Montalcino Holidays

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Top 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
8.8/10 Excellent! (324 reviews)
"We stayed two nights midway through travelling around Tuscany. It was a lovely peaceful break for us. We felt very pampered by all of the staff who were superb. Dining by the pool area was lovely. A very happy couple of days."

Reviewed on 29 Jul, 2025

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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 S$2,823 per night from 16 Aug to 17 Aug
S$2,823
16 Aug - 17 Aug
includes taxes & fees
10/10 Exceptional! (65 reviews)
"Beautiful property and great service. Was a little disappointed they charge double the price for wine they make in their back yard then I pay here in Montreal."

Reviewed on 3 Aug, 2025

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
9.2/10 Wonderful! (349 reviews)
"The hotel is in a great location, and our room had a partial view of the sea. The bed, unfortunately, was not as comfortable as I think it could be. It was relatively hard, and we had two double beds, rather than a full-size bed. Service was good as was the breakfast."

Reviewed on 23 Jul, 2025

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SI Montalcino Hotel
See all 7,250 properties in Montalcino
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.

Popular places to visit

Abbazia di Sant'Antimo

5/5(1 review)

You can learn about the history of Castelnuovo dell'Abate with a visit to Abbazia di Sant'Antimo. Visit the area's spas or simply enjoy its wineries.

Abbazia di Sant'Antimo

What to do in Montalcino

Val d'Orcia Brunello Wine Tour with Montalcino and Montepulciano

Val d'Orcia Brunello Wine Tour with Montalcino and Montepulciano

S$345
per adult
100% of travellers recommend
Val d'Orcia Brunello Wine Tour with Montalcino and Montepulciano
Brunello di Montalcino small-group Wine Tour

Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena

S$271
per adult
100% of travellers recommend
Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena
small town in Italy

Brunello di Montalcino Small Group Wine Tour from Siena

S$239
per adult
98% of travellers recommend
Brunello di Montalcino Small Group Wine Tour from Siena
See all activities in Montalcino

Frequently asked questions

How much does a Montalcino holiday package cost?
Offering great value package deals on Expedia, you'll be thrilled with how little a holiday to Montalcino costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Montalcino?
December, January and February are the best times to look for cheap Montalcino holiday packages. Travelling in less busy months means you can generally find lower prices on flights and accommodation.
How many days is enough for Montalcino?
For a Montalcino holiday, a few days will be enough to explore the highlights. Make sure to stop by Capanna of Cencioni — it's one of the main sights in this destination. If you're looking for more activities, think about basing yourself here and heading off on some trips from Montalcino.
Is it worth booking a holiday package to Montalcino?
Well known for its views, nature and bars and pubs, a Montalcino holiday is a hit with all kinds of travellers. Be sure to visit major sights like Fortress of Montalcino and Civic and Diocesan Museum of Sacred Art of Montalcino, and consider renting a car for day trips to explore even more.
How to find the best Montalcino package deals?
Bagging a cheap Montalcino package deal is easy with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your maximum budget, add a few filters and see what's available. You can customise your search by "Amenities," "Property type," "Traveller experience" and more. Sort the results by "Price: low to high" to view the most wallet-friendly Montalcino package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Montalcino holiday as a package?
You can enjoy significant savings on your next Montalcino getaway by booking a tailored holiday package. Check the "Package" heading, then select your travel dates and destination to see the best airfares and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a holiday package to Montalcino?
If you have your Montalcino holiday dates finalized, book early to score some terrific deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spontaneous getaways? Our last-minute deals are great for quick escapes.
How to plan a trip to Montalcino?

  1. Pick your travel dates: The things you plan to do in Montalcino and your favourite season can help you decide when to go.
  2. Budget wisely: Besides the cost of your accommodation, you should consider other expenses. These include flights, transportation and food. Also, put aside some extra funds for unexpected costs that may crop up during your trip to Montalcino.
  3. Decide how long to go for: Now that you know more about Montalcino, you can figure out the perfect length of your holiday. Create a rough plan and give yourself enough time for all the things you want to do.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to choose a Montalcino holiday package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.