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

Aurum Firenze

4 out of 5
Historic Centre of Florence
Price was CA $2,095, price is now CA $1,375 per person
CA $1,375
per person
Apr 3 - Apr 7
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Florence (FLR)
7.6/10 Good! (1,002 reviews)
Yes, to both questions. Wi-fi needs work.

Reviewed on Feb 7, 2026

Grand Hotel Cavour

Grand Hotel Cavour

4 out of 5
Historic Centre of Florence
Price was CA $3,662, price is now CA $2,543 per person
CA $2,543
per person
May 1 - May 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
9.2/10 Wonderful! (1,002 reviews)
Everything was wonderful. The staff was so helpful. I didn’t eat breakfast so I don’t know how it was

Reviewed on Feb 10, 2026

Il Rivalta - Place of Charme

Il Rivalta - Place of Charme

4 out of 5
Historic Centre of Florence
Price was CA $3,505, price is now CA $2,469 per person
CA $2,469
per person
May 1 - May 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
9.2/10 Wonderful! (420 reviews)
Our room was lovely, clean and well appointed. The staff were very friendly and very helpful!, breakfast was amazing, they cater for everyone. The restaurant staff really friendly and accommodating, we had a birthday meal there which they made extra special too, and overall our stay was made better ( if that’s possible) due to the above. Grazie Mille.

Reviewed on Jan 29, 2026

Relais Uffizi, Tailor made Hotel

Relais Uffizi, Tailor made Hotel

4 out of 5
Historic Centre of Florence
Price was CA $3,223, price is now CA $2,336 per person
CA $2,336
per person
May 1 - May 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
9.4/10 Exceptional! (120 reviews)
Phenomenal location!

Reviewed on Oct 18, 2025

Hotel degli Orafi

Hotel degli Orafi

4 out of 5
Historic Centre of Florence
Price was CA $2,969, price is now CA $2,158 per person
CA $2,158
per person
Mar 21 - Mar 27
found 8 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Florence (FLR)
9.6/10 Exceptional! (1,001 reviews)
Very clean room and great amenities.

Reviewed on Jan 30, 2026

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Castellina in Chianti Hotel Deals

c-hotels Ambasciatori

c-hotels Ambasciatori

4 out of 5
Via Luigi Alamanni 3 Florence FI
Fully refundableReserve now, pay when you stay
The price is CA $165 per night from Feb 18 to Feb 19
CA $165
CA $204 total
Feb 18 - Feb 19
includes taxes & fees
8.2/10 Very Good! (1,000 reviews)
Great location, short walk to the Duomo, museums and shopping. A clean quiet room awaited me.

Reviewed on Jan 21, 2026

c-hotels Ambasciatori
IQ Hotel Firenze

IQ Hotel Firenze

4 out of 5
Via Camillo Cavour, 88 Florence FI
Fully refundableReserve now, pay when you stay
The price is CA $136 per night from Feb 23 to Feb 24
CA $136
CA $172 total
Feb 23 - Feb 24
includes taxes & fees
9.6/10 Exceptional! (1,147 reviews)
Spotless, friendly staff, great breakfast and tram links, perfect safe location and only 9 min walk to Duomo

Reviewed on Feb 9, 2026

IQ Hotel Firenze
Bernini Palace

Bernini Palace

5 out of 5
Piazza San Firenze 29 Florence FI
Fully refundableReserve now, pay when you stay
The price is CA $311 per night from Feb 19 to Feb 20
CA $311
CA $368 total
Feb 19 - Feb 20
includes taxes & fees
9.6/10 Exceptional! (1,008 reviews)
This is a wonderful hotel. Friendly staff, very clean rooms, and great location. Wish I could stay longer.

Reviewed on Feb 9, 2026

Bernini Palace
See all 15,056 properties in Castellina in Chianti
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.
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Discover the most popular places to visit in Castellina in Chianti

Castellina in Chianti showing farmland

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.

Buondonno Winery

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.

Casa Vinicola Luigi Cecchi

What to do in Castellina in Chianti

Siena, San Gimignano, Monteriggioni & Chianti from Florence

Siena, San Gimignano, Monteriggioni & Chianti from Florence

CA $84
per adult
86% of travellers recommend
Siena, San Gimignano, Monteriggioni & Chianti from Florence
Florence: San Gimignano, Siena, Monteriggioni, Chianti & Lunch with Wine

Florence: San Gimignano, Siena, Monteriggioni, Chianti & Lunch with Wine

CA $112
per adult
88% of travellers recommend
Florence: San Gimignano, Siena, Monteriggioni, Chianti & Lunch with Wine
Tuscany in 1 day: Pisa, San Gimignano and Siena with Lunch

Tuscany in 1 day from Florence: Pisa, San Gimignano & Siena with Lunch

CA $79
per adult
78% of travellers recommend
Tuscany in 1 day from Florence: Pisa, San Gimignano & Siena with Lunch
See all activities in Castellina in Chianti

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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.