Montalcino Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Montalcino holiday rentals

B&B Le Scalette di Piazza

B&B Le Scalette di Piazza
Montalcino
9.4 out of 10, Exceptional, (90 reviews)
"Great location and excellent staff. "
Canada
Jacek
B&B Le Scalette di Piazza

Antico Brunello

Antico Brunello
Montalcino
The price is AU$12,198
includes taxes & fees
17 Feb - 18 Feb
Antico Brunello

Borgo Lucignanello Bandini

Borgo Lucignanello Bandini
Montalcino
9.4 out of 10, Exceptional, (12 reviews)
"Beautiful stay "
United States
Marc
The price is AU$513
includes taxes & fees
8 Mar - 9 Mar
Borgo Lucignanello Bandini

Idolina Guest House

Idolina Guest House
Montalcino
9.4 out of 10, Exceptional, (105 reviews)
"Excellent service, ideal location"
United Kingdom
Nigel
The price is AU$157
includes taxes & fees
18 Mar - 19 Mar
Idolina Guest House

La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (133 reviews)
"Spotless, clean. Staff were friendly. Location and view was spectacular"
Australia
Kim
The price is AU$244
includes taxes & fees
24 Feb - 25 Feb
La Locanda di San Francesco

La Piccola Locanda

La Piccola Locanda
Chiusi
8.6 out of 10, Excellent, (9 reviews)
"This was a great place to stay for two nights in late October and to take out and back day trips by train to Siena and Florence on back-to-back days. Very close to the train station - very convenient. Breakfast in the restaurant in the morning was small, but good. Highly recommend this location! It's small, but serviced and supported very well by the staff at the restaurant. "
United States
Jeffery
La Piccola Locanda

Casa di Campagna in Toscana

Casa di Campagna in Toscana
Sovicille
9.4 out of 10, Exceptional, (21 reviews)
"Fantastic experience with friendly hosts and an excellent breakfast! A little rustic here and there but all part of the charm!"
United Kingdom
Alasdair
Casa di Campagna in Toscana

Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.2 out of 10, Wonderful, (79 reviews)
"Fantastic place"
United States
Clifford
The price is AU$309
includes taxes & fees
5 Mar - 6 Mar
Casanova - Panoramic Rooms and Suites

Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (134 reviews)
"Super convenient location steps to the historic center. Possibly the only hotel with its own dedicated secure / covered parking. Well decorated and breakfast was great!"
Canada
Mark
Hotel San Gregorio

Luxury resort in the Tuscan countryside

Luxury resort in the Tuscan countryside
Trequanda
Luxury resort in the Tuscan countryside

Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (51 reviews)
"This property has a lovely view, great garden, attentive staff with good breakfast. Stayed in the cottage and the patio was very sunny and relaxing. "
United States
Lenise
Affitacamere Maria Gabriella

Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso

Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
San Quirico d'Orcia
9.0 out of 10, Wonderful, (46 reviews)
"Our stay was great. "
United States
Elena
Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso

Il Pozzo di Sant'Andrea

Il Pozzo di Sant'Andrea
Siena
9.8 out of 10, Exceptional, (16 reviews)
"Great host, lovely place near Siena"
United Kingdom
Prem
Il Pozzo di Sant'Andrea

Casa Gioia - Casa Olivieri

Casa Gioia - Casa Olivieri
Pienza
The price is AU$155
includes taxes & fees
18 Feb - 19 Feb
Casa Gioia - Casa Olivieri

Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.8 out of 10, Exceptional, (87 reviews)
"Amazing room staff atmoshpehere, there is no other hotel my wife will stay at in the heart of the town."
United States
Michael.
Meublé Il Riccio

Il Battistero Siena - Residenza d'Epoca

Il Battistero Siena - Residenza d'Epoca
Siena City Centre
9.6 out of 10, Exceptional, (196 reviews)
"Great location and friendly staff. "
United States
Parissa
Il Battistero Siena - Residenza d'Epoca

B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (192 reviews)
"Great location"
United Kingdom
Mina
B&B Il Corso

Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (34 reviews)
"Wonderful "
United States
Rocio Q
The price is AU$290
includes taxes & fees
17 Feb - 18 Feb
Delcorto Suites

Artisti del Cavallo Tourism

Artisti del Cavallo Tourism
Foiano della Chiana
8.4 out of 10, Very good, (24 reviews)
"Good house for one night. "
Germany
Heiner
The price is AU$131
includes taxes & fees
19 Mar - 20 Mar
Artisti del Cavallo Tourism

La Locanda Di Cetona

La Locanda Di Cetona
Cetona
9.2 out of 10, Wonderful, (5 reviews)
"A lovely hotel and very welcoming staff. Cetona is a delight. "
Australia
Julian
La Locanda Di Cetona
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.

The Annual Holiday Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Save an average of 15% on thousands of hotels when you're signed in

Top Montalcino Hotel Reviews

Find out more about Montalcino

Everything you need to know about Montalcino holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Montalcino holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Montalcino holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Montalcino holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Montalcino. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Montalcino holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Montalcino holiday rentals we have selected for you start as low as AU$121 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Montalcino rentals

At Expedia, we put the best Montalcino holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Montalcino rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Montalcino holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Montalcino. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Montalcino?

Yes, there are holiday rentals in Montalcino close to Bosco della Ragnaia, or you can select a more secluded option if you're looking for a relaxing stay. Discover why Montalcino is known for its spas and countryside. While you're here, grab a bite or have a drink at the wineries.

What are some of the best holiday rentals that Montalcino has to offer?

The House of Alice, charm and relaxation: This highly rated holiday home rental in Montalcino is located in a rural location, and has a fireplace, a terrace and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a coffee maker. Kick off your shoes and enjoy yourself with a garden and a selection of books.

How many holiday rentals are there in Montalcino?

With 28 Expedia holiday rentals, you're guaranteed to find just the right place for your Montalcino stay.

What’s there to see and do in Montalcino?

Enjoy the outdoors at Val di Merse and Val di Chiana, or simply take in cultural attractions like Museum of Brunello and Civic and Diocesan Museum of Sacred Art of Montalcino. Other places in town to visit include Fortress of Montalcino and Tenuta Greppo Franco Biondi Santi.

What’s a holiday rental in Montalcino like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Montalcino. Holiday rentals offer amenities like kitchens and laundry facilities so your stay will be comfortable. If you're concerned about a clean environment, a holiday rental can offer a sense of seclusion away from shared hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a great choice for family trips or small group gatherings.