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Holiday rentals in Chiareggio

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Top-rated holiday rentals in Chiareggio

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

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Top guest favourite
Home in Bienno
4.99 out of 5 average rating, 185 reviews

Luxury Residence Private Spa Jacuzzi Sauna View of the Alps

✨ La Quercia del Borgo is a Luxury Home in the heart of Bienno: an 18th-century residence, stone and wood, warm design and a 24-hour Private SPA reserved just for you, with a Jacuzzi, Finnish sauna and a view of the Alps. 🛏️ King suite + private bathroom 75”📺Smart TV Memory bed 🛋️ sofa 🍷 Artisanal cuisine and wine cellar + Welcome kit 🌄 Rooftop Fast 📶 Wi-Fi ❤️ A romantic getaway for anniversaries, proposals and honeymoons: privacy, charm and an authentic village, with every detail carefully prepared.

Top guest favourite
Cabin in Postalesio
4.97 out of 5 average rating, 212 reviews

Cabin Nonna Maria - Nature Reserve Chalet

Welcome to Baita Nonna Maria, an intimate and authentic retreat where nature is the real star. The chalet is in a uniquely secluded but easily accessible location, a rare balance that offers absolute privacy without sacrificing comfort. All around, there is only the forest, the scent of resin and a breathtaking view that opens up onto the mountains like a painting that changes with the seasons. It is a place that welcomes, calms and invites you to find time and space for yourself and for those you love.

Guest favourite
A charming stone house is nestled among rows of vibrant grapevines, showcasing autumn foliage. The sloped roof features unique, overlapping tiles, while the surrounding greenery highlights the tranquil setting within the valley.
Home in Castione Andevenno
4.98 out of 5 average rating, 53 reviews

Your house on the Valtellina Wine Road

Casa Seconda is a space that welcomes you when you want to get away from the hustle and bustle of the city for a while, to relax and take a break from the daily grind, as if it were your second home. The simple appearance of the exterior, overlooking the vineyard (we are in the Sassella sub-area), hides large, well-kept and functional interior spaces, in harmony with the spirit of the valley. Designed and cared for in every detail for those who, like us, love nature, but also the right comfort.

Top guest favourite
A terrace offers a scenic view of mountains and valleys bathed in the warm hues of a sunset. A small table is positioned on the wooden deck, surrounded by lush greenery and the silhouette of distant peaks.
Cabin in Ardenno
5.0 out of 5 average rating, 155 reviews

Splendid Chalet in Valtellina, Lombardy Mountains

The stars of a luxury hotel don't always count, try counting the ones you see from the panoramic terrace of our fantastic chalet at 1100 m above sea level, in the heart of the beautiful Valtellina, a short distance from Val Masino, 'Ponte nel Cielo', Valgerola, Lake Como and the Bernina Express -Red Train. In a sunny position all year round, it is ideal for admiring the Alps and enjoying absolute tranquility and privacy. Are you ready to stop and listen to the silence and the chorus of nature?

Guest favourite
The rustic stone exterior of the building is complemented by wooden accents and a balcony, surrounded by vibrant flowers and greenery. The blue sky above enhances the inviting atmosphere, offering a glimpse of the serene natural setting.
Apartment in Carnale
4.93 out of 5 average rating, 203 reviews

"Baita Carnale", Mountain in Valtellina

The apartment is located at 1270 meters in the town of Carnale, just 20 minutes from Sondrio (Lombardy). It is located on the ground floor, under the "Baita Paolo", in a flat area surrounded by the greenery of nature. Ideal for families and couples looking for tranquility and who want to explore a beautiful landscape full of trails and breathtaking views of the Valtellina valley floor and the Valmalenco. The apartment has just been completed and cared for in every detail. 014044-CIM-00001

Guest favourite
A snow-covered exterior of a charming building showcases a light-colored facade with decorative window frames. Several windows are visible, allowing natural light to enter. The surrounding area is blanketed in snow, with evergreen trees adding to the serene landscape.
Flat in Sils im Engadin/Segl
4.94 out of 5 average rating, 120 reviews

Charming Engadine style holiday apartment

Renovation work in building on working days in Oct-Nov 2026. Charming flat (2/F, 72 m2) located in a quiet residential area of Sils Maria. For 4 persons. (Separate bedroom with two beds and two beds in open gallery above living room). Mountain view. Village centre and sports area: 5 mins. on foot. Supermarket and free winter ski bus stop: 3 mins. Closest downhill ski area 5 mins by ski bus. Engadin ski marathon cross-country trail right in front of house. Lots of beautiful hiking trails.

Guest favourite
The exterior of the chalet features a stone facade accented by wooden shutters and balconies. Sunlight illuminates the surrounding meadow filled with wildflowers, while the backdrop showcases majestic mountains with a snow-capped peak.
Chalet in Carnale
4.93 out of 5 average rating, 269 reviews

The Masun: holiday house in the alps

The chalet is located in a small village in the alps, sorrounded by lawns and woods. You can't miss this place and its beautiful panorama. My place is perfect for families and couples who would like to relax, walk into the woods and hike. Exclusive and quiet location to discover a real and clean contact with nature without giving up comfort. There will be a gift for you: organic products made by our farm Azienda Agricola Agneda, the best way to experience Valtellina's flavors.

Top guest favourite
A wooden bedroom is highlighted by natural wood paneling on the walls and ceiling, creating a warm ambiance. A spacious bed sits in the center, flanked by bedside lamps. A small table and chair are positioned nearby, with a cozy rug underfoot, enhancing the room's inviting atmosphere.
Home in Bregaglia
5.0 out of 5 average rating, 35 reviews

Chesa Antica - Historic Charm & Alpine Relax 1601

Chesa Antica is a historic house built in 1601. With its vaulted ceilings and rooms made of larch and Swiss pine, this home fascinates and enchants with its charm. Located at the foot of Piz Lunghin and the Septimer Pass, 10’ from Maloja and 25’ from St. Moritz. A haven for those who love nature and seek beauty and uniqueness. Choose from walks in the woods or along lakes, adventurous hikes, or extreme mountaineering – perfect for families, couples, or friends!

Guest favourite
Cabin in Carnale
4.96 out of 5 average rating, 27 reviews

"Baita Paolo", Mountain in Valtellina

The cabin is located at 1270 meters in the town of Carnale, about 20 minutes from Sondrio. Surrounded by greenery, in a flat and sunny area, it is ideal for families and couples looking for tranquility. Arranged on two floors, it is located above the independent apartment "Baita Carnale" and offers three bedrooms, an equipped kitchen and a wooden living room with a stove. Renovated in a rustic style with artisan care, it offers splendid views of the Valmalenco.

Guest favourite
A traditional wooden building stands on a slight incline, partially surrounded by snow. The structure features a rustic exterior with wooden beams and a balcony, while majestic mountains rise in the background under a partly cloudy sky.
Hut in Bregaglia
4.97 out of 5 average rating, 126 reviews

Barn1686: Your getaway in a renovated barn

Barn1686 is located in the quiet village of Borgonovo, surrounded by stunning mountains. Originally built in 1686, the barn was fully renovated in 2015 and offers 90 m² of modern amenities: electric heating, a modern kitchen, two open bedrooms, two bathrooms, and a cozy fireplace. Need more space? Right next door is the second half of the semi-detached house – Ciäsa7406! Perfect for families or friends traveling together who still value their privacy.

Top guest favourite
A modern chalet is nestled in lush greenery, surrounded by colorful foliage. The exterior features stone accents and large windows. A manicured lawn stretches in front, with a terrace visible at one side, offering seating to enjoy the serene views of the surrounding mountains.
Chalet in Lovero
4.99 out of 5 average rating, 291 reviews

Chalet "The apple blossoms" CIR014038 CNI00002

Chalet surrounded by greenery, in the heart of Valtellina. Located in a quiet but strategic area for travel to the main tourist destinations. Nearby are bike paths and nature trails. Tirano and the departure of the "Red Train" are 7 km away. Bormio with ski slopes and thermal baths is 25 km away. Livigno, the Stelvio National Park, and many other enchanting locations can be reached in about 1 hour. Ideal place for those seeking peace and quiet.

Top guest favourite
Large windows with wooden frames open to a panoramic view of the valley below. Light sheer curtains gently diffuse sunlight while showcasing a scenic landscape with mountains and a small town.
Holiday home in Caspoggio
4.98 out of 5 average rating, 429 reviews

Valmalenco_Attic_Panoramic

Cozy 70 sqm attic with panoramic view of Valmalenco. A two-minute drive from the ski area's ski lifts. Ideal accommodation as a base camp for various types of excursions suitable for beginners and experts (excursions, nature trails, mountain huts, etc.). The house is equipped with everything you need for your stay (WiFi included), independent access and a free reserved parking space.

Popular amenities for Chiareggio holiday rentals