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.
Villa Costanza Boutique Hotel

Villa Costanza Boutique Hotel

Vittoria Apuana
CA $1,480
per person
Oct 14 - Oct 20
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
9.4/10 Exceptional! (6 reviews)
Beautiful chic hotel. I chose the deluxe room with terrace. The terrace spanned the entire face of the building and was styled as a living room ~ wonderful. The perfect space for my German Shepard. Breakfast was to point with delicious cheeses, grain bread and eggs made to order. Staff was gracious and helpful. The only downside is all of the outdoor windows are lined with bright LED lighting. I like to sleep with windows ajar so this was very inconvenient; lights shone directly into the bedroom.

Reviewed on Apr 29, 2026

Aurum Firenze

Aurum Firenze

Historic Centre of Florence
CA $1,788
per person
Oct 17 - Oct 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Florence (FLR)
7.6/10 Good! (1,003 reviews)
The room was clean, staff reasonably friendly, breakfast breads were stale, air conditioning worked well. Conveniently located for train station

Reviewed on Sep 2, 2026

The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

Historic Centre of Florence
CA $1,548
per person
Oct 26 - Oct 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Florence (FLR)
9.6/10 Exceptional! (592 reviews)
The Moon Hotel exceeded my expectations and is highly recommended. The restaurant services and breakfast offerings were excellent Management and particularly Ivan was absolutely outstanding.

Reviewed on Sep 9, 2026

L'Andana

L'Andana

CA $2,156
per person
Oct 25 - Oct 30
found 10 hours ago
Roundtrip flight included
Toronto (YTO) to Florence (FLR)
9.6/10 Exceptional! (94 reviews)
Excellent place

Reviewed on Sep 9, 2026

Hotel La Scaletta Al Ponte Vecchio

Hotel La Scaletta Al Ponte Vecchio

Historic Centre of Florence
CA $2,605
per person
Oct 12 - Oct 17
found 3 hours ago
Roundtrip flight included
Montreal (YMQ) to Florence (FLR)
9/10 Wonderful! (1,005 reviews)
Great staff it’s got a great location cute historic hotel

Reviewed on Sep 6, 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 $1,058
CA $1,179 total
Sep 27 - Sep 28
includes taxes & fees
9/10 Wonderful! (370 reviews)
"Staying here was a wonderful and truly unique experience. The only reason I’m giving it 4 stars instead of 5 was because of the challenges we had with the air conditioning in our room. That said, the staff really did make an effort to find a workaround for us. While it wasn’t a perfect solution, ..."

Reviewed on Sep 9, 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 $3,285
CA $3,630 total
Oct 8 - Oct 9
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 $668
CA $751 total
Oct 5 - Oct 6
includes taxes & fees
9.8/10 Exceptional! (78 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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Capanna of Cencioni

10.0/10 (10 reviews)
You can enjoy a tasting or tour at Capanna of Cencioni during your travels to 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 $1,480. 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.