
Ski-in/Ski-out holiday rentals in Willingen (Upland)
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Top-rated ski-in/out rentals in Willingen (Upland)
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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!

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

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

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 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.

Holiday Appartement Winterberg - Ski slopes 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.

Cozy chalet including hot tub and sauna
We offer a cozy chalet including a hot tub and sauna in the holiday village of Bromskirchen. A beautiful forest property in total privacy and silence. In the winter, you can relax in the sauna and hot tub in the evening after a day in the snow. For nature lovers, summer invites you to numerous hiking trails or to chill on the new sun deck with a cool bathing tub. Our property is open. It is only surrounded by plants!
Popular amenities for Willingen (Upland) ski-in/out rentals
Ski-in/out house rentals

"The Chalets Herzenssache" - Chalet Lebenskunst

Luxury vacation home on the lake

Villa SKYLO, complete prime location in Winterberg!

Chalet on Postwiese

Family Home Winterberg: Space, Nature & Views

Vacation home House by the creek

Dream cottage for relaxing

Wellness & Family Retreat in a 5-Star Holiday Home
Family-friendly, ski-in/out home rentals

Waldchalet in Willingen

Sunshine Lodge

Apartment in Küstelberg/near Winterberg

Centrally located above the rooftops of Willingen

Panoramic apartment with a view ✨

Vacation home 8-10 people 175 m²

"Active time-out" - Ski, bike, hike & relax.

Apartment "Relax" - dogs are welcome
Ski-in/out apartment rentals

Private sauna | 2-4 people | Winterberg Center

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"

2 room apartment - first floor (no. 1.1)
When is the best time to visit Willingen (Upland)?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £71 | £80 | £67 | £71 | £78 | £74 | £68 | £77 | £77 | £73 | £72 | £99 |
| 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 |
Quick stats about holiday rentals that are ski-in/out in Willingen (Upland)

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

Nightly prices starting at
Willingen (Upland) holiday rentals start at £22 per night before taxes and fees

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

Family-friendly holiday rentals
40 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 30 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
80 of Willingen (Upland) holiday rentals include wifi 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
Destinations to explore
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- House rentals Willingen (Upland)
- Family-friendly rentals Willingen (Upland)
- Rentals with outdoor seating Willingen (Upland)
- Pet-friendly rentals Willingen (Upland)
- Rentals with a fireplace Willingen (Upland)
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- Flat rentals Willingen (Upland)
- Fitness-friendly rentals Willingen (Upland)
- Rentals with pools Willingen (Upland)
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- Ski-in/ski-out rentals Hesse
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- Bergpark Wilhelmshöhe
- Willingen Ski Lift
- Kellerwald-edersee National Park
- Skikarussell Altastenberg
- Skiliftcarrousel Winterberg
- Ruhrquelle Ski Resort
- Externsteine
- Fort Fun Abenteuerland
- Sparrenberg Castle
- AquaMagis
- Grimmwelt
- Westfalen-Therme
- Atta Cave
- Karlsaue
- Paderborner Dom
- Hermannsdenkmal
- Fridericianum
- Sababurg Animal Park
- Ruhrquelle




