Search Deals onCastellina in Chianti Vacation Packages
Castellina in Chianti Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Aurum Uffizi
Price was $1,445, price is now $1,075 per person
$1,075
per person
Oct 30 - Nov 3
found 17 hours ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
Stay at this hotel in Florence. Enjoy free breakfast, free WiFi, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Ponte Vecchio and Piazza del Duomo are located nearby.
excellent location, clean and staff helpful
Reviewed on Aug 23, 2026
The Moon Boutique Hotel & Spa
Save 100% on your flight
Price was $2,219, price is now $1,296 per person
$1,296
per person
Oct 29 - Nov 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
Book a stay at this spa hotel in Florence. Enjoy free WiFi, a full-service spa, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Ponte Vecchio and Piazza del Duomo are located nearby.
Eden Rock Resort
Price was $2,177, price is now $1,511 per person
$1,511
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
Book a stay at this business-friendly residence in Florence. Enjoy free WiFi, room service, and parking (surcharge). Popular attractions Piazza del Duomo and Ponte Vecchio are located nearby.
This was a beautiful property about 10 mins away from Florence. You get the beauty of Tuscany without having to go too far. The hotel only has 12 rooms and everyone knows you by name. We traveled with 2 kids and the rooms were very spacious. Staff are wonderful, Onsite restaurant was great. Views were breathtaking. We didn't have a car, and the hotel was able to help us with cabs easily. Service was excellent and we would highly recommend this hotel!
Reviewed on Jul 18, 2026
Grand Hotel Cavour
Price was $1,687, price is now $1,199 per person
$1,199
per person
Oct 31 - Nov 5
found 11 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
Book a stay at this family-friendly hotel in Florence. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Piazza del Duomo and Ponte Vecchio are located nearby.
Precise Tale Poggio Alla Sala
Save 100% on your flight
Price was $3,315, price is now $2,365 per person
$2,365
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip flight included
New York (JFK) to Florence (FLR)
Book a stay at this luxury hotel in Montepulciano. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Archaeological Civic Museum and Terme Sant'Elena are located nearby.
Amazing! If you are a family visiting Tuscany I highly recommend
Reviewed on Aug 27, 2026
Hotel La Scaletta Al Ponte Vecchio
Price was $2,776, price is now $1,986 per person
$1,986
per person
Oct 7 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
Stay at this hotel in Florence. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Ponte Vecchio and Piazza del Duomo are located nearby.
This was my favorite hotel out of all the cities I’ve visited in Italy. The staff are kind and the hotel is in walking distance to everything. I didn’t take any taxis during my stay. It’s a 15 minute walk from the train station. It’s close to many restaurants, attractions and stores to shop. They have a beautiful roof top bar over looking Florence
Reviewed on Aug 25, 2026
The Rif - Boutique Hotel
Price was $2,484, price is now $1,777 per person
$1,777
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
Book a stay at this family-friendly hotel in Pisa. Enjoy free WiFi, breakfast (surcharge), and a sauna. Our guests praise the helpful staff in our reviews. Popular attractions Leaning Tower and Pisa Baptistry are located nearby.
Aurum Firenze
Price was $1,628, price is now $1,202 per person
$1,202
per person
Nov 19 - Nov 25
found 14 hours ago
Roundtrip non-stop flight included
Portland (PDX) to Florence (FLR)
Stay at this hotel in Florence. Enjoy free breakfast, free WiFi, and a 24-hour front desk. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Piazza del Duomo and Ponte Vecchio are located nearby.
Room is very small
Reviewed on Aug 21, 2026
Castellina in Chianti Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Castellina in Chianti Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Tue, Nov 10 - Tue, Nov 17
CDG
Roissy-Charles de Gaulle
FLR
Peretola
$129 Roundtrip, found 2 hours ago
$129
Roundtrip
found 2 hours ago
Sun, Sep 27 - Sat, Oct 17
STN
Stansted
FLR
Peretola
$241 Roundtrip, found 2 days ago
$241
Roundtrip
found 2 days ago
Sun, Nov 8 - Mon, Nov 16
JFK
John F. Kennedy Intl.
FLR
Peretola
$616 Roundtrip, found 5 hours ago
$616
Roundtrip
found 5 hours ago
Tue, Nov 3 - Thu, Nov 12
JFK
John F. Kennedy Intl.
ZMS
Santa Maria Novella Train Station
$905 Roundtrip, found 3 hours ago
$905
Roundtrip
found 3 hours ago
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