
Cottage vacation rentals in Montepulciano
Find and book unique cottages on Airbnb
Top-rated cottage rentals in Montepulciano
Guests agree: these cottages are highly rated for location, cleanliness, and more.

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.

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.

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.

La Quercia Panoramic 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).

Casa La Misura in the heart of 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.

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.
Popular amenities for Montepulciano cottage rentals
Cottage rentals with a hot tub

Romantic House in Tuscany with jacuzzi

"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

EcoLodge – modernes Design in ruhiger Panoramalage

Panoramic view & outdoor jacuzzi - Pienza
Pet-friendly cottage rentals

Romantic lake view cottage (2/4),Tuscany/ Umbria,

Casa Gialla, Cortona-sunsets in the olive grove

Casina Miriano

House in Sogna

a small stone house in the woods

Rustic Tuscan with swimming pool

Villetta Belvedere

Castellin di Bocco Tuscan countryhouse with pool
Private cottage rentals

Old Chianti chapel-style cottage

Small cottage, swimming pool entirely private use

dependance mandriola

La Loggia, cozy stone cottage for 2 with terrace

Il Seccatoio – a stone house with a panoramic view

Casale Poggiolo Basso - The place of silence

Grove Cottage, Immersed in nature & close to town

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

Nightly prices starting at
Montepulciano vacation rentals start at G$75,193 GYD 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
- Pet-friendly rentals Montepulciano
- Smoking-friendly rentals Montepulciano
- Rentals with a fireplace Montepulciano
- Rentals with breakfast Montepulciano
- Bed and breakfasts Montepulciano
- Rentals with a washer and dryer Montepulciano
- Rentals with a hot tub Montepulciano
- Rentals with outdoor seating Montepulciano
- Condo rentals Montepulciano
- Rentals with a patio Montepulciano
- Rentals with pools Montepulciano
- House rentals Montepulciano
- Apartment rentals Montepulciano
- Family-friendly rentals Montepulciano
- Villa rentals Montepulciano
- Cottage rentals Siena
- Cottage rentals Tuscany
- Cottage rentals Italy
- Lake Trasimeno
- Lake Bolsena
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Kite Beach Fiumara
- Avignonesi Winery Fattoria Le Capezzine
- Tenuta Le Velette
- Basilica of St Francis
- Terme Dei Papi
- Cala di Forno
- Castiglion del Bosco Winery
- Golf Club Toscana
- Spiaggia di Marina di Grosseto
- Mount Subasio
- Cantina Colle Ciocco
- Santa Maria della Scala
- Palazzo Pubblico
- Cantina di Montefiascone Soc.Coop.Agr. - Punto di Vendita
- Podere La Marronaia, Sosta alle Colonne
- Ugolino Golf Club
- Abbey of Monte Oliveto Maggiore
- Madonna del Latte
- Podere Il Cocco
- Azienda Agricola Montefioralle Winery
- Cantina de' Ricci
- Things to do Montepulciano
- Things to do Siena
- Sports activities Siena
- Food and drink Siena
- Sightseeing Siena
- Tours Siena
- Art and culture Siena
- Nature and outdoors Siena
- Things to do Tuscany
- Entertainment Tuscany
- Art and culture Tuscany
- Nature and outdoors Tuscany
- Food and drink Tuscany
- Sports activities Tuscany
- Sightseeing Tuscany
- Tours Tuscany
- Things to do Italy
- Art and culture Italy
- Wellness Italy
- Sports activities Italy
- Sightseeing Italy
- Entertainment Italy
- Food and drink Italy
- Nature and outdoors Italy
- Tours Italy






