
Ski-in/Ski-out holiday rentals in Willingen (Upland)
Find and book unique ski-in/out homes on Airbnb
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 £30 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 & child-friendly amenities

Pet-friendly holiday rentals
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

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
Top-rated ski-in/out rentals in Willingen (Upland)
Guests agree: these ski-in/out homes are highly rated for location, cleanliness and more.

*| 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

Centrally located above the rooftops of Willingen
🏡 Central holiday apartment in Willingen – everything within easy walking distance Welcome to our cosy holiday apartment in the heart of Willingen. If you are looking for accommodation in a central location close to nature, with the popular, gently sloping panoramic road, the "Sonnenweg", on the Sonnenhang above the centre, then you've 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.

"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.

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

Prime location with a view of the slopes | 2-room flat | garage included
Modern and spacious 2-room apartment measuring 65m² in a prime central location with a magnificent view of the slopes. Shops such as Rewe and Lidl are just a minute's walk away. A garage is available to you free of charge – ideal for cars, bicycles or skis. There is also a free outdoor parking space right by the property. The perfect starting point for skiing holidays, activities in the mountains and relaxing days, with all the important facilities within easy reach.

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...

Apartment Tokio + Sauna, 100 m to Ski and Bikepark
This modern 70 m² apartment with private sauna is located directly on the ski slope and the bike park – ideal for an active vacation with relaxation. Two bedrooms with box-spring beds and a sofa bed can accommodate up to 6 people. The fully equipped kitchen, a stylish bathroom with shower and two balconies create a cozy atmosphere. Wi-Fi, Netflix and Waipu TV are included. An underground parking space is also at your disposal – for an all-round carefree stay.

"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

Apartment Broche, vacation from everyday life

Luxury childproof holiday home in Winterberg + view

Family holiday home · sauna, hot tub, fireplace

"The Chalets Herzenssache" - Chalet Lebenskunst

Sternenblick Holiday Home

Vacation home House by the creek

Our property in Bödefeld

Haus am Wald
Family-friendly, ski-in/out home rentals

* Adventure overnight stay in one of our yurts *

Holiday apartment in Willingen-Schwalefeld

„Ride & Relax“ Willingen

Quiet apartment near a forest

Willingen modern apartment balcony in the green park free

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

Picturesque apartment Willingen "the water"

Panorama Chalet Winterberg
Ski-in/out apartment rentals

Large deluxe apartment "H1 Winterberg"

Vacation home Bergzauber sauna biker park ski

Apartment Mountain Ski & Bikepark

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
When is the best time to visit Willingen (Upland)?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £96 | £100 | £98 | £90 | £99 | £93 | £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 |
Destinations to explore
- Rentals with a sauna Willingen (Upland)
- Chalet rentals Willingen (Upland)
- Pet-friendly rentals Willingen (Upland)
- Family-friendly rentals Willingen (Upland)
- Flat 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
- Sababurg Animal Park
- Fort Fun Abenteuerland
- Grimmwelt
- Fridericianum
- Atta Cave
- Karlsaue
- Monkey and Bird Park Eckenhagen
- Vogelpark Heiligenkirchen
- Documenta-Halle
- Landgrafen Palace
- Altena Castle
- Wewelsburg
- Willingen Ski Lift
- Natural History Museum Kassel
- Panorama Park
- Schloss Wilhelmsthal
- Möhne Reservoir
- Heimat-Tierpark Olderdissen
- Sparrenberg Castle





