Montalcino Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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

Your Montalcino Vacation

Say goodbye to the hassle of planning and hello to a Montalcino vacation package. With your travel details organized before you take off, you can focus on discovering the best of this city, starting with Montegiovi, which is great for views, walking and nature. Abbazia di SantAntimo, Tenuta Greppo Franco Biondi Santi and Fortress of Montalcino are just some of the sights worth checking out during your trip to Montalcino. Don't delay visiting this city any longer. The ultimate Montalcino vacation is a couple of clicks away with Expedia.

Top Montalcino Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Villa Liana

Hotel Villa Liana

3 out of 5
Historic Centre of Florence
Price was CA $1,506, price is now CA $1,129 per person
CA $1,129
per person
Dec 1 - Dec 7
found 20 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Florence (FLR)
8.8/10 Excellent! (373 reviews)
My first day/night was not good. I was in a room that faced the traffic. Even with the shutters closed, it did nothing to alleviate the noise. The traffic didn't stop until midnight. The next morning I asked if I could be moved. Thankfully a room facing the quiet courtyard was found. Breakfast was very good, with many choices in a charming historic room.

Reviewed on Oct 14, 2026

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was CA $1,948, price is now CA $1,254 per person
CA $1,254
per person
Dec 1 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Florence (FLR)
7.6/10 Good! (1,003 reviews)
A great budget hotel in a fantastic central location. Despite being so central it was in a side street so quiet at night. Rooms were cleaned daily and breakfast was buffet-style with cereal, fruit, croissants etc. I stayed there for 2 weeks and have no complaints at all. Excellent value for money.

Reviewed on Oct 24, 2026

Eurostars Florence Boutique

Eurostars Florence Boutique

4 out of 5
Historic Centre of Florence
Price was CA $2,203, price is now CA $1,535 per person
CA $1,535
per person
Nov 30 - Dec 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
8.6/10 Excellent! (503 reviews)

Hotel Duomo Firenze

Hotel Duomo Firenze

3 out of 5
Historic Centre of Florence
Price was CA $4,007, price is now CA $2,869 per person
CA $2,869
per person
Dec 28 - Jan 1
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Florence (FLR)
9.2/10 Wonderful! (1,000 reviews)
Everything was perfect,we loved everything,staff very nice

Reviewed on Oct 27, 2026

Grand Hotel Cavour

Grand Hotel Cavour

4 out of 5
Historic Centre of Florence
Price was CA $3,910, price is now CA $2,959 per person
CA $2,959
per person
Dec 28 - Jan 1
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Florence (FLR)
9.4/10 Exceptional! (1,000 reviews)

Ready to book your vacation to Montalcino?

 

Choose your dates

Montalcino Hotel Deals

Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel

5 out of 5
Localita Castiglion del Bosco Montalcino SI
Fully refundableReserve now, pay when you stay
The price is CA $1,768 per night from Nov 4 to Nov 5
CA $1,768
CA $1,961 total
Nov 4 - Nov 5
includes taxes & fees
10/10 Exceptional! (86 reviews)
"Fabulous service. Gorgeous location and pristine hotel. Great food choices and services."

Reviewed on Oct 23, 2026

Castiglion del Bosco, A Rosewood Hotel
Corte Francigena - Apartments

Corte Francigena - Apartments

Via Ferretti Montalcino SI
Fully refundableReserve now, pay when you stay
The price is CA $159 per night from Nov 9 to Nov 10
CA $159
CA $188 total
Nov 9 - Nov 10
includes taxes & fees
Corte Francigena - Apartments
Castello di Velona Resort Thermal SPA & Winery

Castello di Velona Resort Thermal SPA & Winery

5 out of 5
Località Velona Montalcino SI
Fully refundableReserve now, pay when you stay
The price is CA $792 per night from Nov 15 to Nov 16
CA $792
CA $887 total
Nov 15 - Nov 16
includes taxes & fees
9/10 Wonderful! (380 reviews)
"Stayed at the hotel for our honeymoon and it was an incredible experience. The view is simply breathtaking and the castle is extremely charming. Food (breakfast and diner) and wine at the restaurants are high quality, inspired and locally sourced, though expensive. Their Brunello is VERY good. The ..."

Reviewed on Oct 23, 2026

Castello di Velona Resort Thermal SPA & Winery
See all 7,099 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Stay near popular Montalcino attractions

Castello Banfi

9.4/10 (51 reviews)
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.
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

CA $189
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

CA $40
per adult
Montepulciano Wine Tasting in the Tuscan Countryside
Vino Nobile di Montepulciano winery tour and tasting

Vino Nobile di Montepulciano winery tour and tasting

CA $48
per adult
Vino Nobile di Montepulciano winery tour and tasting
See all activities in Montalcino

Frequently asked questions

How much does a Montalcino vacation package cost?
You can pick up a vacation package to this destination from CA $1,129 on Expedia. But how much your vacation to Montalcino costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Montalcino?
December, January and February are great times to look for cheap Montalcino vacation packages. Opting to travel in quieter periods means you can typically find lower prices on accommodations and flights.
How many days is enough for Montalcino?
When planning your Montalcino vacation, a few days will be enough to see all the highlights. Make sure to visit Abbazia di Sant'Antimo — it's one of the major sights in this destination. If you're looking for more adventure, consider basing yourself here and heading off on some tours from Montalcino.
Is it worth booking a vacation package to Montalcino?
Montalcino has everything you need for a memorable getaway — views, nature and bars and pubs are just the start. Whether you want to check out attractions like Fortress of Montalcino and Civic and Diocesan Museum of Sacred Art of Montalcino, or take the road less travelled, you'll have plenty to see and do on your Montalcino vacation.
How to find the best Montalcino package deals?
Begin your search for a Montalcino package deal by entering your destination and preferred travel dates under our "Packages" tab. Then apply a few filters, like "Property type" and "Guest rating," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the perfect Montalcino package deal straight away, simply tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Montalcino escape off to a flying start.
Is it cheaper to book a Montalcino vacation as a package?
You can enjoy significant savings on your Montalcino getaway by booking a tailored vacation package. Check the "Package" heading, then enter your destination and travel dates to view some great hotel prices and airfares. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Montalcino?
Enjoy incredible bargains by reserving your flights early with Expedia. If being spontaneous is more your thing, take advantage of our last-minute deals for an impromptu Montalcino break.
How to plan a trip to Montalcino?

  1. Choose the right time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to visit Montalcino.
  2. Calculate your budget: Ensure you have enough money to cover everything from transportation and food to activities and airfares. Your hotel will probably be the largest expense during your trip to Montalcino.
  3. Set the duration of your trip: Start by listing all the attractions and activities you'd like to experience in Montalcino. Then, estimate how long you'll need for each, including any travel time.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. All that's left now is to find 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.