Montalcino Vacations from ¥289,042

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ¥109,000 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Montalcino Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Aurum Firenze

Aurum Firenze

Historic Centre of Florence
¥289,042
per person
Dec 25 - Dec 29
found 20 hours ago
Roundtrip flight included
Tokyo (TYO) to Florence (FLR)
7.4/10 Good! (1,015 reviews)
We encountered ants twice. We were given a bottle of raid and kept food in fridge or hanging up high. Appreciated the 24 hour service. There was a medical emergency and the front desk took great care of us. And they had no problem with us staying for an extra 2 days.

Reviewed on Oct 12, 2026

Aurum Uffizi

Aurum Uffizi

Historic Centre of Florence
¥291,998
per person
Dec 25 - Dec 29
found 20 hours ago
Roundtrip flight included
Tokyo (TYO) to Florence (FLR)
7.6/10 Good! (1,003 reviews)
Hotel La Scaletta Al Ponte Vecchio

Hotel La Scaletta Al Ponte Vecchio

Historic Centre of Florence
¥326,704
per person
Dec 25 - Dec 29
found 20 hours ago
Roundtrip flight included
Tokyo (TYO) to Florence (FLR)
9/10 Wonderful! (1,002 reviews)
Great location! Staff was friendly and helpful. Had a wonderful stay Highly recommend!

Reviewed on Oct 11, 2026

Hotel degli Orafi

Hotel degli Orafi

Historic Centre of Florence
¥336,176
per person
Dec 25 - Dec 29
found 20 hours ago
Roundtrip flight included
Tokyo (TYO) to Florence (FLR)
9.6/10 Exceptional! (1,005 reviews)
Breakfast was delicious.Daurio was very helpful .the room needs maintenance and updating.front desk staff was very good as well as the porter .need extra towels for hair washing and air conditioner needs to be checked functioning beforehand and fix if needed before assignment to guests

Reviewed on Oct 13, 2026

Hotel Ginori al DUOMO

Hotel Ginori al DUOMO

Historic Centre of Florence
¥311,614
per person
Dec 25 - Dec 29
found 20 hours ago
Roundtrip flight included
Tokyo (TYO) to Florence (FLR)
8.8/10 Excellent! (63 reviews)
The hotel is close to everything. Great restaurants near by too. Highly recommend.

Reviewed on Oct 5, 2026

Find the Best Montalcino Vacation Packages

Things to do near Montalcino

Shopping

Montalcino offers unique shopping experiences with local stores like RI Crea RE, located 16.1km away. If you're up for a drive, check out Valdichiana Outlet Village, 32.2km away, for a vibrant shopping atmosphere, or visit Pinzi Pinzuti, 24.1km away, for more local treasures.

Recreation

Experience luxury at the Chapel of Our Lady of Vitaleta, a serene country club offering exquisite surroundings. Enjoy rejuvenating treatments at San Giovanni Terme Rapolano, known for its soothing body treatments. Finally, unwind at Terme di Chianciano, a spa retreat perfect for relaxation and wellness in Tuscany.

Adventure

Experience thrilling adventures in Montalcino. Hit the slopes at Macinaie Ski Lift, located 20.9km away, or challenge yourself at the Amiata Freeride Bike Resort, also 20.9km distant. For a unique thrill, try karting at the Siena Circuit, located 29.0km from Montalcino.

Nightlife

Montalcino offers a charming nightlife with cozy wine bars and vibrant restaurants. Visit Enoteca la Fortezza for exquisite local wines, or enjoy a traditional meal at Trattoria Il Grappolo Blu. For a relaxed evening, stroll through the picturesque streets, soaking in the enchanting Tuscan atmosphere.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in Montalcino

Montalcino, Tuscany, is perfect for romantic and outdoor getaways, offering a blend of culture and entertainment. Explore charming squares, monasteries, and cathedrals while indulging in the local wine scene. Don't miss the Montalcino Fortress, renowned wineries, and picturesque wine estates. The village itself is a delightful spot to experience the local charm and rich heritage of this stunning region.

  • Abbazia di Sant'Antimo: Nestled in the stunning Tuscan countryside, this ancient monastery enchants visitors with its serene atmosphere and beautiful Romanesque architecture. Experience the peaceful chants of the monks during services, which add to the cultural vibes of this spiritual haven.
  • Museum of Brunello: A must-visit for wine lovers, this museum offers an engaging exploration of the Brunello di Montalcino wine-making process. Learn about the region's history, viticulture, and the art of wine through interactive exhibits and tastings.
  • Fortress of Montalcino: Standing proudly atop a hill, this historic fortress provides breathtaking views of the surrounding landscape. Wander through its ancient walls and immerse yourself in Montalcino's rich history while enjoying the stunning vistas.

Best time to go to Montalcino

The best time to visit Montalcino is dependent on what kind of holiday you are seeking. July and August are its hottest month on average. At the time of August, visitor numbers are average and weather is sunny. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January39.4°F (4.1°C)Light RainMostly SunnyAverageSlightly Low
February40.6°F (4.8°C)Light RainMostly SunnyAverageSlightly Low
March45.0°F (7.2°C)Light RainMostly SunnyModerately HighAverage
April50.9°F (10.5°C)Light RainMostly SunnyModerately HighAverage
May57.4°F (14.1°C)Light RainMostly SunnyAverageAverage
June66.7°F (19.3°C)Light RainSunnyAverageSlightly High
July73.0°F (22.8°C)No RainSunnyAverageSlightly High
August73.0°F (22.8°C)No RainSunnyAverageAverage
September64.8°F (18.2°C)Light RainMostly SunnyModerately HighSlightly High
October56.7°F (13.7°C)Light RainMostly SunnyAverageAverage
November48.6°F (9.2°C)Light RainMostly SunnyModerately LowAverage
December42.1°F (5.6°C)Light RainMostly SunnyModerately LowSlightly Low

Tips to save on your trip to Montalcino

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Montalcino.
  • Consider traveling to Montalcino during the low season (December to February) for more affordable options.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Montalcino Hotel Deals

Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel

Localita Castiglion del Bosco Montalcino SI
Fully refundableReserve now, pay when you stay
¥209,349
¥232,056 total
Nov 5 - Nov 6
includes taxes & fees
Castiglion del Bosco, A Rosewood Hotel
Corte Francigena - Apartments

Corte Francigena - Apartments

Via Ferretti Montalcino SI
Fully refundableReserve now, pay when you stay
¥17,419
¥20,580 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

Corte Francigena - Apartments
Castello di Velona Resort Thermal SPA & Winery

Castello di Velona Resort Thermal SPA & Winery

Località Velona Montalcino SI
Fully refundableReserve now, pay when you stay
¥89,511
¥100,235 total
Nov 3 - Nov 4
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

Castello di Velona Resort Thermal SPA & Winery
See all 7,158 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.

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.
See properties

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.
See properties

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.
See properties

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.
See properties

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.
See properties

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.
See properties

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.
See properties

Civic and Diocesan Museum of Sacred Art of Montalcino

9.4/10 (6 reviews)
This intimate museum houses medieval treasures from Sienese masters like Simone Martini in a 13th-century convent. Admire gold-ground paintings and wooden sculptures that showcase Tuscany's sacred art heritage.
See properties

What to do in Montalcino

3 Regions in 1 Day from Rome with Tuscany Wine Tasting & Lunch

From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch

¥19,639
per adult
98% of travellers recommend
From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
Montepulciano Wine Tasting in the Tuscan Countryside

Montepulciano Wine Tasting in the Tuscan Countryside

¥4,504
per adult
Montepulciano Wine Tasting in the Tuscan Countryside
Montepulciano Gran Tour

Montepulciano Gran Tour

¥2,703
per adult
Montepulciano Gran Tour
See all activities in Montalcino

Frequently asked questions

How much does a Montalcino vacation package cost?
Offering great value package deals from ¥289,042 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?
  1. Pick your travel dates: The things you plan to do in Montalcino and your favorite season can help you decide when to go.
  2. 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.
  3. 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.
  4. 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.