
Cottage holiday rentals in Montepulciano
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Top-rated cottage rentals in Montepulciano
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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.

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.

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.

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

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.

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.

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.

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).

Casa Roberta: a beautiful view of the Crete!
Finely renovated stone house, located on the hill of Vescovado di Murlo. It is on the edge of the historical center in a quiet area where you can only hear the sound of nature. Two floors with small garden with beautiful views. It can accommodate four guests. The house is not suitable for people with disabilities (stairs, unsuitable door rooms). Cars must be parked outside, in the many parking lots in the village.

Lakehouse in unique position on Lake Trasimeno
Lang’s Lakehouse is in a unique location, being one of a handful of properties on the banks of Lake Trasimeno, Italy’s fourth largest lake. The property sleeps five upstairs. Directly in front of the property is a large grassed terrace, perfect for relaxation or entertaining. Visitors can swim, paddleboard or fish from the front of the property and even cook pizzas in their own pizza oven.

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

Countryside Cottage With View - Le Rondini apt
The cottage is part of a charming traditional Tuscan farmhouse, built in stone and situated in one of the most beautiful areas of Tuscany.A lovely garden surrounds the house and has magnificent views of the medieval town with its famous towers.
Popular amenities for cottage rentals in Montepulciano
Cottage rentals with a hot tub

Romantic House in Tuscany with jacuzzi

From Simone, podere santi Lucia and Pietro

Cottage in the greenery with private jacuzzi and pool

"Rosso Poggiolo" farmhouse with swimming pool.

NEW Leccino home pool&Jacuzzi a Fontanaro Property

Tuscany Villa Girasole

Independent cottage with private spa

Luxury Cottage Spaccasole - Pool W/Cortona
Pet-friendly cottage rentals

Small cottage, swimming pool entirely private use

Rustic retreat in the Tuscan hills

Casa Gialla, Cortona-sunsets in the olive grove

Cottage in the south of Tuscany

Il Seccatoio - a stone house with panoramic views

Casina Miriano

Villetta Belvedere

Castellin di Bocco Tuscan countryhouse with pool
Private cottage rentals

Old Chianti chapel-style cottage

Crete Senesi - Asciano Cavoni Hut

La Loggia, cozy stone cottage for 2 with terrace

Stone cottage in beautiful Umbrian countryside

Casale Poggiolo Basso - The place of silence

Grove Cottage, Immersed in nature & close to town

Jino House Detached Villa with fireplace

Very cosy cottage with beautiful views
Quick stats about cottage rentals in Montepulciano

Nightly prices starting at
Montepulciano holiday rentals start at $433 SGD 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!
Destinations to explore
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- Cottage rentals Siena
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- Lake Trasimeno
- Del Chianti
- Siena Cathedral
- Lake Bolsena
- Eremo Di Camaldoli
- Terme Dei Papi
- Avignonesi Winery Fattoria Le Capezzine
- Basilica of St Francis
- Mount Subasio
- Palazzo Pubblico
- Cascate del Mulino
- Santa Maria della Scala
- Ugolino Golf Club
- Abbey of Monte Oliveto Maggiore
- Antinori nel Chianti Classico
- Abbazia di San Galgano
- Castello di Verrazzano
- Mount Amiata
- Val di Chiana
- Vulci
- San Gimignano 1300
- Castello di Volpaia
- Pozzo di San Patrizio
- Saturnia Thermal Park
- Things to do Montepulciano
- Things to do Siena
- Food and drink Siena
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- Sightseeing Siena
- Nature and outdoors Siena
- Things to do Tuscany
- Sports activities Tuscany
- Entertainment Tuscany
- Sightseeing Tuscany
- Nature and outdoors Tuscany
- Tours Tuscany
- Food and drink Tuscany
- Art and culture Tuscany
- Things to do Italy
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- Sports activities Italy
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- Entertainment Italy
- Wellness Italy
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