Montalcino Holidays

Book a Hotel + Flight or Car together to unlock savings

Top 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 59.247.051 ₫ per night from 1 Aug to 2 Aug
59.247.051 ₫
65.480.159 ₫ total
1 Aug - 2 Aug
includes taxes & fees
10/10 Exceptional! (64 reviews)
"Peaceful, Relaxing Stay in Tuscany We had a great experience here. The setting is quiet and secluded—felt like a true escape from everyday life. The golf was excellent, the food was consistently good, and the service was friendly and professional. It is remote, which adds to the charm, but just a ..."

Reviewed on 21 Jun 2025

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
8.8/10 Excellent! (318 reviews)
"Gorgeous property Attentive staff Tranquil setting Fresh culinary standards"

Reviewed on 29 Jun 2025

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Castello di Velona Resort Thermal SPA & Winery
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! (342 reviews)
"Overall very good."

Reviewed on 28 Jun 2025

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SI Montalcino Hotel
See all 7,186 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.

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.

Popular places to visit

Castello Banfi

Castello Banfi

5/5(1 review)

You can enjoy a tasting or tour at Castello Banfi during your travels to Poggio alle Mura. Visit the area's spas or simply enjoy its wineries.

Castello Banfi
Fortress of Montalcino

Fortress of Montalcino

3/5(1 review)

Find out about the history of Montalcino when you take a trip to Fortress of Montalcino. Visit the area's spas or simply enjoy its wineries.

Fortress of Montalcino

Tenuta Greppo Franco Biondi Santi

You can enjoy a tasting or tour at Tenuta Greppo Franco Biondi Santi during your travels to Montalcino. Discover the area's countryside and spas.

Tenuta Greppo Franco Biondi Santi