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A stone castle with battlements overlooking a lush valley with vineyards.

Gaiole in Chianti
Tuscany
Italy
Europe
Hotwire.com

Gaiole in Chianti Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.

Hotel Caravaggio

3 out of 5

Price was $1,466, price is now $1,053 per person

$1,053

per person

Oct 24 - Oct 26

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) to Florence (FLR)

Stay at this hotel in Florence. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Piazza del Duomo and Ponte Vecchio are located nearby.

L'Andana

5 out of 5

Price was $1,842, price is now $1,449 per person

$1,449

per person

Oct 18 - Oct 21

found 14 hours ago

Roundtrip flight included

New York (NYC) to Florence (FLR)

Book a stay at this luxury hotel in Castiglione della Pescaia. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Abbazia di San Pancrazio al Fango and Cantina Sociale i Vini di Maremma are located nearby.

What a great experience, the hotel was excellent all the way around

Reviewed on Aug 17, 2026

Precise Tale Poggio Alla Sala

5 out of 5

Save 100% on your flight

Price was $3,388, price is now $2,224 per person

$2,224

per person

Oct 9 - Oct 15

found 14 hours 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.

Horrible service at best. Not a 5 star hotel. Save your money.

Reviewed on Aug 17, 2026

Grand Hotel Cavour

4 out of 5

Save 100% on your flight

Price was $6,265, price is now $4,399 per person

$4,399

per person

Sep 23 - Sep 28

found 3 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 Cathedral of Santa Maria del Fiore are located nearby.

They were very accommodating and helped with suggestions for places to eat local shops and their breakfast buffet was amazing

Reviewed on Aug 23, 2026

The Moon Boutique Hotel & Spa

4 out of 5

Price was $1,572, price is now $1,109 per person

$1,109

per person

Oct 24 - Oct 28

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 Cathedral of Santa Maria del Fiore and Ponte Vecchio are located nearby.

Gorgeous hotel and great staff. Spa was nice

Reviewed on Aug 23, 2026

Hotel Villa Liana

3 out of 5

Price was $1,894, price is now $1,349 per person

$1,349

per person

Oct 11 - Oct 17

found 23 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

Book a stay at this business-friendly hotel in Florence. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular attractions Piazza del Duomo and Cathedral of Santa Maria del Fiore are located nearby.

clean, spacious, well-stocked with toiletries and breakfast items too. walkable distance to all iconic sites. Grace, the breakfast host, did an incredible job, very welcoming & served with options for hot coffee drinks. All together, wonderful, memorable stay!!

Reviewed on May 23, 2026

Hotel Santa Croce

2 out of 5

Price was $1,885, price is now $1,372 per person

$1,372

per person

Oct 11 - Oct 17

found 23 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

Stay at this hotel in Florence. Enjoy free WiFi, room service, and valet parking (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Piazza del Duomo and Ponte Vecchio are located nearby.

Hotel Certosa Di Maggiano

5 out of 5

Price was $2,258, price is now $1,651 per person

$1,651

per person

Nov 4 - Nov 10

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Florence (FLR)

Book a stay at this luxury hotel in Siena. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Piazza del Campo and Porta Romana are located nearby.

Amazing building (old monastery). Staff were very friendly and helpful. Food was lovely.

Reviewed on Aug 21, 2026