Cottage vacation rentals in Montalcino

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Top-rated cottage rentals in Montalcino

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Guest favorite

A wooden barrel with a vibrant red hue stands on a deck surrounded by lush greenery. Colorful flowering plants and an agave plant add to the vibrant landscape, with rolling hills visible in the background under a clear blue sky.

Cottage in San Bartolomeo a Quarate

4.92 out of 5 average rating, 142 reviews

FAETOLE typical Tuscan country house near FLORENCE

My cottage is hidden in Tuscan countryside among olive groves, vineyards and woodland. Nevertheless, downtown Florence is only 16km away! While away, spend your time by relaxing in the garden, where you will find a barbecue and an outdoor shower to cool down while sunbathing. Discover the beauty of surrounding countryside with a hike and unwind with a view of picture-perfect vineyards! One can also easily go for day trips to many tiny medieval towns scattered on the hills of Tuscany from here!

Top guest favorite

The historical Villa di Geggiano is surrounded by lush gardens and vineyards, displaying elegant landscaping. Its stone façade and terracotta roof harmonize with the rolling hills in the distance. A gravel driveway leads to the entrance, providing access to the serene countryside ambiance.

Cottage in Geggiano

4.99 out of 5 average rating, 129 reviews

Villa di Geggiano – Guesthouse

PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI, THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR. The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idyllic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa.

Top guest favorite

Cottage in Monteriggioni

4.96 out of 5 average rating, 234 reviews

Monteriggioni Castello, holiday house in Tuscany

Il nostro alloggio è un edificio storico che risale alla costruzione del castello. È stato recentemente restaurato e arredato con cura in tutti i dettagli. È molto accogliente e dispone di tutti i più moderni servizi. I turisti che decideranno di essere nostri ospiti, avranno il vantaggio di vivere nell' ambiente medievale del castello, usufruendo di tutti i confort. Si sentiranno coccolati e avranno l'opportunità di tornare indientro vivendo un' esperienza unica e indimenticabile.

Top guest favorite

The rustic stone facade of the cottage is framed by lush greenery and potted plants. A covered porch with a wooden roof provides a welcoming entrance. Unique architectural details are showcased in the arched doorway and decorative bricks, enhancing the outdoor appeal.

Cottage in San Casciano In Val di Pesa

4.95 out of 5 average rating, 139 reviews

Il Fienile, Cottage in the country with Jacuzzi

Surrounded by wineyards, close to Florence, a charming accomodation in a cozy cottage with heated jacuzzi at your exclusive use. Rooms sanitized by health protocols. Perfect starting point to discover Florence and Siena. Kitchen, wide living room, bathroom, two double bedroom (one with an extra single bed). In the living room a sofa bed for other 2 people. Tasteful furniture, Air Conditioning, barbecue, private parking. Partnership for: bike rental, private chef, private driver

Top guest favorite

A spacious wooden deck overlooks a panoramic view of rolling hills and distant mountains, with the sea visible on the horizon. Two lounge chairs are positioned for relaxation, surrounded by native plants and trees that enhance the natural setting.

Cottage in Vetulonia

4.96 out of 5 average rating, 120 reviews

La Dolce Vita ~ romantic retreat in quiet nature

Welcome to Il Baciarino! We are a rustic agriturismo in the green hills of Maremma, Toscana's wild and unexplored coastal region. Il Baciarino is a place to come and stay, to escape from the bustle of the city and your busy life, and to unwind in nature; perfect for those who love unspoiled nature, endless views, fresh seafood & good wine. Il Baciarino has various unique rustic cottages nestled in 19 acres of wilderness, on the outskirts of the tiny Etruscan town of Vetulonia.

Guest favorite

An inviting workspace features a large circular window that frames a scenic view of the landscape beyond. Two wooden benches provide ample seating, complemented by a black wire chair. Natural wood paneling creates a warm, comfortable atmosphere for productivity.

Cottage in Castell'Azzara

4.99 out of 5 average rating, 134 reviews

Your Private Tuscan Retreat

This beautiful sheepherder’s stone cottage is equipped with modern comforts and spa facilities free of charge. The large grounds of forest and meadow span a ridge and provide panoramic views of the valley toward Val d’Orcia to the north, the expansive Maremema to the south, and the ancient volcano of Amiata to the west. This is the perfect getaway for those wanting a private retreat from which to explore the rich wine, food, culture, history, and landscape of southern Tuscany.

Guest favorite

A serene private pool is set against a panoramic view of rolling hills and lush greenery. The water reflects the clear sky, while the pool's edge extends into a sunlit patio area, offering an inviting space for relaxation.

Cottage in Pari

4.95 out of 5 average rating, 152 reviews

La Casa del Frantoiano - Pari -

We offer our guests a small apartment in Pari, a charming village in the heart of Tuscany, near the Petriolo Thermal Baths and halfway between Siena and the sea, reachable in about half an hour. Completely and recently renovated, it consists of a kitchen, large bedroom, bathroom, outdoor relaxation space with table available. Equipped with air conditioning and every kind of comfort, it is ideal for 2/3 people, in the kitchen there is a single bed. Private pool by appointment.

Guest favorite

An independent country cottage is framed by lush greenery, with a stone-paved entrance leading to a cozy building. The sunset casts a warm glow, illuminating the surroundings and a fenced garden area. An electronic gate provides access, enhancing privacy and security.

Cottage in Ponte Feccia

4.95 out of 5 average rating, 164 reviews

Country cottage C&M surrounded by greenery, love Tuscany

Country stone cottage, independent in the Tuscan countryside in the province of Siena, with large garden, porch and gazebo. Our house is located in the countryside of the municipality of Chiusdino, just 5 minutes from the two main towns of Monticiano and Chiusdino and 10 minutes from the beautiful Abbey of Galgano. 30 minutes from Siena, from Monteriggioni, an hour from Florence and 30/40 minutes from the sea. Just 20 minutes from the beautiful Terme del Petriolo.

Top guest favorite

A stone house features a rustic charm, framed by lush greenery. In the foreground, a clear, inviting pool reflects the sky. Sun loungers are positioned around the pool area, providing space for relaxation while enjoying the serene landscape.

Cottage in Lucardo

4.99 out of 5 average rating, 244 reviews

Best view ever & private pool

Antique Tuscan barn made into a comfortable home with private swimming pool. Best views ever. Close to Florence, Siena and Pisa. Very quiet, yet easy to reach. Sunsets you can only dream of. Ideal Tuscan getaway for family or two couples. The house has two bedrooms and two bathrooms plus a guest bathroom on the ground floor. The pool has a panoramic edge and whirlpool section. There are two restaurants on walking distance (a few hundred meters).

Superhost

A scenic view of the Orcia Valley is presented, displaying rolling hills adorned with greenery and neatly trimmed cypress trees. The landscape transitions into soft earth tones that blend with the horizon, creating a serene backdrop under a clear sky.

Cottage in Radicofani

4.84 out of 5 average rating, 127 reviews

Cottage "Girasole" in Tuscany

A lovely cottage in the old farmhouse "Podere Maltaia" that overlooks the Unesco's Heritage protected area Orcia Valley, surrounded by large farmyards and 3 hectares of private land that includes an outdoor swimming pool (opened seasonally, based on outside temperature - please ask to know the dates for the upcoming or ongoing summer season), garden, outdoor dining area, BBQ and parking area (not-covered, free of charge).

Guest favorite

Cottage in Casole d'Elsa (SI)

4.85 out of 5 average rating, 132 reviews

Eco-house, pool & garden on beautiful olive farm

New independent eco-house in rural setting, away from the crowds between Florence and Siena. This is an annex building on a family run olive farm surrounded by unspoilt Tuscan countryside. Plenty of shaded outdoor space, barbecue, stunning views, fantastic sunsets and big night skies. We are an official agriturismo, there are two other independent apartments on the olive farm that share the pool and private parking.

Guest favorite

An archway adorned with greenery frames a clear view of a spacious pool, surrounded by manicured grass. A variety of lounge chairs are positioned nearby, inviting relaxation under the bright blue sky with scattered clouds.

Cottage in Montagnano

4.93 out of 5 average rating, 125 reviews

Charming cottage in Tuscany

Charming cottage located on a hill with 360-degree views. An oasis of peace and quiet. Surrounded by greenery. Large swimming pool BBQ Area Inside there is a bedroom with a French bed, a living room with a sofa bed, a bathroom, a kitchenette and an indoor and outdoor dining area. Ideal for couples and families with one/two children. Crib available