of the highest quality! Experience a completely new vacation feeling and enjoy your own outdoor sauna and fireplace.

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 Winterberg
4.98 out of 5 average rating, 44 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, 154 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!

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 Vöhl
4.87 out of 5 average rating, 84 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 favorite
A charming chalet is set against a snowy landscape, featuring a sloped roof and dark wooden accents. A clear pathway leads to the front door, flanked by snow-covered shrubs. Bright blue skies contrast with the tranquil environment, emphasizing the inviting exterior.
Chalet in Winterberg
4.89 out of 5 average rating, 56 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

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, 54 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, 15 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.

Superhost
A modern kitchen space features a central island with pots and utensils stacked below. Large windows draped with light, airy curtains allow natural light to illuminate the room. A wall shelf holds dishware and bowls, enhancing the functional design of the area.
Chalet in Warstein
4.74 out of 5 average rating, 23 reviews

Wohnen im Schweden Chalet (Haus 3)

Modern, cozy and surrounded by nature. Our Swedish house has elegant architecture and invites you to relax and explore the Sauerland. Waking up in the morning and being awakened by cows is something special. The house is also gladly used as a workation place. The large window facade to the west gives you a fabulous view over the Wästertal to Warstein and gives the house a lot of light. We appreciate inquiries for living in Warstein.

Top guest favorite
The image shows a welcoming wooden villa surrounded by lush greenery. The vibrant garden features blooming rhododendrons and tall trees. A grassy area invites relaxation, while a rustic log lies in the foreground, contributing to the natural ambiance.
Chalet in Allendorf / Bromskirchen
4.92 out of 5 average rating, 194 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. You can find various recommendations and tips in the house.

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, 312 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) chalet rentals

Quick stats about chalet rentals in Willingen (Upland)

  • Nightly prices starting at

    Willingen (Upland) vacation rentals start at ﺩ.ﺇ624 per night before taxes and fees

  • Verified guest reviews

    Over 70 verified reviews to help you choose

  • Popular amenities for guests

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

  • 4.8 Average rating

    Willingen (Upland) stays are highly rated by guests—averaging 4.8 out of 5!

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