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Holiday rentals in Cheleiros

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Top-rated holiday rentals in Cheleiros

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
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 Alcabideche
4.86 out of 5 average rating, 301 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.

Guest favourite
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, 111 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)

Guest favourite
Shipping container in Carvoeira
4.97 out of 5 average rating, 125 reviews

Quinta Maresia Tiny House 2

Reconnect with nature at this unforgettable escape. Our 2 tiny houses are in the midst of agricultural landscapes on a horse farm 400 meters from one of the best surf beaches around. The container unit is private only for you. Its entrance is via the the sunroom. This sunroom, as well as laundry space, garden and backoffice / storage space is shared with the other unit (2pax) Our local community also offers a small local beach bar, a pizza place and a micro brewery & hamburger restaurant.

Top guest favourite
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, 346 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.

Guest favourite
An outdoor patio features a wooden dining table surrounded by chairs, illuminated by soft candlelight. A hammock is hung nearby, with potted plants offering greenery. The rustic walls are enhanced by decorations, and a barbecue grill is visible, creating a relaxed outdoor space.
Cottage in Mafra
4.93 out of 5 average rating, 55 reviews

A Sanctuary for the Soul: Country & Sea near Ericeira

🏡 Between the countryside and the sea, just a 6-minute drive from Mafra and 8 minutes from 🌊Ericeira, 🌿Refúgio da Alma is a traditional house that blends comfort and nature. A retreat designed for couples or small families seeking tranquillity. ☀️ In summer, the private patio and barbecue are perfect for outdoor leisure;🔥 in winter, the fireplace ensures a cozy atmosphere. A versatile space offering the perfect balance between cultural heritage and the proximity to the coast.

Guest favourite
Two comfortable chairs are positioned beside a small table, with a large window framing the scenic ocean view. The pool is visible just outside, reflecting the clear sky, while elegant light fixtures enhance the space.
Home in Carvoeira
4.9 out of 5 average rating, 68 reviews

Casa das Rosas, Portugal

- casadasrosasportugal - Villa, 320 m2 with amazing seaview, large pool (heated april-oct.), gym, big size 4K-golf simulator, pool-table, ping-pong, playground, BBQ. 3 big bathrooms with heating floors, 3 small bathrooms, 4 bedrooms. Fully equipped kitchen. Space for 12 people. Located in Carvoeira close to Ericeira, 34 min from airport. Ericeira is one of the most popular surfing destinations in the world. Great combination of privacy and adventure close to Lisbon and Sintra.

Top guest favourite
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.
Flat in Paço de Arcos
5.0 out of 5 average rating, 241 reviews

THE miniPENTHOUSE terrace & SPA

Apartment rebuilt by architect, excellent privacy, solar exposure, with wifi, and beach at 150m. 1 suite with SPA and Turkish bath with aromatherapy. 1 suite with terrace with sea view, cinema projection screen. Room with sea, river and terrace views, where you can enjoy a seating area and barbecue with wrought-iron grill. Close to restaurants, cafes and supermarket, and train station. Air conditioning and heated floor in all areas, 4K TV and independent box per suite.

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
4.86 out of 5 average rating, 107 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 favourite
A spacious villa is framed by vibrant greenery and a clear blue sky. The outdoor area includes a private pool, lounge chairs, and a hammock, providing an inviting space for relaxation. Wide glass doors lead into the living areas, connecting indoor and outdoor environments.
Home in São João das Lampas
4.96 out of 5 average rating, 170 reviews

Spacious Traditional Villa Country Sintra w Pool

Escape to our unique Sintra villa, a serene countryside retreat designed for relaxation and adventure. Enjoy the private pool, lush gardens, and cozy fireplace. Ideal for families, with children's entertainment, baby essentials, and spacious living areas. Perfectly located for exploring Sintra, Ericeira, beaches, and Lisbon. High-speed fiber Wi-Fi internet and fully equipped kitchen included. Experience the perfect blend of comfort, peace and exploration.

Superhost
A spacious interior features a large bed with a light-colored quilt, flanked by soft curtains. A comfy seating area is highlighted by a potted plant and wooden flooring, while a small TV is visible. Natural light filters through large windows, enhancing the serene ambiance.
Cabin in São João das Lampas
4.91 out of 5 average rating, 35 reviews

Casa Seahorses B Cottage

Located 15 minutes from the Romantic Village of Sintra and 15 minutes from the World Surf Reserve - Ericeira, Cabana Janota accommodates 2 people in a double bed and the possibility of a third on a sofa bed. It has a small dining space and seating area. Located on a farm with horses, it has access to the outdoor lawn area that you can enjoy with your dog. Two beaches 5 minutes away, Samarra with the benefit of being Pet-friendly and São Julião.

Guest favourite
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
4.93 out of 5 average rating, 150 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.

Top guest favourite
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, 242 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 holiday rentals