Brunello di Montalcino Wine Area Vacation Packages

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Top Brunello di Montalcino Wine Area Vacation Deals

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

Aurum Uffizi

Historic Centre of Florence
CA $1,297
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Florence (FLR)
7.6/10 Good! (1,003 reviews)
The room was clean and air conditioning worked well for the size of room. However, the room was a little small for a family of four. The location was one of the best aspects of the hotel: it was right in the historic centre and near all the attractions. Staff were also very helpful, promptly responding to our requests.

Reviewed on Aug 2, 2026

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

CA $3,650
per person
Sep 24 - Sep 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
9.6/10 Exceptional! (155 reviews)
The place it’s an Amazing. Very clean. Is more beautiful than the pictures.

Reviewed on Aug 2, 2026

Hotel La Scaletta Al Ponte Vecchio

Hotel La Scaletta Al Ponte Vecchio

Historic Centre of Florence
CA $1,696
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Florence (FLR)
9/10 Wonderful! (1,002 reviews)
Nice modern decor with Jacuzzi in the room!

Reviewed on Aug 8, 2026

Aurum Firenze

Aurum Firenze

Historic Centre of Florence
CA $1,343
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Florence (FLR)
7.4/10 Good! (1,008 reviews)
The hotel is in a great location in terms of the train station, however the neighbourhood and a street that the hotel is located on is very sketchy. There were no good authentic Italian restaurants or cafes near by. There was often a weird lingering smell in the room and the wifi never worked for us once during our entire stay. The hotel is still walking distance to all the main attractions in just a short 10 or 15 minutes. The room was modern and basic, and we really liked the extra security measures like the front door to the hotel locking and and the door to the elevator and stairs locking as well which can only be unlocked with the room key.

Reviewed on Aug 8, 2026

Hotel Caravaggio

Hotel Caravaggio

Historic Centre of Florence
CA $1,797
per person
Sep 24 - Sep 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
9/10 Wonderful! (1,009 reviews)
Very good location for exploring the beautiful city of Florence. We had no issues with accessing the hotel outside of hours and staff were great. Would definitely return.

Reviewed on Aug 7, 2026

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Brunello di Montalcino Wine Area Hotel Deals

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
CA $872
CA $975 total
Aug 31 - Sep 1
includes taxes & fees
9/10 Wonderful! (365 reviews)
"one of the best place to enjoy Tuscany area. there are 2 very beautiful pool in the top of the hill, and a very nice restaurant facing west where you can see fantastic sunset."

Reviewed on Aug 5, 2026

Castello di Velona Resort Thermal SPA & Winery
Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel

Localita Castiglion del Bosco Montalcino SI
CA $4,200
CA $4,636 total
Sep 2 - Sep 3
includes taxes & fees
10/10 Exceptional! (80 reviews)
"Best hotel ever."

Reviewed on Jul 27, 2026

Castiglion del Bosco, A Rosewood Hotel
Mastrojanni Relais - Small Luxury Hotels of the World

Mastrojanni Relais - Small Luxury Hotels of the World

Localita Loreto e San Pio Montalcino SI
CA $716
CA $804 total
Aug 11 - Aug 12
includes taxes & fees
9.8/10 Exceptional! (77 reviews)
"Perfect, pristine, could not be any better!"

Reviewed on Aug 6, 2026

Mastrojanni Relais - Small Luxury Hotels of the World
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Stay near popular Brunello di Montalcino Wine Area 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.
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Fortress of Montalcino

9.2/10 (54 reviews)
Find out about the history of Montalcino with a stop at Fortress of Montalcino. Visit the area's spas, or simply enjoy its wineries.
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Tenuta Greppo Franco Biondi Santi

8.6/10 (8 reviews)
You can enjoy a tasting or tour at Tenuta Greppo Franco Biondi Santi during your travels to Montalcino. Discover the area's countryside and spas.
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Abbazia di Sant'Antimo

9.6/10 (111 reviews)
You can learn about the history of Montalcino when you stop by Abbazia di Sant'Antimo. Visit the area's spas, or simply enjoy its wineries.
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Castiglion del Bosco Winery

9.6/10 (5 reviews)
You can enjoy a tasting or tour at Castiglion del Bosco Winery during your travels to Castiglione del Bosco.
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Poggio Antico

9.6/10 (7 reviews)
You can enjoy a tasting or tour at Poggio Antico during your travels to Montalcino. Discover the area's countryside and wineries.
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Torrenieri Montalcino Station

9.0/10 (2 reviews)
You can take time to visit Torrenieri Montalcino Station during your travels to Torrenieri. Visit the area's spas, or simply enjoy its wineries.
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Civic and Diocesan Museum of Sacred Art of Montalcino

9.4/10 (6 reviews)
You can spend time exploring the galleries in Civic and Diocesan Museum of Sacred Art of Montalcino during your travels in Montalcino. Discover the area's countryside and wineries.
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Frequently asked questions

How much does a Brunello di Montalcino Wine Area vacation package cost?
We make it easy to travel the world, with Brunello di Montalcino Wine Area packages starting from as little as CA $1,297. You'll have the flexibility to combine your favorite hotels, airlines and car rental. For the ultimate escape, why not add a few experiences and tours to your travel itinerary?
How do I get a cheap travel package to Brunello di Montalcino Wine Area?
Creating your own Brunello di Montalcino Wine Area vacation package with Expedia is a simple way to save. We have more than 550 airlines and 1,000,000 hotels throughout the world. With such a wonderful range to pick from, you'll have no difficulty putting together your next dream vacation.
Where should I stay in Brunello di Montalcino Wine Area?
Close to the action. Many visitors book hotels around top attractions, such as Tenuta Greppo Franco Biondi Santi, Fortress of Montalcino and Capanna of Cencioni.
What are the top hotels in Brunello di Montalcino Wine Area?
One of the top places to stay in Brunello di Montalcino Wine Area is Rosewood Castiglion del Bosco, in the Tavernelle area. Explore the city by day and then kick back in your comfortable room at night.
How far in advance should I book my Brunello di Montalcino Wine Area vacation?
It can be hard to know exactly when the best time is to book your vacation to Brunello di Montalcino Wine Area. But usually the earlier you book, the lower the prices. In some cases, you can secure your flights and hotels up to a year before your departure date. If you're considering a last-minute getaway, no need to stress! There are fabulous deals posted on Expedia all the time.
What does an Expedia Brunello di Montalcino Wine Area travel package include?
Expedia has all you need to lock in Brunello di Montalcino Wine Area escape, but how your package is structured is totally up to you. Pick from any combination of rental cars, flights and hotels. Chasing some tours or experiences to keep you entertained? Once you've made your booking, you can add them too. Whatever your style or budget, there's a package deal to meet your needs.
What should I know before booking a Brunello di Montalcino Wine Area travel package?
You can save a tidy sum by bundling your airfares, hotels and rental cars. Once you've made your booking, you can add on things like sightseeing tours or experiences. Your next awesome adventure is only a couple of clicks away.
Can I choose my airline with a Brunello di Montalcino Wine Area Expedia vacation package?
Yes, the choice is all yours. We have access to over 550 airlines around the world, so you can tailor your Brunello di Montalcino Wine Area adventure according to your travel needs.
If I'm not able to travel, can I cancel my Brunello di Montalcino Wine Area vacation package?
Whether it's your flight or hotel, you can cancel and rebook it. Locked in your Brunello di Montalcino Wine Area vacation package in the last 24 hours? You may be able to make changes or cancellations at no cost. If it's been longer than that, you may incur a fee from your airline, hotel or car rental company. For further information, head to our Customer Service Portal. We'll help you every step of the way.

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