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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
A private saltwater pool is framed by wooden decking and equipped with sun loungers. An umbrella provides shade beside the pool, while a light-colored house with large windows is visible in the background, surrounded by trees.
Chalet in Valdemorillo
5 out of 5 average rating, 27 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.

Superhost
A fenced-in area features a swimming pool with a sunbathing space. A thatched-roof pergola provides shade over comfortable lounge chairs. The vibrant red house in the background blends with the lush greenery and landscaped garden, creating a relaxed outdoor environment.
Chalet in San Martín de Valdeiglesias
4.93 out of 5 average rating, 76 reviews

EKOLIBRE FARM

6000 m2 property between Pelayos and San Martín. It is located in an idyllic place in the middle of nature, away from the noise and next to the best beaches of the San Juan swamp. Video surveillance access. It is self-supplied with solar energy and its own well. The road to the house is dirt and has some potholes. Barbecues are not allowed in summer. Six cats live on the property. The house, pool, and property are for the private use of guests. Enjoy a few days of peace at the EKOLIBRE ESTATE.

Guest favourite
Chalet in La Cascabela
4.97 out of 5 average rating, 118 reviews

Oasis with private pool and patio in Madrid!

Enjoy a Premium Experience in Madrid! 🏡Stay in a beautiful house with private pool & patio near Madrid Río, just minutes from the historic city center by metro 2 bedrooms + 2 bathrooms, heated floors, A/C, fast Wi-Fi. 🏊‍♂️ Relax in your private pool (mid-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!!

Superhost
A well-maintained outdoor space features a round table complemented by two metal chairs, situated on a green lawn. Lush shrubs and plants provide a natural backdrop, while a terrace area is visible in the distance, enhancing the outdoor setting.
Chalet in Soto del Real
4.86 out of 5 average rating, 116 reviews

Villa with garden in Soto del Real (9 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 outdoor space showcases a modern swimming pool framed by a stone patio. A vibrant sunset casts warm hues across the sky, while a hammock and sun loungers invite relaxation. Lush greenery and mountains provide a picturesque backdrop.
Chalet in Segovia
4.97 out of 5 average rating, 105 reviews

A chalet with a pool and dreamy sunsets

Enjoy a special getaway in our cozy villa, 45 minutes from Madrid, in the private development Los Angeles de San Rafael (Segovia). A home with charm and modern design, with 3 bedrooms: 2 with a 1.50 bed and 1 with a double bed. It has 2 bathrooms, one en-suite with a dressing room. Everything is ready for you to live a few unique days. Private salt chlorination pool with thermal canvas, barbecue grill and air conditioning in all rooms for your maximum comfort.

Superhost
The independent house is surrounded by tall trees, with a garden showcasing natural stone paths. A staircase leads to the entrance, framed by lush greenery. In the background, the mountains are visible, providing a serene, natural setting.
Chalet in Manzanares el Real
4.87 out of 5 average rating, 414 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.

Superhost
Chalet in Cortos
4.84 out of 5 average rating, 228 reviews

Detached villa 9 km from Ávila in a quiet area.

It is not a rural house, although its surroundings are, it is certainly a good combination of modernity in a rural environment, ideal to enjoy and relax surrounded by nature and tranquility. It has the appeal and comforts of a modern home, where light is the main protagonist. Its perfectly designed courtyards convey peace and quiet, and its plot covers an area of 180 m. We are located just 9 km from Ávila, near the Police School. We allow pets.

Guest favourite
A well-maintained private pool is surrounded by a stone patio, featuring two sun loungers positioned nearby. Lush greenery and palm trees add to the serene atmosphere of the outdoor space. A clear blue sky reflects on the water's surface, inviting relaxation.
Chalet in El Hoyo de Pinares
4.96 out of 5 average rating, 23 reviews

Villa near Madrid

Enjoy a spacious, comfortable villa with a swimming pool, barbecue, gas iron and a small home gym. It is located in a privileged natural environment, with hiking trails already designed. The village is an hour from Madrid and has a regular bus line to the capital, with departures practically every hour. The town is 20 minutes away from two large reservoirs with natural beaches where swimming is allowed: El Burguillo and Pantano de San Juan.

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, 141 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.

Superhost
Chalet in Rozas de Puerto Real
4.62 out of 5 average rating, 26 reviews

Chalet sierra Madrid private pool. WIFI

Modern Chalet in the Sierra de Madrid with Private Pool The house is decorated in a modern and functional style. Spacious fully equipped kitchen and large independent areas, including two living rooms and a large outdoor space with a private pool. The pool is open from mid-May onwards. House with a garden and private pool, designed with style. Very quiet residential area, just 20 minutes from the San Juan Pantano in Madrid.

Top guest favourite
The entryway features a warm and inviting atmosphere, highlighted by a wooden staircase leading to the upper floor. A vintage chest of drawers, a console table, and a comfortable bench provide functional touches. Natural light fills the space, enhancing the neutral color palette and woven area rug.
Chalet in Cercedilla
4.98 out of 5 average rating, 142 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, 53 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!

Popular amenities for chalet rentals in Sierra Oeste

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Avg. price$331 SGD$331 SGD$333 SGD$365 SGD$363 SGD$385 SGD$411 SGD$415 SGD$363 SGD$285 SGD$344 SGD$295 SGD
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Quick stats about chalet rentals in Sierra Oeste

  • Total holiday rentals

    Explore 60 holiday rentals in Sierra Oeste

  • Nightly prices starting at

    Sierra Oeste holiday rentals start at $39 SGD per night before taxes and fees

  • Verified guest reviews

    Over 2,150 verified reviews to help you choose

  • Family-friendly holiday rentals

    50 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 30 rentals that welcome pets

  • Holiday rentals with a pool

    40 properties feature pools

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    50 of Sierra Oeste holiday rentals include wifi 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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