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Cottage vacation rentals in Montepulciano

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Top-rated cottage rentals in Montepulciano

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Top guest favorite

An aerial view showcases the expansive grounds of La settecentesca Villa di Geggiano, surrounded by manicured gardens and lush vineyards. The main villa is prominent, with a circular driveway leading to it, while gentle hills extend into the background.

Cottage in Geggiano

4.99 out of 5 average rating, 135 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.

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, 197 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.

The rustic stone cottage is set in a verdant landscape, surrounded by trees. A spacious outdoor patio with a table and chairs invites relaxation and dining in the sun. The clear blue sky enhances the serene, inviting atmosphere of this countryside retreat.

Cottage in La Cetina

4.96 out of 5 average rating, 104 reviews

Eleutherìa: Cozy Cottage in the heart of Tuscany

Eleutherìa is a recently refurbished cottage, located on the top of the hill surrounded by the stunning Tuscan countryside. It is right in the middle of trekking tracks crossing centuries-old woods and wild nature, those who walk along can feel nature and discover to belong to it.. Offering a 75 sqm (800 sqft) area with patio overlooking the garden to unwind your senses. Just about 18 Km (11 Mi) from the medieval city of Siena, it’s a strategic location to the major Tuscan’s attractions.

Top guest favorite

A serene scene captures the rolling hills of Tuscany at sunrise, enveloped in soft mist. A pergola adorned with vines frames the view, while lush greenery and bushes create a natural border. The sky displays a gradient of warm hues as the day begins.

Cottage in Castellina in Chianti

4.98 out of 5 average rating, 101 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

An aerial view of the historic Monteriggioni Castle showcases its medieval architecture surrounded by lush countryside. The fortified walls encircle the village, which is dotted with trees and buildings, while rolling hills extend into the distance under a sunset sky.

Cottage in Monteriggioni

4.96 out of 5 average rating, 250 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 jacuzzi is featured outdoors, illuminated with blue lights, creating a calming atmosphere at night. The surrounding stone walls provide privacy, and a dining table can be seen nearby. Steam rises, indicating the water is warm and inviting.

Cottage in San Casciano In Val di Pesa

4.95 out of 5 average rating, 154 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

An outdoor wood-fired hot tub is surrounded by lush green grass, offering a scenic view over the expansive landscape. A stone pathway leads to the hot tub, while the rustic stone cottage is visible in the background under a partly cloudy sky.

Cottage in Castell'Azzara

4.99 out of 5 average rating, 141 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.

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

4.9 out of 5 average rating, 143 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.

A stone patio is shown, featuring a small table set with two chairs. The entrance to the cottage is visible, accompanied by wooden shutters. Lush greenery surrounds the area, providing a serene environment.

Cottage in Ponte Feccia

4.94 out of 5 average rating, 175 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.

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

4.85 out of 5 average rating, 131 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).

The garden features a shaded dining area with a large umbrella and a wooden table set with chairs. A brick barbecue stands nearby, surrounded by greenery and well-maintained grass. The entrance to the house is visible through elegant wrought iron doors.

Cottage in La Piazza

4.96 out of 5 average rating, 102 reviews

Casa La Misura in the heart of Chianti

La Misura house is part of Borgo Montecastelli, a beautiful rural complex located right on the border between the provinces of Siena and Florence. Due to its strategic position, straddling two valleys, Borgo Montecastelli enjoys a magnificent panorama from its summit towards the villages that surround it: Panzano, Radda in Chianti, Castellina in Chianti, as well as farmhouses, churches, and towers.

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, 128 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

Vacation rentals for every style

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Popular amenities for Montepulciano cottage rentals

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

Top guest favorite

A stone cottage is surrounded by lush greenery, featuring a rustic facade with wooden accents. Potted plants are placed near the entrance, and the roof is topped with a small chimney. A pathway of stones leads to the door, inviting guests to explore.

Cottage in San Gimignano

4.97 out of 5 average rating, 72 reviews

Romantic House in Tuscany with jacuzzi

A spacious area of well-kept grass is seen in the foreground, with a rustic Tuscan farmhouse in the background. The building features a tiled roof and multiple windows. Bare trees and some greenery surround the property, under a clear blue sky with scattered clouds.

Cottage in Sovicille

4.93 out of 5 average rating, 224 reviews

From Simone, podere santi Lucia and Pietro

A glass-enclosed veranda offers a view of the private garden and pool area. A round dining table with decorative tiles is surrounded by iron chairs. Light filters through the glass, enhancing the rustic charm of the exposed stone walls.

Cottage in Trequanda

4.75 out of 5 average rating, 142 reviews

"Rosso Poggiolo" farmhouse with swimming pool.

A gravel pathway leads through an archway adorned with blooming roses, framed by lush olive trees. The entrance is marked by wooden gates that open into the property, inviting guests to explore the serene surroundings.

Cottage in Paciano

NEW Leccino home pool&Jacuzzi a Fontanaro Property

The two-story villa features a rustic exterior with a tiled roof and brick accents. A private pool is visible in the foreground, surrounded by well-maintained grass. A staircase leads to the upper level, and large windows allow for natural light. Lush greenery frames the property.

Cottage in Montepulciano

4.63 out of 5 average rating, 16 reviews

Tuscany Villa Girasole

A modern villa is surrounded by lush green grass, showcasing a sparkling swimming pool that reflects the evening sky. Lounge chairs are arranged by the poolside, with two shaded areas offering protection from the elements. The villa features multiple large windows, providing a welcoming glow.

Cottage in Foiano della Chiana

Luxury Cottage Spaccasole - Pool W/Cortona

A shaded pergola adorned with grapevines provides a relaxing spot for outdoor dining. A colorful table features a floral design, surrounded by wrought iron chairs. A private jacuzzi sits nearby, with lush greenery and rolling hills visible in the background.

Cottage in Castelmuzio

5 out of 5 average rating, 62 reviews

Panoramic view & outdoor jacuzzi - Pienza

A modern stone house is surrounded by lush greenery, nestled against a hillside. Large glass windows provide ample natural light, showcasing the inviting interior. The roof has a gentle slope, reflecting a blend of traditional and contemporary architecture.

Cottage in Seggiano

4.96 out of 5 average rating, 93 reviews

EcoLodge – modern design in quiet panoramic location

Pet-friendly cottage rentals

A rustic stone house is set against a backdrop of lush trees, featuring a terrace with sun loungers arranged around a central swimming pool. The building's earthy tones complement the natural surroundings, while a chimney adds a touch of charm to the exterior.

Cottage in Roccalbegna

4.91 out of 5 average rating, 78 reviews

Small cottage, swimming pool entirely private use

Two white Adirondack chairs are positioned on a lush green lawn facing the lake, providing a view of the water and a colorful sunset. A firepit is centered between the chairs, adding to the outdoor ambiance. Trees line the edge of the property, enhancing the scenery.

Cottage in Magione

4.96 out of 5 average rating, 97 reviews

Lakehouse in unique position on Lake Trasimeno

A stone house is set in a lush green landscape, surrounded by mature trees and blooming shrubs. The home features a rustic exterior, with a tiled roof and large windows. An open grassy area leads to the house, offering a serene view of the surrounding hills.

Cottage in Santa Fiora

4.85 out of 5 average rating, 27 reviews

Il Seccatoio – a stone house with a panoramic view

A serene exterior view of a rustic brick house surrounded by lush greenery. A large tree provides shade, while a person interacts with a horse nearby. Vibrant shrubs line the pathway, and a gravel area adds texture to the outdoor setting.

Cottage in Castiglione del Lago

4.9 out of 5 average rating, 42 reviews

Casina Miriano

The exterior features a spacious garden surrounded by greenery, showcasing a variety of plants. A shaded area provides seating with lounge chairs and a large tree offers additional shade. The house structure is visible in the background, with large windows reflecting the landscape.

Cottage in Castelfranco Piandiscò

4.89 out of 5 average rating, 74 reviews

Villetta Belvedere

Top guest favorite

A serene view of a swimming pool nestled among lush greenery, framed by vibrant leaves. The water appears inviting and reflects the surrounding foliage, creating a peaceful atmosphere. In the background, gentle hills are visible under a clear sky.

Cottage in Castiglion Fibocchi

5 out of 5 average rating, 46 reviews

Castellin di Bocco Tuscan countryhouse with pool

A rustic two-story building constructed from warm brick is surrounded by lush greenery. Large windows invite natural light, while wooden shutters add charm. The exterior features a gravel path leading to lounge chairs, creating a serene outdoor space for relaxation.

Cottage in Buonconvento

4.84 out of 5 average rating, 62 reviews

QuarterApartment for 6P Agriturismo Quarantallina

A cozy outdoor patio area is featured, showcasing comfortable wicker chairs and a small table. Potted plants add greenery, while a scenic view of rolling hills and lush landscapes creates a serene backdrop.

Cottage in Casole D'Elsa -Siena

4.79 out of 5 average rating, 70 reviews

Villetta with private patio and shared pool

Private cottage rentals

A rustic cottage with traditional stone walls and wooden shutters is set among lush green hedges and olive trees. A clear blue sky filled with fluffy white clouds provides a picturesque backdrop to the charming landscape. The tranquility of the surroundings enhances the natural beauty of the property.

Cottage in Cavriglia

4.85 out of 5 average rating, 74 reviews

Il Fienile, characteristic stone cottage for 2

An exterior view of a rustic stone structure is presented, featuring a covered porch with a wooden table and benches. Olive trees surround the area, providing shade. A barbecue station is visible nearby, with a pathway leading through the outdoor space.

Cottage in Sinalunga

4.87 out of 5 average rating, 83 reviews

Rustic retreat in the Tuscan hills

A rustic stone building is framed by lush greenery and seasonal flowers. Outdoor seating is arranged on a grassy area, including a table and chairs. A swimming pool partially visible in the background invites relaxation. The sky is clear, suggesting a bright day.

Cottage in Fabro

4.89 out of 5 average rating, 88 reviews

dependance mandriola

An outdoor terrace features a rustic wooden ceiling supported by brick columns. Comfortable seating is provided by a light-colored couch and benches, alongside a dining table with chairs. The surrounding greenery and pathways lead to additional buildings, creating a serene and inviting space.

Cottage in Pergine Valdarno

4.75 out of 5 average rating, 59 reviews

Holiday Casa Vacanze Tuscan countryside with swimming pool

A spacious living area features a large arched window offering views of the garden. A modern fireplace is centered within the room, complementing a comfortable seating arrangement. Natural light fills the space, enhancing the rustic wooden beams overhead.

Cottage in San Martino in Grania

5 out of 5 average rating, 46 reviews

Crete Senesi - Asciano Cavoni Hut

A charming stone cottage is displayed, featuring a welcoming entrance and large wooden windows. A round table with green chairs is set in a gravel courtyard surrounded by potted plants. Soft shadows from trees offer a refreshing contrast to the sunlit surroundings.

Cottage in Cortona

4.8 out of 5 average rating, 114 reviews

Tuscan Charm of Cottage Roccaio Cortona

A rustic brick house is surrounded by greenery, with additional trees and shrubs in the background. A dining table set for several, with chairs in blue, is positioned on the grass, suggesting a welcoming outdoor space for gatherings.

Cottage in Frattavecchia

4.89 out of 5 average rating, 56 reviews

Casale Poggiolo Basso - The place of silence

Top guest favorite

The cottage, constructed with Città della Pieve's distinctive red brick, is framed by lush greenery under a clear blue sky. Traditional wooden shutters add character to the windows, while a chimney rises from the roof, suggesting warmth and comfort inside.

Cottage in Città della Pieve

5 out of 5 average rating, 28 reviews

Grove Cottage, Immersed in nature & close to town

Destinations to explore