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 $1,636, price is now CA $1,160 per person
CA $1,160
per person
May 5 - May 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
7.6/10 Good! (1,002 reviews)
Yes, to both questions. Wi-fi needs work.

Reviewed on Feb 7, 2026

Hotel Berchielli

Hotel Berchielli

4 out of 5
Historic Centre of Florence
Price was CA $4,238, price is now CA $2,615 per person
CA $2,615
per person
May 1 - May 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
9.4/10 Exceptional! (1,002 reviews)
Very good Breakfast with many food options. Great service !

Reviewed on Jan 21, 2026

Rivoli Boutique Hotel

Rivoli Boutique Hotel

4 out of 5
Historic Centre of Florence
Price was CA $2,802, price is now CA $1,853 per person
CA $1,853
per person
Apr 17 - Apr 23
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Florence (FLR)
9/10 Wonderful! (1,000 reviews)
Fourth time staying here. Love this hotel - staff, rooms, location and breakfast

Reviewed on Oct 29, 2025

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was CA $1,736, price is now CA $1,199 per person
CA $1,199
per person
May 5 - May 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
7.8/10 Good! (1,000 reviews)
This is not a typical hotel where there is a lobby or staff to greet you . Instead it is a set of apartments in a corner building . The person who let us in was awaiting for us at the door at check in. Breakfast was serve in a buffet style . Staff would ask if you would order something else if you like. Continental breakfast is available .Overall it was comfortable and easy to find . Shops and restaurants are all walking distance.

Reviewed on Jan 15, 2026

Palazzo Firenze by Baglioni Hotels & Resorts

Palazzo Firenze by Baglioni Hotels & Resorts

5 out of 5
Historic Centre of Florence
Price was CA $4,178, price is now CA $2,992 per person
CA $2,992
per person
May 5 - May 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
9.4/10 Exceptional! (233 reviews)
Gorgeous boutique hotel, like museum Beautiful rooms!!! Thank you Giovanni for all ur help and knowledge organizing everything for us, and breakfast waiters were great!!!

Reviewed on Aug 21, 2025

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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 $122 per night from Feb 22 to Feb 23
CA $122
CA $157 total
Feb 22 - Feb 23
includes taxes & fees
8.2/10 Very Good! (1,001 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 $137 per night from Feb 26 to Feb 27
CA $137
CA $173 total
Feb 26 - Feb 27
includes taxes & fees
9.6/10 Exceptional! (1,134 reviews)
Fantastic service, exceptionallly clean room, free drink and minibar was a nice addition. Highly recommend. Lovely coming home after a day sightseeing.

Reviewed on Feb 1, 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 $321 per night from Feb 19 to Feb 20
CA $321
CA $379 total
Feb 19 - Feb 20
includes taxes & fees
9.6/10 Exceptional! (1,005 reviews)
Staff very helpful Rooms very clean Good breakfast options

Reviewed on Jan 30, 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 romantic 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
88% of travellers recommend
Siena, San Gimignano, Monteriggioni & Chianti from Florence
Siena: Civic Museum and Palazzo Pubblico Entry Ticket

Siena: Civic Museum and Palazzo Pubblico Entry Ticket

CA $16
per adult
Siena: Civic Museum and Palazzo Pubblico Entry Ticket
Wine Tasting in Tuscany

Casa Emma Wine Tasting

CA $57
per adult
Casa Emma Wine Tasting
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.