Ski-in/Ski-out vacation rentals in Olsberg

Apartment in Schmallenberg

A green, grassy area features a white horse and two brown horses roaming freely. Surrounding the scene are clusters of tall trees and shrubs, with a wooden fence enclosing the pasture. Natural sunlight highlights the lush greenery and tranquil setting.

4.77 out of 5 average rating, 83 reviews

Cozy nostalgic country house apartment, Schanze

The apartment (approx. 42 square meters) overlooking forest and pasture is quietly located in the hilltop village of Schanze (720 m above sea level). Wonderful area for hikers, riders, mountain bikers and winter sports enthusiasts. Cross-country ski trail network and toboggan run in the village. The ski lift in Schmallenberg can be reached in about 10 minutes and the lifts in Winterberg can be reached in about 20 minutes by car. Ideal for those who seek tranquility and love nature.

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.

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.

4.92 out of 5 average rating, 126 reviews

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, 311 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.

4.77 out of 5 average rating, 31 reviews

A snow-covered landscape features a white building with a sloped roof in the background. In the foreground, a ski lift is visible, with people skiing in the distance under a clear blue sky and bright sunlight.

Apartment in Brilon

Comfort apartment | Sauna | 4 people | 4 stars

Feel-good apartment with large terrace & access to the garden in the immediate vicinity of the ski slope. The 51 sqm apartment is well-equipped and offers everything you need. → Box spring bed → large lounge/dining area with sofa bed → Flat screen and smart TV → Kitchen with coffee machine → Terrace & large garden → own parking space → sauna → directly on the ski slope → quiet and picturesque, yet just 15 minutes on foot for the historic old town

4.99 out of 5 average rating, 95 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.

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.

4.89 out of 5 average rating, 164 reviews

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.

A living area features a green sofa accented with orange cushions, set against large glass doors that open to a scenic view. A coffee table with decorative items is situated in front of the sofa, and natural light fills the space.

4.89 out of 5 average rating, 18 reviews

Hillside apartment with a view! Lake balcony

Beautiful apartment with a great view! Right outside the front door you can reach countless hiking trails, bike trails, toboggan runs, golf courses, ski slopes, Lake Hillebachsee (water skiing, beach and playground), restaurants and much more. The apartment has 4 sleeping places (1 double bed, 1 sofa bed) and leaves nothing to be desired. We look forward to seeing you!

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, 139 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.

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

Houses

A space thats all yours, with room for everyone

Villas

Luxurious estates for the ultimate escape

Popular amenities for Olsberg 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 🙏🏻

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

4.84 out of 5 average rating, 37 reviews

A spacious holiday home stands amidst lush greenery, featuring a dark roof and contrasting white walls. Tall trees provide shade, while two cyclists ride along the road in the foreground, highlighting the peaceful surroundings. A clear blue sky completes the serene outdoor setting.

Home in Medebach

Spacious, vintage holiday home with a view.

RubenRating, 5 stars3 months ago

Enjoyed a ski weekend with friends. Daan gave us good tips and the house was great. Location super close to Winterberg.

The exterior of a renovated detached vacation home is shown, featuring a mix of wood and white siding. A gentle slope leads to the house, surrounded by a green lawn and a flower bed with colorful blooms. Street lighting is visible near the entrance.

4.8 out of 5 average rating, 10 reviews

Haus Ludwiges (Winterberg)

NicoleRating, 5 stars3 months ago

Rustic, cozy cottage in a great location. We had a great time and would be happy to come back!

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

A snow-covered landscape is showcased, featuring a large ski jump structure against a clear blue sky. The gently sloping ground invites outdoor activities, and the peaceful surroundings highlight the winter environment.

4.7 out of 5 average rating, 174 reviews

Goski & Gobike Winterberg (Netflix, Waipu.tv free)

SibanyoniRating, 5 stars5 months ago

GREAT LOCATION, here you will be close to the skii resort and town for eating out. everything is within walking distance.

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.

4.87 out of 5 average rating, 85 reviews

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!

4.75 out of 5 average rating, 141 reviews

A modern living area features a light-colored couch with decorative pillows, complemented by a stylish armchair and small side tables. A soft area rug in neutral tones is placed on the wooden floor. The room is brightened by natural light, showcasing clean, minimalist design.

Apartment in Korbach

Beautiful living on the Sauerland Höhenflug

NadineRating, 5 stars2 weeks ago

We enjoyed it very much. The apartment is nicely furnished, there is everything you need. There are plenty of options to store your things in both bedrooms and the bathroom. In the kitchen, we lacked a bit of space in the cupboard for food, so the sideboard had to do. But it wasn't a problem. There are a lot of dishes and everything else you need. We had a lovely stay.

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.

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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.

4.83 out of 5 average rating, 23 reviews

A modern kitchen features a spacious countertop with a sink and kettle, surrounded by sleek cabinetry. Sunlight filters through large windows dressed in sheer curtains, illuminating the room. Kitchen appliances such as a coffee maker and microwave are neatly arranged on the shelves.

Condo in Schmallenberg

Gierse Vacation Rental

EugenRating, 5 stars1 week ago

A little paradise – highly recommended! 🌿✨ We were very lucky to be able to spend a few days in this fantastic apartment – and it was just perfect! As soon as you enter, you can feel how much love for detail everything was designed here. The décor is stylish, cozy and modern at the same time – you immediately feel at home. The apartment was sparkling clean, well-equipped and really left nothing to be desired – from the fully equipped kitchen to small touches. The location is also ideal – quiet, but still close to everything you need: nature, shopping, restaurants and great excursion destinations in the area. A big compliment also to the hostess: communication, cordiality and helpfulness were exceptional. We highly recommend this wonderful place to anyone looking for relaxation, style and genuine hospitality! 5 out of 5 stars ⭐⭐⭐⭐⭐

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.

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.

A comfortable living area is shown, featuring a gray sectional sofa adorned with teal cushions. A small white coffee table is positioned in front, with decorative items placed on it. Natural light enters through a nearby window, and a tall indoor plant adds a touch of greenery to the space.

4.94 out of 5 average rating, 17 reviews

vacation apartment Bergpanorama - TV, parking lot

MariannaRating, 5 stars3 months ago

We felt completely comfortable and had a wonderful stay. The apartment is furnished with attention to detail and my 6-year-old son was also enthusiastic about the play and entertainment offer. Great view, we would have liked to have stayed longer. 😊

A modern living area features a dark blue sofa with decorative cushions, accompanied by an ottoman. A round white coffee table sits on a woven rug, with tranquil artwork depicting outdoor scenes displayed on the wall. Natural light filters in through the window, accented by a soft roller blind.

Condo in Willingen

4.79 out of 5 average rating, 33 reviews

Your dream apartment in Willingen

OlegRating, 5 stars6 days ago

The apartment is small but super cozy and absolutely clean – you feel right at home. The host was always available and super friendly, which really makes a difference. For the price, a real hit. Clear recommendation!

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

SimoneRating, 5 stars2 weeks ago

The accommodation, the host Uwe, the cleanliness and extensive amenities, where nothing is missing and above all the communication with Uwe was extremely accommodating, helpful and exceeded our expectations. Location was perfect for us. Beautiful view, on foot you are in 10-15 min at the foot of the Ettelsberg (Seilbar), in 15 min. at shopping stores, 3 min. to the restaurant Vis a Vis Hütte, 3 min. to the chairlift for mountain biking, summer toboggan run and Co in about 10 min., to the brewery/barn 15 min. and to the center about 25-30 min. Perfect for us. The equipment is absolutely amazing, nothing is really missing. We were allowed to enter much earlier and enjoy the check-out a little later on the day of departure. I highly recommend this place and would love to come back

A modern living space features a wooden dining table with placemats, surrounded by stylish chairs. A gray sofa and a bright yellow loveseat provide comfortable seating. Large windows allow natural light to fill the room, showcasing a view of greenery outside.

5 out of 5 average rating, 5 reviews

Maisonette am Bikepark#Terrasse#Loggia#Garage#

JanRating, 5 stars10 months ago

Overall, the time in the accommodation was a very successful vacation. We were here for the bike park and especially for that it was really perfect. There was nothing wrong with your own garage for the bikes and the optimal location. You feel right at home, everything was super clean and the hostess is always very quick and easy to reach. I would definitely go there again.