Brunello di Montalcino Wine Area Vacation Packages 2026 from $996

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The Latest Brunello di Montalcino Wine Area vacation packages

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

Aurum Uffizi

Historic Centre of Florence

$996

per person

Oct 21 - Oct 25

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

7.6/10 Good! (1,003 reviews)

Clean room, convenient location. has AC and lift. Breakfast was ok. Would stay again

Reviewed on Aug 12, 2026

Hotel La Scaletta Al Ponte Vecchio

Historic Centre of Florence

$1,244

per person

Oct 21 - Oct 25

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

9/10 Wonderful! (1,006 reviews)

Precise Tale Poggio Alla Sala

Save 100% on your flight

$3,170

per person

Sep 22 - Sep 27

found 17 hours ago

Roundtrip flight included

Dallas (DFW) to Florence (FLR)

9.6/10 Exceptional! (156 reviews)

The Moon Boutique Hotel & Spa

Historic Centre of Florence

$1,247

per person

Oct 23 - Oct 28

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

9.6/10 Exceptional! (580 reviews)

Stunning hotel and maintained to a spotless standard. Bit of a trek to the centre and parking not cheap but good services just outside (tram, bus) - just takes some working out. We probably didn't need to go for the suite considering the time of year (Sauna and jacuzzi not overly used after stomping streets in near 40deg heat!). Breakfast good and staff super friendly/informative.

Reviewed on Aug 11, 2026

The Rif - Boutique Hotel

Pisa City Centre

$1,646

per person

Oct 9 - Oct 12

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Florence (FLR)

8.8/10 Excellent! (69 reviews)

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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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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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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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Brunello di Montalcino Wine Area Hotel Deals

Castello di Velona Resort Thermal SPA & Winery

Località Velona Montalcino SI

Fully refundableReserve now, pay when you stay

$681 nightly

$761 total

Aug 28 - Aug 29

Total with taxes and fees

9/10 Wonderful! (367 reviews)

"This property was amazing from the moment we booked. Chiara was extremely helpful with looking into horseback riding and other tours for us. I made a mistake in booking and she caught it and corrected it before we even arrived. She was great. Additionally, the room was beautiful and really clean. ..."

Reviewed on Aug 14, 2026

Mastrojanni Relais - Small Luxury Hotels of the World

Localita Loreto e San Pio Montalcino SI

$636 nightly

$711 total

Sep 15 - Sep 16

Total with taxes and fees

9.8/10 Exceptional! (77 reviews)

"Perfect, pristine, could not be any better!"

Reviewed on Aug 6, 2026

Castiglion del Bosco, A Rosewood Hotel

Localita Castiglion del Bosco Montalcino SI

10/10 Exceptional! (80 reviews)

"Best hotel ever."

Reviewed on Jul 27, 2026

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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.