Montalcino Vacations
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Find the Best Montalcino Vacation Packages
Montalcino Hotel Deals
Castiglion del Bosco, A Rosewood Hotel
Localita Castiglion del Bosco Montalcino SI
Fully refundableReserve now, pay when you stay
₩1,573,431
₩1,745,822 total
Nov 3 - Nov 4
includes taxes & fees
Corte Francigena - Apartments
Via Ferretti Montalcino SI
₩162,822
₩191,142 total
Nov 8 - Nov 9
includes taxes & fees
9.8/10 Exceptional! (19 reviews)
"The unit is very clean, awesome breakfast, beautiful view"
Reviewed on Sep 24, 2026
Castello di Velona Resort Thermal SPA & Winery
Località Velona Montalcino SI
Fully refundableReserve now, pay when you stay
₩757,292
₩848,023 total
Nov 15 - Nov 16
includes taxes & fees
9/10 Wonderful! (378 reviews)
"Amazing views. Relaxing stay! A very romantic hotel, though I was surprised by the number of families there; given its location and amenities, I had assumed it was geared towards couples. That isn't a negative comment, though—it was simply a case of my own mistaken perception."
Reviewed on Sep 27, 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.
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.
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.
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 savoring wine pairings with local cheeses amid the Tuscan countryside.
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.
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.
Museum of Brunello
9.4/10 (12 reviews)
Explore Brunello di Montalcino's history through artifacts, photographs, and films at this immersive museum. The guided tour ends at the Brunello Labyrinth, featuring over 200 bottles from local wineries.
Capanna of Cencioni
10.0/10 (10 reviews)
This family-run Tuscan winery crafts prestigious Brunello di Montalcino wines using traditional methods since 1957. Tour their hillside vineyards and cellars, then enjoy tastings paired with local delicacies.
Frequently asked questions
How much does a Montalcino vacation package cost?
Offering great value package deals on Expedia, you'll be thrilled with how little a vacation 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 vacation packages. Traveling in less busy months means you can generally find lower prices on flights and accommodations.
How many days is enough for Montalcino?
For a Montalcino vacation, 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 vacation package to Montalcino?
Well known for its views, nature and bars and pubs, a Montalcino vacation is a hit with all kinds of travelers. 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 customize your search by "Amenities," "Property type," "Traveler 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 vacation as a package?
You can enjoy significant savings on your next Montalcino getaway by booking a tailored vacation package. Check the "Package" heading, then select your travel dates and destination to see the best airfares and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Montalcino?
If you have your Montalcino vacation 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 favorite season can help you decide when to go.
- Budget wisely: Besides the cost of your accommodations, 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 vacation. 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 vacation 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.
