
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 $119 NZD 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, Wi-Fi 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.
FamilyLocationNearby

Centrally located above the rooftops of Willingen
🏡 Central apartment in Willingen – everything within easy walking distance Welcome to our cozy holiday apartment in the heart of Willingen. If you are looking for accommodation in a central and nature-oriented location with the popular, gently sloping panoramic road, the "Sonnenweg," on the sunny slope above the center, then you have come to the right place. The apartment can accommodate up to 9 people and has a spacious living and dining area with direct access to the sunny balcony.
ValueFamilyHiking

Top location with a view of the slopes | 2-room apartment | Including garage
Modern and spacious 2-room apartment with 65 m² in a prime downtown location with a magnificent view of the slopes. Shopping facilities such as Rewe and Lidl are easily accessible in just 1 minute on foot. A garage is available to you free of charge – ideal for a car, bicycles, or skis. There is also a free outdoor parking space directly at the property. Perfect base for ski vacations, activities in the mountains and relaxing days with short distances to all important facilities.
LocationNearbyWalkability

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
ValueLocationAmenities

Luxury, kid-proof vacation home in Winterberg + views
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!
LocationFamilyBiking

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.
FamilyValueView

Apartment Sunlife Winterberg 4**** Sterne (NEU)
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...
ValueLocationAccuracy

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
LocationValueParking

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.
FamilyLocationAccess

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.
ValueFamilyGetting around

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).
LocationValueWi-Fi

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

Apartment Broche, vacation from everyday life
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Family holiday home · sauna, hot tub, fireplace
FamilyValueDecor

"The Chalets Herzenssache" - Chalet Lebenskunst
LocationSleep qualityPets

Our property in Bödefeld
LocationFamilyOutdoor spaces

Sternenblick Vacation Home
FamilyQuietAmenities

Haus am Wald
LocationFamilyBathroom

Dream cottage for relaxing
FamilyLocationComfort

Stylish villa near Winterberg
LocationFamilyIndoor spaces
Family-friendly, ski-in/ski-out home rentals

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

A little time out
LocationCleanlinessDecor

Chalet with fireplace in prime location Willingen.
LocationFamilyPets

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

Vacation apartment in Willingen-Schwalefeld
LocationValueQuiet

FeWo Natali
ValueLocationView

Panorama Chalet Winterberg
LocationFamilyAccuracy

Vacation home 8-10 people 175 m²
FamilyValueSleep quality
Ski-in/ski-out condo rentals

"The Nest" | Modern apartment with a view
LocationFamilyGetting around

Large deluxe apartment "H1 Winterberg"
FamilyValueKitchen

Vacation home Bergzauber sauna biker park ski
LocationValueKitchen

Fichtenblick in Winterberg directly at the bike park
FamilyValueAmenities

Apartment Mountain Ski & Bikepark
LocationFamilyIndoor spaces

Apartment with a view + 50 sqm + covered balcony
FamilyLocationIndoor spaces

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

Luxury studio apartment (no. 5)
LocationValueCleanliness
When is the best time to visit Olsberg?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $236 NZD | $221 NZD | $218 NZD | $211 NZD | $219 NZD | $216 NZD | $214 NZD | $204 NZD | $207 NZD | $211 NZD | $199 NZD | $221 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 |
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
- Westfalen Park
- Hermannsdenkmal
- Fort Fun Abenteuerland
- Sababurg Animal Park
- Grimmwelt
- German Football Museum
- Fridericianum
- Atta Cave
- Fredenbaumpark
- Karlsaue
- Monkey and Bird Park Eckenhagen
- Schloss Nordkirchen
- Vogelpark Heiligenkirchen
- Documenta-Halle
- Landgrafen Palace
- Wewelsburg
- Altena Castle
- Willingen Ski Lift
- Natural History Museum Kassel
- Panorama Park





