
Ski-in/Ski-out vacation rentals in Olsberg
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Top-rated ski-in/ski-out rentals in Olsberg
Guests agree: these ski-in/ski-out homes are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Olsberg ski-in/ski-out rentals
Ski-in/ski-out house rentals

BergZauber - up to 22 people, 10 bathrooms, sauna
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 🙏🏻

Home with sauna close to Winterberg and Willingen
The house was designed in a charming old German style, creating a warm and inviting atmosphere. It felt cozy and comfortable throughout our stay.

Luxury Block House A
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 Chalets Herzenssache" - Chalet Lebenskunst
Great accommodation, extremely clean and looked after by very friendly hosts

Villa SKYLO, complete top location in Winterberg !
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!

Cozy detached house with Hot Tub
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

Spacious, vintage holiday home with a view.
Enjoyed a ski weekend with friends. Daan gave us good tips and the house was great. Location super close to Winterberg.

Haus Ludwiges (Winterberg)
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

Goski & Gobike Winterberg (Netflix, Waipu.tv free)
GREAT LOCATION, here you will be close to the skii resort and town for eating out. everything is within walking distance.

Luxury apartment with garden and unique view!
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!

Apartment (bedroom, living room, bath room)
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

Landhaus Schlossberg Apartment 2
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!

GENIETEN EVE's CHALET NEUASTENBERG
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.

F****Vacation Rental Country House Postwiese
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!

Beautiful living on the Sauerland Höhenflug
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.

Luxury chalet in dream location in Willingen.
Getting to the driveway was a bit exciting. Otherwise, everything is great and satisfactory! Everything worked.
Ski-in/ski-out condo rentals

Beautiful ski and hiking domicile with south balcony
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.

Gierse Vacation Rental
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 ⭐⭐⭐⭐⭐

Private sauna | 2-4 people | Winterberg Center
We really enjoyed our stay here. Lots of space, everything you need, and great location. Would definitely stay again.

vacation apartment Bergpanorama - TV, parking lot
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. 😊

Your dream apartment in Willingen
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!

"The Nest" | Modern apartment with a view
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

Maisonette am Bikepark#Terrasse#Loggia#Garage#
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.

Large deluxe apartment "H1 Winterberg"
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
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