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

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

Nightly prices starting at
Willingen (Upland) holiday rentals start at $57 AUD per night before taxes and fees

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

Family-friendly holiday rentals
40 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 40 rentals that welcome pets

Holiday 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) holiday 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.

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

„Black+Beauty“ die Design-Hütte mit 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
🏡 Zentrale Ferienwohnung in Willingen – alles bequem zu Fuß erreichbar Willkommen in unserer gemütlichen Ferienwohnung im Herzen Willingens. Wer eine Unterkunft in zentraler sowie naturverbundenen Lage mit der beliebten, sanft ansteigenden Panoramastraße dem "Sonnenweg" am Sonnenhang oberhalb des Zentrums sucht, ist bei uns genau richtig. Die Wohnung bietet Platz für bis zu 9 Personen und verfügt über einen großzügigen Wohn- und Essbereich mit direktem Zugang zum sonnigen Balkon.

Holiday apartment in Willingen-Schwalefeld
Genießen Sie erholsame Tage in unserem gemütlichen Apartment in Willingen-Schwalefeld – perfekt für alle, die Natur, Ruhe und Aktivurlaub verbinden möchten.Nach einem erlebnisreichen Tag können Sie auf dem Balkon den Abend gemütlich ausklingen lassen. Ausstattung & Komfort: • Smart-TV • Balkon mit Sitzgelegenheit und Grillmöglichkeit • Voll ausgestattete Küche (inkl. Kochutensilien) • Schlafmöglichkeiten für 4 Personen: Doppelbett + Schlafsofa • Ruhige Lage ohne Durchgangsverkehr

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 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 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!

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

House Waldblick Bromskirchen

"The Chalets Herzenssache" - Chalet Lebenskunst

Our property in Bödefeld

Luxury vacation home on the lake

Villa SKYLO, complete prime location in Winterberg!

Haus am Wald

Luxury, childproof holiday home in Winterberg with a view

Vacation home House by the creek
Family-friendly, ski-in/ski-out home rentals

Picturesque apartment Willingen "the water"

Lovely accommodation near the centre, ski slope/ice rink

Panorama Chalet Winterberg

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

Willingen modern apartment balcony in the green park free

Quiet apartment near a forest

Deluxe Apartment | Sauna & Pool | Free Parking

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

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

Your dream apartment in Willingen

Apartment Mountain Ski & Bikepark

Ski and pedal your XL pad 08

Apartment with a view + 50 sqm + covered balcony

Large deluxe apartment "H1 Winterberg"

Nora apartment Winterberg with balcony city close

Vacation home "Schanze" in Willingen
When is the best time to visit Willingen (Upland)?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $185 AUD | $193 AUD | $188 AUD | $138 AUD | $151 AUD | $144 AUD | $131 AUD | $148 AUD | $148 AUD | $141 AUD | $140 AUD | $191 AUD |
| 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 washing machine and dryer Willingen (Upland)
- Rentals with an EV charger Willingen (Upland)
- Chalet rentals Willingen (Upland)
- House rentals Willingen (Upland)
- Rentals with pools Willingen (Upland)
- Pet-friendly rentals Willingen (Upland)
- Rentals with a fire pit Willingen (Upland)
- Villa rentals Willingen (Upland)
- Rentals with a patio Willingen (Upland)
- Fitness-friendly rentals Willingen (Upland)
- Rentals with outdoor seating Willingen (Upland)
- Apartment rentals Willingen (Upland)
- Family-friendly rentals Willingen (Upland)
- Rentals with a sauna Willingen (Upland)
- Rentals with a fireplace Willingen (Upland)
- Ski-in/ski-out rentals Hesse
- Ski-in/ski-out rentals Germany
- Bergpark Wilhelmshöhe
- Kellerwald-edersee National Park
- Externsteine
- Willingen Ski Lift
- Sparrenberg Castle
- Hermannsdenkmal
- Grimmwelt
- Sababurg Animal Park
- Fridericianum
- Fort Fun Abenteuerland
- Atta Cave
- Karlsaue
- Monkey and Bird Park Eckenhagen
- Vogelpark Heiligenkirchen
- Documenta-Halle
- Wewelsburg
- Altena Castle
- Landgrafen Palace
- Natural History Museum Kassel
- Panorama Park
- Schloss Wilhelmsthal
- Möhne Reservoir
- Heimat-Tierpark Olderdissen





