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Ski-in/Ski-out vacation rentals in Olsberg

Find and book unique ski-in/ski-out homes on Airbnb

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

Ski-in/ski-out house rentals

Superhost
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.
Home in Winterberg
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 🙏🏻
Guest favorite
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
5 out of 5 average rating, 9 reviews

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.
Superhost
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
4.85 out of 5 average rating, 20 reviews

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.
Top guest favorite
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.
Home in Winterberg
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
Superhost
Home in Winterberg
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!
Superhost
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.
Home in Winterberg
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
Superhost
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
4.84 out of 5 average rating, 37 reviews

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.
Home in Winterberg
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!

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.
Apartment in Winterberg
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.
Guest favorite
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
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!
Guest favorite
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
4.71 out of 5 average rating, 107 reviews

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
Superhost
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
4.64 out of 5 average rating, 14 reviews

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!
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, 47 reviews

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.
Guest favorite
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
4.85 out of 5 average rating, 46 reviews

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!
Superhost
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
4.75 out of 5 average rating, 141 reviews

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.

Ski-in/ski-out condo rentals

Superhost
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
4.83 out of 5 average rating, 58 reviews

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.
Guest favorite
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
4.83 out of 5 average rating, 23 reviews

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.
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.
Guest favorite
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.
Condo in Winterberg
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!
Top guest favorite
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
4.98 out of 5 average rating, 42 reviews

"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.
Condo in Winterberg
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.
Guest favorite
A spacious bedroom features wooden beams along the ceiling, enhancing the open feel. An elegant freestanding bathtub is situated on a light-colored floor, while a cozy area rug adds warmth. Natural light enters through a skylight, illuminating the neutral color palette and calming atmosphere.
Condo in Winterberg
4.94 out of 5 average rating, 16 reviews

Large deluxe apartment "H1 Winterberg"

Maria HeleneRating, 5 stars1 month ago
The place was great and we had a wonderful weekend. Everything was great!

Quick stats about vacation rentals that are ski-in ski-out in Olsberg

  • Total rentals

    30 properties

  • Nightly prices starting at

    G$14,651 GYD before taxes and fees

  • Total number of reviews

    820 reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

Destinations to explore