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Featured Holiday Homes in Montalcino

Borgo Argiano

Borgo Argiano

Loc. Argiano, Pianella, Castelnuovo Berardenga, Siena
Located in Castelnuovo Berardenga, Borgo Argiano is on a river, within a 10-minute drive of Chianti Sculpture Park and La Fornace Art Gallery.
Borgo Argiano
The House of Alice, charm and relaxation

The House of Alice, charm and relaxation

Montalcino (SI)
The price is AU$293 per night from 25 Nov to 26 Nov
AU$293
includes taxes & fees
25 Nov - 26 Nov
Located in Montalcino, this vacation home is by the sea, a 4-minute drive from Abbazia di Sant'Antimo and 9 minutes from Museum of Brunello.
The House of Alice, charm and relaxation
Welcome to Sarteano Look forward to a holiday in Italy.

Welcome to Sarteano Look forward to a holiday in Italy.

Sarteano
With a stay at this vacation home in Sarteano, you'll be on a lake, just steps from Val di Chiana and a 4-minute drive from Archaeological Museum of ...
Welcome to Sarteano Look forward to a holiday in Italy.
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The Gelda house, relax with a view

The Gelda house, relax with a view

Castelnuovo dell'Abate
The price is AU$231 per night from 24 Nov to 25 Nov
AU$231
includes taxes & fees
24 Nov - 25 Nov
Located in Montalcino, this vacation home is by the sea, a 5-minute drive from Abbazia di Sant'Antimo and 8 minutes from Museum of Brunello.
The Gelda house, relax with a view
Casa delle Rose: charming house with stunning balcony in the heart of Cortona

Casa delle Rose: charming house with stunning balcony in the heart of Cortona

Cortona
With a stay at this vacation home in Cortona (Cortona Old Town), you'll be within a 15-minute drive of Lake Trasimeno and Cortona Cathedral.
Casa delle Rose: charming house with stunning balcony in the heart of Cortona
Terre di Maremma, Ciclamino Apartment, Tuscany

Terre di Maremma, Ciclamino Apartment, Tuscany

Sticciano
With a stay at this vacation home in Roccastrada, you'll be 8.9 mi (14.4 km) from Baluardo a tre punte and 9 mi (14.5 km) from Torre del Belvedere.
Terre di Maremma, Ciclamino Apartment, Tuscany
Old Tuscan house in the medieval village of Castiglione d'Orcia

Old Tuscan house in the medieval village of Castiglione d'Orcia

Castiglione d'Orcia
A stay at this vacation home places you in the heart of Castiglione d'Orcia, a 1-minute drive from Fortress of Tentennano and 7 minutes from Piazza delle ...
Old Tuscan house in the medieval village of Castiglione d'Orcia
Podere Casorbica with free parking, large garden, swimming pool.

Podere Casorbica with free parking, large garden, swimming pool.

cortona
Located in Cortona, this vacation home is in a rural location, a 4-minute drive from Santa Maria delle Grazie and 5 minutes from Cortona Cathedral.
Podere Casorbica with free parking, large garden, swimming pool.
Townhouse in ancient tower in medieval Cetona

Townhouse in ancient tower in medieval Cetona

Cetona
A stay at this vacation home places you in the heart of Cetona, a 1-minute drive from Val di Chiana and 8 minutes from Archaeological Museum of Sarteano.
Townhouse in ancient tower in medieval Cetona
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Montalcino Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Montalcino vacation homes are the perfect way for you to wing it.

Holiday houses in Montalcino let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Montalcino in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Montalcino adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Montalcino with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Montalcino vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Montalcino Holiday Homes essential information

Accommodation
1204 Holiday Homes
Lowest Price
AU$231
Highest Price
AU$1,724
Popular accommodation
Borgo Argiano, The House of Alice, charm and relaxation, Welcome to Sarteano Look forward to a holiday in Italy., The Gelda house, relax with a view, Casa delle Rose: charming house with stunning balcony in the heart of Cortona, Terre di Maremma, Ciclamino Apartment, Tuscany, Old Tuscan house in the medieval village of Castiglione d'Orcia, Podere Casorbica with free parking, large garden, swimming pool., Townhouse in ancient tower in medieval Cetona

Top trending hotels in Montalcino

Rosewood Castiglion del Bosco

Rosewood Castiglion del Bosco

5 out of 5
Localita Castiglion del Bosco, Montalcino, SI
Fully refundableReserve now, pay when you stay
The price is AU$1,724 per night from 1 Dec to 2 Dec
AU$1,724
includes taxes & fees
1 Dec - 2 Dec
With a stay at Rosewood Castiglion del Bosco in Montalcino, you'll be 7.8 mi (12.5 km) from Fortress of Montalcino and 11.7 mi (18.8 km) from Monte Oliveto Maggiore ...
Rosewood Castiglion del Bosco
Castello di Velona Resort Thermal SPA & Winery

Castello di Velona Resort Thermal SPA & Winery

5 out of 5
Località Velona, Castelnuovo dell'Abate, Montalcino, SI
Fully refundableReserve now, pay when you stay
The price is AU$848 per night from 27 Nov to 28 Nov
AU$848
includes taxes & fees
27 Nov - 28 Nov
Located in Montalcino, Castello di Velona Resort Thermal SPA & Winery is in a national park, within a 15-minute drive of Abbazia di Sant'Antimo and Fortress ...
Castello di Velona Resort Thermal SPA & Winery
SI Montalcino Hotel

SI Montalcino Hotel

3 out of 5
Via Osticcio 21, Montalcino, SI
Located in Montalcino, SI Montalcino Hotel is a 2-minute drive from Fortress of Montalcino and 6 minutes from Poggio Antico.
SI Montalcino Hotel
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Hotel Dei Capitani

Hotel Dei Capitani

3 out of 5
Via Lapini 6, Montalcino, SI
The price is AU$234 per night from 23 Nov to 24 Nov
AU$234
includes taxes & fees
23 Nov - 24 Nov
Located in Montalcino, Hotel Dei Capitani is in a rural location, within a 15-minute walk of Civic and Diocesan Museum of Sacred Art of Montalcino and Fortress ...
Hotel Dei Capitani
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.