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

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

4.89 out of 5 average rating, 209 reviews

Apartamento Ocejón Parejas

Places of interest: Valverde de los Arroyos, Tamajón, Incredible views, Incredible views, Hayedo Tejera Negra. Leafy oak forests, Pico Ocejón, Despeñalagua, the route of the Black Villages, the light, the comfort of the bed, the comfort of the bed, the cozy space. You will love my place because it is newly opened, everything is designed to be very comfortable, incredible views and very individual. Ideal for couples getaways.. My accommodation is good for couples, business travelers, and pets.

LocationFamilyDecor

Guest favourite

The house is viewed through a natural wooden frame, showcasing its spacious design and large windows. The exterior features a mix of neutral colors, with greenery surrounding the structure, enhancing its connection to the natural environment.

Home in Duruelo

5.0 out of 5 average rating, 14 reviews

Casa Teja Vieja

Discover a peaceful corner in Duruelo, Segovia, where time seems to stand still. It's the perfect place to disconnect from the daily rhythm and immerse yourself in nature, with the comfort of a cozy house and spectacular views of the mountains. • Private pool overlooking the mountains • Privileged environment • Large garden and outdoor areas: Perfect for barbecue • Connection to nature: Surrounded by hiking trails, country lanes and charming villages to explore at your own pace.

LocationFamilyKitchen

Top Guest favourite

Home in Prádena

5.0 out of 5 average rating, 7 reviews

Casa La Huertona in Castroserna

Large house ideal for families and groups of friends, spacious and very bright, designed for everyone's maximum comfort. Outside, enjoy the barbecue and paella area for unforgettable outdoor meals and evenings. We are in a beautiful natural setting, perfect for quiet walks discovering rivers and waterfalls. A unique experience: watch the majestic flight of the vultures and visit the nearby vulture breeding centers. Prime location near Hoces del Duratón, Sepúlveda and Riaza.

FamilyLocationBarbecue

Guest favourite

A shared swimming pool is featured within a stone-walled enclosure, surrounded by green grass. Sunlight reflects on the pool's water while shadows are cast from nearby structures, creating a serene outdoor space. The rustic surroundings enhance the tranquil ambiance.

Home in El Espinar

4.97 out of 5 average rating, 62 reviews

Casa Carma

Area of the black villages of Guadalajara nestled in front of the Ocejon peak and different routes that make waterfalls, Campillo de Ranas Majaelrayo reservoirs, a great place. Rooms with Smart TV, board games, oven, Nespresso, microwave, etc. 85 square meter house, 2 bedrooms, 1 toilet, full bathroom, living room, kitchen, outdoor table, extendable dining table, fireplace in living room, smart TV in living room, Wi-Fi available. And dishwasher. The pool and garden are shared

ValueLocationWalkability

Top Guest favourite

An overhead view captures a serene outdoor space, featuring a lawn bordered by a swimming pool and sun loungers. The rustic stone walls and wooden beams contribute to a harmonious setting, while an umbrella provides shade over a dining area with modern furnishings.

Home in Rascafría

4.97 out of 5 average rating, 29 reviews

The Rascafria granary

Escape the daily grind at this unique accommodation in the Sierra de Guadarrama, IG @elpajarderascafria. Located in the beautiful town of Rascafría, the starting point for the best trails to Peñalara. Perfect for a family holiday at any time of the year. We also organise retreats (IG @nkalmaretreats) for groups or celebrations, featuring a range of workshops. The pool has a massage bench in summer. In winter you can enjoy the fireplace. One hour from Madrid and Segovia.

LocationFamilyPool

Guest favourite

Loft in La Pinilla

4.87 out of 5 average rating, 126 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.

FamilyLocationAmenities

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, 104 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.

LocationValueOutdoor spaces

Guest favourite

The exterior of the house features a distinctive stone façade, complemented by large windows. A spacious lawn surrounds the property, and a patio area is visible. The roof is sloped, and greenery from nearby trees adds a natural touch to the setting.

Cottage in Riaza

4.98 out of 5 average rating, 44 reviews

Country House "El Rebeco"

Fabulous country house on the outskirts of Riaza. Newly renovated, comfortable, and with plenty of space for groups of friends or families. It has 5 bedrooms, 4 bathrooms and a large living room with a fully equipped open kitchen. The house is surrounded by a large garden with an outdoor porch, gazebo, and barbecue. Just a 15-minute walk to downtown Riaza, a 10-minute drive to La Pinilla and many other countryside and mountain activities.

FamilyLocationDecor

Superhost

A bell is positioned above a wooden table set with glassware, suggesting a communal dining experience. A small red birdhouse adds a charming touch to the scene. Outside, a pool area is enclosed by transparent walls, allowing for natural views while offering privacy.

Home in Segovia

4.91 out of 5 average rating, 34 reviews

La Lumbre: Charm with a year-round pool

La Lumbre, available for 22 guests, is located in a natural setting and has a heated indoor pool available year-round, private for our guests. Due to its size and layout, it is ideal for families and large groups who want to enjoy a charming and quiet accommodation, with multiple options for leisure and relaxation both without leaving the house and enjoying the surroundings: Riaza, La Pinilla, Sepúlveda, the Hoces del Duratón (gorge)...

LocationFamilyIndoor spaces

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, 107 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

FamilyLocationCleanliness

Guest favourite

A stone-clad entrance presents a welcoming exterior, featuring a shaded seating area with wooden chairs and a table beneath a large umbrella. Greenery enhances the environment, while rustic details add character to the facade of the house.

Cottage in Montejo de la Sierra

4.95 out of 5 average rating, 55 reviews

Comfortable Country House with fireplace (3 bedrooms + 3 bathrooms)

Rural House in Montejo de la Sierra within the Sierra del Rincón Biosphere Reserve and just 8 km from the Hayedo de Montejo. This accommodation exudes tranquility and comfort: relax with the whole family! Stay in its three bedrooms with bathroom, fully equipped kitchen, TV, independent heating and a small terrace area with barbecue outside. Come and discover the Sierra Norte de Madrid and you will come back!

ValueLocationView

Guest favourite

A rural house constructed of stone and wood is set against a clear blue sky. Wooden shutters accent the windows, and a spacious garden features a small seating area with tables and chairs. Lush green grass and flowering plants enhance the surroundings.

Cottage in Prádena

4.96 out of 5 average rating, 109 reviews

El Covanchon Rural House

Cozy country house on the outskirts of a village in Segovia. Built in wood and stone and surrounded by a beautiful garden with excellent views. The location is ideal as it is within the village but maintains privacy by being on the outskirts and you can walk to many routes in the area. The village has a municipal swimming pool located in a magnificent juniper forest 5 minutes from the house.

LocationFamilyLong stay