
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 G$142,186 GYD per night before taxes and fees

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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.

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.

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.

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

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.

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.

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.

EcoLodge – modern design in a peaceful panoramic location
The EcoLodge, modern, ecological, comfortable, is in the middle of nature in a peaceful, fertile cultural landscape on Monte Amiata in the quiet southern Tuscany. It belongs to an old farmhouse with plenty of space, beautiful views, many old fruit, chestnut, olive trees and our vineyard. It's an ideal location. From here you can explore world-famous sights, do a lot and enjoy the tranquility of Tuscan country life away from the hordes of tourists.

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

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).

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!

Casa Roberta: a beautiful view of the Crete!
Beautifully renovated stone house, located on the hill of Vescovado di Murlo. It is on the edge of the historic center in a quiet area where you can only hear the sound of nature. Two floors with a small garden with a beautiful view. It can accommodate four guests. The house is not suitable for disabled people (presence of stairs, unsuitable doorways). Cars must be parked outside, in the many parking lots of the Borgo.
Popular amenities for Montepulciano cottage rentals
Cottage rentals with a hot tub

From Simone, podere santi Lucia and Pietro

Panoramic view & outdoor jacuzzi - Pienza

Il Picchio Verde

"Rosso Poggiolo" farmhouse with swimming pool.

Cottage in the countryside with private jacuzzi and swimming pool

NEW Leccino home pool&Jacuzzi a Fontanaro Property

Farmhouse with Private Saltwater Pool • Montepulciano

Capanna at S. Carlo in Buonconvento
Pet-friendly cottage rentals

Countryside, 10 min from Siena

Chianti Barn with Pool and Vineyard View

La Casa del Frantoiano - Pari -

Tuscan Barn Apartment for 6 with panoramic pool

Villetta Belvedere

Typical Tuscan Cottage with swimming pool and park

Charming Cottage with Pool

House in Sogna
Private cottage rentals

Angalia Guesthouse

Grove Cottage, Immersed in nature & close to town

Crete Senesi - Asciano Cavoni Hut

Il Villino

Chianti Loft (AC & Pool)

Casale Poggiolo Basso - The place of silence

Casetta Di Pietra 2-bed cottage with private pool

CASA MARIA
Destinations to explore
- Smoking-friendly rentals Montepulciano
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- Rentals with a hot tub Montepulciano
- Pet-friendly rentals Montepulciano
- Rentals with breakfast Montepulciano
- Villa rentals Montepulciano
- Rentals with a fireplace Montepulciano
- Condo rentals Montepulciano
- Rentals with a washer and dryer Montepulciano
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- Rentals with outdoor seating Montepulciano
- Apartment rentals Montepulciano
- Rentals with a patio Montepulciano
- Rentals with pools Montepulciano
- Family-friendly rentals Montepulciano
- Cottage rentals Siena
- Cottage rentals Tuscany
- Cottage rentals Italy
- Lake Trasimeno
- Lake Bolsena
- Parco Regionale Della Maremma
- Del Chianti
- Basilica of St Francis
- Centro Storico Orvieto
- Terme Dei Papi
- Mount Amiata
- Avignonesi Winery Fattoria Le Capezzine
- La Scarzuola
- Eremo Di Camaldoli
- Antinori nel Chianti Classico
- Siena Cathedral
- Palazzo Pubblico
- Vulci
- Mount Subasio
- Val di Chiana
- Valdichiana Outlet Village
- Abbey of Sant'Antimo
- Saturnia Thermal Park
- Rocca Maggiore
- Antiporto Camollia
- Piazza del Campo
- Abbazia di San Galgano
- Things to do Montepulciano
- Food and drink Montepulciano
- Things to do Siena
- Sports activities Siena
- Sightseeing Siena
- Art and culture Siena
- Entertainment Siena
- Nature and outdoors Siena
- Food and drink Siena
- Tours Siena
- Things to do Tuscany
- Nature and outdoors Tuscany
- Art and culture Tuscany
- Sports activities Tuscany
- Tours Tuscany
- Entertainment Tuscany
- Food and drink Tuscany
- Sightseeing Tuscany
- Things to do Italy
- Food and drink Italy
- Wellness Italy
- Art and culture Italy
- Nature and outdoors Italy
- Sports activities Italy
- Sightseeing Italy
- Tours Italy
- Entertainment Italy







