
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$142,270 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.
FamilyLocationCheckout
4.95 out of 5 average rating, 297 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.
ValueLocationTV
4.99 out of 5 average rating, 155 reviews
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
LocationFamilyCleanliness
4.96 out of 5 average rating, 117 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.
LocationFamilyBathroom
4.97 out of 5 average rating, 115 reviews
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.
LocationFamilyOutdoor spaces
4.98 out of 5 average rating, 218 reviews
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.
ValueLocationDecor
4.94 out of 5 average rating, 111 reviews
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.
FamilyValueCheckout
5.0 out of 5 average rating, 116 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.
LocationFamilyAccess
4.94 out of 5 average rating, 203 reviews
Tuscan Barn Apartment for 6 with panoramic pool
Panoramic Tuscan apartment converted from an old barn, with direct access to the garden and a shared panoramic swimming pool overlooking the Senese hills. Ideal for families or small groups of friends looking to enjoy for an authentic rural experience, privacy and relax. The apartment features three double bedrooms each with private bathroom, air-conditioning and WI-FI. A perfect place to enjoy nature, silence and unforgettable Tuscan sunsets.
FamilyLocationAccuracy
4.89 out of 5 average rating, 100 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. 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
FamilyLocationBackyard
4.96 out of 5 average rating, 197 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).
LocationFamilyQuiet
4.85 out of 5 average rating, 140 reviews
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!
ValueFamilyWifi
4.9 out of 5 average rating, 106 reviewsPopular amenities for Montepulciano cottage rentals
Cottage rentals with a hot tub

From Simone, podere santi Lucia and Pietro
LocationValueGrill
4.94 out of 5 average rating, 242 reviews
Panoramic view & outdoor jacuzzi - Pienza
LocationBikingView
5.0 out of 5 average rating, 81 reviews
Il Picchio Verde
LocationFamilyAccuracy
4.97 out of 5 average rating, 65 reviews
"Rosso Poggiolo" farmhouse with swimming pool.
FamilyValueSleep quality
4.75 out of 5 average rating, 144 reviews
NEW Leccino home pool&Jacuzzi a Fontanaro Property
Indoor spacesHospitality

Podere Coreno / Authentic Tuscan Peace & Relaxation
FamilyLocationIndoor spaces
5.0 out of 5 average rating, 6 reviews
Farmhouse with Private Saltwater Pool • Montepulciano
FamilyLocationParking
4.55 out of 5 average rating, 22 reviews
Capanna at S. Carlo in Buonconvento
LocationFamilyDecor
4.95 out of 5 average rating, 39 reviewsPet-friendly cottage rentals

The Five Oaks Cottage
LocationFamilyAir conditioning
4.83 out of 5 average rating, 175 reviews
Countryside, 10 min from Siena
ValueFamilyGetting around
4.84 out of 5 average rating, 289 reviews
Chianti Barn with Pool and Vineyard View
FamilyValueBeach
4.79 out of 5 average rating, 289 reviews
La Casa del Frantoiano - Pari -
ValueLocationHospitality
4.94 out of 5 average rating, 179 reviews
Casina Miriano
LocationFamilyHeating
4.93 out of 5 average rating, 59 reviews
Private Country House with swimming pool -Chianti
LocationValueCondition
4.95 out of 5 average rating, 57 reviews
Castagnatello Country House - Noce cottage
ValueLocationCheck-in
4.92 out of 5 average rating, 12 reviews
Stunning cottage on the Tuscan hills
ValueFamilyBathroom
4.85 out of 5 average rating, 98 reviewsPrivate cottage rentals

Casa Roberta: a beautiful view of the Crete!
FamilyLocationBeach
4.83 out of 5 average rating, 161 reviews
Historic Mill in the Countryside -Chianti Classico
LocationFamilyCleanliness
4.83 out of 5 average rating, 132 reviews
Grove Cottage, Immersed in nature & close to town
LocationValueCondition
5.0 out of 5 average rating, 53 reviews
Casale Poggiolo Basso - The place of silence
FamilyLocationDecor
4.9 out of 5 average rating, 63 reviews
Angalia Guesthouse
LocationFamilyAmenities
4.92 out of 5 average rating, 39 reviews
CASA MARIA
LocationFamilyQuiet
5.0 out of 5 average rating, 20 reviews
Crete Senesi - Asciano Cavoni Hut
LocationFamilyDecor
5.0 out of 5 average rating, 57 reviews
Il Villino
LocationFamilyView
4.95 out of 5 average rating, 59 reviewsDestinations to explore
- Bed and breakfasts Montepulciano
- Pet-friendly rentals Montepulciano
- Rentals with breakfast Montepulciano
- Villa rentals Montepulciano
- Condo rentals Montepulciano
- House rentals Montepulciano
- Apartment rentals Montepulciano
- Rentals with pools Montepulciano
- Family-friendly rentals Montepulciano
- Rentals with a hot tub Montepulciano
- Cottage rentals Siena
- Cottage rentals Tuscany
- Cottage rentals Italy
- Lake Trasimeno
- Lake Bolsena
- Parco Regionale Della Maremma
- Del Chianti
- Basilica of St Francis
- Mount Amiata
- Centro Storico Orvieto
- Cascate del Mulino
- Terme Dei Papi
- Eremo Di Camaldoli
- La Scarzuola
- Antinori nel Chianti Classico
- Siena Cathedral
- Avignonesi Winery Fattoria Le Capezzine
- Vulci
- Val di Chiana
- Mount Subasio
- Palazzo Pubblico
- Valdichiana Outlet Village
- Saturnia Thermal Park
- Terme San Filippo
- Abbey of Sant'Antimo
- Abbey of Monte Oliveto Maggiore
- Piazza del Campo
- Things to do Montepulciano
- Tastings Montepulciano
- Things to do Siena
- Art workshops Siena
- Tastings Siena
- Museums Siena
- Food tours Siena
- Dining Siena
- Cultural tours Siena
- Outdoors Siena
- Landmarks Siena
- Wildlife Siena
- Cooking Siena
- Things to do Tuscany
- Water sports Tuscany
- Flying Tuscany
- Cooking Tuscany
- Wildlife Tuscany
- Landmarks Tuscany
- Workouts Tuscany
- Tastings Tuscany
- Galleries Tuscany
- Outdoors Tuscany
- Food tours Tuscany
- Dining Tuscany
- Museums Tuscany
- Performances Tuscany
- Shopping and fashion Tuscany
- Art workshops Tuscany
- Cultural tours Tuscany
- Things to do Italy
- Workouts Italy
- Shopping and fashion Italy
- Food tours Italy
- Cooking Italy
- Flying Italy
- Cultural tours Italy
- Wellness Italy
- Tastings Italy
- Wildlife Italy
- Landmarks Italy
- Museums Italy
- Performances Italy
- Art workshops Italy
- Dining Italy
- Galleries Italy
- Outdoors Italy
- Architecture Italy
- Water sports Italy







