
Ski-in/Ski-out holiday rentals in Willingen (Upland)
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Top-rated ski-in/out rentals in Willingen (Upland)
Guests agree: these ski-in/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.

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

Luxury chalet in a dream location in Willingen.
Deze vrijstaande woning met onlangs gerenoveerde (2024) benedenverdieping beschikt over talrijke voorzieningen, waaronder een sauna, en drie slaapkamers met badkamer. De voorzijde heeft een veranda met panoramisch uitzicht over de dorpsvallei en de Ettelsberg. Achtertuin(1100m2) met terras, voorzien van verwarming, grenst direct aan de bosrand, alwaar diverse wandelpaden en winters aansluiting op de skicarrousel. De woning is bij uitstek geschikt voor een verblijf van vier tot zes personen.

"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

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/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: Ruimte, Natuur & Uitzicht

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

Schöne Unterkunft nahe Zentrum, Skipiste/Rodelbahn

Waldchalet in Willingen

Pistenblume Apartment - ski slope, city center

Luxury log cabin Willingen - right on the ski slope

Luxury apartment at 710 m above sea level: unique views!

Centrally located above the rooftops of Willingen

Panoramic apartment with a view ✨

"Active time-out" - Ski, bike, hike & relax.
Ski-in/out apartment rentals

Gierse Vacation Rental

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 | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $166 SGD | $173 SGD | $169 SGD | $124 SGD | $136 SGD | $129 SGD | $118 SGD | $133 SGD | $133 SGD | $127 SGD | $125 SGD | $172 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 |
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 $38 SGD 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
- Rentals with a washing machine and dryer Willingen (Upland)
- Rentals with a fireplace Willingen (Upland)
- Chalet rentals Willingen (Upland)
- Rentals with outdoor seating Willingen (Upland)
- Rentals with an EV charger Willingen (Upland)
- Pet-friendly rentals Willingen (Upland)
- Rentals with pools Willingen (Upland)
- Rentals with a sauna Willingen (Upland)
- Villa rentals Willingen (Upland)
- Family-friendly rentals Willingen (Upland)
- House rentals Willingen (Upland)
- Fitness-friendly rentals Willingen (Upland)
- Flat rentals Willingen (Upland)
- Rentals with a patio Willingen (Upland)
- Rentals with a firepit Willingen (Upland)
- Ski-in/ski-out rentals Hesse
- Ski-in/ski-out rentals Germany
- Bergpark Wilhelmshöhe
- Kellerwald-edersee National Park
- Skikarussell Altastenberg
- Skiliftcarrousel Winterberg
- Willingen Ski Lift
- Ruhrquelle Ski Resort
- Externsteine
- Paderborner Dom
- Sparrenberg Castle
- Fort Fun Abenteuerland
- Westfalen-Therme
- Atta Cave
- Grimmwelt
- Hermannsdenkmal
- AquaMagis
- Sababurg Animal Park
- Karlsaue
- Ruhrquelle
- Fridericianum
- Sauerlandpark Hemer





