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Cottage vacation rentals in Montepulciano

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Quick stats about cottage rentals in Montepulciano

  • Nightly prices starting at

    Montepulciano vacation rentals start at ﺩ.ﺇ 2,497 per night before taxes and fees

  • Verified guest reviews

    Over 20 verified reviews to help you choose

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Montepulciano rentals

  • 4.9 Average rating

    Montepulciano stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated cottage rentals in Montepulciano

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

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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

Monteriggioni Castello, holiday house in Tuscany

Our accommodation is a historic building that dates back to the construction of the castle. It has been recently restored and furnished with attention to every detail. It is very welcoming and has all the most modern amenities. Tourists who decide to be our guests will have the advantage of living in the medieval environment of the castle, taking advantage of all the conveniences. They will feel pampered and have the opportunity to return home having lived a unique and unforgettable experience.

4.95 out of 5 average rating, 295 reviews
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

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.

4.99 out of 5 average rating, 155 reviews
Guest favorite
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

Lakefront House | Private Access & Sunsets

Langs Lakehouse: Wake up just steps from the water in one of the very few true lakefront homes on Lake Trasimeno. Spend your days swimming, paddleboarding, or cycling quiet Umbrian roads, and your evenings dining outdoors as the sun sets across the lake. This is not just a place to stay—it’s a slower, more beautiful way of living for a while. Paddleboards and bikes included Large outdoor terrace for dining and relaxing Pizza oven for long summer evenings Sleeps up to 5 guests comfortably

4.96 out of 5 average rating, 116 reviews
Top 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

Stone House with Exclusive Pool Codilungo in Chianti

Welcome to your Tuscan dream between Florence & Siena. Perfect for families or romantic getaways. • 360° views of iconic Chianti hills. •Huge Exclusive Infinity Pool (17x9m), lit at night (open from May 1st to October 15th) • Total privacy, yet restaurants/shops are 10-15 mins away. • Comfort for 6: 3 bedrooms (2 double, 1 twin) & 3 full baths. • Modern amenities: Fully equipped kitchen area, Smart TV. • Outdoor bliss: Large dining loggia, professional BBQ, poolside porch & bath.

4.98 out of 5 average rating, 216 reviews
Guest favorite
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

EcoLodge – modern design in a peaceful panoramic location

The modern, ecological and comfortable EcoLodge is quiet and secluded, surrounded by olive groves, chestnut and fruit trees, vines and meadows. In front of you are the hills of the Val d'Orcia; behind you is Monte Amiata. Three worlds meet here: Val d'Orcia, Monte Amiata, and Maremma. The Vielfältigkeit is an ideal base for culture, wine, hiking, mountain biking, hot springs and the sea – and at the same time a place to enjoy Tuscan country life away from the crowds of tourists.

4.94 out of 5 average rating, 110 reviews
Top guest favorite
A charming stone cottage is set within lush greenery, featuring a covered porch with outdoor seating. Olive trees surround the area, enhancing the natural beauty. A bicycle leans against the wall, inviting exploration of the peaceful countryside.
Cottage in Osteria delle Noci

Your Tuscan oak tree house, enchanting Val d'Orcia

The house enjoys a rare and enchanting view of the Val d’Orcia and Monte Amiata, ensuring maximum privacy. The interiors mirror the charm of the Tuscan style, with antique furniture and finishes made by local artisans. It is equipped with a double bedroom, a large living room with a big table, a fully equipped kitchenette, a double sofa bed in front of the fireplace, in the living room. Outside, the patio will allow you to eat with the colors of the sunset as a backdrop.

5.0 out of 5 average rating, 115 reviews
Top guest favorite
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

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.

4.95 out of 5 average rating, 200 reviews
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

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. 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

4.96 out of 5 average rating, 194 reviews
Top guest favorite
Cottage in Castellina in Chianti

Cottage Leccio - Masseto In Chianti

MASSETO IN CHIANTI, located in La Piazza, between Panzano and Castellina in Chianti, is a private village where you can relax in the garden and near the pool, play sports, or pivot to visit many surrounding Renaissance towns like Firenze, Siena, San Giminiano, Arezzo, Volterra. Kids can move carefree in the village. We offer four indipendent ancient cottages : Quinto (2 beds), Vittoria (4 beds), Cappero (4 beds), Leccio (6 beds).

4.96 out of 5 average rating, 102 reviews
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

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).

4.85 out of 5 average rating, 140 reviews
Guest favorite
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

dependance mandriola

The mandriola is our annex, a truly cozy and charming nest, renovated and furnished in a rustic Umbrian-Tuscan style. It has a unique dining-kitchen area with a fireplace and sofa, a large bedroom with a canopy bed, a bathroom with a shower and washing machine, and a comfortable loft with a double bed. All set in a large garden with panoramic terraces. New in 2021: large private jacuzzi and tree house for the little ones!

4.9 out of 5 average rating, 105 reviews
Guest favorite
Cottage in Sovicille

Lovely apartment with garden and views near Siena

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

4.89 out of 5 average rating, 160 reviews

Popular amenities for Montepulciano cottage rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Cottage rentals with a hot tub

Top guest favorite
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

From Simone, podere santi Lucia and Pietro

4.94 out of 5 average rating, 240 reviews
Top guest favorite
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

Panoramic view & outdoor jacuzzi - Pienza

5.0 out of 5 average rating, 79 reviews
Superhost
The two-story country house is surrounded by a spacious garden featuring mature olive trees. Large windows and an inviting porch are visible, blending harmoniously with the natural landscape. The site is well-maintained, showcasing greenery and a fence that marks the property's boundaries.
Cottage in Città della Pieve

Il Picchio Verde

4.97 out of 5 average rating, 64 reviews
Superhost
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

"Rosso Poggiolo" farmhouse with swimming pool.

4.75 out of 5 average rating, 144 reviews
Guest favorite
Cottage in Colle di Val d'Elsa

Cottage in the countryside with private jacuzzi and swimming pool

4.87 out of 5 average rating, 79 reviews
Superhost
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

Farmhouse with Private Saltwater Pool • Montepulciano

4.52 out of 5 average rating, 21 reviews
Top guest favorite
Cottage in Buonconvento

Capanna at S. Carlo in Buonconvento

4.95 out of 5 average rating, 39 reviews

Pet-friendly cottage rentals

Superhost
Cottage in Montespertoli

Chianti Barn with Pool and Vineyard View

4.79 out of 5 average rating, 288 reviews
Guest favorite
A cozy bedroom features a large bed framed by elegant wrought-iron headboards. Textured stone walls complement the cream-colored backdrop. A small table displays travel brochures and decorative elements, providing a homely touch.
Cottage in Pari

La Casa del Frantoiano - Pari -

4.94 out of 5 average rating, 179 reviews
Top guest favorite
An aerial view captures the agriturismo's lush green landscape, featuring neatly arranged cypress trees lining the path. A sparkling swimming pool glimmers amidst the foliage, while sprawling fields extend into the background under a clear sky, showcasing the beauty of the Tuscan countryside.
Cottage in Buonconvento

Tuscan Barn Apartment for 6 with panoramic pool

4.89 out of 5 average rating, 99 reviews
Top guest favorite
Cottage in Monticiano

Typical Tuscan Cottage with swimming pool and park

5.0 out of 5 average rating, 40 reviews
Guest favorite
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

Villetta Belvedere

4.91 out of 5 average rating, 87 reviews
Superhost
Cottage in Cortona

Casale Cantalena | Farmhouse with private pool

4.9 out of 5 average rating, 21 reviews
Superhost
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

Stunning cottage on the Tuscan hills

4.85 out of 5 average rating, 97 reviews
Guest favorite
A rustic stone farmhouse with a tiled roof is set against a clear blue sky. Two chimneys rise from the roof, while a spacious outdoor area showcases green grass and a gravel driveway. Small patio furniture is visible near the entrance.
Cottage in Seggiano

Castagnatello Country House - Noce cottage

4.91 out of 5 average rating, 11 reviews

Private cottage rentals

Guest favorite
A stone exterior is presented, showcasing a well-maintained garden with various plants and flowers. A staircase leads from the garden to an entrance, while a wrought-iron gate opens onto a pathway. The structure is flanked by a neighboring building visible in the background.
Cottage in Vescovado

Casa Roberta: a beautiful view of the Crete!

4.83 out of 5 average rating, 160 reviews
Superhost
A bright living room is presented, featuring exposed wooden beams and a colorful woven rug. Two pink sofas provide comfortable seating, while a white fireplace adds a cozy touch. Natural light enters through a window, illuminating the neutral tones of the walls and furnishings.
Cottage in Figline e Incisa Valdarno

Historic Mill in the Countryside -Chianti Classico

4.83 out of 5 average rating, 130 reviews
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

Grove Cottage, Immersed in nature & close to town

5.0 out of 5 average rating, 51 reviews
Guest favorite
A sunlit outdoor space features a wooden deck with a dining table and chairs, overlooking lush green fields. A circular stone seating area surrounds a wooden hot tub, providing a tranquil spot to enjoy the serene landscape.
Cottage in Montepulciano

Angalia Guesthouse

4.92 out of 5 average rating, 39 reviews
Guest favorite
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

Casale Poggiolo Basso - The place of silence

4.9 out of 5 average rating, 62 reviews
Guest favorite
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

Crete Senesi - Asciano Cavoni Hut

5.0 out of 5 average rating, 57 reviews
Top guest favorite
A charming stone house showcases a rustic design with wooden shutters and a balcony. The front porch features seating areas, surrounded by lush greenery and well-maintained gardens. An elegant pathway leads to the house, enhancing its countryside appeal.
Cottage in Villa A Sesta

CASA MARIA

5.0 out of 5 average rating, 20 reviews
Guest favorite
A charming stone villa is surrounded by lush greenery, featuring a shaded terrace with a wooden awning. Six outdoor chairs are arranged on a stone patio overlooking a well-kept lawn. A staircase leads to the upper level of the villa, framed by olive trees.
Cottage in Montisi

Il Villino

4.95 out of 5 average rating, 59 reviews

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