
Ski-in/Ski-out holiday 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.

Apartment Tokio + Sauna, 100 m to Ski and Bikepark
Diese moderne 70 m² Ferienwohnung inkl. privater Sauna liegt direkt an der Skipiste und dem Bikepark – ideal für einen Aktivurlaub mit Entspannung. Zwei Schlafzimmer mit Boxspringbetten und eine Schlafcouch bieten Platz für bis zu 6 Personen. Die voll ausgestattete Küche, ein stilvolles Bad mit Dusche und zwei Balkone schaffen eine gemütliche Atmosphäre. WLAN, Netflix und Waipu-TV sind inklusive. Ein Tiefgaragenstellplatz steht dir ebenfalls zur Verfügung – für einen rundum sorglosen Aufenthalt.

*| Chalet-Suite |* by Meis I Willingen (Upland)
Welcome to the chalet suite in the heart of Willingen – pure relaxation awaits! This stylishly furnished suite combines the charm of the region with modern comforts and offers everything you need for a relaxing stay: → King-size bed for a restful sleep → Smart TV + comfortable seating areas → Free Wi-Fi → Parking included + private bicycle storage → Fully equipped kitchen with automatic coffee machine + dishwasher → Bathroom with modern shower → Washing machine + large balcony for relaxation

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.

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

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.

Wellness & Family Retreat in a 5-Star Holiday Home
Your wellness getaway in Winterberg! Our 5-star holiday home accommodates up to 8 guests. Relax in the panoramic sauna with direct forest views or unwind in the hot tub on the large terrace. A cozy fireplace and two wellness areas guarantee ultimate relaxation. Great for families too: a garden playground and a kids' lounge keep the little ones happy. High-end, thoughtful, and perfect for your premium retreat in the Sauerland region.

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!

* 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.

Wi-Fi, 72 m², Nature, Cozy, Lake, Glücksklee 4YOU
Unsere gemütliche Ferienwohnung liegt in Niedersfeld, einem schönen und ruhigen Vorort von Winterberg. Auf der östlich gelegenen sonnen reichen Bergseite oberhalb der Kerngemeinde Niedersfeld, wohnst du in einer modern eingerichteten Ferienwohnung auf 573 Höhenmetern.
Popular amenities for Olsberg ski-in/ski-out rentals
Ski-in/ski-out house rentals

Waldchalet in Willingen

New | Comfort Chalet | Sauna | 5 people | Skiing

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: Ruimte, Natuur & Uitzicht
Family-friendly, ski-in/ski-out home rentals

Sunshine Lodge

Winterberg Centrum apartment privet bike cellar

Apartment in Küstelberg/near Winterberg

Quiet apartment near a forest

"Active time-out" - Ski, bike, hike & relax.

Hutstyle - *Direct piste access*SNES*Parking

Deluxe Apartment for 5| Sauna & Pool |Free Parking

„Ride & Relax“ Willingen
Ski-in/ski-out condo rentals

Gierse Vacation Rental

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

Your dream apartment in Willingen

"The Nest" | Modern apartment with a view

Apartment with a view + 50 sqm + covered balcony

Holiday apartment in beautiful Sauerland

Large deluxe apartment "H1 Winterberg"

2 room apartment - first floor (no. 1.1)
When is the best time to visit Olsberg?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $232 NZD | $217 NZD | $214 NZD | $211 NZD | $207 NZD | $209 NZD | $211 NZD | $201 NZD | $204 NZD | $207 NZD | $196 NZD | $217 NZD |
| 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 ski-out in Olsberg

Total holiday rentals
Explore 30 holiday rentals in Olsberg

Nightly prices starting at
Olsberg holiday rentals start at $100 NZD 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 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

4.8 Average rating
Olsberg stays are highly rated by guests—averaging 4.8 out of 5!
Destinations to explore
- Rentals with a sauna Olsberg
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- Rentals with a fireplace Olsberg
- Pet-friendly rentals Olsberg
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- House rentals Olsberg
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- Ski-in/ski-out rentals North Rhine-Westphalia
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- Bergpark Wilhelmshöhe
- Kellerwald-edersee National Park
- Signal Iduna Park
- Externsteine
- Willingen Ski Lift
- Sparrenberg Castle
- German Football Museum
- Hermannsdenkmal
- Fort Fun Abenteuerland
- Grimmwelt
- Dortmunder U
- Sababurg Animal Park
- Westfalen Park
- Atta Cave
- Fridericianum
- Karlsaue
- Heimat-Tierpark Olderdissen
- Documenta-Halle
- Schloss Nordkirchen
- Monkey and Bird Park Eckenhagen
- Panorama Park
- Thier-Galerie
- Vogelpark Heiligenkirchen
- Altena Castle





