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Montalcino Vacations from $971

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The Latest Montalcino Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Premium bedding, in-room safe, cribs (free), WiFi (free)
    Oct 21 - Oct 26

    Aurum Uffizi + Flight

    Historic Centre of Florence
    4 nights
    4.0 star property
    7.6/10 - Good (1,001 reviews)
    "Great little hotel in heart of city"
    Reviewed July 30, 2026
    Roundtrip • New York (EWR) - Florence (FLR)
    EWR - FLR • 1 stop FLR - EWR • 2 stops
    $1,374
    $971
    per traveler
    found 8 hours ago
    Aurum Uffizi
  • Exterior
    Sep 5 - Sep 11

    Precise Tale Poggio Alla Sala + Flight

    Montepulciano
    5 nights
    5.0 star property
    9.6/10 - Exceptional (155 reviews)
    "Magical location, pools, staff, property."
    Reviewed July 19, 2026
    Roundtrip • New York (JFK) - Florence (FLR)
    JFK - FLR • 1 stop FLR - JFK • 1 stop
    Save 100% on your flight
    $5,077
    $3,278
    per traveler
    found 14 hours ago
    Precise Tale Poggio Alla Sala
  • Front of property
    Oct 7 - Oct 11

    Albergo Firenze + Flight

    Historic Centre of Florence
    3 nights
    3.0 star property
    9.0/10 - Wonderful (262 reviews)
    Roundtrip • New York (JFK) - Florence (FLR)
    JFK - FLR • 1 stop FLR - JFK • 1 stop
    $1,664
    $1,215
    per traveler
    found 13 hours ago
    Albergo Firenze
  • Interior detail
    Oct 9 - Oct 13

    Alfieri9 + Flight

    Historic Centre of Florence
    3 nights
    3.0 star property
    9.6/10 - Exceptional (170 reviews)
    "More quiet residential area of Firenze in walking distance of center but away from the crowds. No elevator and two flight of stairs."
    Reviewed July 5, 2026
    Roundtrip • New York (EWR) - Florence (FLR)
    EWR - FLR • 1 stop FLR - EWR • 2 stops
    $1,433
    $1,060
    per traveler
    found 9 hours ago
    Alfieri9
  • Daily buffet breakfast for a fee
    Oct 17 - Oct 22

    Grand Hotel Cavour + Flight

    Historic Centre of Florence
    4 nights
    4.0 star property
    9.2/10 - Wonderful (1,003 reviews)
    "The check in lady said"
    Reviewed July 31, 2026
    Roundtrip • New York (NYC) - Florence (FLR)
    JFK - FLR • 1 stop FLR - EWR • 1 stop
    $1,858
    $1,386
    per traveler
    found 20 hours ago
    Grand Hotel Cavour

Discover the most popular places to visit in Montalcino

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.

What to do in Montalcino

Montalcino: Guided Winery Tour and Wine Tasting

Montalcino: Guided Winery Tour and Wine Tasting

$51
per adult
0% of travelers recommend
Montalcino: Guided Winery Tour and Wine Tasting
See all activities in Montalcino

Montalcino Hotel Deals

Seasonal outdoor pool, open 9:30 AM to 7:00 PM, pool umbrellas

SI Montalcino Hotel

SI Montalcino Hotel
3.0 star property
0.7 mi from Montalcino
9.2 out of 10, Wonderful, (399 reviews)
"Excellent hotel and friendly staff. Good location to explore Tuscany."
$104 nightly
The price is $123
Aug 10 - Aug 11
Total with taxes and fees
SI Montalcino Hotel
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.
See all properties in Montalcino

Frequently Asked Questions

How much does a Montalcino vacation package cost?

Offering great value package deals from $971 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?

You're likely to find lower rates and better availability in September, October and December. Take a look at our cheap Montalcino vacation packages and you could land some great off-season deals.

How many days is enough for Montalcino?

Typically, a few days is enough for a Montalcino vacation. With a carefully crafted itinerary, you can see all the popular sights such as Capanna of Cencioni, as well as explore some hidden gems along the way.

Is it worth booking a vacation package to Montalcino?

Whether you want to explore major attractions such as Fortress of Montalcino and Civic and Diocesan Museum of Sacred Art of Montalcino on your Montalcino vacation, or coming for its excellent walking trails, views and history, there's something for everyone here. With so many things to do, you'll soon discover why so many visitors think Montalcino is a good vacation destination.

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. Choose your dates: What you'd like to do in Montalcino and your favorite season can help you decide when to travel.
  2. Set your budget: Factor in costs like flights, food and transportation when working out how much to set aside for your trip to Montalcino. Then, choose a property that works with your budget, whether that's a low-cost option or a more upscale getaway.
  3. Organize your Montalcino escape with our trip planning tool: Search for and book hotels and experiences all in one place. You can also collaborate with family and friends to plan an unforgettable trip to Montalcino together.
  4. Decide your trip length: Consider how much time you'd like to spend discovering Montalcino. Plan your days so you can get to all the attractions and activities you're interested in without rushing.
  5. Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to pick a Montalcino vacation package that brings all your bookings together.
  6. Book activities and experiences ahead of time: Whether it's a ticket to a major attraction or a walking tour, you won't have to worry about missing out on the highlights of Montalcino. Find all the exciting things to do in Montalcino with our dedicated travel guide.

Does Expedia offer Book Now, Pay Later Montalcino vacation packages?

Your Montalcino trip is meant to be a relaxing escape from your busy life, not a reason for money worries. So to allow you a bit more flexibility, we've joined up with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.

Book with confidence

Things to do near Montalcino

Montalcino, Tuscany, is perfect for a romantic and entertaining getaway, offering a range of outdoor activities. Explore the renowned Montalcino wineries with wine tours and tastings, or indulge in spa and body treatments for ultimate relaxation. Don't miss the chance to enjoy local theater and plan a memorable day trip to soak in the stunning landscapes and rich culture of this charming town.

Shopping

For unique gifts and souvenirs, visit RI Crea RE, just 10 miles from Montalcino, or Pinzi Pinzuti, located 15 miles away. If you're up for a drive, check out Valdichiana Outlet Village, 20 miles away, offering a vibrant atmosphere with a mix of shopping and entertainment.

Recreation

Experience tranquility at the Chapel of our Lady of Vitaleta, a luxurious country private club just 7 miles from Montalcino. Indulge in wellness at Terme di Chianciano, a serene spa 17 miles away, or rejuvenate with body treatments at San Giovanni Terme Rapolano, located 16 miles from Montalcino.

Adventure

The Macinaie Ski Lift, located 13 miles from Montalcino, offers thrilling skiing experiences against breathtaking alpine scenery. For adrenaline seekers, the Siena Circuit, situated 18 miles away, features exciting karting races. Additionally, the Saltalbero Adventure Park, 17 miles away, boasts ziplining and ropes courses amidst beautiful outdoor landscapes.

Nightlife

Montalcino offers a charming nightlife with cozy wine bars and local trattorias. Enjoy live music at venues like Il Grappolo, or sip Brunello at La Fortezza. The atmosphere is relaxed, perfect for mingling with locals and savoring Tuscan cuisine under the stars.

Find the best attractions in and around Montalcino

Experience the charm of Montalcino, Tuscany, perfect for a romantic and outdoor getaway. Explore the picturesque piazzas, historic monasteries, and beautiful churches, while immersing yourself in the local culture. Don’t miss the stunning Brunello vineyards, the scenic village of Montalcino, and the majestic fortress. For a comfortable stay, check out the best hotels in the area, ensuring a memorable Italian vacation filled with delightful sights and experiences.

  • Fortress of Montalcino: This historic fortress offers a journey back in time, showcasing stunning architecture and panoramic views of the surrounding vineyards and countryside. The cultural vibe here immerses you in Montalcino's rich history, making it a perfect spot for photography and exploration.
  • Monte Amiata: Just 13 miles from Montalcino, this majestic mountain is ideal for outdoor enthusiasts. With breathtaking scenery, hiking trails, and the thrill of adventure, it offers a perfect escape into nature, whether you're skiing in winter or enjoying wildflower hikes in spring.
  • Abbazia di Sant'Antimo: Nestled in the countryside, this stunning monastery is a serene place to experience spirituality and history. Its Romanesque architecture and tranquil surroundings create a peaceful atmosphere, perfect for reflection and appreciating the local culture.

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.

Tips to save on your trip to Montalcino

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling during the off-peak season (typically December to February) for more affordable package holidays to Montalcino.
  • 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.

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