Sierra de Guadarrama Vacation Rentals from CA $117: Short-Term Rentals for 2026

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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

Segovia Old Town

Shauna

CA $139 total

includes taxes & fees

Dec 13 - Dec 14

A building with a stone facade, wooden shutters, and a fenced courtyard.

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

Real Sitio de San Ildefonso

CA $170 total

includes taxes & fees

Nov 15 - Nov 16

A rustic courtyard with potted plants, a red wheelbarrow, and a stone wall.

3. Villa Don Juan II

Segovia Old Town

Mike

CA $274 total

includes taxes & fees

Nov 16 - Nov 17

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

Real Sitio de San Ildefonso

CA $1,222 total

includes taxes & fees

Nov 16 - Nov 17

A reception desk with a framed welcome sign, a potted plant, and two desk lamps.

5. La Arbolada

Navacerrada

ROSANA G.

CA $221 total

includes taxes & fees

Nov 17 - Nov 18

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

Navacerrada

Aa A.

CA $271 total

includes taxes & fees

Nov 17 - Nov 18

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

Navacerrada

CA $238 total

includes taxes & fees

Nov 17 - Nov 18

A dining area with a white table set for four, a potted plant, and a painting on the wall.

8. Apartamento El Sauce

Navacerrada

CA $266 total

includes taxes & fees

Nov 17 - Nov 18

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

Segovia Old Town

Jeremy K.

CA $254 total

includes taxes & fees

Nov 15 - Nov 16

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

Becerril de la Sierra

Anonymous traveller

CA $326 total

includes taxes & fees

Nov 15 - Nov 16

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

Torrecaballeros

"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...

Anonymous traveller

CA $683 total

includes taxes & fees

Nov 15 - Nov 16

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

Espirdo

Gueorgui Stoyanov

CA $299 total

includes taxes & fees

Nov 15 - Nov 16

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

Segovia

CA $936 total

includes taxes & fees

Nov 14 - Nov 15

A neatly arranged bedroom with a bed, bedside tables, and a wall-mounted picture.

14. Beautiful duplex in an unbeatable location.

Segovia Old Town

Laura U.

CA $407 total

includes taxes & fees

Dec 6 - Dec 7

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

Miraflores de la Sierra

CA $138 total

includes taxes & fees

Nov 16 - Nov 17

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

Guadarrama

CA $123 total

includes taxes & fees

Nov 15 - Nov 16

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

Ortigosa del Monte

CA $519 total

includes taxes & fees

Dec 1 - Dec 2

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

La Higuera

Anonymous traveller

CA $1,384 total

includes taxes & fees

Nov 15 - Nov 16

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

Sotosalbos

CA $491 total

includes taxes & fees

Nov 15 - Nov 16

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

CA $290 total

includes taxes & fees

Nov 25 - Nov 26

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Find vacation rentals that suit your style

Top Sierra de Guadarrama Hotel Reviews

A pool area with lounge chairs and umbrellas, surrounded by a well-maintained lawn and a view of a distant town with historic buildings.

Parador de Segovia

Segovia

10/10 Excellent

miguel

A building named 'El Rancho' with a stone facade, a statue in the foreground, and a well-maintained lawn.

Hotel El Rancho

Torrecaballeros

10/10 Excellent

Denis

A table set outdoors with a castle in the background.

Hotel Don Felipe

Segovia Old Town

10/10 Excellent

If you're debating travelling to Segovia, definitely do it. The aqueduct is amazing and so is the castle. AND if you go to Segovia, stay at Don Felipe's. It's a fantastic hotel, very modern and the pictures don't do it justice. Definitely pay for the upgraded room. It was only about 5 Euro for us to upgrade which is less than some restaurants charge for a seat with a view here.(seriously). Stop debating, go to Segovia, and stay at Don Felipe's it could easily be the best choice you make on your...

Matt

A lobby with a reception desk, patterned tiles, a chandelier, and a staircase leading to another area.

Hotel Cetina Palacio Ayala Berganza.

Segovia

10/10 Excellent

Claudiu

Real Segovia Apartments

Segovia Old Town

10/10 Excellent

Shauna

A room with a view of a courtyard, a statue, a table with a vase of flowers, and a framed picture on the wall.

Hotel Infanta Isabel

Segovia Old Town

10/10 Excellent

Kate

A hotel with a covered entrance, outdoor seating, and a large tree in the foreground.

Hotel Puerta de Segovia

La Lastrilla

10/10 Excellent

Janusz

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, cottages, cabins, villas... 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Sierra de Guadarrama vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Sierra de Guadarrama vacation rentals we have selected for you start as low as CA $117 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Sierra de Guadarrama rentals

At Expedia, we put the best Sierra de Guadarrama vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Sierra de Guadarrama rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Sierra de Guadarrama vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Sierra de Guadarrama. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Sierra de Guadarrama Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Sierra de Guadarrama vacation rentals

1. Real Segovia Apartments

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

3. Villa Don Juan II

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

5. La Arbolada

6. Apartamento en Pleno Centro de Navacerrada

7. Apartamento El Roble

8. Apartamento El Sauce

9. Studio 'Judería' with Wi-Fi

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

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

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

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

14. Beautiful duplex in an unbeatable location.

15. EL ENCANTO LAS NIEVES APARTMENT IN MIRAFLORES

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

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

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

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

20. El Espinar Cottage

Find vacation rentals that suit your style

Top Sierra de Guadarrama Hotel Reviews

Parador de Segovia

10/10 Excellent

Find out more about Sierra de Guadarrama

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

How to find incredible deals on Sierra de Guadarrama rentals

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