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Family-friendly holiday rentals in Olsberg

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Olsberg

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Top guest favourite
A modern, multi-level house is shown against a clear blue sky. The exterior features a combination of white and black accents, with multiple balconies and large windows that allow natural light. A paved driveway leads up to the garage, surrounded by landscaped greenery.
Flat in Elpe
4.97 out of 5 average rating, 133 reviews

Apartment "Kiek ma rin"

Our cozy apartment( (approx. 40 sqm) is located in the beautiful village of Elpe. It has a living-dining area, a bathroom with shower, as well as a bedroom. The entire apartment is equipped with underfloor heating. Cabinets for wardrobe are present. In the summer, the outdoor terrace (garden furniture ,charcoal grill ) offers time to relax, or just enjoy the beautiful view. In the village there is the South Tyrolean bakery house with excellent baked goods, as well as the paragliding school Papillon

Top guest favourite
A charming cabin is nestled in a snowy landscape, surrounded by trees coated in white frost. The clear blue sky provides a bright backdrop to the scene, enhancing the serene winter atmosphere.
Cabin in Willingen
4.99 out of 5 average rating, 107 reviews

Black+Beauty Design Cabin in Willingen / Sauerland

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.

Top guest favourite
A modern wooden chalet is set against a backdrop of lush greenery and a serene lake. The structure features large windows and a spacious deck with outdoor seating. A hot tub is visible on one side, adding to the outdoor amenities.
Chalet in Windebruch
5 out of 5 average rating, 303 reviews

Design chalet with lake view, sauna, fireplace & Jacuzzi

Nestled in nature, in an idyllic forest edge location with breathtaking lake views, this chalet allows you to escape everyday life. Hike in the forest or by the lake and enjoy a bike ride with our e-bikes. When it's cool, warm up in the sauna or heated pool before settling in with a glass of red wine by the fireplace. In the warm season, enjoy a swim in the pool or in the crystal clear lake (SUP/kayak are also available) before watching the stars in the evening.

Guest favourite
An inviting living space features a wooden dining table with dark chairs, a wall-mounted television, and a cozy seating area with a gray couch. Large windows provide views of the outdoors, while warm lighting enhances the serene ambiance.
Flat in Stryck
4.83 out of 5 average rating, 175 reviews

Mellie’s Fewo Willingen

Unsere Ferienwohnung liegt im malerischen Strycktal, mit herrlicher Sonnenterasse. Es erwartet Sie ein 32qm² Apartment, mit einer vollausgestatteten Küche und einem eigenen Bad. Das Apartment verfügt außerdem über einen Flachbild TV, ein Doppelbett, eine Schlafcouch, einem Elektrokamin und eine Sonnenterasse mit Gartenblick. Die helle Ferienwohnung ist gemütlich und stilvoll eingerichtet, so können Sie sich gleich wie zu Hause fühlen. Hunde nach Rücksprache.

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
4.94 out of 5 average rating, 339 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.

Guest favourite
The ecological A-frame house features wooden siding and a triangular roof, surrounded by trees. A welcoming porch with a railing extends out front. Large windows allow natural light to enter, and a patio umbrella is visible, providing shade for outdoor relaxation.
Cabin in Eslohe
4.94 out of 5 average rating, 104 reviews

BergesGlück log cabin, edge of forest, fireplace, Sauerland

Our ecological log cabin, built in 2022, is located on the edge of an oak grove on a 550 m high plateau called Oesterberge, in the middle of the Sauerland Nature Park. When furnishing, we placed special emphasis on stylish and comfortable furnishings. For hikers, mountain bikers, but also for families with children, it becomes a small paradise. Located on the edge of our farm, guests of all ages can experience pure nature, tranquility and spectacular views.

Guest favourite
A wooden cabin is set on a grassy area, surrounded by vibrant flowers and trees. The porch features steps leading up to the entrance, and two small tables are positioned outside. An inviting outdoor space is visible, complete with colorful chairs and decorations.
Farm stay in Siddinghausen
4.93 out of 5 average rating, 197 reviews

Enjoy nature in an apple tree house and shepherd's wagon

Outdoor fans, take note! On our farm we have just the thing for you: A cozy wooden car with a loft bed (1.40 m) and sofa bed (1.20 m) and a shepherd's wagon with a large lying area (2 m x 2.20 m). There is also a shower house with toilet in the meadow. Our ducks and pigs live right next door. There is electricity. Wi-Fi is available in the farmhouse 150 meters away. There you can use a kitchen. Breakfast basket (also vegetarian) can be booked for €9/person

Top guest favourite
The exterior of Bamenohler Schloss is showcased, featuring an ivy-covered tower and a well-manicured lawn. Surrounding trees provide shade, while a pathway leads to the main entrance, which is marked by a red carpet. A scenic green landscape is visible in the background.
Castle in Finnentrop
4.98 out of 5 average rating, 318 reviews

Bamenohl Castle - Fireplace room apartment

The over 700 year old castle Haus Bamenohl is hidden behind old trees in the middle of an idyllic park in the heart of the Sauerland hills. As guest of the Vicounts of Plettenberg, who have been living here since 1433, you can relax for some quiet days alone, spend a romantic weekend for two at the fireplace or take a family outing. Whether it's hiking in the wonderful nature, cycling, sailing, golfing, skiing - Bamenohl is worth a visit.

Superhost
A wooden cabin is nestled among lush greenery, accented by blooming flowers in vibrant colors. The sloped roof and large windows hint at a welcoming interior. The surrounding trees provide a natural backdrop, enhancing the serene atmosphere of the location.
Cabin in Bömighausen
4.9 out of 5 average rating, 367 reviews

Woody Willingen - The wooden hut in beautiful nature

This cozily furnished Scandinavian wooden cabin in Willingen-Bömighausen will delight you. Surrounded by forest, meadows and pastures, this charming cabin is not only suitable for recreation and relaxation. In addition to its ideal starting point for hiking (directly on the Uplandsteig), cycling and excursions to the beautiful region, it is only a few kilometers away from the Willingen ski area. Dogs are welcome! (€30 fee per stay)

Superhost
The image features the exterior of the Ferienwohnung, showcasing a well-maintained garden with lush greenery. A wooden sign indicates the entrance, while the building displays a sloped roof and solar panels. A paved area in the foreground provides access to the property.
Holiday home in Elpe
4.83 out of 5 average rating, 106 reviews

FeWo Elpetalblick

Die Fewo befindet sich in 59939 Olsberg-Elpe. Wanderwege sind direkt ab Haus möglich. Wasserfall NRW 3 km Freizeitpark Fort-Fun 4 km Wasserfall Besucherbergwerk Ramsbeck 5 km Bruchhauser Steine 12 km Niedersfeld 15 km Kart Bahn, Kinderland, Wasserski Olsberg 15 km Freizeit Sole/Bad Aqua , Kneip Themen Park Winterberg ca. 14 km Willingen ca.20 km Meschede 26 km Hennesee mit Schifffahrt

Guest favourite
Apartment in Brilon
4.96 out of 5 average rating, 104 reviews

Cozy quiet apartment in Brilon

Our private second apartment is on the 2nd floor of a modern 3-family house from 2015. The location is central yet pleasantly quiet – perfect for exploring Brilon in a relaxed way. From the apartment you can enjoy a beautiful view of the Propsteikirche and the charming town. The decor is modern, bright and carefully selected, so you can feel comfortable from the first moment.

Superhost
Cottage in Bruchhausen
4.9 out of 5 average rating, 209 reviews

Charming house "Alte Försterei" in Sauerland

This historic 19th century house with modern interior (6-10 Guests) is part of the Bruchhausen Castle Estate with a view on the Castle and the park. The house is very bright, has a private garden and terrasse as well as outside parkingspace for two cars. From the house you can see on top of the mountaine the 4 massiv rocks "Bruchhauser Steine".

Popular amenities for Olsberg family-friendly rentals

When is the best time to visit Olsberg?

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Quick stats about holiday rentals that are family-friendly in Olsberg

  • Total holiday rentals

    Explore 180 holiday rentals in Olsberg

  • Nightly prices starting at

    Olsberg holiday rentals start at $51 SGD per night before taxes and fees

  • Verified guest reviews

    Over 3,580 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 70 rentals that welcome pets

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

  • Wifi availability

    170 of Olsberg holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Olsberg rentals

  • 4.8 Average rating

    Olsberg stays are highly rated by guests – averaging 4.8 out of 5!