Vacation rentals in Sierra de Guadarrama

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Top-rated vacation rentals in Sierra de Guadarrama

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favourite

Home in San Martín de Valdeiglesias

4.91 out of 5 average rating, 101 reviews

Casa Salamandra. With pool, by the swamp

Privileged environment, surrounded by pine forests next to the swamp, located between three of the most representative cities of Spain: Toledo, Ávila and Madrid. Very interesting design house in the shape of an A, with a lot of light, in the middle of nature, with views of the lake and mountains. Private garden of 1500 m2 with private pool. Furnished terrace with BBQ. 7 km from San Martín de Valdeiglesias (where all kinds of services are available). Possibility of carrying out a variety of aquatic activities.

Guest favourite

Cottage in Cerro Matallera

4.91 out of 5 average rating, 137 reviews

Casa Matallera - Mountain Retreat near Madrid

Beautiful house in Sierra de la Cabrera Guadarrama, 40 minutes from Madrid. Hiking, cycling, horse riding, leisure activities for families & a varied gastronomic offer. The loveliest municipal pool is just 10 km away. Very quiet area, ideal for disconnecting, resting, or working remotely. Large dining room, living room. Amazing fireplace and very well-equipped kitchen. Ideal for family gatherings, reduced weddings (30/40 pax) in spring and autumn (events subject to small extra payment to agree).

Guest favourite

Cottage in El Espinar

4.95 out of 5 average rating, 153 reviews

The corner of your dreams.

Isolation, peace, and enjoyment in its purest state. A unique experience, a magical feeling of having your own wooden house in the middle of the mountain. A 3000m2 private oak wood house (for you) within a community with 24-hour security, swimming pools, hiking trails, golf courses, horseback riding, restaurants, a supermarket, a lake with water activities, and a spa. Each season offers its possibilities, from its cozy fireplace to its barbecues, through a spring full of flowers.

Superhost

Cottage in Miraflores de la Sierra

4.91 out of 5 average rating, 287 reviews

Amazing garden and charming villa in the mountains

Beautiful house of the 60s rehabilitated, on a large plot of 1500m with private pool and large trees. Tranquility and privacy in the heart of the forest in one of the most beautiful villages in the Sierra de Madrid. You can walk for days through the forests and mountains of Guadarrama National Park from the very doorstep. Ideal for sharing two families. Fully equipped with lots of charm. Fireplace, barbecue, table tennis, trampoline, slide, basketball basket, wi-fi...

Superhost

Cottage in Río Cofio

4.85 out of 5 average rating, 197 reviews

Cozy and bright country house. 22-meter terrace

CLOSED PLOT WITH ANTI CATERPILLAR TREATMENT Murmullo del Río..Nature tops..Relax..Evening in the company of the moon... Unique skies.. Unique views of the majestic Mount of Sta Catalina. Águilas .. rides to the river that is 50 meters away... smell of green.. cozy house.. umbrella hammocks.. barbecue .....pool in the development ... fresh nights.. pure air... quiet mornings and also everything you need: wifi, air conditioning, coffee, TV, board games

Guest favourite

Cottage in Los Molinos

4.94 out of 5 average rating, 210 reviews

The Casita de El Montecillo

Charming and fully equipped mountain house. Located in a unique natural setting: a private 65-hectare estate full of holm oaks, with a lake and a hermitage, perfect for walking, hiking in the mountains... You will be in the middle of the Sierra de Guadarrama, surrounded by mountains and nature. The perfect place for a romantic weekend, with a fireplace and jacuzzi for two. Perfect for coming with children. NO PETS ALLOWED. NO SMOKING ALLOWED.

Top guest favourite

Chalet in El Boalo

4.98 out of 5 average rating, 119 reviews

Beautiful rustic house in the mountains of Madrid

Very comfortable rustic house located in the heart of the "Sierra de la Pedriza", that belongs to the Guadarrama regional park, and just half an hour from Madrid. The land of this house has an area of 3000 square meters with natural vegetation in the area. 5 minutes walk you will find the beautiful town "El Boalo". Impressive views of the Sierra de Madrid. Possibility of beautiful excursions, horse riding and multiple activities.

Guest favourite

Home in La Losa

5 out of 5 average rating, 11 reviews

Casa Josephine Riofrío - retreat 1 hour from Madrid

Casa Josephine Riofrío B&B is a capsule of peace and rest an hour from Madrid, in a quiet village in a protected landscape at the foot of the mountain. A place where time runs differently. A retreat, one place to create, rest, or work at a different pace. A fully renovated house in 2022 with an architectural and interior design project paused in geometry, materials and proportions, signed by Casa Josephine Studio. Permit VUT 40/718

Guest favourite

Home in Uceda

4.96 out of 5 average rating, 103 reviews

Rural Boutique with Jacuzzi and Garden

Welcome to the Pertenera house. Immerse yourself in the luxury of our stone-surrounded Jacuzzi for two, where elegance and good taste are present in every detail of this charming house. From the comfortable bed, you can gaze at the stars through the window on clear nights. Relax in our charming courtyard with a cactus garden. Your perfect getaway less than an hour from Madrid, where style meets rural!

Guest favourite

Villa in El Gasco

4.92 out of 5 average rating, 24 reviews

Villa Sierra Madrid (7 bedroom villa with pool)

In the mountains 30km from Madrid we rent out our villa with more than 400 m2 of living space and a garden with pool. That garden is 4000 m2 and has more than 100 trees. From the house and outside terrace you have a fantastic view and at the pool there is lounge area. The pool is 13m long en 6m wide. The villa has been recently fully renovated and everything is new. The climate is nice, warm and dry.

Top guest favourite

Cottage in Los Molinos

4.99 out of 5 average rating, 182 reviews

Recoveco Cottage

Lovely cottage, completely detached, located in the northern mountains of Madrid. Just a 5-minute walk from Los Molinos train/suburban station. And from downtown. The house is fully equipped and has 1G fiber, making your stay a perfect place for leisure, rest, or teleworking. Your perfect choice to enjoy nature with all the amenities the city can offer. No pets allowed.

Top guest favourite

Apartment in El Boalo

4.98 out of 5 average rating, 257 reviews

The Sound of Silence, Guadarrama National Park, La Pedriza

The accommodation is a small house, made with mostly ecological materials and furnished and decorated with love to make your stay as comfortable and enjoyable as possible. The cottage is in our garden, but it is totally independent. The plot has direct views of the Guadarrama National Park and is a very quiet place of spectacular beauty.