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.
Hotel Miceli - Civico 50
Historic Centre of Florence
Price was CA $2,333, price is now CA $1,692 per person
CA $1,692
per person
Jun 2 - Jun 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
9/10 Wonderful! (247 reviews)
I loved everything on and around this property. Sitting at the heart of that shopping district, every place I wanted to visit, was just max 15 mins walking distance.
Reviewed on Dec 29, 2025
Eurostars Florence Boutique
Historic Centre of Florence
Price was CA $2,536, price is now CA $1,786 per person
CA $1,786
per person
Jun 2 - Jun 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
8.6/10 Excellent! (484 reviews)
The room was clean and the staff very accommodating. The breakfast was quite sufficient and had a good variety. The location is great. It's a short walk from the square, shopping and from restaurants.
Reviewed on Dec 13, 2025
Hotel La Scaletta Al Ponte Vecchio
Historic Centre of Florence
Price was CA $4,250, price is now CA $3,010 per person
CA $3,010
per person
Jun 2 - Jun 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
8.8/10 Excellent! (991 reviews)
The hotel was amazing. The location was fantastic for our short city break and the staff on reception could not have been more helpful. Our room was clean and the beds were so comfortable. We got great nights sleeps as it was so quiet. Would highly recommend.
Reviewed on Apr 19, 2026
Monastero di Cortona Hotel & Spa
Cortona Old Town
Price was CA $2,651, price is now CA $1,920 per person
CA $1,920
per person
Jun 2 - Jun 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
10/10 Exceptional! (262 reviews)
Staff was phenomenal!! Great team every accomplished
Reviewed on Apr 20, 2026
Il Rivalta - Place of Charme
Historic Centre of Florence
Price was CA $3,981, price is now CA $2,946 per person
CA $2,946
per person
May 29 - Jun 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
9.4/10 Exceptional! (498 reviews)
Good continental breakfast and great location.
Reviewed on Apr 23, 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 $239 per night from May 3 to May 4
CA $239
CA $285 total
May 3 - May 4
includes taxes & fees
9/10 Wonderful! (1,341 reviews)
Great rooftop gym with views of the skyline! Wish the site mentioned the pool was closed for maintenance (which was the main reason I booked the property) but I still got to enjoy laying in the sun on the rooftop. The courtyard was open and comfortable with nice seating, great spot to have an espresso. ...
Reviewed on Apr 21, 2026
Plus Florence - Hostel
Via Santa Caterina D'Alessandria, 15 Florence FI
Fully refundableReserve now, pay when you stay
The price is CA $103 per night from Apr 26 to Apr 27
CA $103
CA $126 total
Apr 26 - Apr 27
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
Everything was good
Reviewed on Apr 22, 2026
IQ Hotel Firenze
Via Camillo Cavour, 88 Florence FI
Fully refundableReserve now, pay when you stay
The price is CA $316 per night from Apr 25 to Apr 26
CA $316
CA $370 total
Apr 25 - Apr 26
includes taxes & fees
9.6/10 Exceptional! (1,228 reviews)
A superb location, about 10-15 minutes walk to the centre, great breakfast and coffee. The staff were all really friendly and helpful.
Reviewed on Apr 21, 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 Castellina in Chianti
Buondonno Winery
You can enjoy a tasting or tour at Buondonno Winery during your travels to Castellina in Chianti. Discover the beautiful countryside and wineries in this quaint area.
Casa Vinicola Luigi Cecchi
You can enjoy a tasting or tour at Casa Vinicola Luigi Cecchi during your travels to Castellina in Chianti. Discover the beautiful countryside in this walkable area, or enjoy its local tours.
What to do in Castellina in Chianti
Siena, San Gimignano, Monteriggioni & Chianti from Florence
CA $74
per adult
86% of travellers recommend
Florence: San Gimignano, Siena, Monteriggioni, Chianti & Lunch with Wine
CA $128
per adult
88% of travellers recommend
Chianti Half Day Wine Tour from Florence
CA $40
per adult
88% of travellers recommend
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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.
