Montalcino Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top hotels in Montalcino
Castello di Velona Resort Thermal SPA & Winery
Località Velona Montalcino SI
Fully refundableReserve now, pay when you stay
S$953
25 Aug - 26 Aug
includes taxes & fees
9/10 Wonderful! (367 reviews)
"This property was amazing from the moment we booked. Chiara was extremely helpful with looking into horseback riding and other tours for us. I made a mistake in booking and she caught it and corrected it before we even arrived. She was great. Additionally, the room was beautiful and really clean. ..."
Reviewed on 14 Aug, 2026
Mastrojanni Relais - Small Luxury Hotels of the World
Localita Loreto e San Pio Montalcino SI
S$909
15 Sept - 16 Sept
includes taxes & fees
9.8/10 Exceptional! (77 reviews)
"Perfect, pristine, could not be any better!"
Reviewed on 6 Aug, 2026
Castiglion del Bosco, A Rosewood Hotel
Localita Castiglion del Bosco Montalcino SI
10/10 Exceptional! (80 reviews)
"Best hotel ever."
Reviewed on 27 Jul, 2026
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.
Stay near popular Montalcino attractions
Castello Banfi
9.4/10 (51 reviews)
This medieval estate blends Tuscan tradition with world-renowned winemaking excellence. Sample award-winning Brunello di Montalcino while overlooking rolling vineyards from the restored 18th-century village.
Fortress of Montalcino
9.2/10 (54 reviews)
This pentagonal medieval stronghold was the final bastion of Siena's resistance against Medici conquest. Climb its historic ramparts for panoramic Tuscan views before sampling Brunello wines at the fortress enoteca.
Tenuta Greppo Franco Biondi Santi
8.6/10 (8 reviews)
Birthplace of Italy's prestigious Brunello di Montalcino wine, Tenuta Greppo has defined excellence since 1888. Tour the historic cellars and vineyards where the Biondi-Santi family's winemaking traditions thrive.
Abbazia di Sant'Antimo
9.6/10 (111 reviews)
This medieval Romanesque abbey offers a serene glimpse into monastic life amid Tuscan olive groves. Explore the intricate stone carvings and listen for occasional Gregorian chants echoing through its ancient walls.
Castiglion del Bosco Winery
9.6/10 (5 reviews)
This historic estate, a founding consortium member, produces Italy's finest Brunello di Montalcino wines. Tour the vineyard and cellars before savouring wine pairings with local cheeses amid the Tuscan countryside.
Poggio Antico
9.6/10 (7 reviews)
Perched at one of Montalcino's highest elevations, Poggio Antico produces exceptional Brunello wines in a stunning Tuscan setting. Tour the vineyards and cellar, then sample their distinguished vintages.
Bosco della Ragnaia
10.0/10 (1 review)
Explore the great outdoors at Bosco della Ragnaia, a lovely green space in San Giovanni d'Asso. Take in the museums while you're in the area.
Museum of Brunello
9.4/10 (12 reviews)
Explore Brunello di Montalcino's history through artefacts, photographs, and films at this immersive museum. The guided tour ends at the Brunello Labyrinth, featuring over 200 bottles from local wineries.
What to do in Montalcino
From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
S$139
per adult
98% of travellers recommend
Tasting Tour in One of The Most Beautiful Cellars in the World
S$49
per adult
100% of travellers recommend
Horseback riding through the vineyards in Montepulciano Tuscany
S$118
per adult
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?
- Pick your travel dates: The things you plan to do in Montalcino and your favourite season can help you decide when to go.
- 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.
- 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.
- 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.
