Winterberg holiday rentals

We found 2,267 holiday rentals — enter your dates for availability
Discover a selection of 246 homes, 1004 apartments and other holiday rentals in Winterberg that are perfect for your trip. Whether you're staying in a holiday rental with a group or just with your pet, you'll find the best amenities for hanging out with the people that matter most, which might include a pool and a washer and dryer. You'll be sure to find a property to rent that has what everyone needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Winterberg

Showing deals for:13 Nov - 20 Nov

Dining
Living area
Property grounds
Room
Exceptional
(8 reviews)

Villa Annabelle, Luxe vakantiehuis in Winterberg

Winterberg

31% off
S$4,031
for 7 nights, 1 villa
S$576 per night
includes taxes & fees
Villa Annabelle, Luxe vakantiehuis in Winterberg
Exterior
Property grounds
Property grounds
Room
Exceptional
(12 reviews)

Nature House. Great for the family

Medebach

13% off
S$1,055
for 7 nights, 1 home
S$151 per night
includes taxes & fees
Nature House. Great for the family
Dining
Private kitchen
Interior
Interior
Exceptional
(9 reviews)

Modern Renovierte Wohnung in Zentraler Lage

Hallenberg

8% off
S$840
for 7 nights, 1 apartment
S$120 per night
includes taxes & fees
Modern Renovierte Wohnung in Zentraler Lage
Interior
Dining
Exterior
Property grounds
Exceptional
(5 reviews)

Bright apartment for 6 people on the ground floor with a terrace in the garden right by the forest

Olsberg

8% off
S$1,052
for 7 nights, 1 apartment
S$150 per night
includes taxes & fees
Bright apartment for 6 people on the ground floor with a terrace in the garden right by the forest
Interior
Living area
Room
Interior
Exceptional
(7 reviews)

Neu und Liebevoll Eingerichtete Fewo am Skihang und Waldrand Nähe Willingen!

Willingen

8% off
S$1,250
for 7 nights, 1 apartment
S$179 per night
includes taxes & fees
Neu und Liebevoll Eingerichtete Fewo am Skihang und Waldrand Nähe Willingen!
Room
Interior
Exterior
Dining
Wonderful
(71 reviews)

Non smoking!! Dogs welcome family house near Willingen with panoramic view.

Olsberg

8% off
S$2,607
for 7 nights, 1 home
S$372 per night
includes taxes & fees
Non smoking!! Dogs welcome family house near Willingen with panoramic view.
Interior
Outdoor dining
Interior
Dining
Excellent
(56 reviews)

beautifully furnished apartment right on the lake Hillebachstausee

Winterberg

6% off
S$761
for 7 nights, 1 apartment
S$109 per night
includes taxes & fees
beautifully furnished apartment right on the lake Hillebachstausee
Interior
Terrace/patio
Exterior detail
Interior
Exceptional
(9 reviews)

"Old town jewel" in the heart of Brilon

Brilon

8% off
S$873
for 7 nights, 1 apartment
S$125 per night
includes taxes & fees
"Old town jewel" in the heart of Brilon
Interior
Private kitchen
Property grounds
Dining
Exceptional
(58 reviews)

Hermann's winter dream on the ski carousel / ski jump !!!!

Winterberg

11% off
S$983
for 7 nights, 1 apartment
S$140 per night
includes taxes & fees
Hermann's winter dream on the ski carousel / ski jump !!!!
Living area
Interior
Dining
Interior
Exceptional
(71 reviews)

Holidays in Winterberg-Silbach

Winterberg

8% off
S$1,187
for 7 nights, 1 apartment
S$170 per night
includes taxes & fees
Holidays in Winterberg-Silbach
Property grounds
Dining
Interior
Living area
Exceptional
(11 reviews)

Ferienwohnung Hof Wehlenbach

Hallenberg

8% off
S$988
for 7 nights, 1 apartment
S$141 per night
includes taxes & fees
Ferienwohnung Hof Wehlenbach
Interior
Pool
Exterior
Dining
Exceptional
(25 reviews)

Pino24 Comfort vacation apartment 127m², pool and sauna, 3 bathrooms/WC, max. 12 persons

Hallenberg

9% off
S$2,438
for 7 nights, 1 apartment
S$348 per night
includes taxes & fees
Pino24 Comfort vacation apartment 127m², pool and sauna, 3 bathrooms/WC, max. 12 persons
Living area
Exterior
Private kitchen
Exterior
Exceptional
(77 reviews)

House lagoon in Willingen

Willingen

7% off
S$1,162
for 7 nights, 1 apartment
S$166 per night
includes taxes & fees
House lagoon in Willingen
Marina
Terrace/patio
Exterior
Property grounds
Exceptional
(91 reviews)

☎️Gemütlich furnished vacation apartment with balcony for 2-8 Personen☎️

Willingen

9% off
S$2,832
for 7 nights, 1 apartment
S$405 per night
includes taxes & fees
☎️Gemütlich furnished vacation apartment with balcony for 2-8 Personen☎️

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Take in the majestic beauty of Winterberg

The mountains and parks create a pretty picture of Winterberg. Well known for its skiing, golfing and spas, this scenic city won't disappoint. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in Winterberg

Do you want to find attractions to visit in the area? Venture out of your cosy holiday rental and check out everything that makes Winterberg a fun place to get away to. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Skiliftkarussell Winterberg (0.6 mi / 1 km)
  • Bobbahn Winterberg (1.2 mi / 2 km)
  • Winterberg Mountain Adventure (1.4 mi / 2.2 km)
  • Bikepark Winterberg (1.4 mi / 2.2 km)
  • Postwiese Ski Resort (2.8 mi / 4.6 km)
  • Bikepark Willingen (7.1 mi / 11.4 km)

Exploring the natural landscape of Winterberg

Whether you're an active traveller or just want to spend some time taking in the scenery, Winterberg is a great place to spend some time outside. Here are some of the area’s most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Kahler Asten (2.2 mi / 3.5 km)
  • Lake Diemelsee (14.3 mi / 23 km)
  • Rothaargebirge Nature Park (14.5 mi / 23.3 km)
  • Hennetalsperre (15 mi / 24.1 km)
  • Rothaar Mountains Nature Park (18.9 mi / 30.5 km)
  • Kellerwald-Edersee National Park (19.5 mi / 31.5 km)

Seasonal weather averages in Winterberg

Travellers enjoy Winterberg for its skiing. If you've planned your trip around snowy activities, consider visiting in January, February, March or April, when snowfall averages 0 cm and temperatures average 1°C.

How to get to and around Winterberg

The nearest airport is in Paderborn (PAD-Paderborn - Lippstadt), located 29 mi (46.7 km) from the city centre. If you're unable to find a flight that fits your schedule, you could book a flight to Dortmund (DTM), which is 45.4 mi (73.1 km) away.

If you prefer to travel by train, Winterberg (Westfalen) Station, Winterberg Silbach Station and Siedlingausen Station are the main stations in the city.

Frequently asked questions

What is the most popular type of holiday rental accommodation in Winterberg?
Apartments are the most popular kind of holiday rental in Winterberg, according to our data. Even if you've got a different idea in mind, Vrbo has properties in a variety of shapes and sizes. Compare our options to find your perfect Winterberg pad.
How much does it cost to rent a holiday rental in Winterberg?
The average price for a holiday rental in Winterberg is based on several factors, such as property type, length of stay and time of year. Whether you're dreaming about a sprawling house with room for friends and family or a cosy cottage for you and your other half, just add your travel dates to find stays with unbeatable value.
How much does it cost to rent a beach house in Winterberg?
Prices for beach houses in Winterberg can differ depending on the style and size of the property and time of year you're travelling. All you need to do is enter your travel dates into Vrbo and the number of guests to view your options and prices. From there you can use our filters to narrow your search by nearby activities, amenities, ratings and more.
Are there pet-friendly holiday rentals in Winterberg?
Pack a travel bag and a bone for the pup in your life because Winterberg has 396 holiday homes that put out the welcome mat to pets. Let your happy hound join in with the family fun at one of our pet-friendly holiday rentals on Vrbo. Simply enter your dates then check the "Pets allowed" filter box.
Can I rent a house with a pool in Winterberg?
Pack your swimsuit and inflatable unicorn, because there are 20 houses with a private pool in Winterberg. Unwind at one of these sought-after holiday homes and every day will be a pool day. Simply enter your dates into Vrbo, then check the "pool" filter to find the perfect place for a splashing good time!
What are popular rental amenities in Winterberg?
When it comes to rental amenities that guests are searching for in Winterberg, a sauna, a swimming pool and an ocean view rank the highest. With Vrbo holiday rentals, you'll find options to suit your style and taste, whether you're going on a trip with your partner, your friends or even pets.
Are there large group holiday rentals in Winterberg?
Winterberg has 32 holiday homes that can accommodate 10 or more people. These stays come with the privacy and space you need to enjoy good times with your favourite people.
Are there holiday rentals in Winterberg that welcome kids?
With 394 family-friendly holiday rentals available in Winterberg, now is the perfect time to introduce your children to the wonders of travel. Just click on our "Properties good for families" filter to discover stays packed with conveniences ideal for travelling families, such as full kitchens, private pools, entertainment areas and hot tubs.
What are the top attractions for families in Winterberg?
Keep the kids busy at these awesome family-friendly attractions in Winterberg:
  • Fort Fun
  • Lagunen-Erlebnisbad
  • Freizeitwelt Willingen
Are there one-bedroom holiday rentals in Winterberg?
Yes, there are 148 one-bedroom properties in Winterberg to pick from. A one-bedroom holiday home is an excellent choice if it's only you and your partner or if you're travelling alone. Add in more space, privacy and convenience than a hotel, and you'll be sure to have a memorable trip.
Can I find two-bedroom holiday rentals in Winterberg?
Take your pick of 151 two-bedroom holiday rentals in Winterberg. Put the kids in the second room or maybe fill it with a couple of your best friends. There's plenty of space for whoever's lucky enough to be joining in on the fun.
Are there holiday rentals with WiFi in Winterberg?
Pick from 122 holiday rentals with WiFi in Winterberg. If you want to disconnect from the world during your escape, but still need to be connected to the internet, these getaways are for you. Narrow your search by applying the WiFi filter on Vrbo.
How can I find holiday rentals with air conditioning in Winterberg?
Select your travel dates and then use our filters to locate holiday rentals with air conditioning in Winterberg on Vrbo. With four air-conditioned properties on offer here, you can look forward to a cool and comfy break.
How old do you have to be to rent a holiday rental in Winterberg?
You'll need to check with the Winterberg holiday rental you'd like on Vrbo as the minimum age varies. However, it's normally 16, 18 or 21.
How long can I rent a holiday rental in Winterberg for?
It really depends on the Winterberg property. To view all available options offering extended stays, simply type your travel dates and number of guests into Vrbo's search page. You can look forward to having the entire property to yourself, along with comforts such as a fully-equipped kitchen and a yard where the kids can run around and play. Keep your eyes open for long-term stays that offer weekly or monthly discounts.

More holiday ideas