
Ski-in/Ski-out holiday rentals in Olsberg
Find and book unique ski-in/ski-out homes on Airbnb
Quick stats about holiday rentals that are ski-in ski-out in Olsberg

Total holiday rentals
Explore 30 holiday rentals in Olsberg

Nightly prices starting at
Olsberg holiday rentals start at $97 AUD per night before taxes and fees

Verified guest reviews
Over 1,030 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
30 of Olsberg holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Olsberg rentals

4.7 Average rating
Olsberg stays receive an average rating of 4.7 out of 5 from guests
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.

"Black+Beauty" the design hut with sauna
New location right on the Uplandsteig. In this cozy cabin you can enjoy the view and silence - relax by the fireplace - put on an LP… The sun shines through the large windows all day. Ideal starting point for hiking, biking and skiing. Great location on the edge of Willingen/Usseln. Restaurants, Graf Stollberghütte and the Skywalk are within walking distance. With a chic mirror sauna in the garden. Black+Beauty the place of well-being in nature - be active and recharge your batteries.

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

Luxury, childproof holiday home in Winterberg with a view
Get away together to Goldilocks Chalet and enjoy peace, nature and comfort. Wake up with unobstructed views, go out among the autumn colors, and then come home to your own chalet. 🧸 Great for families: trampoline, toys, table soccer, cot, high chair and safety outlets. ✨ Comfort for the parents: a luxurious kitchen with Bora induction, a cozy Wintergarten and, in the evening, watching Netflix together or reading a book by the fireplace! Enjoyment with the whole family!

The little black dress
The little black one! A charming cottage on the Musenberg. A beautiful colorful cottage garden welcomes guests. The covered terrace invites you to enjoy the outdoors. For grilling and cooking, use the outdoor oven. (Spring to fall) The bright house, which is converted into the roof, is decorated 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.

Apartment Sunlife Winterberg 4**** stars (NEW)
Our modern equipped apartment is 68 m² and is designed for 1-5 people. The flat has: 2 double bedrooms with box spring bed 1 living & dining room with sofa bed 1 kitchen with dishwasher, oven, stove, fridge, freezer, microwave... 1 bathroom 1 hallway 1 large terrace 2 parking spaces 1 safe Wifi Amenities for the kids: 2 travel cribs 2 high chairs 1 changing table with diaper bin 1 baby tub 1 crib bumper 1 toilet seat 1 baby monitor 1 crawling blanket Toys...

Design Apartment - Ski. Bike. Sauna.
Welcome to our beautiful apartment in Winterberg! This cozy and newly renovated apartment can accommodate up to 4 people and is located directly at the ski slope and bike park. The location is perfect for those looking for central accommodation near the main attractions. . private sauna . private balcony with hammock . newly renovated 2023 . 100m to the bike park/ski slope . fireplace (elect.) . King size box spring bed . free, fast WIFI . Bicycle/ski cellar

Apartment Tokio + Sauna, 100 m to Ski and Bikepark
This modern 70 m² apartment with private sauna is located directly on the ski slope and the bike park – ideal for an active vacation with relaxation. Two bedrooms with box-spring beds and a sofa bed can accommodate up to 6 people. The fully equipped kitchen, a stylish bathroom with shower and two balconies create a cozy atmosphere. Wi-Fi, Netflix and Waipu TV are included. An underground parking space is also at your disposal – for an all-round carefree stay.

"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.

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 little time out
Welcome to our little time-out. Our 45 sqm apartment is located right on the edge of the forest, not far from the Brilon ski slope. From here you can go hiking (Rothaarsteig), cycling or activities in nearby Willingen. The center of the cozy Brilon old town is a 15-minute walk. With 6500 m² of water, Brilon has the largest forest outdoor pool in North Rhine-Westphalia and can be reached by car in 5 minutes.

Apartment (bedroom, living room, bath room)
Apartment with separate entrance. bath room with shower bedroom with 2 beds (+ baby bed) living room with sleeping couch for up to two persons TV, WLAN and towels/bed linen are available. The apartment has a small terrace. The apartment is located in the village 'Eimelrod' (about 12km from Willingen).

* 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.
Popular amenities for Olsberg ski-in/ski-out rentals
Ski-in/ski-out house rentals

Apartment Broche, vacation from everyday life

"The Chalets Herzenssache" - Chalet Lebenskunst

Family holiday home · sauna, hot tub, fireplace

Sternenblick holiday home

Our property in Bödefeld

Haus am Wald

Dream cottage for relaxing

Villa SKYLO, complete prime location in Winterberg!
Family-friendly, ski-in/ski-out home rentals

Prime location with a view of the slopes | 2-room apartment | garage included

*| Chalet-Suite |* by Meis I Willingen (Upland)

Holiday apartment in Willingen-Schwalefeld

Vacation home directly in nature

Chalet with fireplace in prime location Willingen.

Centrally located above the rooftops of Willingen

"Leo's Cottage" Recreation in the nature and ski area

FeWo Natali
Ski-in/ski-out condo rentals

Large deluxe apartment "H1 Winterberg"

Apartment Mountain Ski & Bikepark

Vacation home Bergzauber sauna biker park ski

Fichtenblick in Winterberg directly at the bike park

Apartment with a view + 50 sqm + covered balcony

Bergpanorama – Family & Bike | 5 min. to "Kappe"

Luxury studio apartment (no. 5)

Nora apartment Winterberg with balcony city close
When is the best time to visit Olsberg?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $194 AUD | $181 AUD | $178 AUD | $173 AUD | $180 AUD | $177 AUD | $175 AUD | $167 AUD | $170 AUD | $173 AUD | $163 AUD | $181 AUD |
| Avg. temp | -2°C | -1°C | 1°C | 6°C | 10°C | 13°C | 15°C | 15°C | 11°C | 7°C | 2°C | -1°C |
Destinations to explore
- Rentals with lake access Olsberg
- Chalet rentals Olsberg
- House rentals Olsberg
- Pet-friendly rentals Olsberg
- Rentals with a sauna Olsberg
- Villa rentals Olsberg
- Family-friendly rentals Olsberg
- Apartment rentals Olsberg
- Waterfront rentals Olsberg
- Ski-in/ski-out rentals North Rhine-Westphalia
- Ski-in/ski-out rentals Germany
- Bergpark Wilhelmshöhe
- Signal Iduna Park
- Kellerwald-edersee National Park
- Externsteine
- Hermannsdenkmal
- Westfalen Park
- Fort Fun Abenteuerland
- Sababurg Animal Park
- Grimmwelt
- German Football Museum
- Fridericianum
- Atta Cave
- Karlsaue
- Fredenbaumpark
- Monkey and Bird Park Eckenhagen
- Schloss Nordkirchen
- Vogelpark Heiligenkirchen
- Documenta-Halle
- Landgrafen Palace
- Altena Castle
- Wewelsburg
- Willingen Ski Lift
- Natural History Museum Kassel
- Panorama Park





