
Ski-in/Ski-out holiday rentals in Olsberg
Find and book unique ski-in/out homes on Airbnb
Top-rated ski-in/out rentals in Olsberg
Guests agree: these ski-in/out homes are highly rated for location, cleanliness and more.

Mellie’s Fewo Willingen 2
Herzlich willkommen in unserer frisch renovierten Ferienwohnung! Die Unterkunft befindet sich im wunderschönen Strycktal, unweit des Skywalks. Genießt eure Auszeit im stilvoll eingerichteten Wohnbereich mit Elektrokamin für gemütliche Abende oder auf dem Balkon mit traumhaftem Fernblick in die Natur. Die Wohnung bietet Platz für 4 Personen und verfügt über ein separates Schlafzimmer, eine Ausziehcouch, sowie eine vollausgestatteten Küche. Hunde auf Anfrage willkommen. Ankommen und Genießen!

Apartment Sunlife Winterberg 4**** Sterne (NEU)
Unsere modern ausgestattete Ferienwohnung hat 68m² und ist für 1-5 Personen ausgelegt. Die Wohnung hat: 2 Doppelzimmer mit Boxspringbett 1 Wohn-& Esszimmer mit Schlafsofa 1 Küche mit Spülmaschine, Backofen, Herd, Kühlschrank, Gefrierschrank, Mikrowelle... 1 Badezimmer 1 Flur 1 große Terrasse 2 Parkplätze 1 Tresor / Safe WLAN Ausstattung für die Kids: 2 Reisebetten 2 Hochstühle 1 Wickeltisch mit Windeltonne 1 Babywanne 1 Rausfallgitter 1 Toilettensitz 1 Babyphone 1 Krabbeldecke Spielzeug….

"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

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.

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 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!

Sauerland Panorama Vacation Home in Elpe (Olsberg)
Luxury holiday home (sleeps 7) by stream. Large garden and panoramic views, near Winterberg. Child-friendly house with large living room with wood-burning stove, upstairs 3 spacious bedrooms, 2 bathrooms. Table tennis and bicycles in garage. Energy surcharge applies in October-April. From 11/2/2025, the downstairs apartment (1-4 persons) plus infrared sauna is not automatically available anymore for rental; only for previous bookings and on request.

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.

Cozy chalet including hot tub and sauna
We offer a cozy chalet including a hot tub and sauna in the holiday village of Bromskirchen. A beautiful forest property in total privacy and silence. In the winter, you can relax in the sauna and hot tub in the evening after a day in the snow. For nature lovers, summer invites you to numerous hiking trails or to chill on the new sun deck with a cool bathing tub. Our property is open. It is only surrounded by plants!

FeWo Natali
Welcome to the new apartment in beautiful Winterberg! The lovingly furnished apartment has enough space for 6 people. Size: 76 square meters Rooms: Living room, 2 separate bedrooms, kitchen and bathroom. Small highlight: the bathroom is equipped with an infrared cabin. The tourist tax of 3.00 euros per person / night will be charged separately on site. We live on the first floor. We'd love to have you stay with us.

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

Waldchalet in Willingen

House with sauna 15 min. from Winterberg and Willingen

"The Chalets Herzenssache" - Chalet Lebenskunst

Luxury vacation home on the lake

Villa SKYLO, complete prime location in Winterberg!

Chalet on Postwiese

Family Home Winterberg: Space, Nature & Views

Dream cottage for relaxing
Family-friendly, ski-in/out home rentals

Sunshine Lodge

Winterberg Centrum apartment privet bike cellar

Apartment in Küstelberg/near Winterberg

StayCozy Gray Bike&Ski Apartment, animal friendly

Panoramic apartment with a view ✨

Vacation home 8-10 people 175 m²

Villa Nordhang - Apartment 3

Cozy cottage in Winterberg Altastenberg
Ski-in/out apartment rentals

Gierse Vacation Rental

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

Your dream apartment in Willingen

"The Nest" | Modern apartment with a view

Apartment Mountain Ski & Bikepark

Apartment with a view + 50 sqm + covered balcony

Holiday apartment in beautiful Sauerland

Large deluxe apartment "H1 Winterberg"
When is the best time to visit Olsberg?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £98 | £97 | £86 | £93 | £92 | £92 | £93 | £89 | £90 | £92 | £87 | £96 |
| 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 |
Quick stats about holiday rentals that are ski-in/out in Olsberg

Total holiday rentals
Explore 30 holiday rentals in Olsberg

Nightly prices starting at
Olsberg holiday rentals start at £44 per night before taxes and fees

Verified guest reviews
Over 990 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
30 of Olsberg holiday rentals include wifi access

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

4.8 Average rating
Olsberg stays are highly rated by guests – averaging 4.8 out of 5!
Destinations to explore
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- Rentals with a sauna Olsberg
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- Ski-in/ski-out rentals North Rhine-Westphalia
- Ski-in/ski-out rentals Germany
- Bergpark Wilhelmshöhe
- Willingen Ski Lift
- Kellerwald-edersee National Park
- Skikarussell Altastenberg
- Skiliftcarrousel Winterberg
- Signal Iduna Park
- Ruhrquelle Ski Resort
- Externsteine
- Fort Fun Abenteuerland
- Sparrenberg Castle
- Dortmunder U
- AquaMagis
- Grimmwelt
- Westfalen-Therme
- German Football Museum
- Atta Cave
- Fredenbaumpark
- Paderborner Dom
- Karlsaue
- Hermannsdenkmal
- Fridericianum
- Sababurg Animal Park
- Ruhrquelle
- Westfalen Park




