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Cottage vacation rentals in Montalcino

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Top-rated cottage rentals in Montalcino

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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, 139 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, 200 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

Cottage in La Cetina

4.96 out of 5 average rating, 109 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

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, 257 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

4.96 out of 5 average rating, 160 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, 146 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.

A wooden deck offers a serene view of rolling green hills extending into the distance. Two sun loungers are placed on the deck, inviting relaxation amid the natural surroundings. Trees frame the scene, creating a peaceful atmosphere, ideal for enjoying the landscape.

Cottage in Vetulonia

4.96 out of 5 average rating, 124 reviews

La Dolce Vita Romantic Sea-view Cottage. Tuscany

Welcome to Il Baciarino, a rustic agriturismo in the green hills of Maremma, Tuscany’s wild and less-traveled coastal region. Our property offers unique, handcrafted cottages with sea views, privacy, and direct contact with nature. Set within 19 acres of hillside wilderness in the charming Etruscan town of Vetulonia, Il Baciarino is the perfect place to escape the city, slow down, and enjoy unspoiled landscapes, fresh seafood, and good wine.

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, 178 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 .

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, 136 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

4.95 out of 5 average rating, 107 reviews

Casa La Misura nel cuore del 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 rustic stone building is set amidst a large, green lawn dotted with olive trees. The facade features multiple windows with arched tops, reflecting the characteristic Tuscan architecture. Natural scenery and gentle hills in the background suggest a peaceful, rural atmosphere.

Cottage in Fungaia, Monteriggioni

4.84 out of 5 average rating, 280 reviews

Countryside, 10 min from Siena

Apartment and large garden for exclusive use. It's a must for countryside, peace and relaxation, close to major places of cultural interest, trekking, biking trails. In a hilly area characterized by beautiful oak and holm oak forests, it enjoys a quiet location and a beautiful view of Siena, which is only 7 km away. (2 km are dirt road).

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, 133 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

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Popular amenities for Montalcino 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, 75 reviews

Romantic House in Tuscany with jacuzzi

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, 144 reviews

"Rosso Poggiolo" casale con piscina.

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

4.61 out of 5 average rating, 18 reviews

Tuscany Villa Girasole

A stone villa is surrounded by a lush green lawn, with a pathway leading to the entrance. Sun loungers are positioned nearby for relaxation. The landscape includes distant hills, complementing the serene outdoor environment.

Cottage in Reggello

5 out of 5 average rating, 11 reviews

Cottage indipendente con Spa Privata

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 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

4.95 out of 5 average rating, 95 reviews

EcoLodge – modernes Design in ruhiger Panoramalage

A private outdoor jacuzzi is presented in the foreground, with bubbling water inviting relaxation. In the background, a rustic cottage made of stone is framed by flowering plants and a large olive tree, amidst the scenic landscape of Tuscan rolling hills.

Cottage in Castelmuzio

5 out of 5 average rating, 66 reviews

Panoramic view & outdoor jacuzzi - Pienza

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

4.9 out of 5 average rating, 84 reviews

Small cottage, swimming pool entirely private use

A dining area features a dark wooden table with black chairs, adorned with a floral centerpiece. Light-colored stone walls and wooden beams create a rustic charm. A blue sofa with floral cushions is positioned against a large window, allowing natural light to fill the space.

Cottage in Quarate

4.92 out of 5 average rating, 151 reviews

FAETOLE typical Tuscan country house near FLORENCE

Cottage in Magione

4.96 out of 5 average rating, 98 reviews

Lakehouse in unique position on Lake Trasimeno

Cottage in Lubriano

4.97 out of 5 average rating, 139 reviews

Farmhouse between Orvieto and Civita di Bagnoregio

A charming cottage is positioned in a well-kept garden, surrounded by vibrant greenery and colorful flower pots. The exterior features a warm-toned facade with a sloped roof and large glass doors, inviting natural light into the space. A paved pathway leads to the entrance.

Cottage in Florence

4.84 out of 5 average rating, 179 reviews

Cottage Michelangelo,verde in città

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

4.88 out of 5 average rating, 32 reviews

Il Seccatoio – house in stone with panoramic view

Two lounge chairs with cushions are positioned beside a private pool, overlooking rolling hills at sunset. A small table holds a bottle of sparkling beverage, enhancing the serene atmosphere. Lush greenery and trees frame the view, creating a sense of tranquility.

Cottage in San Casciano dei Bagni

4.89 out of 5 average rating, 20 reviews

Toscana, Country house with exclusive pool

Top guest favorite

A charming stone house is framed by greenery, with a covered porch featuring wooden beams. Colorful flowers in bloom line a path leading to the entrance, enhancing the natural surroundings. The setting conveys tranquility and a connection to nature.

Cottage in San Venanzo

5 out of 5 average rating, 38 reviews

a small stone house in the woods

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

4.86 out of 5 average rating, 77 reviews

Il Fienile, characteristic stone cottage for 2

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, 91 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, 61 reviews

Casa Vacanze campagna toscana con piscina

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, 49 reviews

Crete Senesi - Asciano Capanna Cavoni

A charming stone house is viewed from a grassy area, framed by olive trees. Two yellow chairs sit invitingly on the lawn, while a small table is arranged on the terrace. The sky displays a mix of blue and wispy white clouds.

Cottage in Localita' Pievescola

4.92 out of 5 average rating, 97 reviews

Antico Borgo Ripostena – n. 1 Casa Bertilla

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

4.91 out of 5 average rating, 44 reviews

Casina Miriano

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, 35 reviews

Grove Cottage, Immersed in nature & close to town

Top guest favorite

The exterior of a charming stone cottage features large windows and a distinctive roof design. Surrounding the cottage, a well-maintained garden showcases colorful roses, while seating options are positioned on a stone patio, inviting relaxation amidst natural scenery.

Cottage in Greve in Chianti

5 out of 5 average rating, 39 reviews

Very cosy cottage with beautiful views

Destinations to explore