Ski-in/Ski-out vacation rentals in Willingen

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.

4.88 out of 5 average rating, 166 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

4.97 out of 5 average rating, 106 reviews

The bathroom features wooden accents on the walls, creating a warm atmosphere. A walk-in shower with a glass enclosure is present alongside a modern toilet. Natural light fills the space through a window that overlooks greenery, complemented by a small indoor plant on the sill.

Home in Hilchenbach

Apartment Broche, vacation from everyday life

Cozy apartment since September 2017 in a very quietly located former farmhouse on the edge of the forest. If you are looking for hustle and bustle, you will not find it here. However, if you want to switch off and are looking for relaxation, you have come to the right place. Certified by the DTV with 3 stars. If desired, the refrigerator (for a fee) can be filled. In the garden there is a spacious garden house, which we also make available to our guests by arrangement.

4.92 out of 5 average rating, 126 reviews

The living area features a comfortable couch arranged facing a flat-screen TV. A dining table with dark leather chairs sits nearby. Large windows allow natural light to fill the space, showcasing views of the surrounding landscape. Decorative items and artwork add character to the room.

Condo in Winterberg

Apartment with fantastic views

Experience the perfect holiday with a breathtaking view of the valley and the slopes from our apartment. This cozy apartment is ideal for 2 people and offers a living room and bedroom with panoramic views. In summer you can reach the Kahler Asten in just 15 minutes on foot, while in winter you are right on the slopes. The apartment has a fully equipped kitchen and a bathroom with a bathtub and hairdryer. Discover the perfect retreat for your next vacation!

4.95 out of 5 average rating, 310 reviews

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

The little black dress

The little black one! A charming vacation home on the Musenberg. A beautiful colorful farm garden welcomes the guests. The covered patio invites you to enjoy outside. For grilling and cooking, use the outdoor oven. (spring to autumn) The bright house, built into the roof, is furnished 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.

4.98 out of 5 average rating, 42 reviews

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.

Condo in Willingen

"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.

4.99 out of 5 average rating, 94 reviews

Cabin in Willingen

Black+Beauty Design Cabin in Willingen / Sauerland

New location right on the Uplandsteig. At this cozy cabin you can enjoy the view and silence - relax by the fireplace - put on an LP…The sun shines through the large window all day. Ideal starting point for hiking, biking and skiing. Great location on the edge of Willingen/Usseln. You can walk to restaurants, Graf Stollberghütte and the Skywalk. With chic mirror sauna in the garden. Black+beauty the feel-good place in nature - be active & refuel.

4.89 out of 5 average rating, 164 reviews

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.

Apartment in Winterberg

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.

Vacation home in Winterberg

A multi-level building with multiple balconies is visible, featuring wooden railings and large windows. Snow covers the ground, creating a wintery ambiance. The architecture highlights natural materials, with sections of the building showcasing varying window arrangements.

4.93 out of 5 average rating, 138 reviews

AparmentRIO🌴Netflix❤️100m to Ski⛷ PlayStation4 ✔️

Die Wohnung, ca. 35 qm ist einem dschungelartigen Stil gehalten. Die Einrichtung überzeugt durch einen trendigen Style und frischen Farben, damit die Feriengäste sich wohl fühlen. In der Wohnung ist Platz für 2 Erwachsene. Das Apartment liegt direkt an der Skipiste Kahler Asten. Zur Innenstadt von Winterberg könnt ihr in ca. 2 Minuten mit dem Auto hinfahren.

5 out of 5 average rating, 20 reviews

A snow-covered path is flanked by tall evergreen trees, their branches heavy with white snow. The clear blue sky above contrasts with the tranquil winter landscape, creating a serene atmosphere. A hint of moon is visible, adding a touch of wonder to the scene.

Apartment in Willingen

Apartment with fantastic views

Kick back and relax in this calm, stylish, newly renovated 47 sqm apartment. It is furnished for 2 adults + max. 1 child. Well-signposted hiking trails, cross-country ski runs, and ski lifts are in the immediate vicinity. You can reach Willingen with further, numerous leisure activities in a few minutes (4 km). Unfortunately no pets are permitted!

4.88 out of 5 average rating, 16 reviews

A modern bedroom features a spacious bed with soft linens, complemented by colorful wall art above the headboard. A stylish light fixture illuminates a nearby seating area, which includes a soft blanket draped over an extra bed, creating a cozy ambiance.

Apartment in Willingen

Inside Willingen - Design Apartment mit Balkon

Discover our stylish designer apartment in Willingen! In our newly renovated 33m² apartment located in the idyllic Stryck Valley, you will find a modern atmosphere with space for up to 3 guests. Perfect for active holidaymakers and those seeking relaxation, it is situated in one of the most beautiful and popular areas of Willingen.

4.93 out of 5 average rating, 153 reviews

A yurt is illuminated at dusk, showcasing a wooden door and a chimney. Surrounding the yurt, natural grass and stones create a rustic atmosphere. Wooden seating options, including benches, are positioned nearby, offering a space for relaxation amid serene natural surroundings.

Yurt in Olsberg

* Adventure overnight stay in one of our yurts *

Watch the starry sky from bed. Enjoy the sounds of nature when you stay in this unique place. A living space without corners and edges, to relax and experience time together. The yurts are located on a 2500 sqm nature reserve with a lake and view of the natural monument Bruchhauser Steine.

Chalet in Allendorf / Bromskirchen

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.

4.92 out of 5 average rating, 167 reviews

Your place to feel good - Villa Milan log cabin

Your "feel-good place" right by the forest. Villa Milan is a true paradise for nature lovers, walkers, mountain bikers and winter sports enthusiasts and is located at 600m altitude in the middle of a picturesque landscape. Pure peace and relaxation, where fox and rabbit say good night.

Vacation rentals for every style

Get the amount of space that is right for you

Chalets

Adventure-ready homes with après-ski style

Apartments

Convenient locations with everyday essentials

Houses

A space thats all yours, with room for everyone

Popular amenities for Willingen ski-in/ski-out rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Ski-in/ski-out house rentals

An aerial view of the BergZauber holiday house showcases its charming architecture and scenic surroundings. The building features a classic design with a gabled roof and a welcoming entrance. Lush greenery surrounds the property, emphasizing its peaceful location in nature.

5 out of 5 average rating, 3 reviews

BergZauber - up to 22 people, 10 bathrooms, sauna

LeaRating, 5 stars1 month ago

Great place and highly recommended! We were there with our team from Fr. Were received super nicely, even with a personal welcome 😊 The amenities were great, the rooms and bathrooms super clean and nicely furnished. The sauna was used daily 😍 With foosball, ping pong table, barbecue hut and much more, we didn't miss anything. On Sunday, we received a personal farewell. All communication was super easy and fast and really very warm. We will be happy to come back and can only recommend the accommodation and the two "landlords" Sandra and Christoph. High praise to the two of them 🙏🏻

4.67 out of 5 average rating, 30 reviews

An open dining area features a large wooden table surrounded by four chairs in varying colors. A modern pendant light hangs above the table, and a television is mounted on a textured stone wall. Light wood flooring adds warmth to the inviting space.

Home in Brilon

New | Comfort Chalet | Sauna | 5 people | Skiing

TunahanRating, 5 stars2 months ago

The place was in a very quiet place as expected and highly recommended for a relaxing holiday. The property is on a steep path (ski facility) that leads to other places where it also goes up and down. The host was really always very responsive and helpful. We really enjoyed our vacation there and can only recommend the accommodation.

5 out of 5 average rating, 5 reviews

A cozy living area is presented with a grey sectional sofa featuring plush cushions. A wooden coffee table with a star design sits at the center, next to a decorative candle. Natural light enters through glass doors, highlighting warm wood accents and a rustic dining area.

Home in Allendorf (Eder)

Haus Waldblick Bromskirchen

Marie-AngeRating, 5 stars2 weeks ago

We had a lovely quiet stay with the dog at Marvin's house. Everything was nice, clean and well equipped. We will definitely come back. Marie-Ange

5 out of 5 average rating, 9 reviews

The exterior of a classic detached house is surrounded by lush greenery, featuring a spacious garden area. Patio furniture is visible, offering an inviting spot for relaxation. The two-story structure displays a wooden roof and windows, blending harmoniously with the natural landscape.

Home in Olsberg

Home with sauna close to Winterberg and Willingen

BarthRating, 5 stars3 months ago

The house was designed in a charming old German style, creating a warm and inviting atmosphere. It felt cozy and comfortable throughout our stay.

4.85 out of 5 average rating, 20 reviews

The log cabin features a striking wooden exterior with expansive windows that invite natural light. A well-maintained lawn is framed by colorful flowers, while a paved driveway leads to the entrance and a carport. The sloped roof and natural materials contribute to its inviting charm.

Home in Willingen

Luxury Block House A

TheresaRating, 5 stars5 months ago

The log cabin half is modern and lovingly furnished, everything was right. Kitchen is well equipped and the beds are comfortable. We will be happy to come back.

The chalet exterior is illuminated against the evening sky, featuring a modern design with large windows. A gentle slope leads to the entrance, bordered by greenery. Warm lights highlight architectural details, inviting relaxation in the tranquil setting.

5 out of 5 average rating, 7 reviews

"The Chalets Herzenssache" - Chalet Lebenskunst

HannoRating, 5 stars10 months ago

Great accommodation, extremely clean and looked after by very friendly hosts

4.86 out of 5 average rating, 28 reviews

Villa SKYLO, complete top location in Winterberg !

StephanieRating, 5 stars1 week ago

We (4 adults, 3 children) felt very comfortable here! A very cozy and lovingly furnished house with everything you need. Plenty of space to get together, but also to retreat in between. We can imagine booking again very well!

An outdoor hot tub is shown, featuring a wooden exterior and a smooth, light-colored inner surface. A small wooden step is visible, allowing easy access. Surrounding greenery adds a natural touch to the tranquil setting.

4.75 out of 5 average rating, 8 reviews

Cozy detached house with Hot Tub

AntoniaRating, 5 stars4 months ago

Tom has a beautiful large apartment and a large garden which we did not want to use because of winter - snow and a lot of cold - many possibilities to do, the bus goes to the ski slopes and to Winterberg We 5 women had a lovely few days in the apartment

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Family-friendly, ski-in/ski-out home rentals

4.87 out of 5 average rating, 85 reviews

The contemporary building features multiple balconies with wooden accents, overlooking a colorful array of blooming flowers. The vibrant purple lupines and other wildflowers fill the foreground, enhancing the natural appeal of the surrounding landscape under clear blue skies.

Apartment in Winterberg

Luxury apartment with garden and unique view!

IlonaRating, 5 stars3 months ago

What a lovely apartment, with all the comforts and very warm and cozily furnished. We felt right at home! The apartment is on the slopes and the view is breathtaking. It was nice that we received all the necessary information in advance, it was very complete. Questions were answered almost immediately. We can recommend this accommodation to everyone!

4.71 out of 5 average rating, 107 reviews

An outdoor terrace area is visible, featuring a round table and two black chairs. A sun umbrella stands to one side, and a trellis is situated nearby. The entrance door to the holiday apartment is also visible in the background, framed by a small garden area.

Apartment in Willingen

Apartment (bedroom, living room, bath room)

BeccsRating, 5 stars2 weeks ago

We were guests for the second time. I would be happy to come back☺️. Thank you also for the small gift for my daughter. We will be happy to come back again and again. Thank you

4.64 out of 5 average rating, 14 reviews

A spacious room contains two wooden beds with soft blue-striped bedding. Two bedside tables with lamps are positioned next to each bed. A doorway leads to a modern bathroom, visible in the background. The tile flooring adds to the cozy atmosphere.

Apartment in Medebach

Landhaus Schlossberg Apartment 2

NaomiRating, 5 stars78 months ago

Perfect place to stay and enjoy the area! The appartement was very clean and the communication was good. All basic services were available (kitchen and bathroom). Also a nice garden!

4.89 out of 5 average rating, 47 reviews

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

GENIETEN EVE's CHALET NEUASTENBERG

JörgRating, 5 stars1 month ago

We stayed there with our group of men for 2 nights. Everything went well from the arrival to everything else. We were satisfied and would come back.

4.85 out of 5 average rating, 46 reviews

A charming chalet-style building is nestled in a snowy landscape, featuring traditional wooden beams and a sloped roof. Large windows allow natural light to illuminate the interior. Snow blankets the ground, providing a serene winter ambiance.

Townhouse in Winterberg

F****Vacation Rental Country House Postwiese

KristinRating, 5 stars5 months ago

We had a lovely time at Landhaus Postwiese. The apartment was super clean. We didn't miss anything in terms of furnishings and amenities! The location was super central for tobogganing/skiing at the Postwiese. It was also nice that the swimming pool and wellness area of the nearby hotel could be used. The contact with the landlord was quick and very friendly. Thank you!

Apartment in Schmallenberg

The image captures a serene landscape featuring rolling hills covered in a light mist. Lush greenery is visible, interspersed with trees showcasing autumn hues. In the distance, a swing set is positioned in a meadow, adding a touch of leisure to the tranquil setting.

4.84 out of 5 average rating, 85 reviews

Country house idyll: apartment with beautiful views

JustusRating, 5 stars2 weeks ago

beautiful spacious accommodation, easy check-in, Christiane showed us the accommodation briefly and was a very kind host

The exterior of a rustic vacation home is shown, framed by snow-dusted trees. A wooden balcony extends from the upper level, and large windows allow natural light to enter. A small terrace and pathway leading to the entrance are visible, surrounded by wintry vegetation.

Chalet in Willingen

4.77 out of 5 average rating, 48 reviews

Luxury chalet in dream location in Willingen.

marvinRating, 5 stars1 week ago

Getting to the driveway was a bit exciting. Otherwise, everything is great and satisfactory! Everything worked.

The exterior of the chalet features a wooden balcony that overlooks the surrounding greenery and forest. The combination of natural wood and white walls creates a harmonious look, while large windows invite ample natural light into the space.

Chalet in Diemelsee

4.57 out of 5 average rating, 116 reviews

Cosy chalet on a hill in the forest

ElenaRating, 5 stars1 month ago

We had a lovely time in the house. We particularly liked the large sun terrace with garden.

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Ski-in/ski-out condo rentals

4.83 out of 5 average rating, 58 reviews

A well-lit room features a spacious bed with a soft throw, complemented by a television mounted on the wall. Two chairs are positioned next to a small table, with natural light flowing through large windows overlooking a balcony adorned with greenery.

Condo in Medebach

Beautiful ski and hiking domicile with south balcony

NinaRating, 5 stars1 week ago

Our stay at Tina's apartment was exactly as we had imagined, we were very satisfied and felt comfortable. The apartment is exactly as described in the listing and perfect for short stays. Tina is very nice, helpful and quickly accessible.

A bright seating area features a black chair beside a warm wooden side table. Large windows allow ample natural light, offering views of the landscaped exterior. Wooden cabinetry provides storage and displays decorative items. A cozy blanket and a small lamp complete the inviting setup.

Condo in Willingen

4.5 out of 5 average rating, 36 reviews

Chic apartment for 2 people

NicoleRating, 5 stars4 months ago

We stayed at Axel's place last year and felt very comfortable again this time. The apartment is well-equipped, nothing is missing and you have everything you need. As always, the contact with Axel was very nice and straightforward. Check-in was quick and easy. We appreciate the good value and will definitely be happy to come back! A completely successful stay.

A wooden table holds two glasses of sparkling wine and a lit candle, adding a soft glow. In the background, a sleek television is mounted above a low wooden cabinet. Soft curtains frame the space, enhancing the light and airy feel.

Condo in Winterberg

4.82 out of 5 average rating, 57 reviews

Private sauna | 2-4 people | Winterberg Center

DanielRating, 5 stars16 months ago

We really enjoyed our stay here. Lots of space, everything you need, and great location. Would definitely stay again.