Cottage vacation rentals in Montepulciano

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Top-rated cottage rentals in Montepulciano

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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, 133 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.

Guest favorite

The stone house features a welcoming entrance with large arched windows. A vibrant flower box filled with geraniums complements the lush green lawn. A shaded area with wooden seating offers a place to relax, while the infinity pool and surrounding vineyards are visible in the background.

Cottage in Barberino Tavarnelle

4.98 out of 5 average rating, 192 reviews

Stone House with Exclusive Pool Codilungo in Chianti

Spend a holiday in the heart of the Tuscan countryside in this cozy stone house with terracotta floors and beamed ceilings in solid oak, furnished with paintings of author , equipped with all comforts. Enjoy yourself by swimming in the large infinity pool (18m X 9m, open from May 1st to October 15th for guests of Stone house use only) or relax in an armchair under the loggia, tasting a glass of Chianti wine in front of the rolling hills of vineyards, olive groves, woods and medieval villages.

Top guest favorite

A charming stone house is set amidst lush greenery, featuring a wooden door and small windows. A golden retriever sits contentedly on the grass, surrounded by white flowers and shrubs, contributing to the inviting ambiance of the property.

Cottage in Castellina in Chianti

4.98 out of 5 average rating, 100 reviews

Cottage Cappero – Masseto In Chianti

MASSETO IN CHIANTI è un villaggio privato dove potrete rilassarvi nel vostro giardino privato e in piscina, fare sport, o utilizzare come base per visitare città rinascimentali: Firenze, Siena, San Gimignano, Arezzo, Volterra. Offriamo altri tre cottage con accesso indipendente e giardinetto privato: Quinto (2 letti), Vittoria (4 letti), Leccio (6 letti). La piscina è condivisa dai 4 cottage, ciascuno dispone di un gazebo privato, con distanze garantite e sanificazione a norma Covid-19.

Top guest favorite

Cottage in Monteriggioni

4.96 out of 5 average rating, 239 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, 147 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

Guest favorite

A rustic dining table is set outdoors with plates of food, glasses of water, and red wine, overlooking a serene landscape of green hills. Natural light highlights the meal, creating a warm and inviting atmosphere for enjoying food in nature.

Cottage in Vetulonia

4.96 out of 5 average rating, 121 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.

Top guest favorite

The kitchen area features wooden cabinets and modern appliances, including a gas stove and oven. A round table with a colorful design is surrounded by black wire chairs. Large windows provide natural light and views of the surrounding landscape.

Cottage in Castell'Azzara

4.99 out of 5 average rating, 139 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

An exterior view of a rustic farmhouse features weathered stone walls and dark wooden shutters. Lavender flowers bloom nearby, adding a touch of color to the scene. Two doors offer access to the home, and a small potted plant is visible in the ground floor window.

Cottage in Sovicille

4.91 out of 5 average rating, 138 reviews

Apartment for 2 with super views+pool near Siena

Located just 18km from Siena, the apartment is part of a traditional Tuscan farmhouse tucked away in the scenic rolling hills of Tuscany. The uniquely positioned grounds dominate the valley, allowing for stunning views from all angles, with the most enchanting sunsets, or sunrises for those early birds! With its idilic views and peaceful surroundings, the apartment allows for a relaxing and recharging break, as well as being in the perfect location to go out and explore.

Guest favorite

The country cottage is surrounded by tall trees and lush greenery, softly illuminated at dusk. The rustic stone exterior features warm light emanating from the windows, highlighting the tranquil setting in the Tuscan countryside. A wooden fence outlines the property, enhancing its privacy.

Cottage in Ponte Feccia

4.94 out of 5 average rating, 170 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.

Guest favorite

Cottage in Radicofani

4.84 out of 5 average rating, 129 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

A spacious covered porch is equipped with a long wooden table surrounded by various chairs. Potted plants and greenery enhance the natural setting, while large windows allow for ample light. A decorative flower arrangement sits at the center of the table.

Cottage in Onano

4.89 out of 5 average rating, 101 reviews

Between nature and culture

The renovated tuff cottage, surrounded by greenery, is located at the crossroads between Umbria, Lazio and Tuscany, a few minutes from Lake Bolsena and about an hour from the sea. Just over half an hour's drive away are the most famous spas in Italy, such as Saturnia, Bagno Vignoni, Bagni San Filippo, Sorano and the Terme dei Papi in Viterbo, ideal even in the middle of winter. For cultural tourism and relaxation.

Guest favorite

A charming cottage is surrounded by lush green grass and decorative plants. The rustic brick exterior features large windows framed with climbing vines. A cozy seating area on a tiled porch offers a relaxing view of the garden and the inviting countryside.

Cottage in Montagnano

4.93 out of 5 average rating, 127 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