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Family-friendly holiday rentals in Winterberg

Find and book unique family-friendly homes on Airbnb

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

  • Total holiday rentals

    Explore 590 holiday rentals in Winterberg

  • Nightly prices starting at

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

  • Verified guest reviews

    Over 10,450 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 250 rentals that welcome pets

  • Holiday rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    130 properties have a dedicated workspace

  • Wifi availability

    570 of Winterberg holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Winterberg rentals

  • 4.7 Average rating

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

Top-rated family-friendly rentals in Winterberg

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

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Top guest favourite
Chalet in Bromskirchen
4.98 out of 5 average rating, 161 reviews

Waldliebe - your retreat in the countryside

Welcome to Waldliebe 🌲❤️ – your nature retreat in the Sauerland A cozy vacation home with a fireplace, a conservatory, and a large, fenced-in garden—perfect for anyone seeking peace, nature, and relaxation. Your vacation starts right here, on your doorstep: go hiking, relax, ski, take your dog for a walk through the woods, or simply sit in the conservatory and gaze into the fire. Here, you'll find everything you need for a relaxing getaway away from the hustle and bustle of everyday life.

FamilyKitchenSleep quality

Top guest favourite
The exterior of a two-story house is depicted, showcasing a mix of white plaster and wooden beams. Lush greenery surrounds the property, with carefully manicured shrubs and flower beds visible. The clear blue sky adds tranquility to the setting, enhancing the inviting atmosphere.
Farm stay in Bad Berleburg
4.96 out of 5 average rating, 113 reviews

Vacation home in the Edertal

Our cozy furnished apartment with views of the beautiful Edertal is located directly on the Ederauen bike path. Our farm is located on the edge of the small village of Berghausen in the Wittgensteiner Land. The nearby Rothaarsteig offers great hiking opportunities. In Winterberg, 20 km away, you will find sports and leisure activities in summer and winter. The apartment has a double bedroom and a sofa bed in the living room. A travel crib is available for toddlers.

Indoor spacesKitchenPool

Guest favourite
Flat in Bestwig
4.95 out of 5 average rating, 104 reviews

Experience FeWo-Dörnberg in the Sauerland, near Winterberg

The apartment is located at 550 meters above sea level, in the heart of the Sauerland. A little paradise, as we call it. Perfect for nature lovers who need a break from everyday stress. For children, we offer an experience with tame sheep, chickens and rabbits that roam freely on the property. Our happy chickens provide you with fresh breakfast eggs in the morning. By arrangement, there are also fresh trout from the fish pond. A small home to feel good and enjoy.

Indoor spacesKitchenParking

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
5.0 out of 5 average rating, 354 reviews

Wellness chalet by the lake with 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.

Indoor spacesKitchenCheck-in

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, 376 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.

Indoor spacesKitchenParking

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

Indoor spacesFamilyTV

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.
Flat in Winterberg
4.92 out of 5 average rating, 123 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.

KitchenFamilyNearby

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, 118 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.

FamilyKitchenDecor

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, 353 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.

FamilyKitchenCleanliness

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 Willingen (Upland)
4.9 out of 5 average rating, 407 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)

Indoor spacesFamilyValue

Guest favourite
The grey house features multiple windows and a charming roof, surrounded by lush greenery and colorful flowers. A stone path leads to the entrance, inviting guests to explore the natural surroundings, including tall trees that provide a serene atmosphere.
Home in Winterberg
4.95 out of 5 average rating, 74 reviews

Asten-Lodge

Directly on the Rothaarsteig at an altitude of 800 meters, the Asten-Lodge is located in the middle of a 7000 sqm large natural estate. The idyllic house can accommodate six people in three double rooms and is ideal for couples and families. There is a barrel sauna and outdoor shower in the garden. In the certified five star cottage in the middle of nature, far from noisy streets, you can spend a relaxing time with family or friends.

FamilyKitchenBathroom

Guest favourite
A dining table is set with green plates and wine glasses, with a bouquet of yellow flowers as the centerpiece. The view beyond features rolling hills under a partly cloudy sky, allowing natural light to illuminate the inviting dining space.
Flat in Winterberg
4.96 out of 5 average rating, 152 reviews

Sun Panorama - Adventurers and Explorers

Welcome to Sonnen Panorama in Grönebach near Winterberg! Enjoy the magnificent view over the Sauerland, the quiet location and the comfort of our modern ground-floor apartment. With a balcony, fireplace, private garage, dog-friendly and child-friendly amenities, and a perfect location for hikers, cyclists, families, and winter sports enthusiasts, it is the ideal base for your getaway in nature.

Indoor spacesKitchenAccess

Popular amenities for Winterberg family-friendly rentals