
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 G$6,273 GYD per night before taxes and fees

Verified guest reviews
Over 2,310 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Vacation rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
10 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.

Mellie’s Fewo Willingen 2
Herzlich willkommen in unserer frisch renovierten Ferienwohnung! Die Unterkunft befindet sich im wunderschönen Strycktal, unweit des Skywalks. Genießt eure Auszeit im stilvoll eingerichteten Wohnbereich mit Elektrokamin für gemütliche Abende oder auf dem Balkon mit traumhaftem Fernblick in die Natur. Die Wohnung bietet Platz für 4 Personen und verfügt über ein separates Schlafzimmer, eine Ausziehcouch, sowie eine vollausgestatteten Küche. Hunde auf Anfrage willkommen. Ankommen und Genießen!

*| 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

„Ride & Relax“ Willingen
Das neue Ferienhaus "Ride & Relax" hat eine perfekte Lage im Willinger Hoppecketal. Vom Balkon und der privaten Terrasse bietet sich ein atemberaubender Blick auf die besten Skipisten, die sich im Sommer zum Mountainbikeparadies "Bikepark Willingen" verwandeln. Trotzdem liegt das Haus so zentral, dass man den Ort und fast alle Sehenswürdigkeiten zu Fuß erreichen kann. Das Ferienhaus wird ab Ende 2025 vermietet nach vollständiger Sanierung aller Räume und komplett neuer stylischer Möblierung.

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.

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

Luxury chalet in a dream location in Willingen.
This detached house with recently renovated (2024) ground floor has numerous amenities, including a sauna, and three bedrooms with bathroom. The front has a veranda with panoramic views over the village valley and the Ettelsberg. Backyard (1100m2) with terrace, equipped with heating, directly adjacent to the edge of the forest, where various hiking trails and winter connection to the ski carousel. The home is ideally suited for stays of four to six people.

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!

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.)

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

Vacation home Bergzeit Karles – Rothaarsteig Heimat

"The Chalets Herzenssache" - Chalet Lebenskunst

Luxury vacation home on the lake

Villa SKYLO, complete prime location in Winterberg!

Chalet on Postwiese

Luxury Chalet Winterberg: Quiet, Views & Kid-Proof

Vacation home House by the creek

Dream cottage for relaxing
Family-friendly, ski-in/ski-out home rentals

Waldchalet in Willingen

Sunshine Lodge

Winterberg Centrum apartment privet bike cellar

Vacation home directly in nature

Luxury log cabin Willingen - right on the ski slope

Easter nest - with pool & sauna & Wi-Fi near ski lift

Centrally located above the rooftops of Willingen

Panoramic apartment with a view ✨
Ski-in/ski-out condo rentals

Beautiful ski and hiking domicile with south balcony

Apartment Forest Ski & Bikepark

Gierse Vacation Rental

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

Your dream apartment in Willingen

Ski and pedal your XL pad 08

Apartment with a view + 50 sqm + covered balcony

Large deluxe apartment "H1 Winterberg"
When is the best time to visit Willingen (Upland)?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$27,181 GYD | G$28,227 GYD | G$27,600 GYD | G$20,282 GYD | G$22,163 GYD | G$21,118 GYD | G$19,236 GYD | G$21,745 GYD | G$21,745 GYD | G$20,700 GYD | G$20,491 GYD | G$28,018 GYD |
| 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 |
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- 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
- Fort Fun Abenteuerland
- Atta Cave
- Fridericianum
- Karlsaue
- Heimat-Tierpark Olderdissen
- Vogelpark Heiligenkirchen
- Documenta-Halle
- Monkey and Bird Park Eckenhagen
- Panorama Park
- Natural History Museum Kassel
- Altena Castle
- Möhne Reservoir
- Wewelsburg
- Landgrafen Palace
- Schloss Wilhelmsthal





