Castellina in Chianti Vacation Packages
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Your Castellina in Chianti Vacation
An easy way to experience this city is with a tailor-made Castellina in Chianti vacation package. Base yourself in the neighborhood of Badia Coltibuono, which is good for families, nature and walking or go someplace else — our package deals are all about you. If sightseeing is on the cards during your trip to Castellina in Chianti, look around well-known attractions like Isole e Olena Winery, Il Molino di Grace Winery and Castello di Radda Winery. Check out Expedia's wide range of travel options and begin planning your ultimate vacation to Castellina in Chianti now.
Top Castellina in Chianti Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Aurum Firenze
Historic Centre of Florence
Price was CA $2,642, price is now CA $1,637 per person
CA $1,637
per person
Aug 8 - Aug 14
found 2 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Florence (FLR)
7.4/10 Good! (1,014 reviews)
It was not entirely clean, the staff don't do much. Breakfast is from the day before. Air conditioning excellent.
Reviewed on Jul 3, 2026
Precise Tale Poggio Alla Sala
Price was CA $6,611, price is now CA $4,066 per person
CA $4,066
per person
Sep 6 - Sep 12
found 7 hours ago
Roundtrip flight included
Montreal (YMQ) to Florence (FLR)
9.6/10 Exceptional! (147 reviews)
It’s a beautiful property, but be aware that it is secluded and that the restaurant menu is quite limited and after a couple of days, we were happy to go elsewhere. The waiting staff was attentive and nice, front desk not as much (maybe the la guard barrier?)
Reviewed on Jun 19, 2026
Residenza Florentia
Historic Centre of Florence
Price was CA $2,733, price is now CA $1,875 per person
CA $1,875
per person
Sep 20 - Sep 26
found 6 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
8.4/10 Very good! (53 reviews)
Staff was helpful, the property was not very well maintained.
Reviewed on Jun 1, 2026
Hotel Caravaggio
Historic Centre of Florence
Price was CA $2,633, price is now CA $1,904 per person
CA $1,904
per person
Sep 20 - Sep 26
found 9 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
9/10 Wonderful! (1,008 reviews)
We enjoyed our stay at Hotel Caravaggio. The location was excellent with a lovely large park in front of the hotel and only 8-10 minutes from the duomo and 6 minute walk from the T2 tram which takes you to the airport. We enjoyed all the surrounding small businesses- shops, cafes, restaurants, etc. The AC worked beautifully and the staff was very helpful. They made great recommendations to us.
Reviewed on Jul 6, 2026
Il Malaspina
Historic Centre of Florence
Price was CA $3,433, price is now CA $2,485 per person
CA $2,485
per person
Sep 6 - Sep 12
found 7 hours ago
Roundtrip flight included
Montreal (YMQ) to Florence (FLR)
9.8/10 Exceptional! (147 reviews)
We had a lovely stay. The room was great and the location was solid.
Reviewed on Jul 3, 2026
Castellina in Chianti Hotel Deals
The Social Hub Florence Lavagnini
Viale Spartaco Lavagnini 70 72 Florence FI
Fully refundableReserve now, pay when you stay
The price is CA $203 per night from Jul 29 to Jul 30
CA $203
CA $246 total
Jul 29 - Jul 30
includes taxes & fees
9/10 Wonderful! (1,441 reviews)
"Great location and great view from the rooftop bar"
Reviewed on Jul 4, 2026
The Social Hub Florence Belfiore
Viale Belfiore, 55 Florence FI
Fully refundableReserve now, pay when you stay
The price is CA $182 per night from Jul 12 to Jul 13
CA $182
CA $223 total
Jul 12 - Jul 13
includes taxes & fees
9.4/10 Exceptional! (613 reviews)
"The location was great- right across the street from the train stop. The staff was friendly and very helpful. We stayed for 2 nights and although the rooftop and hotel were busy, we did not hear any hustle and bustle in the hotel room. The only complaint was there was a musty smell when we got off ..."
Reviewed on Jul 5, 2026
Plus Florence - Hostel
Via Santa Caterina D'Alessandria, 15 Florence FI
Fully refundableReserve now, pay when you stay
The price is CA $115 per night from Jul 12 to Jul 13
CA $115
CA $139 total
Jul 12 - Jul 13
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
"Plus Florence was awesome! The atmosphere is really fun and there are lots of people to meet and hang out with! The room was clean and the ac worked wonderfully! I would definitely go back next time I’m in Florence."
Reviewed on Jun 27, 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 Castellina in Chianti attractions
What to do in Castellina in Chianti
Tuscany in 1 day from Florence: Pisa, San Gimignano & Siena with Lunch
CA $80
per adult
78% of travellers recommend
Chianti Half Day Wine Tour from Florence
CA $36
per adult
88% of travellers recommend
Florence: San Gimignano, Siena, Monteriggioni, Chianti & Lunch with Wine
CA $128
per adult
88% of travellers recommend
Frequently asked questions
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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.
