
Ski-in/Ski-out holiday rentals in Olsberg
Find and book unique ski-in/out homes on Airbnb
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 $90 SGD 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 & 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

4.7 Average rating
Olsberg stays receive an average rating of 4.7 out of 5 from guests
Top-rated ski-in/out rentals in Olsberg
Guests agree: these ski-in/out homes are highly rated for location, cleanliness and more.

*| 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

"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, kid-proof vacation home in Winterberg + views
Welcome to Winterberg! 🌲 Relax with the family: wake up to unobstructed views, have breakfast on the terrace and BBQ in the evening sun. 🧸 100% kid-proof: trampoline, toys, cot, high chair and safe power sockets. Enjoy the luxury kitchen (Bora induction), table football in the cozy Wintergarten, or just relax with Netflix. Your vacation starts off right: upon arrival at Goldilocks Chalet, the beds are already wonderfully made. 🛏️ Enjoy our Superhost service!

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 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...

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.

* 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
Our cozy apartment is located in Niedersfeld, a nice and quiet suburb of Winterberg. On the sunny east-facing mountain side above the core municipality of Niedersfeld, you will stay in a modern furnished apartment at 573 meters above sea level.
Popular amenities for Olsberg ski-in/out rentals
Ski-in/out house rentals

Apartment Broche, vacation from everyday life

Autumn escape by forest · Sauna, hot tub, fire pit

Luxury vacation home on the lake

Sternenblick Vacation Home

Dream cottage for relaxing

Our property in Bödefeld

Haus am Wald

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

FeWo Natali

A little time out

Vacation home directly in nature

Vacation apartment in Willingen-Schwalefeld

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

Best View Winterberg - Kleines Studioapartment

Luxury chalet in a dream location in Willingen.

Easter nest - with pool & sauna & Wi-Fi near ski lift
Ski-in/out apartment rentals

Large deluxe apartment "H1 Winterberg"

Apartment Forest 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 | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $178 SGD | $166 SGD | $164 SGD | $159 SGD | $165 SGD | $162 SGD | $161 SGD | $154 SGD | $156 SGD | $159 SGD | $150 SGD | $166 SGD |
| 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
- Chalet rentals Olsberg
- Rentals with lake access Olsberg
- House rentals Olsberg
- Pet-friendly rentals Olsberg
- Rentals with a sauna Olsberg
- Family-friendly rentals Olsberg
- Villa rentals Olsberg
- Flat 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
- Willingen Ski Lift
- Sparrenberg Castle
- Westfalen Park
- Hermannsdenkmal
- Sababurg Animal Park
- German Football Museum
- Fort Fun Abenteuerland
- Grimmwelt
- Dortmunder U
- Fridericianum
- Atta Cave
- Karlsaue
- Fredenbaumpark
- Monkey and Bird Park Eckenhagen
- Schloss Nordkirchen
- Vogelpark Heiligenkirchen
- Documenta-Halle
- Landgrafen Palace
- Altena Castle
- Wewelsburg





