Castiglione del Bosco Vacation Packages
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Your Castiglione del Bosco Vacation
Take the guesswork out of travel planning with a Castiglione del Bosco vacation package. A great neighborhood to stay in this vibrant city is Poggioferro, which is great for views and much more. Like to start exploring your surroundings? Tenuta Greppo Franco Biondi Santi, Fortress of Montalcino and Museum of Brunello are among the top places to visit during your trip to Castiglione del Bosco. That dream Castiglione del Bosco vacation is just clicks away. Search flights, accommodations and more on Expedia for an adventure that's tailored just for you.
Top Castiglione del Bosco Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Aurum Uffizi
Historic Centre of Florence
Price was CA $2,717, price is now CA $1,649 per person
CA $1,649
per person
May 27 - May 31
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Florence (FLR)
7.6/10 Good! (1,006 reviews)
The room was clean and newly renovated. Having breakfast included was great for a quick bite so I could focus on exploring instead of searching and waiting in line. Would definitely recommend a stay here
Reviewed on Apr 9, 2026
Precise Tale Poggio Alla Sala
Price was CA $4,250, price is now CA $2,657 per person
CA $2,657
per person
May 29 - Jun 1
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
9.4/10 Exceptional! (124 reviews)
Absolutely an amazing stay. Very charming and well kept. Essentially a resort with a palatial feel. Loved walking the grounds and relaxing. Excellent restaurant, breakfast was included. The setting is quiet and beautiful. Will book again.
Reviewed on Apr 13, 2026
EXE Toscana
Lucca Historical Center
Price was CA $3,722, price is now CA $2,492 per person
CA $2,492
per person
May 19 - May 25
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
8.4/10 Very Good! (822 reviews)
Room was run down and the breakfast was included in the past but not now. Staff said that the name change and rebranding was meant to attract business people but there were no working outlets in the room and no usb or other charging outlets apart from one socket in the bathroom. Very inconvenient. The place was much nicer to stay at in the past 15 years but has been let down by its owners sadly.
Reviewed on Apr 14, 2026
The Moon Boutique Hotel & Spa
Historic Centre of Florence
Price was CA $3,983, price is now CA $2,738 per person
CA $2,738
per person
Jun 8 - Jun 13
found 5 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Florence (FLR)
9.6/10 Exceptional! (515 reviews)
Five STAR! Amazing Hotel! Spa Perfecto! Lovely Stay!
Reviewed on Apr 16, 2026
The Hoxton Florence
Historic Centre of Florence
Price was CA $3,670, price is now CA $2,539 per person
CA $2,539
per person
Jun 5 - Jun 11
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Florence (FLR)
9.6/10 Exceptional! (241 reviews)
The Hoxton never disappoints. 3rd stay at a Hoxton after Rome and Edinburgh. They are all on par. The staff are lovely. The rooms are gorgeous and just the whole vibe of the place is good. Slightly out from the centre about a 15 minute walk to the Duomo but nice as quiet. Coffee shop in the hotel served nice coffee and there was a small pizzeria over the road ran by the loveliest old man. Drinks in the restaurant were also delicious.
Reviewed on Apr 15, 2026
Castiglione del Bosco Hotel Deals
Castiglion del Bosco, A Rosewood Hotel
Localita Castiglion del Bosco Montalcino SI
The price is CA $2,439 per night from Apr 29 to Apr 30
CA $2,439
CA $2,699 total
Apr 29 - Apr 30
includes taxes & fees
10/10 Exceptional! (75 reviews)
If you don’t like th it s place, then there will never be a place on earth that you like.. it’s actually above a 5 star!! Over the top service.. food seasons breakfast fantastic…fell very lucky to have stayed here.. thank you
Reviewed on Apr 8, 2026
Hotel Athena
P Mascagni 55 Siena SI
Fully refundableReserve now, pay when you stay
The price is CA $279 per night from Apr 23 to Apr 24
CA $279
CA $314 total
Apr 23 - Apr 24
includes taxes & fees
9.2/10 Wonderful! (1,012 reviews)
Cafeteria buffet breakfast. Loads of food. But we didn't come to Italy to eat American-style big breakfasts. Everything else was fine.
Reviewed on Apr 15, 2026
Palazzo Ravizza
Pian dei Mantellini 34 Siena SI
Fully refundableReserve now, pay when you stay
The price is CA $305 per night from Apr 21 to Apr 22
CA $305
CA $344 total
Apr 21 - Apr 22
includes taxes & fees
9.4/10 Exceptional! (778 reviews)
Excellent all around
Reviewed on Apr 15, 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.
Discover the most popular places to visit in Castiglione del Bosco
Tenuta Greppo Franco Biondi Santi
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.
Fortress of Montalcino
Find out about the history of Montalcino with a stop at Fortress of Montalcino. Visit the area's spas, or simply enjoy its wineries.
What to do in Castiglione del Bosco
From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
CA $124
per adult
98% of travellers recommend
Seggiano: Guided Tour of the Olive Grove and Food Tasting
CA $40
per adult
Montepulciano Wine Tasting in the Tuscan Countryside
CA $39
per adult
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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.
