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Chalet vacation 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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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

Estate of 6000 m2 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 marsh of San Juan. Video-monitored access. It is self-sufficient 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. Live a few days of peace on the EKOLIBRE ESTATE.

Top guest favorite
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, 26 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 favorite
Chalet in La Cascabela
4.96 out of 5 average rating, 113 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!!

Guest favorite
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
4.88 out of 5 average rating, 409 reviews

Independent house in the mountains

Charming detached house with charm at the foot of La Pedriza. Beautiful garden to enjoy the singing of the birds and the tranquility that the environment offers. Built in harmony with the very stones that nature gives us. Ideal para relajarse 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
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
4.91 out of 5 average rating, 133 reviews

Family-friendly villa with a pool and garden

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 favorite
Chalet in Robledo de Chavela
5 out of 5 average rating, 13 reviews

Bergidum

Desconecta de la rutina de la ciudad en Bergidum. Disfruta de las puestas de sol y atardeceres increíbles. Si te gusta la naturaleza explora nuestra de red de senderos y miradores . No olvides tus prismáticos, Robledo; en la zona ZEPA, alberga aves de gran envergadura como el águila imperial y el buitre negro. En verano acércate a las instalaciones del Club con piscina y restaurante. Por la noche, observa las estrellas bajo un cielo despejado. ¡Te esperamos en Bergidum!

Guest favorite
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)

Detached villa in the Sierra de Madrid, in the urban area of Soto del Real. Unbeatable location. Perfectly connected. All amenities within a 5-minute walk. Perfect for spending a few days with family or friends. Living room, kitchen, dining room, 1 bedroom and full bathroom on the ground floor. 3 bedrooms, another full bathroom and terrace overlooking Sierra de la Pedriza on the top floor. It has a BBQ. Parking available inside the plot. We are pet friendly. VT-15209.

Top guest favorite
A saltwater pool is visible on a terrace, framed by sleek glass fencing. The sunset casts vibrant colors in the sky, reflecting on the water's surface. The modern architectural features and stone tiles create a serene environment.
Chalet in Segovia
4.97 out of 5 average rating, 104 reviews

A chalet with a pool and dreamy sunsets

Enjoy a special getaway in our cozy villa, 45 minutes from Madrid, in the private Los Angeles de San Rafael (Segovia) development. A charming home with 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 tarp, barbecue grill and air conditioning in all rooms for your maximum comfort.

Top guest favorite
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, 137 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 favorite
The exterior of the house features a rustic stone façade, a tiled roof, and a spacious covered porch. Comfortable seating is arranged on the porch, which overlooks a well-maintained lawn and panoramic views of the surrounding landscape.
Chalet in El Espinar
4.96 out of 5 average rating, 55 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.

Guest favorite
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, 141 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 favorite
A clear blue pool is situated beside a well-maintained lawn, surrounded by tall, green hedges. The house features a modern exterior with wooden accents and large windows, offering views of the rocky landscape in the background.
Chalet in Manzanares el Real
4.88 out of 5 average rating, 101 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.

Popular amenities for Sierra Oeste chalet rentals

When is the best time to visit Sierra Oeste?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$53,956 GYDG$53,956 GYDG$54,165 GYDG$59,394 GYDG$59,185 GYDG$62,740 GYDG$66,923 GYDG$67,550 GYDG$59,185 GYDG$46,428 GYDG$56,048 GYDG$48,101 GYD
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Quick stats about chalet rentals in Sierra Oeste

  • Total vacation rentals

    Explore 60 vacation rentals in Sierra Oeste

  • Nightly prices starting at

    Sierra Oeste vacation rentals start at G$6,274 GYD per night before taxes and fees

  • Verified guest reviews

    Over 2,160 verified reviews to help you choose

  • Family-friendly vacation rentals

    50 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Vacation rentals with a pool

    40 properties feature pools

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Sierra Oeste vacation 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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