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Vacation rentals in La Pinilla

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Top-rated vacation rentals in La Pinilla

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

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Top guest favourite
The exterior of the house is constructed from stone and wood, featuring a large porch with comfortable seating. Lush greenery surrounds the property, while the upper balcony offers views of the garden below. A prominent stone chimney adds character to the inviting façade.
Cottage in Cerro Matallera
4.91 out of 5 average rating, 150 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).

Top guest favourite
A welcoming entrance is framed by rustic stone walls, leading into a softly lit interior. The threshold opens to a glimpse of warm wooden beams and cozy furnishings, with a doormat positioned at the doorway. A potted plant sits beside the entrance.
Place to stay in Brieva
4.97 out of 5 average rating, 100 reviews

La Casa de Brieva

Charming stone country house in Brieva, declared a Cultural Heritage Site (Bien de Interés Cultural), just an hour and a half from Madrid. A place to slow down, reconnect with nature and enjoy the silence. Perfect for family getaways, romantic escapes or a few days of remote work during the week. Wake up without rushing, stroll through the surroundings, read or write in peace and enjoy the fireplace at the end of the day. A fully equipped home designed to make you feel at home

Guest favourite
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.

Guest favourite
A modern bathroom features a freestanding white tub and a glass shower. Natural light enters through a round window, highlighting the smooth, neutral wall textures. A small wooden table holds two glasses, a bottle of wine, and a candle, adding a subtle touch of elegance.
Home in Madrid
4.95 out of 5 average rating, 113 reviews

Dreamy treehouse

Discover the magic of this charming wooden house, an oasis of tranquility surrounded by trees and nature. Its unique design integrates modernity with the natural environment. Here, you will wake up to the sound of birds and the breeze through the trees, enjoying a cozy and sophisticated atmosphere. A few meters away, you will find hiking trails that cross landscapes where you can see horses, bulls and the beauty of the countryside. Perfect for disconnecting and relaxing.

Guest favourite
The exterior of the house is adorned with lush green vines, blending seamlessly with the surrounding nature. A stone pathway leads up to the property, with decorative planters featuring flowers and shrubs. Tall trees and a lamp post contribute to the tranquil ambiance.
Cottage in Miraflores de la Sierra
4.91 out of 5 average rating, 315 reviews

Amazing garden and charming villa in the mountains

A beautiful renovated house from the 60s on a large 1500m plot with a 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 your doorstep. Great for two families to share. Totally charmingly equipped. Fireplace, gas BBQ, ping-pong, trampoline, slide, basketball basket, Wi-Fi, and more

Top guest favourite
Cottage in Los Molinos
4.94 out of 5 average rating, 241 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.

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, 249 reviews

Stone cabin (Painting workshop)

Vivienda de uso turístico (N°licencia: 42/000223) La cabaña de piedra es una acogedora casita de piedra y madera en la que conectas contigo mismo y la naturaleza que te rodea. Es una casa muy especial, hecha casi a mano con gran esfuerzo y mucho cariño. Pero NO ES UN HOTEL, es una casa particular con sus características y condiciones, que no siempre coinciden con las de un hotel!!. Asegúrate de que cumple con tus espectativas.

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
4.9 out of 5 average rating, 105 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
An outdoor patio area features a stone structure with wooden beams. A small white table and two chairs are positioned on a stone floor. Colorful flowers bloom in the background, and a lush green lawn extends beyond the patio.
Home in Palancares
4.88 out of 5 average rating, 201 reviews

Apartamento Ocejón I mean Parents

Sights: Valverde de los Arroyos, Tamajón, Incredible views, Hayedo Tejera Negra. lush oak forests, Pico Ocejón, Despeñalagua jetties, the route of the Black Towns, the light, the comfort of the bed, the cozy space. You'll love my place because of its newly opened, all designed to be very comfortable, incredible views and very individual. Ideal for couples getaways.. My place is good for couples, adventurers, and pets.

Guest favourite
A relaxing jacuzzi for two is set against a textured stone wall, featuring subtle blue lighting that highlights the water's surface. The clean lines of the simple design contribute to a tranquil ambiance. A woven basket with a cushion is positioned nearby.
Home in Uceda
4.96 out of 5 average rating, 150 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!

Top guest favourite
Cottage in Los Molinos
4.99 out of 5 average rating, 228 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.

Guest favourite
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, 203 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.

Popular amenities for La Pinilla vacation rentals

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