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Ski-in/Ski-out holiday rentals in Olsberg

Find and book unique ski-in/ski-out homes on Airbnb

Quick stats about holiday rentals that are ski-in ski-out in Olsberg

  • Total holiday rentals

    Explore 30 holiday rentals in Olsberg

  • Nightly prices starting at

    Olsberg holiday rentals start at $97 AUD per night before taxes and fees

  • Verified guest reviews

    Over 1,030 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Olsberg holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Olsberg rentals

  • 4.7 Average rating

    Olsberg stays receive an average rating of 4.7 out of 5 from guests

Top-rated ski-in/ski-out rentals in Olsberg

Guests agree: These ski-in/ski-out homes are highly rated for location, cleanliness and more.

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Guest favourite
A warm interior of a sauna features wooden benches and a window showcasing a sunset over trees. A wood-burning stove stands prominently, providing comfort. Sunlight filters through the structure, creating a serene and inviting atmosphere.
Cabin in Willingen (Upland)
4.98 out of 5 average rating, 122 reviews

"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.

Superhost
A modern house with a sloped roof is set in a landscaped garden. Large windows reflect the sky, while a patio area with seating is visible in front. Lush greenery surrounds the property, with additional structures on the property, contributing to a spacious outdoor environment.
Home in Winterberg
4.87 out of 5 average rating, 196 reviews

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

Guest favourite
Home in Winterberg
4.96 out of 5 average rating, 25 reviews

Luxury, childproof holiday home in Winterberg with a view

Get away together to Goldilocks Chalet and enjoy peace, nature and comfort. Wake up with unobstructed views, go out among the autumn colors, and then come home to your own chalet. 🧸 Great for families: trampoline, toys, table soccer, cot, high chair and safety outlets. ✨ Comfort for the parents: a luxurious kitchen with Bora induction, a cozy Wintergarten and, in the evening, watching Netflix together or reading a book by the fireplace! Enjoyment with the whole family!

Top Guest favourite
The exterior of a black vacation home features a prominent chimney and large windows that allow natural light inside. Surrounding greenery includes a lush bush and a well-maintained garden, providing a serene outdoor ambiance.
Cottage in Willingen (Upland)
4.95 out of 5 average rating, 372 reviews

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.

Top Guest favourite
Apartment in Winterberg
4.97 out of 5 average rating, 113 reviews

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...

Guest favourite
A modern bathroom features a walk-in shower with a rain showerhead and stylish cabinetry. A private balcony displays a hammock, inviting relaxation amidst greenery. The cozy living area includes a gray sofa, a wooden coffee table, and artwork on a light wall. A sauna is equipped with wooden seating and complimentary towels.
Holiday home in Winterberg
4.97 out of 5 average rating, 118 reviews

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

Guest favourite
A bright living area features a large, light-colored sectional sofa adorned with an accent pillow. A round wooden coffee table rests on a circular area rug, and a decorative plant adds greenery. Large glass doors lead to a balcony, framed by sheer drapes.
Apartment in Winterberg
4.92 out of 5 average rating, 121 reviews

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.

Top Guest favourite
A bedroom is featured with a spacious bed dressed in white linens, complemented by neutral-toned cushions. A large mural of leaf patterns decorates the wall behind the bed. A minimalistic side table with an elegant lamp is positioned next to the bed.
Condo in Willingen (Upland)
4.99 out of 5 average rating, 74 reviews

"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.

Guest favourite
A dining table is set with white plates and glasses, surrounded by black placemats. Soft natural light filters through large windows, illuminating the space. In the background, a cozy seating area is visible, featuring dark furniture and decorative elements.
Apartment in Winterberg
4.88 out of 5 average rating, 193 reviews

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.

Guest favourite
Apartment in Brilon
5.0 out of 5 average rating, 10 reviews

A little time out

Welcome to our little time-out. Our 45 sqm apartment is located right on the edge of the forest, not far from the Brilon ski slope. From here you can go hiking (Rothaarsteig), cycling or activities in nearby Willingen. The center of the cozy Brilon old town is a 15-minute walk. With 6500 m² of water, Brilon has the largest forest outdoor pool in North Rhine-Westphalia and can be reached by car in 5 minutes.

Superhost
An outdoor terrace area is visible, featuring a round table and two black chairs. A sun umbrella stands to one side, and a trellis is situated nearby. The entrance door to the holiday apartment is also visible in the background, framed by a small garden area.
Apartment in Willingen (Upland)
4.73 out of 5 average rating, 120 reviews

Apartment (bedroom, living room, bath room)

Apartment with separate entrance. bath room with shower bedroom with 2 beds (+ baby bed) living room with sleeping couch for up to two persons TV, WLAN and towels/bed linen are available. The apartment has a small terrace. The apartment is located in the village 'Eimelrod' (about 12km from Willingen).

Superhost
A yurt is illuminated at dusk, showcasing a wooden door and a chimney. Surrounding the yurt, natural grass and stones create a rustic atmosphere. Wooden seating options, including benches, are positioned nearby, offering a space for relaxation amid serene natural surroundings.
Yurt in Olsberg
4.94 out of 5 average rating, 172 reviews

* Adventure overnight stay in one of our yurts *

Watch the starry sky from bed. Enjoy the sounds of nature when you stay in this unique place. A living space without corners and edges, to relax and experience time together. The yurts are located on a 2500 sqm nature reserve with a lake and view of the natural monument Bruchhauser Steine.

Popular amenities for Olsberg ski-in/ski-out rentals

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