
Ski-in/Ski-out vacation rentals in Willingen (Upland)
Find and book unique ski-in/ski-out homes on Airbnb
Quick stats about vacation rentals that are ski-in ski-out in Willingen (Upland)

Total vacation rentals
Explore 80 vacation rentals in Willingen (Upland)

Nightly prices starting at
Willingen (Upland) vacation rentals start at ﺩ.ﺇ 147 per night before taxes and fees

Verified guest reviews
Over 2,450 verified reviews to help you choose

Family-friendly vacation rentals
40 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Vacation rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
80 of Willingen (Upland) vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Willingen (Upland) rentals

4.7 Average rating
Willingen (Upland) stays receive an average rating of 4.7 out of 5 from guests
Top-rated ski-in/ski-out rentals in Willingen (Upland)
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.

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.

Chalet with fireplace in prime location Willingen.
Wooden chalet on the edge of the forest with a unique panorama of Willingen village and valley. Winters directly from the back garden on ski slopes and other seasons connection to numerous hiking trails and mountain bike trails. Village center, toboggan run and playground and restaurants are within walking distance. Almost all day sun all around. The house is one of the highest houses in the village of Willingen. The house is characterized by its cozy appearance and "outside" feeling.

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

„Ride & Relax“ Willingen
The new vacation home "Ride & Relax" has a perfect location in the Willinger Hoppecketal. From the balcony and the private terrace there is a breathtaking view of the best ski slopes, which in summer turn into the mountain bike paradise "Bikepark Willingen". Nevertheless, the house is so central that you can walk to the place and almost all the sights. The cottage will be rented from the end of 2025 after complete renovation of all rooms and completely new stylish furniture.

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**** 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...

"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.

Quiet apartment near a forest
Relax with the whole family in this beautiful apartment on the edge of a forest. You will find many hiking trails to enjoy in nature, the center of Willingen is close by for a snack and a drink, or for skiing. You will find a nice apartment with a studio upstairs (bedroom 3), which can be reached via the stairs. (parties, smoking and noise are prohibited. We ask all guests to keep in mind that it is quiet in the building between 10 p.m. and 8 a.m.)

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.

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).
Popular amenities for Willingen (Upland) ski-in/ski-out rentals
Ski-in/ski-out house rentals

Luxury, kid-proof vacation home in Winterberg + views

"The Chalets Herzenssache" - Chalet Lebenskunst

Vacation home House by the creek

Haus am Wald

Dream cottage for relaxing

Bergwild vacation home

House Waldblick Bromskirchen

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

Vacation apartment in Willingen-Schwalefeld

Willingen modern apartment balcony in the green park free

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

Picturesque apartment Willingen "the water"

PanoramaChalet Winterberg

Panoramic balcony · Shared pool & sauna

Nice place to stay near the center, ski slope/ice rink

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

Large deluxe apartment "H1 Winterberg"

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

Winterberg guest house, hallway D

Your dream apartment in Willingen
When is the best time to visit Willingen (Upland)?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 477 | ﺩ.ﺇ 496 | ﺩ.ﺇ 485 | ﺩ.ﺇ 448 | ﺩ.ﺇ 492 | ﺩ.ﺇ 463 | ﺩ.ﺇ 338 | ﺩ.ﺇ 382 | ﺩ.ﺇ 382 | ﺩ.ﺇ 364 | ﺩ.ﺇ 360 | ﺩ.ﺇ 492 |
| 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 a sauna Willingen (Upland)
- Chalet rentals Willingen (Upland)
- Pet-friendly rentals Willingen (Upland)
- Family-friendly rentals Willingen (Upland)
- Apartment rentals Willingen (Upland)
- Villa rentals Willingen (Upland)
- House rentals Willingen (Upland)
- Rentals with pools Willingen (Upland)
- Ski-in/ski-out rentals Hesse
- Ski-in/ski-out rentals Germany
- Bergpark Wilhelmshöhe
- Kellerwald-edersee National Park
- Externsteine
- Hermannsdenkmal
- Fort Fun Abenteuerland
- Sababurg Animal Park
- Grimmwelt
- Fridericianum
- Atta Cave
- Karlsaue
- Monkey and Bird Park Eckenhagen
- Vogelpark Heiligenkirchen
- Documenta-Halle
- Willingen Ski Lift
- Wewelsburg
- Landgrafen Palace
- Altena Castle
- Natural History Museum Kassel
- Panorama Park
- Sparrenberg Castle
- Möhne Reservoir
- Schloss Wilhelmsthal
- Heimat-Tierpark Olderdissen





