A pine tree with snow-covered ground and a lake in the background.

Sierra de Guadarrama 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 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Sierra de Guadarrama vacation rentals

A rooftop terrace with outdoor seating and a view of historic buildings.

1. Real Segovia Apartments

Real Segovia Apartments
4.0 star property
Segovia Old Town
9.8 out of 10, Exceptional, (58 reviews)
"Loved the view from room and access to rooftop. Location was close to everything. Restaurant in hotel was very good and reasonably priced. Excellent overall. Would stay there again."
Canada
Shauna
The price is ￥14,198
￥15,618 total
includes taxes & fees
Dec 2 - Dec 3
Real Segovia Apartments
A building with a stone facade, wooden shutters, and a fenced courtyard.

2. Holiday Home 'Casa De Los Abuelos' with Wi-Fi

Holiday Home 'Casa De Los Abuelos' with Wi-Fi
Real Sitio de San Ildefonso
The price is ￥31,188
￥34,732 total
includes taxes & fees
Nov 16 - Nov 17
Holiday Home 'Casa De Los Abuelos' with Wi-Fi
A rustic courtyard with potted plants, a red wheelbarrow, and a stone wall.

3. Villa Don Juan II

Villa Don Juan II
3.5 star property
Segovia Old Town
9.8 out of 10, Exceptional, (35 reviews)
"Location could not be beat! Lots of space, well appointed, and great AC.Would definitely stay here again."
Canada
Mike
The price is ￥28,326
￥31,158 total
includes taxes & fees
Nov 22 - Nov 23
Villa Don Juan II
Living area

4. Holiday Home 'Río Tío Cocinas' with Mountain Views, Balcony and Wi-Fi

Holiday Home 'Río Tío Cocinas' with Mountain Views, Balcony and Wi-Fi
Real Sitio de San Ildefonso
The price is ￥124,516
￥137,488 total
includes taxes & fees
Nov 15 - Nov 16
Holiday Home 'Río Tío Cocinas' with Mountain Views, Balcony and Wi-Fi
A reception desk with a framed welcome sign, a potted plant, and two desk lamps.

5. La Arbolada

La Arbolada
Navacerrada
10.0 out of 10, Exceptional, (2 reviews)
"Encantada con todo, el sitio, el anfitrión y los innumerables detalles ☺️. Repetiré sin duda"
Spain
ROSANA G.
The price is ￥17,544
￥23,746 total
includes taxes & fees
Nov 13 - Nov 14
La Arbolada
A modern hotel room with a large bed, a TV mounted on the wall, a small kitchenette, and a wooden accent wall.

6. Apartamento en Pleno Centro de Navacerrada

Apartamento en Pleno Centro de Navacerrada
Navacerrada
8.0 out of 10, Very good, (1 review)
"Todo correcto, la unica pega, mi pareja no podía acceder (no le funcionaba) las llaves 🔑 del teléfono, solo introduciendo el número en la puerta directamente, lo que lo hacia mas incómodo sobre todo al ir con 2 niñas pequeñas."
Spain
Aa A.
The price is ￥23,037
￥29,416 total
includes taxes & fees
Nov 13 - Nov 14
Apartamento en Pleno Centro de Navacerrada
A modern hotel room with a large bed, a TV mounted on the wall, a small kitchenette, and a wooden wardrobe.

7. Apartamento El Roble

Apartamento El Roble
Navacerrada
The price is ￥19,493
￥26,936 total
includes taxes & fees
Nov 15 - Nov 16
Apartamento El Roble
A dining area with a white table set for four, a potted plant, and a painting on the wall.

8. Apartamento El Sauce

Apartamento El Sauce
Navacerrada
The price is ￥20,733
￥30,302 total
includes taxes & fees
Nov 16 - Nov 17
Apartamento El Sauce
A stone building with a wooden door, a window with metal bars, and a black metal railing on the upper floor.

9. Studio 'Judería' with Wi-Fi

Studio 'Judería' with Wi-Fi
Segovia Old Town
10.0 out of 10, Exceptional, (2 reviews)
"Wonderful host who explained the history of the place. Great central location in the middle of everything. Cathedral around the corner. Easy walking through town from the central bus drop off near the aqueduct."
United States
Jeremy K.
The price is ￥25,934
￥31,121 total
includes taxes & fees
Nov 15 - Nov 16
Studio 'Judería' with Wi-Fi
A house with a stone facade, a patio with chairs, and a tree in the yard.

10. El Nido del Águila: Mountain House for 8 in Sierra de Guadarrama, near Madrid

El Nido del Águila: Mountain House for 8 in Sierra de Guadarrama, near Madrid
Becerril de la Sierra
10.0 out of 10, Exceptional, (2 reviews)
"Pros: Excellent, clean apartment with top end bedding and well stocked kitchen."
United States
Anonymous traveler
The price is ￥36,682
￥36,682 total
includes taxes & fees
Nov 18 - Nov 19
El Nido del Águila: Mountain House for 8 in Sierra de Guadarrama, near Madrid
A covered patio with a table and chairs, stone steps, and a view of the surrounding area.

11. Country House in Torrecaballeros with Mountain Views, Private Pool, and Wi-Fi

Country House in Torrecaballeros with Mountain Views, Private Pool, and Wi-Fi
Torrecaballeros
10.0 out of 10, Exceptional, (6 reviews)
"Pros: La casa es muy grande y aunque íbamos 8 parejas y 4 niños, todos teníamos nuestro espacio vital para estar cómodos. Habitaciones con baño y tele como en un hotel, zonas comunes muy grandes, jardín con césped para jugar y piscina vallada Cons: Nos gustó todo. Quizás si pudiese tener rampa la entrada por el porche de la barbacoa hacia el salon, que hay unos escalones y con niños pequeños teníamos que estar atentos de que no se cayeran. Supongo que tambien si alguien va en silla de ruedas se...
Spain
Anonymous traveler
The price is ￥153,653
￥153,653 total
includes taxes & fees
Nov 15 - Nov 16
Country House in Torrecaballeros with Mountain Views, Private Pool, and Wi-Fi
A bedroom with a bed, a window, wooden beams, a radiator, and wall art.

12. Country House in La Higuera – Rural Charm 10 km from Segovia

Country House in La Higuera – Rural Charm 10 km from Segovia
Espirdo
10.0 out of 10, Exceptional, (1 review)
"Excellent house,15 min by car from Segovia,small village vibe,restaurants in Segovia and near towns available. Very accommodating host. Only wish I would have is Air-conditioning available-usually Segovia area don't need one."
United States
Gueorgui Stoyanov
The price is ￥33,669
￥33,669 total
includes taxes & fees
Nov 15 - Nov 16
Country House in La Higuera – Rural Charm 10 km from Segovia
A rustic outdoor seating area with a wooden table and chairs, a covered table, and a large tree.

13. Rural House 'Casa Agapito Marazuela' with Mountain Views, Private Garden, and Wi-Fi

Rural House 'Casa Agapito Marazuela' with Mountain Views, Private Garden, and Wi-Fi
Segovia
The price is ￥105,261
￥105,261 total
includes taxes & fees
Nov 13 - Nov 14
Rural House 'Casa Agapito Marazuela' with Mountain Views, Private Garden, and Wi-Fi
A neatly arranged bedroom with a bed, bedside tables, and a wall-mounted picture.

14. Beautiful duplex in an unbeatable location.

Beautiful duplex in an unbeatable location.
Segovia Old Town
8.2 out of 10, Very good, (10 reviews)
"We loved the location and the wonderful communication! It was like staying with family! "
United States
Laura U.
The price is ￥35,441
￥45,719 total
includes taxes & fees
Dec 6 - Dec 7
Beautiful duplex in an unbeatable location.
A white door with a brass handle, leading to a room with a chandelier and a table.

15. EL ENCANTO LAS NIEVES APARTMENT IN MIRAFLORES

EL ENCANTO LAS NIEVES APARTMENT IN MIRAFLORES
Miraflores de la Sierra
The price is ￥14,354
￥15,240 total
includes taxes & fees
Nov 28 - Nov 29
EL ENCANTO LAS NIEVES APARTMENT IN MIRAFLORES
A courtyard with stone steps leading to a yellow building with arched doorways, outdoor seating, and potted plants.

16. Room 'Habitación Doble Estandard' with Shared Terrace, Wi-Fi and Air Conditioning

Room 'Habitación Doble Estandard' with Shared Terrace, Wi-Fi and Air Conditioning
Guadarrama
The price is ￥13,822
￥13,822 total
includes taxes & fees
Nov 15 - Nov 16
Room 'Habitación Doble Estandard' with Shared Terrace, Wi-Fi and Air Conditioning
A small building with a tiled roof, a wooden door, a window with metal bars, and a small table.

17. Holiday Home 'De Los Abuelos' with Mountain Views, Private Terrace and Wi-Fi

Holiday Home 'De Los Abuelos' with Mountain Views, Private Terrace and Wi-Fi
Ortigosa del Monte
The price is ￥58,349
￥58,349 total
includes taxes & fees
Dec 1 - Dec 2
Holiday Home 'De Los Abuelos' with Mountain Views, Private Terrace and Wi-Fi
A stone gate with a wooden door, surrounded by greenery and a stone wall.

18. Dalt La Figuera Country House — Guadarrama, Mountain Views, Pool & Wi-Fi

Dalt La Figuera Country House — Guadarrama, Mountain Views, Pool & Wi-Fi
La Higuera
9.0 out of 10, Wonderful, (4 reviews)
"Pros: La casa está decorada con un gusto exquisito y pese a estar ubicada en una zona árida el jardín está lleno de vegetación. Cons: Por decir algo las camas son un poco blandas y la vitro tiene los mandos borrados."
Spain
Anonymous traveler
The price is ￥155,597
￥155,597 total
includes taxes & fees
Nov 15 - Nov 16
Dalt La Figuera Country House — Guadarrama, Mountain Views, Pool & Wi-Fi
A snowy street with a sign for 'Sarosalo' and a building labeled 'Iglesia románica'.

19. Holiday Home 'Las Marias' with Private Garden, Wi-Fi and Air Conditioning

Holiday Home 'Las Marias' with Private Garden, Wi-Fi and Air Conditioning
Sotosalbos
The price is ￥57,415
￥57,415 total
includes taxes & fees
Dec 8 - Dec 9
Holiday Home 'Las Marias' with Private Garden, Wi-Fi and Air Conditioning
A cozy room with a stone wall, a round mirror, a desk with a basket, and a bed with a pillow.

20. El Espinar Cottage

El Espinar Cottage
El Espinar
The price is ￥31,233
￥31,233 total
includes taxes & fees
Nov 22 - Nov 23
El Espinar Cottage
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 Sierra de Guadarrama Hotel Reviews

Hotel Real Segovia

Hotel Real Segovia

10/10 Excellent
"Exclente el hotel, habitaciones amplias, muy bien localizado, cerca de todo lo turístico. Vale mucho la pena"
Alfonso 1-night trip
Posted 1 day ago
Hotel Real Segovia

Find out more about Sierra de Guadarrama

Search for holiday rentals in Sierra de Guadarrama on Expedia! You can easily find your home rentals, villas, holiday apartments in Sierra de Guadarrama using one of the methods below:

  • View our selection of featured holiday rentals in Sierra de Guadarrama
  • Use the map to find apartments and other holiday homes in the Sierra de Guadarrama neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Sierra de Guadarrama while they last

Look no further and take a look at our great range of rental properties in Sierra de Guadarrama!