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Chalet holiday rentals in Sierra Oeste

Find and book unique chalets on Airbnb

Top-rated chalet rentals in Sierra Oeste

Guests agree: These chalets are highly rated for location, cleanliness and more.

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Top Guest favourite
An inviting outdoor space features a salt-water pool surrounded by wooden decking and white stones. Comfortable blue cushions are placed on the decking. An umbrella provides shade over the pool area, with lounge chairs positioned nearby for relaxing.
Chalet in Valdemorillo
5 out of 5 average rating, 32 reviews

Family Villa with Private Pool

¡Escápate al campo! Descanso y relax a tan solo 45 minutos de Madrid en coche. Amplia y cómoda casa situada en un entorno tranquilo con piscina privada. Ideal para unas vacaciones aptas para niños: Parque Infantil y Casita en el árbol. Ideal para invitar a amigos y familiares: barbacoa y cenas al aire libre. Destino popular para senderistas. Explora las cercanías de El Escorial y la Sierra de Guadarrama, Ávila, Segovia y San Ildefonso. Parque Acuático Aquopolis a tan solo 15 minutos en coche.

Guest favourite
Chalet in Soto del Real
4.87 out of 5 average rating, 122 reviews

Chalet with garden in Soto del Real (10 pax)

Individual villa in the Sierra de Madrid, in the urban center of Soto del Real. Unbeatable location. Perfectly connected. All services are a 5-minute walk away. Perfect for spending a few days with family or friends. Living room, kitchen, dining room, 1 bedroom and a full bathroom on the ground floor. 3 bedrooms, another full bathroom and terrace overlooking the Sierra de la Pedriza on the upper floor. It has a barbecue. Parking is available on the property. Pets are allowed. VT-15209.

Top Guest favourite
A serene private swimming pool is framed by a wooden patio and a wall adorned with greenery. Two lounge chairs are positioned beside the pool, bathed in sunlight. The water’s clarity reflects the blue sky with fluffy clouds above.
Chalet in Madrid
4.97 out of 5 average rating, 145 reviews

Private pool and patio, a true Oasis in Madrid.

Enjoy a Premium Experience in Madrid. 🏡Stay in a beautiful chalet with private plunge pool & patio near Madrid Río, just minutes from the historic city center. 2 bedrooms + 2 bathrooms, heated floors, A/C, fast Wi-Fi. 🏊‍♂️ Relax in your private pool (April to early October) or stroll to nearby park & cafés. 🚇 Direct metro to El Rastro, Royal Palace & Gran Vía. Quick access to main attractions. ✨ Perfect for families or friends looking for a stylish, peaceful stay 😉 You Will ❤️ it!!

Guest favourite
Chalet in Las Rozas de Madrid
4.96 out of 5 average rating, 26 reviews

Designer Chalet with a garden and pool

Beautiful family townhouse chalet. Designer interior and garden, with swimming pool and open interior and exterior living-dining room. Open kitchen with bar and professional appliances. Designer furniture and lamps. Ideal for spending a season near the center of Madrid with good access to the city center by highway and public transport (bus and train). Surrounded by parks and green areas, forest, municipal and private sports areas (tennis, paddle, bike, swimming) and shopping centers

Guest favourite
A rectangular salt-water pool is surrounded by a well-maintained green lawn. Several white lounge chairs are positioned alongside the pool, facing a warm sunset sky punctuated by scattered clouds. A stone wall encloses the area, providing privacy.
Chalet in Las Ventas de Retamosa
4.92 out of 5 average rating, 143 reviews

Villa with Pool Near Puy du Fou, Toledo

Family-friendly villa, 30 minutes from Madrid and 30 minutes from Toledo. It has a swimming pool, garden, barbecue and porch to enjoy outdoor meals, open kitchen with American fridge. It has 4 bedrooms + 3 bathrooms, a basement with beds, a ping pong table, foosball, darts and games. Ideal to get away and have a good time. Close to 2 parks, sports center, country walks, Dia supermarkets. Unide and shops. Close to Puy du Fou, Xanadú Shopping Center. No groups that throw parties

Guest favourite
A natural swimming pool is surrounded by wooden fencing and bordered by tall trees. A stone area with some rocks is visible in the foreground, contributing to the peaceful, rustic setting.
Chalet in Manzanares el Real
4.87 out of 5 average rating, 434 reviews

Independent house in the mountains

Charming detached house at the foot of La Pedriza. Beautiful garden to enjoy the birdsong and the tranquility offered by the surroundings. Built in harmony with the very stones that nature gives us. Ideal for relaxing Charming relaxing little house very close to the mountains. There is a beautiful garden where you will enjoy while hearing the birds singing and the relaxing atmosfere. It is built harmoniosuly within the nature of the surrounding enviroment.

Top Guest favourite
A rustic stone house is positioned amid a natural landscape, featuring a wooden staircase leading to the entrance. Lush greenery surrounds the property, with expansive views of the mountains in the background under a clear blue sky.
Chalet in El Boalo
4.99 out of 5 average rating, 157 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
The exterior of a stone house features a large wooden balcony with a metal railing. A gabled roof and chimney add to the architecture, while ample windows allow natural light to fill the interior. The surrounding area showcases a clear blue sky.
Chalet in El Espinar
4.97 out of 5 average rating, 67 reviews

A nice chalet with an indoor fireplace and views.

CASA TOMILLAR is nestled in a privileged location, a few hundred meters from the mountain and in a very quiet urban area where silence and rest prevail. Just 30 minutes by road from three very important cities, Segovia, Ávila and Madrid. Distributed over three floors, with four bedrooms, a spacious living room, full kitchen, three bathrooms or a toilet, gym, ping pong, foosball, parking and porch with garden area.

Top Guest favourite
A cozy outdoor seating area is created with four wicker chairs arranged around a wooden table. A colorful blanket drapes over one chair, and a soft cushion rests on another. The natural stone columns and distant mountain view add a serene touch.
Chalet in Cercedilla
4.98 out of 5 average rating, 148 reviews

la rama_ nature and tranquility, as a family.

la rama_ is our beautiful family home in Cercedilla. Max. 8 adults (other places are for children). In a spacious, simple and very cozy atmosphere, we welcome you to spend relaxing days surrounded by nature; movie afternoons, bike rides, barbecues with friends in the garden and long walks with the children in the surrounding area. La Rama is located a few kilometers from the Navacerrada and Valdesquí ski resorts.

Guest favourite
Chalet in La Estación
4.91 out of 5 average rating, 54 reviews

Casa Zúrich: swimming pool, jacuzzi and incredible views

Mountain chalet with stunning views, surrounded by terraces, pool and private jacuzzi (see opening dates in the ad). It has a large barbecue, a fully equipped kitchen, 3 bedrooms with 4 double beds, air conditioning and ceiling fans. Ideal for sharing unique moments with family and friends!

Guest favourite
A modern structure with large glass windows allows ample natural light, framed by a green lawn and hedge. The design emphasizes a connection to the outdoor space, while the clear blue sky enhances the overall ambiance.
Chalet in Manzanares el Real
4.89 out of 5 average rating, 105 reviews

Nature paradise 30 min from Madrid

Casa La Pedriza is a unique, peaceful, and confortable house located in the heart of the Guadarrama National Park only 30 minutes from the cosmopolitan city of Madrid. Perfect location for a wide array of nature, cultural and entertainment options.

Guest favourite
A black metal gate is set within a stone wall, surrounded by lush greenery. A green mailbox stands to the left of the gate, which opens to a gravel path leading towards a distant structure partially visible through the foliage.
Chalet in La Estación
4.93 out of 5 average rating, 123 reviews

The house in the woods

This accommodation has been decorated and renovated with patience, care and love for the spaces that convey comfort, tranquility and peace, in the middle of a pine garden that makes this place a special place to spend a few days.

Popular amenities for Sierra Oeste chalet rentals

When is the best time to visit Sierra Oeste?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$411 NZD$415 NZD$450 NZD$475 NZD$473 NZD$502 NZD$535 NZD$540 NZD$473 NZD$473 NZD$405 NZD$498 NZD
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Quick stats about chalet rentals in Sierra Oeste

  • Total holiday rentals

    Explore 50 holiday rentals in Sierra Oeste

  • Nightly prices starting at

    Sierra Oeste holiday rentals start at $50 NZD per night before taxes and fees

  • Verified guest reviews

    Over 1,960 verified reviews to help you choose

  • Family-friendly holiday rentals

    50 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 30 rentals that welcome pets

  • Holiday rentals with a pool

    40 properties feature pools

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Sierra Oeste holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Sierra Oeste rentals

  • 4.7 Average rating

    Sierra Oeste stays receive an average rating of 4.7 out of 5 from guests

Destinations to explore

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