
Cottage holiday rentals in Montepulciano
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Top-rated cottage rentals in Montepulciano
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EcoLodge – modernes Design in ruhiger Panoramalage
Die EcoLodge, modern, ökologisch, komfortabel, liegt mitten in der Natur in einer friedlichen, fruchtbaren Kulturlandschaft am Monte Amiata in der stillen Südtoskana. Sie gehört zu einem alten Bauernhaus mit viel Platz, wunderschöner Aussicht, vielen alten Obst-, Marroni-, Olivenbäumen und unserem Weinberg. Es ist ein idealer Standort. Von hier aus können Sie weltberühmte Sehenswürdigkeiten erkunden, viel unternehmen und abseits der Touristenströme die Ruhe des toskanischen Landlebens genießen.

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 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.

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

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.

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).

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

Lovely countryhouse on Chiant hills
Lovely view on the valley, sweet relax in the smelling garden under a very old tree tasting a good wine and then to visit Firenze, Pisa, Siena only 30 km far from here and medieval castles,little churchs ,winery,across the beautiful Chianti road.....
Popular amenities for cottage rentals in Montepulciano
Cottage rentals with a hot tub

Podere Coreno / autentica pace toscana & relax

Romantic House in Tuscany with jacuzzi

Da Simone, podere santi Lucia e Pietro

Cottage nel verde con jacuzzi privata e piscina

"Rosso Poggiolo" casale con piscina.

NEW Leccino home pool&Jacuzzi a Fontanaro Property

Casale con Piscina Privata Salata • Montepulciano

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

Castagnatello Country House - Noce cottage

Small cottage, swimming pool entirely private use

Stunning cottage on the Tuscan hills

Casa Vacanze campagna toscana con piscina

Casa Gialla, Cortona-sunsets in the olive grove

Cottage in the south of Tuscany

Casina Miriano

Villetta Belvedere
Private cottage rentals

Old Chianti chapel-style cottage

Il Fienile, characteristic stone cottage for 2

dependance mandriola

Il Seccatoio – house in stone with panoramic view

Stone cottage in beautiful Umbrian countryside

Chianti Loft (AC & Pool)

Private pool nature Hideway

Casale Poggiolo Basso - The place of silence
Quick stats about cottage rentals in Montepulciano

Nightly prices starting at
Montepulciano holiday rentals start at $501 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!
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- Lake Trasimeno
- Lake Bolsena
- Centro Storico Orvieto
- Basilica of St Francis
- Terme Dei Papi
- Del Chianti
- Avignonesi Winery Fattoria Le Capezzine
- La Scarzuola
- Cascate del Mulino
- Parco Regionale Della Maremma
- Mount Subasio
- Palazzo Pubblico
- Siena Cathedral
- Ugolino Golf Club
- Valdichiana Outlet Village
- Eremo Di Camaldoli
- Antinori nel Chianti Classico
- Abbey of Sant'Antimo
- Santa Maria della Scala
- Vulci
- Val di Chiana
- Mount Amiata
- Terme San Filippo
- Abbey of Monte Oliveto Maggiore
- Things to do Montepulciano
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- Things to do Siena
- Nature and outdoors Siena
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- Sightseeing Siena
- Art and culture Siena
- Food and drink Siena
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- Things to do Italy
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