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, SI
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
INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING

INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING

Montepulciano
Book a stay at this family-friendly vacation home in Montepulciano. Enjoy a water park, a garden, and patios. Popular attractions Torre del Pulcinella and Dome ...
INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING
Farmhouse in the greenery of the Tuscany countryside with private pool and view

Farmhouse in the greenery of the Tuscany countryside with private pool and view

Murlo
Stay at this vacation home in Murlo. Enjoy free WiFi, private pools, and a garden. Popular attractions Castello di Montepescini and Castiglion del Bosco Winery ...
Farmhouse in the greenery of the Tuscany countryside with private pool and view
Save an average of 15% on thousands of hotels when you're signed in
Porcilaia tiny countryside property, shared pool, ideal base to discover Tuscany

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

Siena
Stay at this vacation home in Siena. Enjoy free WiFi, private pools, and a garden. Popular attractions Siena Cathedral and Piazza del Campo are located ...
Porcilaia tiny countryside property, shared pool, ideal base to discover Tuscany
Beautiful home in Sarteano with WiFi

Beautiful home in Sarteano with WiFi

Via di Moggiano 17, Sarteano
Stay at this vacation home in Sarteano. Enjoy free WiFi, balconies, and cable/satellite TV service. Popular attractions Archaeological Museum of Sarteano and ...
Beautiful home in Sarteano with WiFi
Casa Fontelunga, Tuscan holiday villa with private pool

Casa Fontelunga, Tuscan holiday villa with private pool

cortona
Stay at this vacation home in Cortona. Enjoy free WiFi, private pools, and a garden. Popular attractions Santa Maria delle Grazie and Villa Bramasole are located ...
Casa Fontelunga, Tuscan holiday villa with private pool
Charming apartment in the Historic Center of Siena

Charming apartment in the Historic Center of Siena

Siena
Stay at this vacation home in Siena. Enjoy free WiFi, bathrobes, and an in-room coffeemaker. Popular attractions Piazza del Campo and Siena Cathedral are located ...
Charming apartment in the Historic Center of Siena
Villa surrounded by greenery a few minutes and in agreement with the Terme di Saturnia

Villa surrounded by greenery a few minutes and in agreement with the Terme di Saturnia

semproniano
Stay at this vacation home in Semproniano. Enjoy a garden, tennis courts, and patios. Popular attractions Terme di Saturnia and Cascate del Mulino are located ...
Villa surrounded by greenery a few minutes and in agreement with the Terme di Saturnia
Beautiful stone house with garden and private pool.

Beautiful stone house with garden and private pool.

Sovicille - Siena
Stay at this vacation home in Siena. Enjoy free WiFi, private pools, and a garden. Popular attractions Siena Cathedral and Piazza del Campo are located ...
Beautiful stone house with garden and private pool.
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
1335 Holiday Homes
Lowest Price
NZ$274
Highest Price
NZ$2,379
Popular accommodation
Borgo Argiano, INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING, Farmhouse in the greenery of the Tuscany countryside with private pool and view, Porcilaia tiny countryside property, shared pool, ideal base to discover Tuscany, Beautiful home in Sarteano with WiFi, Casa Fontelunga, Tuscan holiday villa with private pool, Charming apartment in the Historic Center of Siena, Villa surrounded by greenery a few minutes and in agreement with the Terme di Saturnia, Beautiful stone house with garden and private pool.

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$2,379 per night from 6 Apr to 7 Apr
NZ$2,379
includes taxes & fees
6 Apr - 7 Apr
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
The price is NZ$1,154 per night from 17 Apr to 18 Apr
NZ$1,154
includes taxes & fees
17 Apr - 18 Apr
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
Mastrojanni Relais

Mastrojanni Relais

Localita Loreto e San Pio, Castelnuovo dell'Abate, Montalcino, SI
Fully refundableReserve now, pay when you stay
The price is NZ$725 per night from 29 Apr to 30 Apr
NZ$725
includes taxes & fees
29 Apr - 30 Apr
Book a stay at this business-friendly farm stay in Montalcino. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Abbazia di Sant'Antimo ...
Mastrojanni Relais
Save an average of 15% on thousands of hotels when you're signed in
SI Montalcino Hotel

SI Montalcino Hotel

3 out of 5
Via Osticcio 21, Montalcino, SI
Fully refundableReserve now, pay when you stay
The price is NZ$274 per night from 13 Apr to 14 Apr
NZ$274
includes taxes & fees
13 Apr - 14 Apr
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
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.