Book Holiday Homes in Montalcino

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Montalcino

Borgo Argiano

Borgo Argiano

Loc. Argiano, Pianella, Castelnuovo Berardenga, Siena
Book a stay at this business-friendly vacation home in Castelnuovo Berardenga. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Piazza ...
Borgo Argiano
The House of Alice, charm and relaxation

The House of Alice, charm and relaxation

Montalcino (SI)
The price is NZ$320 per night from 2 Dec to 3 Dec
NZ$320
includes taxes & fees
2 Dec - 3 Dec
Stay at this vacation home in Montalcino. Enjoy cable/satellite TV service, an in-room coffeemaker, and in-room fireplaces. Popular attractions Abbazia di Sant'Antimo ...
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
Stay at this vacation home in Sarteano. Enjoy private pools, a garden, and balconies. Popular attractions Archaeological Museum of Sarteano and Sarteano Castle ...
Welcome to Sarteano Look forward to a holiday in Italy.
Save an average of 15% on thousands of hotels when you're signed in
The Gelda house, relax with a view

The Gelda house, relax with a view

Castelnuovo dell'Abate
The price is NZ$254 per night from 2 Dec to 3 Dec
NZ$254
includes taxes & fees
2 Dec - 3 Dec
Stay at this vacation home in Montalcino. Enjoy an in-room coffeemaker and in-room fireplaces. Popular attractions Abbazia di Sant'Antimo and 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
Stay at this vacation home in Cortona. Enjoy patios, an in-room coffeemaker, and air conditioning. Popular attractions Piazza della Repubblica and Palazzo Comunale ...
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
Stay at this vacation home in Roccastrada. Enjoy free breakfast, free WiFi, and private pools. Popular attractions Torre del Belvedere and Church of Saints Stephen ...
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
Stay at this vacation home in Castiglione d'Orcia. Enjoy free WiFi, balconies, and in-room fireplaces. Popular attractions Fortress of Tentennano and Piazza ...
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
Stay at this vacation home in Cortona. Enjoy private pools, a garden, and balconies. Popular attractions Santa Maria delle Grazie and Giuseppe Garibaldi Memorial ...
Podere Casorbica with free parking, large garden, swimming pool.
Townhouse in ancient tower in medieval Cetona

Townhouse in ancient tower in medieval Cetona

Cetona
Stay at this vacation home in Cetona. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Archaeological Museum of Sarteano and Sarteano ...
Townhouse in ancient tower in medieval Cetona
Don't see what you're looking for?
See all available properties in Montalcino
View all properties
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
NZ$254
Highest Price
NZ$1,916
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 NZ$1,916 per night from 6 Dec to 7 Dec
NZ$1,916
includes taxes & fees
6 Dec - 7 Dec
Stay at this 5-star luxury hotel in Montalcino. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Castiglion del Bosco Winery and Corte ...
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 NZ$843 per night from 2 Dec to 3 Dec
NZ$843
includes taxes & fees
2 Dec - 3 Dec
Stay at this 5-star luxury hotel in Montalcino. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Abbazia di Sant'Antimo and Museum of Brunello ...
Castello di Velona Resort Thermal SPA & Winery
SI Montalcino Hotel

SI Montalcino Hotel

3 out of 5
Via Osticcio 21, Montalcino, SI
Stay at this 3-star hotel in Montalcino. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
SI Montalcino Hotel
Save an average of 15% on thousands of hotels when you're signed in
Hotel Dei Capitani

Hotel Dei Capitani

3 out of 5
Via Lapini 6, Montalcino, SI
The price is NZ$259 per night from 23 Nov to 24 Nov
NZ$259
includes taxes & fees
23 Nov - 24 Nov
Stay at this 3-star hotel in Montalcino. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
Hotel Dei Capitani
Don't see what you're looking for?
See all available properties in Montalcino
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.