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

4.97 out of 5 average rating, 193 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, 240 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 immerso nel verde love Tuscany

Country cottage in pietra , indipendente nella campagna Toscana in provincia di Siena ,con ampio giardino, portico e gazebo. La nostra casa e' situata nella campagna del comune di Chiusdino, a soli 5 minuti dai due paesi principali Monticiano e Chiusdino e 10 minuti dalla splendida Abbazia di.Galgano . 30 minuti da Siena , da Monteriggioni , un'ora da Firenze e 30/40min minuti dal mare. Soli 20 minuti dalle belle Terme del Petriolo .

Guest favorite

The charming cottage is set against a backdrop of lush greenery, featuring a natural stone facade and a tiled roof. A swimming pool is visible in the foreground, accompanied by sun loungers and umbrellas, while well-maintained gardens and trees surround the property.

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

Cottage in Casole d'Elsa (SI)

4.85 out of 5 average rating, 137 reviews

Eco Escape in Tuscan hills - Design, Nature, Peace

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

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

Affascinante cottage in Toscana

Affascinante cottage situato su collina con vista a 360 gradi . Oasi di pace e tranquillità. Immersa nel verde. Ampia piscina Area barbecue All'interno camera con letto francese, salotto con divano letto, bagno, cucinino e spazio pranzo interno ed esterno . Ideale per coppie e famiglie con uno / due figli . Disponibilità culla