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Featured Holiday Homes in Montalcino

Borgo Argiano

Borgo Argiano

Loc. Argiano, Pianella, Castelnuovo Berardenga, SI
The price is AU$1,078 per night from 31 Aug to 1 Sept
AU$1,078
31 Aug - 1 Sept
includes taxes & fees
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
Il Palazzetto

Il Palazzetto

Strada del Lucherino, 31, Siena, SI
Located in Siena, Il Palazzetto is in a rural location, within a 5-minute drive of Orto Botanico dell'Universita di Siena and Sant'Agostino Monastery.
Il Palazzetto
Private House with Exclusive Swimming Pool Heated and Amazing View

Private House with Exclusive Swimming Pool Heated and Amazing View

Boccheggiano
When you stay at this vacation home in Montieri, you'll be by the sea and 12 minutes by car from Val di Merse.
Private House with Exclusive Swimming Pool Heated and Amazing View
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Villa Le Tortore Tuscany private luxury pool relax

Villa Le Tortore Tuscany private luxury pool relax

Siena
With a stay at this vacation home in Siena, you'll be within a 5-minute drive of Piazza del Campo and Porta Romana.
Villa Le Tortore Tuscany private luxury pool relax
Villa il Giuggiolo, ancient country house with pool at Azienda Fontelunga

Villa il Giuggiolo, ancient country house with pool at Azienda Fontelunga

cortona
Located in Cortona, this vacation home is in a rural location, a 4-minute drive from Santa Maria delle Grazie and 6 minutes from Cortona Cathedral.
Villa il Giuggiolo, ancient country house with pool at Azienda Fontelunga
A MAGICAL HOLIDAY IN TUSCANY

A MAGICAL HOLIDAY IN TUSCANY

Montepulciano
A stay at this vacation home places you in the heart of Montepulciano, steps from Val di Chiana and Cantina Contucci.
A MAGICAL HOLIDAY IN TUSCANY
Eco house with pool and fantastic views

Eco house with pool and fantastic views

Scansano
Located in Scansano, this vacation home is in the mountains, within a 15-minute drive of Tiaso Bioviticulturists - Cellar and Museo della Vite e del Vino di ...
Eco house with pool and fantastic views
Porcilaia tiny countryside property, shared pool, ideal base to discover Tuscany

Porcilaia tiny countryside property, shared pool, ideal base to discover Tuscany

Siena
Located in Siena, this vacation home is in a rural location, a 1-minute drive from Val di Merse and 9 minutes from Museo dell'Acqua.
Porcilaia tiny countryside property, shared pool, ideal base to discover Tuscany
The Casetta di Brunello, quiet and breathtaking views

The Casetta di Brunello, quiet and breathtaking views

Montalcino
The price is AU$429 per night from 18 Aug to 19 Aug
AU$429
18 Aug - 19 Aug
includes taxes & fees
Located in Montalcino, this vacation home is in a rural location, a 5-minute drive from Abbazia di Sant'Antimo and 8 minutes from Museum of Brunello.
The Casetta di Brunello, quiet and breathtaking views
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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
1367 Holiday Homes
Lowest Price
AU$429
Highest Price
AU$3,369
Popular accommodation
Borgo Argiano, Il Palazzetto, Private House with Exclusive Swimming Pool Heated and Amazing View, Villa Le Tortore Tuscany private luxury pool relax, Villa il Giuggiolo, ancient country house with pool at Azienda Fontelunga, A MAGICAL HOLIDAY IN TUSCANY, Eco house with pool and fantastic views, Porcilaia tiny countryside property, shared pool, ideal base to discover Tuscany, The Casetta di Brunello, quiet and breathtaking views

Top trending hotels in Montalcino

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
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
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$3,369 per night from 16 Aug to 17 Aug
AU$3,369
16 Aug - 17 Aug
includes taxes & fees
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
SI Montalcino Hotel

SI Montalcino Hotel

3 out of 5
Via Osticcio 21, Montalcino, SI
Fully refundableReserve now, pay when you stay
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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Mastrojanni Relais

Mastrojanni Relais

Localita Loreto e San Pio, Castelnuovo dell'Abate, Montalcino, SI
The price is AU$751 per night from 12 Sept to 13 Sept
AU$751
12 Sept - 13 Sept
includes taxes & fees
Located in Montalcino, Mastrojanni Relais is in the mountains, within a 15-minute drive of Museum of Brunello and Abbazia di Sant'Antimo.
Mastrojanni Relais
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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.