
Ski-in/Ski-out vacation rentals in Olsberg
Find and book unique ski-in/ski-out homes on Airbnb
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
Get the amount of space that is right for you
Popular amenities for Olsberg ski-in/ski-out rentals
Ski-in/ski-out house rentals

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 & Modern House | Garden & Nature
We spent a wonderfully long weekend at the Goldilocks Chalet with our family and two children. What a beautiful property! Even on the rainy day, the children had a great time in the house. The spacious floor offered plenty of play space and the interior is modern, cozy and equipped with every comfort. The kitchen is equipped with nice, new equipment and the shower is really fantastic. The location is also ideal: all child-friendly activities are only a 15-minute drive away, so we could easily make trips. The contact with the owner was smooth and pleasant, although we actually hardly needed anything because everything was perfectly arranged. Our kids already want to go back – and so do we! Highly recommended for families looking for comfort, peace and fun for the children.
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

Cozy nostalgic country house apartment, Schanze
Christiane is very welcoming. The place is quiet and peaceful as described. Everything was very good. The only concern we had is that there is no real bike room even though it's in the description. There was just a small outdoor shed with no lock and no attachment point. But we had two valuable bikes... But Christiane was very accommodating and let us use a storage room for one of the two bikes (too small to put both). We left the 2nd in the car. Other than that, no worries. In short, we highly recommend the accommodation but perhaps not to cyclists who come with their bikes 😉

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.

Luxury chalet in dream location in Willingen.
Getting to the driveway was a bit exciting. Otherwise, everything is great and satisfactory! Everything worked.

Vacation Rental Annelie
it was exactly as the description indicated. i would go there again in no time. Nice to walk close to the slopes. Small kilometers. The house looked neat and well cared for. Everything was there what we needed. great Matthias
Ski-in/ski-out condo rentals

Chic apartment for 2 people
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.

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 ⭐⭐⭐⭐⭐

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!

Super cozy and in the middle of nature with pool
We definitely want to come back. The place is very quiet and peaceful, beautiful nature. Prompt responses from the host were very helpful.

"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

Apartment Pönblick
Top location for visiting bike park in Willingen.

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$14,645 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
- Cologne Vacation rentals
- Düsseldorf Vacation rentals
- Utrecht Vacation rentals
- Hamburg Vacation rentals
- Amsterdam Vacation rentals
- Nuremberg Vacation rentals
- Antwerp Vacation rentals
- Rotterdam Vacation rentals
- Stuttgart Vacation rentals
- Brussels Vacation rentals
- The Hague Vacation rentals
- Baden Vacation rentals
- Chalet rentals Olsberg
- Rentals with outdoor seating Olsberg
- Pet-friendly rentals Olsberg
- Apartment rentals Olsberg
- Rentals with a fire pit Olsberg
- Rentals with an EV charger Olsberg
- Kid-friendly rentals Olsberg
- Rentals with a sauna Olsberg
- Villa rentals Olsberg
- House rentals Olsberg
- Waterfront rentals Olsberg
- Rentals with a fireplace Olsberg
- Rentals with a patio Olsberg
- Rentals with a washer and dryer Olsberg
- Ski-in/ski-out rentals North Rhine-Westphalia
- Ski-in/ski-out rentals Germany
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom