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 $2,439, price is now CA $1,655 per person
CA $1,655
per person
Jul 7 - Jul 13
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Florence (FLR)
7.6/10 Good! (1,007 reviews)
The bed sheets had a yellow stain. Spent 4 nights and towels or bed sheets were not changed. There’s an awful smell from the bathroom and hallway. Morning breakfast was ok. Staff was helpful and location was great.
Reviewed on May 17, 2026
Dimora Palanca Boutique & SPA
Historic Centre of Florence
Price was CA $2,851, price is now CA $2,026 per person
CA $2,026
per person
Aug 11 - Aug 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Florence (FLR)
9.2/10 Wonderful! (65 reviews)
I particularly love the authenticity of the building being hundreds of hundreds of years old and yet well cut, beautiful staff beautiful spa only lacking in the dining aspect but everything else was perfect. Highly recommend but recommend going out for dinner.
Reviewed on Nov 5, 2025
Hotel La Scaletta Al Ponte Vecchio
Historic Centre of Florence
Price was CA $2,462, price is now CA $1,780 per person
CA $1,780
per person
Aug 11 - Aug 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Florence (FLR)
8.8/10 Excellent! (996 reviews)
Our experience was consistent with previous reviews. Location is ideal. Easy entrance into main attraction area and with rooms off an interior courtyard property is super quiet at night.
Rooftop terrace is ideal. Relaxing, great cocktails and a perfect way to end a day sightseeing in the crowds of Florence.
We didn't realize the restaurant is not open for dinner. Breakfast was crowded, food ok.
Overall a nice property.
Reviewed on May 17, 2026
The Moon Boutique Hotel & Spa
Historic Centre of Florence
Price was CA $2,505, price is now CA $1,835 per person
CA $1,835
per person
Aug 11 - Aug 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Florence (FLR)
9.6/10 Exceptional! (533 reviews)
Great staff, clean rooms and all good on everything.
Reviewed on May 17, 2026
Aurum Uffizi
Historic Centre of Florence
Price was CA $2,385, price is now CA $1,761 per person
CA $1,761
per person
Aug 3 - Aug 8
found 6 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
7.6/10 Good! (1,006 reviews)
I had a wonderful stay at Aurum Uffizi. The staff were kind, friendly, and very helpful throughout my stay. The room was clean and comfortable, and the AC worked perfectly. The food was always fresh and enjoyable. Even though the hotel is close to shops, restaurants, and major tourist attractions, the area felt very safe and quiet, making it a perfect place to relax during my holiday. Highly recommended!
Reviewed on May 14, 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 $220 per night from Jun 2 to Jun 3
CA $220
CA $265 total
Jun 2 - Jun 3
includes taxes & fees
9/10 Wonderful! (1,370 reviews)
"This hotel exceeded our expectations. The rooftop bar was delightful, with an amazing view of Florence. The gym was well-equipped and just adjacent to the bar, so you could enjoy the view from there. We had a few things we needed help with, and the staff were so helpful"
Reviewed on May 18, 2026
Hotel Paris
Via Banchi 2 Florence FI
Fully refundableReserve now, pay when you stay
The price is CA $343 per night from Jun 8 to Jun 9
CA $343
CA $396 total
Jun 8 - Jun 9
includes taxes & fees
8.8/10 Excellent! (1,004 reviews)
"Reserved months in advance for a May stay. Minutes walk from S.M. Novella train station, major sites, central market and restaurants / shopping. The buildings is 14th-century old, with thick walls, high ceilings and atmosphere. That is part of its charm. Nevertheless, the beds were clean and comfortable, ..."
Reviewed on May 17, 2026
Plus Florence - Hostel
Via Santa Caterina D'Alessandria, 15 Florence FI
Fully refundableReserve now, pay when you stay
The price is CA $180 per night from Jun 8 to Jun 9
CA $180
CA $211 total
Jun 8 - Jun 9
includes taxes & fees
8.6/10 Excellent! (1,007 reviews)
"Cuarto privado con baño, limpio y lo necesario, el desayuno muy bueno, el staff muy amable y servicial, tiene lavandería, cafetería, piscina y además muy cerca caminando a la estación de trenes y a las atracciones turísticas Muy recomendable"
Reviewed on May 18, 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 romantic 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 $73
per adult
86% of travellers recommend
Tuscany in 1 day from Florence: Pisa, San Gimignano & Siena with Lunch
CA $79
per adult
78% of travellers recommend
Florence: San Gimignano, Siena, Monteriggioni, Chianti & Lunch with Wine
CA $127
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.
