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Top Brunello di Montalcino Wine Area Vacation Deals
Price found within the past 48 hours. Click for updated prices.

Art Hotel Villa Agape - Place of Charme
Oltrarno
Price was CA $1,655, price is now CA $1,395 per person
CA $1,395
per person
Jan 11 - Jan 16
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Florence (FLR)
9.8/10 Exceptional! (1,000 reviews)
Amazing property highly recommended
Reviewed on Nov 7, 2026


Villa Tolomei Hotel & Resort
Oltrarno
Price was CA $3,811, price is now CA $3,039 per person
CA $3,039
per person
Dec 27 - Jan 2
just found
Roundtrip non-stop flight included
Montreal (YUL) to Florence (FLR)
8.8/10 Excellent! (445 reviews)
The property was lovely. A former 15th(?) century monastery located on a hilltop overlooking parts of Florence. Surrounded by olive and fruit trees, and gardens. It's past the Roman gate, about a 30 euro cab ride from the center of town. Though they didn't tell us until we asked, there's a shuttle that will take you down the hill to the Roman Gate where taxis and busses can be found.
We arrived just after the hotel restaurant had closed for the afternoon by a minute. They were kind/professional enough to serve us something from the cold selections; and it was delicious. The breakfast buffet the next day was outstanding with excellent selection and quality. The usual 3 or 4 hot items: scrambled eggs, breakfast meat, roasted tomatoes. Where it really excelled were the cold items. Fresh juices, local yogurts, fruits, meats, cured salmon. Perfectly executed pastry, and breads with honeycomb stood out. Dinner was a mixed bag.
The big downside was that we arrived in October. Apparently, the property has to commit each year to the local authorities when they will close the pool, and switch from A/C to heat in the rooms. We booked through Expedia and therefore information on things may be incomplete. No mention that the pool was closed. It was almost worse that it was too warm to sleep well at night. We had even contacted the front desk after the first night and they said they'd send someone to look at it. Which we learned later made no sense BC it was off for the season.
Reviewed on Nov 6, 2026

The Hoxton, Florence
Historic Centre of Florence
Price was CA $3,720, price is now CA $2,971 per person
CA $2,971
per person
Dec 27 - Jan 2
just found
Roundtrip non-stop flight included
Montreal (YUL) to Florence (FLR)
9.4/10 Exceptional! (370 reviews)
Nice quiet location with well appointed rooms.
Reviewed on Nov 7, 2026

Hotel Calimala Florence
Historic Centre of Florence
Price was CA $2,034, price is now CA $1,651 per person
CA $1,651
per person
Jan 11 - Jan 16
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Florence (FLR)
9.6/10 Exceptional! (1,004 reviews)
Great hotel, good location, staff was great, would recommend.
Reviewed on Nov 7, 2026
Brunello di Montalcino Wine Area Hotel Deals

Castiglion del Bosco, A Rosewood Hotel
Localita Castiglion del Bosco Montalcino SI
Fully refundableReserve now, pay when you stay
The price is CA $1,275 per night from Dec 5 to Dec 6
CA $1,275
CA $1,418 total
Dec 5 - Dec 6
includes taxes & fees
10/10 Exceptional! (87 reviews)
"Unique property well maintained and quite Serene , great staff"
Reviewed on Oct 30, 2026

Corte Francigena - Apartments
Via Ferretti Montalcino SI
Fully refundableReserve now, pay when you stay
The price is CA $164 per night from Nov 9 to Nov 10
CA $164
CA $192 total
Nov 9 - Nov 10
includes taxes & fees

Castello di Velona Resort Thermal SPA & Winery
Località Velona Montalcino SI
Fully refundableReserve now, pay when you stay
The price is CA $708 per night from Nov 30 to Dec 1
CA $708
CA $794 total
Nov 30 - Dec 1
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
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
Frequently asked questions
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- Visit Val d'Orcia
- Pienza Cathedral
- Visit Lupompesi
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- Art Studio di Adelina Quadri
- Visit Casciano di Murlo
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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.







