Sierra de Guadarrama Vacation Rentals

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Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Sierra de Guadarrama vacation rentals

Estudio Familiar | Premium bedding, down comforters, in-room safe, desk
Hotel Apartamentos Aralso

Hotel Apartamentos Aralso

2.0 star property
Segovia
9.8 out of 10, Exceptional, (37)
"Great affordable place to spend a few days roaming Segovia, it met all our expectations, highly recommended!"
Canada
Bobby
$72 nightly
The price is $79
Jan 7 - Jan 8, 2026
Total with taxes and fees
Hotel Apartamentos Aralso
Rooftop terrace
Real Segovia Apartments

Real Segovia Apartments

4.0 star property
Segovia Old Town
9.6 out of 10, Exceptional, (53)
"Great location in the middle of everything we wanted to do!"
United States
Clarissa
Real Segovia Apartments
Outdoor pool
Hotel El Rancho

Hotel El Rancho

4.0 star property
Torrecaballeros
9.4 out of 10, Exceptional, (63)
"Stayed there before. An excellent hotel. "
United Kingdom
William
$83 nightly
The price is $92
Dec 15 - Dec 16
Total with taxes and fees
Hotel El Rancho
Deluxe Villa, Pool Access (Ángeles) | Living area | 55-inch Smart TV with digital channels, TV, fireplace
Casas Rurales Collarubio

Casas Rurales Collarubio

3.0 star property
Collado Mediano
Casas Rurales Collarubio
Balcony
Villa Don Juan II

Villa Don Juan II

3.5 star property
Segovia Old Town
9.8 out of 10, Exceptional, (33)
"Really nice place, close to everything, very nice private parking spot. Host is amazing, very friendly and helpful."
United States
Manuel
$181 nightly
The price is $199
Dec 10 - Dec 11
Total with taxes and fees
Villa Don Juan II
Indoor pool, outdoor pool
Large family country house in Rascafría,1 h from Madrid, 12 to 24 people

Large family country house in Rascafría,1 h from Madrid, 12 to 24 people

Rascafría
9.8 out of 10, Exceptional, (24)
"A"
Spain
Rafael E.
Large family country house in Rascafría,1 h from Madrid, 12 to 24 people
Standard Studio (+ Sofa Bed) | In-room safe, laptop workspace, soundproofing, iron/ironing board
Hotel Apartamentos Aralso Sotillo

Hotel Apartamentos Aralso Sotillo

2.0 star property
La Lastrilla
9.4 out of 10, Exceptional, (18)
"The manager was most helpful and courteous. "
United States
Steven
Hotel Apartamentos Aralso Sotillo
Pool
CASA RURAL MANSION VILLA ADELA DE LUXE

CASA RURAL MANSION VILLA ADELA DE LUXE

Collado Mediano
9.2 out of 10, Wonderful, (10)
"The property was stunning, absolutely massive, very clean, had so much to do there and the views were gorgeous. The hosts were so easy to communicate with and any problems were fixed immediately. Close to local supermarkets and cafes and a train station to get into main Madrid. We had the most amazing time and thank the hosts for making it so lovely."
United States
Brianna S.
CASA RURAL MANSION VILLA ADELA DE LUXE
Dining
Casa Puente Albor for 22 people

Casa Puente Albor for 22 people

Espinar (El)
9.8 out of 10, Exceptional, (12)
"Great house with indoor pool and great outdoor area. Sergio is the host: he is terrific in customer service and friendly. Strongly recommended."
Spain
Jose Miguel H.
Casa Puente Albor for 22 people
Property grounds
Colmenar Viejo: House / Villa - Colmenar Viejo

Colmenar Viejo: House / Villa - Colmenar Viejo

Colmenar Viejo
9.2 out of 10, Wonderful, (27)
"We loved the place, but the house is in need of some maintenance and repair. The hosts were very kind and gracious and we were grateful to have stayed there."
Spain
Scot M.
Colmenar Viejo: House / Villa - Colmenar Viejo
Outdoor pool
Bonito Chalet Excelente Ubicación

Bonito Chalet Excelente Ubicación

Navacerrada
10.0 out of 10, Exceptional, (15)
"It was great and Carlos went above and beyond to welcome my daughter and i."
United States
Laurence B.
Bonito Chalet Excelente Ubicación
Indoor pool, a heated pool
La Casa Pico de la Miel Incluye Piscina Privada de Agua Salada de 8 x 4 con Espectaculares Vistas

La Casa Pico de la Miel Incluye Piscina Privada de Agua Salada de 8 x 4 con Espectaculares Vistas

La Cabrera
10.0 out of 10, Exceptional, (3)
"Hemos ido un grupo de amigos y hemos disfrutado mucho de la casa. Está bien ubicada y contaba con muchas cosas indispensables que en otros alojamientos hay que comprar (bollería, papel higiénico, leche, sal, aceite...). Los dueños de la casa nos trataron muy bien en el check-in. Lo que más nos ha gustado ha sido que la casa tenga dos cocinas y la piscina climatizada que nos ha dado mucho juego. También destacamos la comodidad de las camas y los tres baños (éramos 13 por lo que nos vino genial)....
Spain
Silvia A.
La Casa Pico de la Miel Incluye Piscina Privada de Agua Salada de 8 x 4 con Espectaculares Vistas
Property grounds
House in Miraflores, for groups with pool, barbecue, bar, billiards, pi

House in Miraflores, for groups with pool, barbecue, bar, billiards, pi

Miraflores de la Sierra
7.4 out of 10, Good, (3)
"El estaso de la casa es lamentable, es muy vieja y los muebles estan viejos y sucios , las fotografias de la casa no tienen nada que ver con la realidad , la verdad es que hemos quedado muy descontentos. Lo unico jueno es que la calefacion una vez solucionado el problema funciono perfectamente y la localizacion es estupenda. "
Spain
Alicia R.
House in Miraflores, for groups with pool, barbecue, bar, billiards, pi
Outdoor pool
EL ESCORIAL HOUSE

EL ESCORIAL HOUSE

Navalquejigo
10.0 out of 10, Exceptional, (2)
"Nos encanto la casa de Andres especialmente el jardin con la picina y la barbacoa. El proprietario fue muy atento, siempre dispuesto a responder cualquier pregunta y con una gran flexibilidad respecto a la hora de llegada y salida. Ademas tuvo el detalle de dejarnos algo de comida y huevos de las gallinas del jardin. Todo un lujo!! Recomiendo esta casa sin dudarlo y su cercania a la estacion de tren la hace aun más practica!! Gracias por todo Andrès !! "
United States
Pauline M.
EL ESCORIAL HOUSE
Interior
El Rincón de Pilar - Rural house

El Rincón de Pilar - Rural house

Fuentemilanos
10.0 out of 10, Exceptional, (5)
"La casa es grande y muy cómoda! Es perfecta para pasar unos días con familia o amigos. Pilar es muy amable y te ayuda en lo que sea."
Spain
Pablo G.
El Rincón de Pilar - Rural house
Interior
Farmhouse Apartment with Pool

Farmhouse Apartment with Pool

Galapagar
9.4 out of 10, Exceptional, (18)
"A fantastic choice for families, The kids loved the outdoor space, and we felt right at home in the apartment, The hosts were friendly and responsive, making our stay even more enjoyable"
United States
Anonymous traveler
Farmhouse Apartment with Pool
Fridge, microwave, oven, stovetop
Romantic and beautiful apartment 65 m2 new in the main square of Segovia.

Romantic and beautiful apartment 65 m2 new in the main square of Segovia.

Segovia Old Town
8.8 out of 10, Excellent, (6)
"The apartment is too near to the pubs. On the Saturday evening, the noise was very loud till 7 o'clock in the morning. It is impossible to sleep in the living room. There is a noise in the wall due to water piping."
Germany
KIAT MENG C.
$154 nightly
The price is $154
Dec 14 - Dec 15
Total with taxes and fees
Romantic and beautiful apartment 65 m2 new in the main square of Segovia.
Outdoor pool, a heated pool
Torrelodones: House with shared garden and pool 25 min from Madrid. Wifi

Torrelodones: House with shared garden and pool 25 min from Madrid. Wifi

Torrelodones
9.8 out of 10, Exceptional, (74)
"Lovely property/accommodations close to a quaint town with stores and restaurants and a short walk to public transportation. "
United States
Will C.
Torrelodones: House with shared garden and pool 25 min from Madrid. Wifi
Outdoor dining
Rural apartment Colla - Rubio for 2 people

Rural apartment Colla - Rubio for 2 people

Collado Mediano
9.4 out of 10, Exceptional, (25)
"Nos ha gustado mucho, todo perfecto."
Spain
Sergio M.
Rural apartment Colla - Rubio for 2 people
Smart TV, books
Detached house with garage and private garden in the center of Segovia

Detached house with garage and private garden in the center of Segovia

Segovia
Detached house with garage and private garden in the center of Segovia
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.
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Top Sierra de Guadarrama Hotel Reviews

Hotel Cetina Palacio Ayala Berganza.

Hotel Cetina Palacio Ayala Berganza.

10/10 Excellent
"Todo ok, cava y seleccion de cafes!!"
Yolanda 1-night trip
Posted 4 days ago
Hotel Cetina Palacio Ayala Berganza.

Find out more about Sierra de Guadarrama

Everything you need to know about Sierra de Guadarrama vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Sierra de Guadarrama vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Sierra de Guadarrama vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Sierra de Guadarrama vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Sierra de Guadarrama. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Sierra de Guadarrama in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $79 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Sierra de Guadarrama rentals

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