A snow-covered ski slope with a forested valley, a ski lift, and distant mountains.

Winterberg Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Winterberg vacation homes

A hallway with a wooden bench, a radiator, a TV, and a mirror on the wall.

1. Winterberg Lodge: 8 Bathrooms, Near Ski Slopes – Family Retreat in Sauerland

Winterberg Lodge: 8 Bathrooms, Near Ski Slopes – Family Retreat in Sauerland
Winterberg
The price is CA $1,503
CA $2,526 total
includes taxes & fees
Nov 2 - Nov 3
Winterberg Lodge: 8 Bathrooms, Near Ski Slopes – Family Retreat in Sauerland
A hot tub with a chimney, surrounded by a deck with a chair and a towel, set against a backdrop of trees and a wooden fence.

2. Skiing & Winter Hiking · Sauna, Hot Tub, Fireplace

Skiing & Winter Hiking · Sauna, Hot Tub, Fireplace
Winterberg
9.0 out of 10, Wonderful, (2 reviews)
"Pros: Ruimte, rust. Het huis is groot genoeg om je terug te trekken en goed ingericht, zodat je ook gezellig samen kunt zijn. Heel mooi vakantiehuis, prima hottub, groot genoeg om ook in de zomer af te koelen. Omgeving is prachtig."
Netherlands
Anonymous traveller
The price is CA $799
CA $1,189 total
includes taxes & fees
Nov 16 - Nov 17
Skiing & Winter Hiking · Sauna, Hot Tub, Fireplace
A stone building with a distinctive arched entrance and a metal gate.

3. Jagdschloss Siedlinghausen: 3 Apartments for up to 16 Guests

Jagdschloss Siedlinghausen: 3 Apartments for up to 16 Guests
Winterberg
The price is CA $1,618
CA $1,618 total
includes taxes & fees
Oct 29 - Oct 30
Jagdschloss Siedlinghausen: 3 Apartments for up to 16 Guests
A modern living room with a sofa, a coffee table, and a chair, a large window with a view of the countryside, and a balcony with outdoor seating.

4. Holiday Home 'Winterberg D4' with Mountain View, Shared Terrace and Wi-Fi

Holiday Home 'Winterberg D4' with Mountain View, Shared Terrace and Wi-Fi
Winterberg
8.0 out of 10, Very good, (2 reviews)
"Die FeWo ist sehr schön und man fühlt sich auch wohl. Jedoch ist die FeWo mit 4 Bädern und Dusche ausgeschrieben allerdings sind 3 Bäder mit Dusche und ein Bad mit WC vorhanden."
United States
Anja W.
The price is CA $1,236
CA $1,243 total
includes taxes & fees
Nov 16 - Nov 17
Holiday Home 'Winterberg D4' with Mountain View, Shared Terrace and Wi-Fi
A dining area with a wooden table, chairs, and a wine glass holder.

5. Grenzweg Holiday Home for 8 People (130 m²) in Winterberg

Grenzweg Holiday Home for 8 People (130 m²) in Winterberg
Winterberg
The price is CA $907
CA $1,150 total
includes taxes & fees
Nov 4 - Nov 5
Grenzweg Holiday Home for 8 People (130 m²) in Winterberg
A two-story wooden house with a gabled roof, surrounded by lush greenery and a well-maintained garden.

6. Holiday Home 'Bauernschänke'

Holiday Home 'Bauernschänke'
Schmallenberg
10.0 out of 10, Exceptional, (1 review)
"Pros: Die ruhige Lage und die schöne, gemütliche Ausstattung im Haus. Es hat uns nichts gefehlt. Wir kommen gerne wieder. Cons: War alles Top!"
Germany
Anonymous traveller
The price is CA $287
CA $295 total
includes taxes & fees
Oct 29 - Oct 30
Holiday Home 'Bauernschänke'
A room with a dining table, chairs, a sofa, a floor lamp, a window with curtains, and a view of the outdoors.

7. Apartment 'Ferienwohnung, 60qm' with Shared Terrace, Shared Garden and Wi-Fi

Apartment 'Ferienwohnung, 60qm' with Shared Terrace, Shared Garden and Wi-Fi
Olsberg
The price is CA $267
CA $272 total
includes taxes & fees
Nov 4 - Nov 5
Apartment 'Ferienwohnung, 60qm' with Shared Terrace, Shared Garden and Wi-Fi
A modern living room with a sofa, dining table, and a chair. There is a window with a view of the outside.

8. Cozy Apartment in Willingen, Usseln – Lovingly Furnished for a Relaxing Atmosphere

Cozy Apartment in Willingen, Usseln – Lovingly Furnished for a Relaxing Atmosphere
Willingen (Upland)
The price is CA $206
CA $245 total
includes taxes & fees
Nov 4 - Nov 5
Cozy Apartment in Willingen, Usseln – Lovingly Furnished for a Relaxing Atmosphere
A dining area with a table set for two, a white cabinet, and a wood-burning stove.

9. Apfelhaus am Hennesee

Apfelhaus am Hennesee
Meschede
8.0 out of 10, Very good, (2 reviews)
"Das Ferienhaus ist toll, ruhig Lage, wunderschöne Natur, sehr sauber. Nur die Wärmepumpen ist gewöhnungsbedürftig aber es gab einen Ölradiator.Hätte der Vermieter nicht doppelt abgebucht, wäre der Urlaub eine 5 mit * gewesen."
Germany
Sandra E.
The price is CA $120
CA $355 total
includes taxes & fees
Oct 31 - Nov 1
Apfelhaus am Hennesee
A modern kitchen with a wooden countertop, built-in appliances, and grey cabinetry.

10. Holiday Home 'Haus Waldesruh' with Private Terrace, Balcony and Wi-Fi

Holiday Home 'Haus Waldesruh' with Private Terrace, Balcony and Wi-Fi
Medebach
9.0 out of 10, Wonderful, (4 reviews)
"Pros: Sehr gastfreundlich! Wir kommen sehr gerne wieder! 🤗 Cons: Es gab nichts zu meckern😅"
Germany
Anonymous traveller
The price is CA $458
CA $790 total
includes taxes & fees
Nov 1 - Nov 2
Holiday Home 'Haus Waldesruh' with Private Terrace, Balcony and Wi-Fi
A modern room with a large sliding glass door leading to a garden, a sofa, a small table, and a cabinet with a plant.

11. Bungalow 'Ferienwohnung Traumblick' with Mountain View, Private Terrace and Wi-Fi

Bungalow 'Ferienwohnung Traumblick' with Mountain View, Private Terrace and Wi-Fi
Bestwig
9.8 out of 10, Exceptional, (8 reviews)
"Pros: Die Gastgeber waren sehr zuvorkommend und freundlich. Die Wohnung war sauber und liebevoll eingerichtet"
Germany
Anonymous traveller
The price is CA $339
CA $586 total
includes taxes & fees
Nov 4 - Nov 5
Bungalow 'Ferienwohnung Traumblick' with Mountain View, Private Terrace and Wi-Fi
A modern living room with a wooden wall, a dining table, chairs, a sofa, and a large window with a view.

12. Holiday Home 'Am Scheidt' with Private Terrace, Private Garden and Wi-Fi

Holiday Home 'Am Scheidt' with Private Terrace, Private Garden and Wi-Fi
Medebach
8.0 out of 10, Very good, (1 review)
"Pros: Rustige omgeving, huisje was super schoon. Alle voorzieningen zijn aanwezig. Genoeg restaurants in de omgeving"
Netherlands
Anonymous traveller
The price is CA $430
CA $531 total
includes taxes & fees
Oct 29 - Oct 30
Holiday Home 'Am Scheidt' with Private Terrace, Private Garden and Wi-Fi
A dining area with a wooden table, chairs, and a blue decorative bowl.

13. Berganker Holiday Home Willingen

Berganker Holiday Home Willingen
Willingen
10.0 out of 10, Exceptional, (1 review)
"Pros: Sehr netter Gastgeber. Sehr schönes Haus mit umzäuntem Garten. Sehr gut für Hundebesitzer"
Germany
Anonymous traveller
The price is CA $1,260
CA $1,383 total
includes taxes & fees
Nov 22 - Nov 23
Berganker Holiday Home Willingen
A wooden interior with a spiral staircase, a cabinet with glass doors, and a radiator.

14. Casa Brocktega

Casa Brocktega
Bestwig
The price is CA $149
CA $240 total
includes taxes & fees
Nov 1 - Nov 2
Casa Brocktega
A wooden ceiling, a bed with pillows and a blanket, and a wall with a forest view.

15. Holiday Home 'Zum Radekopf' with Hot Tub, Terrace, Garden and Sauna

Holiday Home 'Zum Radekopf' with Hot Tub, Terrace, Garden and Sauna
Medebach
10.0 out of 10, Exceptional, (6 reviews)
"Toll ausgestattete Unterkunft mit äußerst freundlicher Begrüßung durch die Gastgeberin!"
Germany
Tim K.
The price is CA $822
CA $828 total
includes taxes & fees
Nov 23 - Nov 24
Holiday Home 'Zum Radekopf' with Hot Tub, Terrace, Garden and Sauna
A modern house with a stone pathway, a front door, and a balcony.

16. Holiday Home 'Schillings Häusken' – Retro Style & Modern Comfort in Sauerland

Holiday Home 'Schillings Häusken' – Retro Style & Modern Comfort in Sauerland
Brilon
9.4 out of 10, Exceptional, (3 reviews)
"Pros: Das Haus ist wunderschön geworden und wir kommen gerne wieder."
Germany
Anonymous traveller
The price is CA $253
CA $331 total
includes taxes & fees
Oct 29 - Oct 30
Holiday Home 'Schillings Häusken' – Retro Style & Modern Comfort in Sauerland
A wooden balcony overlooking a rural landscape with houses, trees, and rolling hills.

17. Holiday Home 'Landhaus' with Mountain View, Private Terrace and Wi-Fi

Holiday Home 'Landhaus' with Mountain View, Private Terrace and Wi-Fi
Bad Berleburg
10.0 out of 10, Exceptional, (1 review)
"War alles super. Schönes Haus in toller Umgebung mit schönem Ausblick. "
Germany
Jan W.
The price is CA $549
CA $795 total
includes taxes & fees
Nov 4 - Nov 5
Holiday Home 'Landhaus' with Mountain View, Private Terrace and Wi-Fi
A spacious kitchen with a large island, wooden cabinetry, and a view of the outdoors.

18. Holiday Home 'Zum Holzknecht' with Private Terrace, Large Garden and Sauna

Holiday Home 'Zum Holzknecht' with Private Terrace, Large Garden and Sauna
Willingen (Upland)
9.8 out of 10, Exceptional, (6 reviews)
"Schönes Haus. Naturnahe Umgebung. "
Germany
Daniel K.
The price is CA $1,888
CA $1,895 total
includes taxes & fees
Oct 29 - Oct 30
Holiday Home 'Zum Holzknecht' with Private Terrace, Large Garden and Sauna
A house surrounded by snow-covered trees.

19. Holiday Home 'Tannenhäuschen' with Mountain View, Private Terrace and Wi-Fi

Holiday Home 'Tannenhäuschen' with Mountain View, Private Terrace and Wi-Fi
Schmallenberg
10.0 out of 10, Exceptional, (1 review)
"Pros: Das Haus ist groß, sehr sauber, liebevoll eingerichtet und super ausgestattet – zudem herrlich abseits gelegen. Die Gastgeber waren unkompliziert und sehr herzlich. Absolute Empfehlung! Cons: es gab nichts auszusetzen."
Germany
Anonymous traveller
The price is CA $862
CA $862 total
includes taxes & fees
Nov 16 - Nov 17
Holiday Home 'Tannenhäuschen' with Mountain View, Private Terrace and Wi-Fi
A bedroom with a large bed, a wooden desk, a chair, a window with a view of greenery, and a nightstand with a lamp.

20. Holiday Home 'Hallmanns Hof' with Private Garden, Dogs Allowed, Wi-Fi

Holiday Home 'Hallmanns Hof' with Private Garden, Dogs Allowed, Wi-Fi
Schmallenberg
10.0 out of 10, Exceptional, (2 reviews)
"Pros: Das Haus ist mit ganz viel Liebe eingerichtet worden. Die Küche ist top ausgestattet. Unsere Kleinsten haben sich besonders wohlgefühlt mit eigener Küche und Kaufladen. Alle Zimmer sind top. Auch das Aussengelände ist perfekt für gross und klein. Wir kommen sehr gerne wieder"
Germany
Anonymous traveller
The price is CA $1,671
CA $1,679 total
includes taxes & fees
Nov 17 - Nov 18
Holiday Home 'Hallmanns Hof' with Private Garden, Dogs Allowed, Wi-Fi
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winterberg Hotel Reviews

Fletcher Berghotel Astenkrone - Winterberg

Fletcher Berghotel Astenkrone - Winterberg

10/10 Excellent
"Beautiful property! Fantastic breakfast. Very much enjoyed our stay."
Aleasha 3-night trip
Posted 1 month ago
Fletcher Berghotel Astenkrone - Winterberg

Find out more about Winterberg

Winterberg Vacation Homes information

Number of reviews
28
Accommodation
261 Vacation Homes
Lowest Price
CA $240
Highest Price
CA $2,526