Brunello di Montalcino Wine Area Holidays

Photo by Xandrah Fuentes

  • Plan, book, travel with confidence

  • Better together

    Save up to €900 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

Top Flight + Hotel Deals in Brunello di Montalcino Wine Area

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

Villa Olmi Firenze

€1,211
per person
6 Jan - 10 Jan
found 12 hours ago
Return direct flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
9.4/10 Exceptional! (807 reviews)
Plaza Hotel Lucchesi

Plaza Hotel Lucchesi

Historic Centre of Florence
€1,337
per person
6 Jan - 10 Jan
found 12 hours ago
Return direct flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
9.4/10 Exceptional! (1,002 reviews)
Hotel was wonderful. Stayed in the superior room which had a beautiful view over the city. Staff were incredibly helpful and the rooftop bar was fantastic.

Reviewed on 21 Oct 2026

Bernini Palace

Bernini Palace

Historic Centre of Florence
€1,440
per person
6 Jan - 10 Jan
found 12 hours ago
Return direct flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
9.8/10 Exceptional! (1,006 reviews)
We were very happy with our stay at the bernini Palace. The hotel waas beautifully appointed, and the staff was helpful and friendly.

Reviewed on 24 Oct 2026

Hotel L'Orologio Firenze

Hotel L'Orologio Firenze

Historic Centre of Florence
€1,284
per person
6 Jan - 10 Jan
found 12 hours ago
Return direct flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
9.6/10 Exceptional! (1,000 reviews)
It gave a old school elegant feel. The rooms was very spacious and the staff was friendly and informative.

Reviewed on 23 Oct 2026

Hotel degli Orafi

Hotel degli Orafi

Historic Centre of Florence
€1,427
per person
6 Jan - 10 Jan
found 12 hours ago
Return direct flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
9.6/10 Exceptional! (1,005 reviews)
Everything was wonderful! Perfect location, beautiful rooms and the breakfast room looks like a museum with an incredible breakfast buffet. The staff couldn't have been more helpful. I watched the sunset from the rooftop bar and listened to opera coming from the plaza below. Fantastic experience!

Reviewed on 24 Oct 2026

Top hotels in Brunello di Montalcino Wine Area

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
€1,235
3 Nov - 4 Nov
includes taxes & fees
10/10 Exceptional! (86 reviews)
"Fabulous service. Gorgeous location and pristine hotel. Great food choices and services."

Reviewed on 23 Oct 2026

Castiglion del Bosco, A Rosewood Hotel
Corte Francigena - Apartments

Corte Francigena - Apartments

Via Ferretti Montalcino SI
Fully refundableReserve now, pay when you stay
€127
1 Nov - 2 Nov
includes taxes & fees
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
€565
15 Nov - 16 Nov
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 23 Oct 2026

Castello di Velona Resort Thermal SPA & Winery
See all 5,424 properties in Brunello di Montalcino Wine Area
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 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.
See properties

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.
See properties

Fortress of Montalcino

9.2/10 (54 reviews)
Find out about the history of Montalcino when you take a trip to Fortress of Montalcino. Visit the area's spas or simply enjoy its wineries.
See properties

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.
See properties

Abbazia di Sant'Antimo

9.6/10 (111 reviews)
You can learn about the history of Montalcino with a visit to Abbazia di Sant'Antimo. Visit the area's spas or simply enjoy its wineries.
See properties

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.
See properties

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.
See properties

Civic and Diocesan Museum of Sacred Art of Montalcino

9.4/10 (6 reviews)
You can spend time browsing the exhibits at Civic and Diocesan Museum of Sacred Art of Montalcino during your travels in Montalcino. Discover the area's countryside and wineries.
See properties

Frequently asked questions

How much does a Brunello di Montalcino Wine Area holiday package cost?
We make it easy to travel the world, with Brunello di Montalcino Wine Area packages starting from as little as €1,211. You'll have the flexibility to combine your favourite 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 holiday 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 holiday.
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 holiday?
It can be hard to know exactly when the best time is to book your holiday 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 holiday 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 holiday package?
Whether it's your flight or hotel, you can cancel and rebook it. Locked in your Brunello di Montalcino Wine Area holiday 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.

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.