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Vacation rentals in Cheleiros

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Top-rated vacation rentals in Cheleiros

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Guest favorite
A spacious garden area is visible, featuring a serene infinity pool bordered by sun loungers and palm trees. Lush greenery surrounds the pool, while ocean views extend in the background under a clear sky.
Home in Cascais
4.86 out of 5 average rating, 293 reviews

Charm & Design in a House with a Pool and Magnificent View of the Sea and Mountains

Watch the “blackbirds” in the morning, the sunset, enjoy the calm and tranquility. Enjoy the unique sea and mountain view from the private lounge, the infinity pool, the “Serra de Sintra” - the magical mountain, its enchanted forests, convents and palaces. Possibility to include a work desk. There is also the possibility of accepting wedding celebrations, if it is for small groups, for an additional fee. For more information, contact the host directly. A mountain Villa built over 100 years ago, set on an imposing rock with a unique setting and a breathtaking view over the sea, the city, Cascais and the mountain where it is located. The house has been recently remodeled and expanded with a modern and design construction enjoying the view and the surroundings. You can see from the top of the Sintra Mountains, to Guincho to Cabo Espichel. A stone's throw from the hiking trails of the Sintra Mountains and its monuments, and next to good restaurants and cafés with a good atmosphere, the small village has a supermarket and pharmacy for your peace of mind. Guests have at their disposal a house with 2 bedrooms, living room and kitchen, fully private and access to a large garden with an infinity pool where they can enjoy the wonderful view. I live on the property and am available to share stories and information about the area. I love cycling and I know the Serra like the back of my hand. I can share the secrets of the mountains and advise on the best restaurants in the region. Malveira da Serra, a picturesque village near Cascais and Lisbon (20 min), with hiking trails in the Sintra Mountains and its monuments. Guincho Beach and its wild dunes with their unique beauty are a paradise for Surf/Kite-surf/Windsurf. I advise using your own car.

Top guest favorite
A spacious living area features large windows offering expansive views of the sea and city. Soft natural light floods the room, highlighting a comfortable sofa and a contemporary television. A cozy armchair adds to the inviting atmosphere, while a wood-paneled accent wall provides texture.
Apartment in Paço de Arcos
5 out of 5 average rating, 227 reviews

THE miniPENTHOUSE terrace & SPA

Apartamento reconstruído por arquitecto, excelente privacidade, exposição solar, com wifi, e praia a 150m. 1 suite com SPA e banho turco com aromaterapia. 1 suíte com terraço com vista mar, tela de projeção de cinema. Sala com vista de mar, rio, e terraço, onde poderá disfrutar de uma zona de estar e de um barbecue com grelha em ferro forjado. Perto de restaurantes, cafés e supermercado, e estação de comboio. Ar condicionado e piso aquecido em todas as áreas, TV 4K e box independente por suíte.

Top guest favorite
A charming house is nestled among greenery, featuring a well-maintained lawn and a variety of outdoor seating options. The exterior showcases a blend of stone and modern architecture, complemented by a shaded area adorned with a sun umbrella. The backdrop includes gently sloping hills and vibrant blue sky.
Cottage in Cheleiros
4.99 out of 5 average rating, 102 reviews

Cosy house in the valley & hottub -Casas Rio Verde

A cosy house set in a beautiful valley. Enjoy the home comfort while in the beauty of nature trees and stars.Fully-equipped with everything you need for a romantic getaway, it's the perfect little nest for nature lovers. A pellet stove warms your winter. It has a private outdoor space with dining table and bbq with direct access to the house. You can relax in our big shared garden with jacuzzi and daybed. Close to Lisbon (40 minutes),Sintra (15 minutes), Ericeira (20 minutes), Mafra (10 minutes)

Top guest favorite
A warm living space features a large red sofa and a small wooden chair. The room is enhanced by a light-colored wooden floor and natural light flooding in through tall windows. A low coffee table is placed on a green area rug, with a small vase at its center.
Home in Sintra
4.98 out of 5 average rating, 333 reviews

Beautiful apartment w/ fabulous views!Free Parking

This beautiful apartment is part of the charming house Cerrado dos Pinheiros. Located in an exclusive area close to the historical center of Sintra with only a short walk from everything you need and easy access to Lisbon, beautiful beaches and peaceful countryside. The house was recently renovated offering modern facilities, whilst maintaining the original historical aspect. It's a perfect retreat for families, couples and friends who are looking for a private and peaceful place to stay.

Top guest favorite
An outdoor dining area is presented, featuring a mosaic table surrounded by black chairs and a wooden chair. Potted plants add touches of greenery, while rolling hills and cloudy skies are visible in the background, enhancing the tranquil ambiance of the space.
Cottage in Igreja Nova
4.96 out of 5 average rating, 47 reviews

Casa das Janelinhas (near Sintra, Mafra and Ericeira)

Situada entre Sintra, Mafra e Ericeira, a Casa das Janelinhas tem excelentes vistas sobre o vale e sobre a montanha e tem um espaço exterior perfeito para refeições ao ar livre. É uma casa com arquitetura típica da região saloia, renovada respeitando a tradição e mantendo o encanto de antigamente, com as necessárias alterações de conforto e modernidade. Mafra - 10 min. Ericeira e as suas praias - 15 min. Sintra - 20 min. Cascais - 30 min. Lisboa - 30 min. Aeroporto de Lisboa - 30 min.

Guest favorite
A bright window frame painted in turquoise is open, revealing a stunning view of the ocean and rugged coastline. The sunlight reflects off the water, creating a serene atmosphere. The interior walls feature natural textures, complementing the coastal landscape.
Apartment in Praia das Maçãs
4.94 out of 5 average rating, 326 reviews

Life is better with a beachfront - Azenhas do Mar

The West Coast Design and Surf Villas (WCDS n10) allow the visitor to be part of the unique setting of the place, located in the central area of ​​Azenhas do Mar with easy access and front sea views. The houses have been rehabilitated using traditional materials and ancient techniques to provide a unique and memorable experience for the guests. A unique location like Azenhas do Mar deserves unique accommodations like Azenhas do Mar WCDS Villas , where the past meets the future.

Top guest favorite
Guest suite in Cascais
4.98 out of 5 average rating, 389 reviews

Cascais Amazing GardenHouse With Shared PlungePool

The Garden House is a cosy and secluded studio apartment for two people that overlooks our lush garden and is the ideal choice for a peaceful and relaxing getaway. Appointed to a high standard with natural materials, such as oak parquet ceiling and floors and linen curtains, and decorated in soothing natural colours, it blends harmoniously with its surroundings. Large patio doors lead out onto a spacious and private terrace with a dining table and chairs and a wooden sofa.

Superhost
A spacious living area features exposed stone walls and a high, wooden-beamed ceiling. Comfortable seating is arranged around a wooden coffee table, with a flat-screen television mounted on the wall. Natural light filters in through a window, enhancing the warm tones of the decor.
Villa in Terrugem
4.85 out of 5 average rating, 101 reviews

Village and Sea - Country House

Casa de Campo is situated between the stunning Serra de Sintra and the Atlantic, offering the best of both worlds! It is just a few minutes from the most incredible beaches – such as Praia do Magoito, Praia Grande, Praia das Maçãs and Azenhas do Mar (7 Wonders of Portugal - Aldeias award) – and 15 minutes from Ericeira, a surfer's paradise. Lisbon is 35 minutes away, perfect for those who want to explore the city and, at the same time, escape its hustle and bustle.

Top guest favorite
The modern house features an outdoor pool surrounded by sun loungers, framed by expansive views of the countryside. A large tree and rolling hills can be seen beyond the pool, suggesting a peaceful, natural setting.
Villa in Dois Portos
5 out of 5 average rating, 34 reviews

Quinta da Estima | House & Farm

Quinta da Estima House & Farm is a vacation home located in Folgorosa, a small village near Lisbon, in the wine circuit. Contemporary villa with wonderful pool and fantastic views. There is internet and quiet to work or rest. The Quinta is perfect for strolling and breathing fresh air. You can pick ripe fruit directly from the trees and shrubs to savor at the moment. Enjoy incredible scenery, leisure, sustainable agriculture and traditional Portuguese cuisine.

Top guest favorite
The treehouse, elevated on stilts, features a unique wooden structure surrounded by native pine trees. A staircase leads to the entrance, where individuals can be seen approaching. The natural greenery provides a serene backdrop, enhancing the treehouse's secluded location.
Treehouse in Assafora
4.98 out of 5 average rating, 43 reviews

The Coconut Treehouse awaits you

We offer an unique 17m2 treehouse for up to 2 people (from 14 years old and over) with 1 small double bed, 1 single pull-out bed and 1 bathroom with shower. You have access to a kitchenette with an electric hob, mini fridge, kettle, utensils and basic condiments such as olive oil, sugar, tea, and coffee. The treehouse is located in a small neighbourhood, a 5-minute drive from São Julião and Vigia's beaches and a 15-minute drive from Ericeira Village.

Top guest favorite
The exterior of Moinho das Longas is illuminated at dusk, showcasing its round, white structure and traditional windmill features. A softly glowing sign at the base presents the name 'Moinho das Longas,' complemented by a subtle backdrop of natural foliage.
Windmill in Montelavar
4.95 out of 5 average rating, 120 reviews

Moinho das Longas

In the heart of the rural area of the Sintra municipality, in the picturesque village of Anços, the Moinho das Longas is reborn — a traditional Portuguese windmill carefully renovated in 2025 to offer you a unique local accommodation experience. Perfect for unplugging, breathing fresh air, and enjoying special moments, book your stay now at Moinho das Longas in Anços — where tradition meets tranquility.

Guest favorite
A charming cottage exterior is surrounded by lush greenery, with a terracotta facade and arched doorways. A patio area is visible, featuring a small table and a parasol, providing a shaded spot to enjoy the serene environment.
Cottage in Sintra
4.98 out of 5 average rating, 233 reviews

Cozy Private Cottage with Fireplace & Outdoor Tub

Tranquil and secluded cottage in the hills of Sintra, set within a private historic estate once home to Sir Arthur Conan Doyle. Casa Bohemia offers absolute privacy, a light-filled living room with wood-beamed ceiling and fireplace, a queen bedroom with en-suite bathroom, and a private courtyard with an antique stone bath for romantic outdoor bathing. Garden, terrace, parking, and nature all around.

Popular amenities for Cheleiros vacation rentals

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