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Holiday houses in La Pinilla

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Top-rated holiday rentals in La Pinilla

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

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Guest favourite
Cottage in Cerro Matallera
4.91 out of 5 average rating, 145 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
A heated indoor pool is surrounded by large floor-to-ceiling windows, providing views of the forest outside. Soft light filters in, highlighting the serene water as a person floats effortlessly on the surface. The atmosphere is inviting and tranquil.
Loft in La Pinilla
4.86 out of 5 average rating, 125 reviews

"Snow escape with sauna and heated pool".

If you are preparing your getaway to disconnect from the routine, look at this charming studio of 45 m2. What gives a touch of distinction, is to be able to enjoy the relaxing HEATED-WARM POOL in winter, contemplating the nature and the landscape. You can also enjoy the warmth of a SAUNA, with its therapeutic benefits, in the Nordic style. They really are Little Whims that undoubtedly make a difference !. Ideal for couples and friends. Families, to value the limited space.

Superhost
An indoor pool features crystal-clear water and is surrounded by large windows that offer views of the forest. The area is designed with light blue tiles and a stone perimeter, allowing for a serene swimming experience.
Loft in La Pinilla
4.67 out of 5 average rating, 55 reviews

Last corner, heated pool, sauna, duplex

Precioso Dúplex de 3 alturas, en la zona más elevada de La Pinilla. En pleno bosque de la Sierra de Ayllón, a pie de pistas de esquí y bicicleta de montaña. Cocina independiente perfectamente equipada. Dos cuartos de baño completos. Amplio y acogedor salón comedor con mesa de hasta seis comensales. Conexión wifi. Espaciosa terraza con magníficas vistas. Dormitorio con armarios empotrados y cuarto de baño con bañera independiente. Se suministran toallas y ropa de cama.

Top Guest favourite
A bright living area features a spacious sofa and a small glass table. A flat-screen television is positioned on a white cabinet against the wall. Large windows provide ample natural light and offer views of the surrounding landscape.
Apartment in Segovia
4.99 out of 5 average rating, 148 reviews

Apartment with panoramic views in Segovia

Fully renovated apartment, very bright and with wonderful views of the city of Segovia. Free street parking and just a 15-minute walk from the aqueduct. Spacious entrance, large kitchen, two bedrooms each with a 1.50 m bed, living room with a 90 cm sofa bed, two full bathrooms with shower and a cozy terrace. It is on the fifth floor with an elevator. Central heating and hot water by electric thermos. Bus and supermarket 200 meters away. No parties and no pets allowed.

Top Guest favourite
A spacious living area features natural wood beams and a large window offering views of the greenery outside. Seating includes a wooden chair, a large round coffee table, and a long couch with cushions, providing a comfortable and inviting space.
Chalet in Orejanilla
4.95 out of 5 average rating, 93 reviews

Old barn, renovated

Old stone barn completely renovated. We have respected its rustic spirit by integrating it with a modern architectural design intervention and warm decoration. Take the opportunity to stay in a unique space and environment. Idyllic setting to disconnect from the city in a small village that is secluded but very close to the monumental town of Pedraza, which is a 3 km walk away. There are numerous hiking, cycling, and other activity trails in the surrounding area.

Guest favourite
An elevated view captures a cozy interior with wooden beams and stone walls. A hammock is suspended nearby a rustic dining table. A sofa and armchair are placed in a relaxing corner, while a kitchen area is visible, equipped with wooden cabinetry and essential appliances.
Cabin in Cuevas de Ayllón
4.88 out of 5 average rating, 245 reviews

Stone cabin (Painting workshop)

Tourist accommodation (license number: 42/000223) The stone cabin is a cozy little stone and wood house where you soon connect with yourself and the nature that surrounds you. It is a very special house, made almost by hand with great effort and a lot of love. But IT IS NOT A HOTEL, it is a private house with its own characteristics and conditions, which do not always match those of a hotel!! Before you book, make sure it meets your expectations.

Superhost
A spacious living area features comfortable seating arranged around a central fireplace, with large windows providing views of the garden. Natural light bathes the room, highlighting the wooden ceiling and warm interior design.
Chalet in Riaza
4.91 out of 5 average rating, 104 reviews

Spectacular house with 3 floors and garden in Riaza

(*) CHECK SPECIAL OFFERS: Weekdays (except high season) for groups of less than 10 people // Stays from 1 to 4 weeks. An incredible villa (corner townhouse), close to downtown, ideal for enjoying nature and tranquility. A cozy house with 3 floors, a garage, a garden, a barbecue grill, and Wi-Fi. Next to La Pinilla ski resort in an environment of culture, gastronomy, leisure, and sports in the middle of nature. VuT JCyL

Guest favourite
A spacious bedroom is highlighted by large glass doors that open to a patio and garden. A comfortable bed is adorned with light linens. The outdoor area features a small table and chairs surrounded by greenery, providing a peaceful and relaxing view.
Home in Uceda
4.96 out of 5 average rating, 140 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
A wooden house with a welcoming porch is surrounded by lush greenery. Potted plants adorn the porch, while the stone wall and textured pathway complement the natural setting. Large windows provide ample light, enhancing the connection between the indoor and outdoor spaces.
Cabin in Uceda
4.88 out of 5 average rating, 543 reviews

Miguel's Cabin

Cozy wooden house with fireplace and 2700 Mt of wooded plot, fully fenced and private. Ideal for city getaways, enjoying nature, clean air and tranquility, 45 min from downtown Madrid. In a sparsely populated development in the municipality of Uceda, Guadalajara (400 meters bordering the community of Madrid). Near Patones de Arriba, Atazar, Jarama River.

Superhost
A transparent dome structure is nestled among trees, revealing an interior with a spacious bed and soft lighting. Surrounding greenery and flowers create a natural, serene setting, enhancing the unique design of this accommodation.
Dome in Soto del Real
4.91 out of 5 average rating, 199 reviews

Transparent Dome Room Madrid - Natura Domo

Do you want to be at one with nature as you've always dreamed of? Stay in this unique place and enjoy the sounds of nature while looking at the stars. We are the only transparent dome to enjoy with your partner in the Sierra de Madrid, just 40km from the city, with an ecosystem that surrounds it to have an unforgettable experience.

Guest favourite
The stone and wood house features a traditional tile roof, complemented by large windows allowing natural light. Surrounding structures include a stone wall and another building with wooden balcony, under a clear blue sky.
Cottage in Braojos
4.93 out of 5 average rating, 405 reviews

Rustic house near National Park

DISCOUNT 7 NIGHTS OR MORE 20%, ENTIRE MONTH 47% !!! Rustic house, made of stone and timber. It is localization in a little town, Braojos, 1.200 metres high, in the Central Mountains of Spain. The house is surrounded by mountains and forests, 50 minutes drive from the city of Madrid

Guest favourite
A stone exterior is featured with a charming balcony above a sunlit terrace, equipped with two lounge chairs. Potted plants line the stone walls, adding greenery to the inviting outdoor space. Large glass doors provide a view into the interior.
Cottage in Tenzuela
4.9 out of 5 average rating, 262 reviews

Veranoor- Designer Country House

Veranoor is a country house in Tenzuela (Segovia) , 1 hour from Madrid, that combines the charm of rural architecture with spacious, and minimalist design and large windows. Located near Torrecaballeros, La Granja, Pedraza and Segovia. Min. 2 nights.

Popular amenities for La Pinilla holiday rentals

  1. Airbnb
  2. Spain
  3. Castile and León
  4. La Pinilla