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Chianti Region Vacation Packages

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A vineyard with rows of grapevines, a house surrounded by trees, and a road with vehicles.

Chianti Region
Tuscany
Italy
Europe
Hotwire.com

Chianti Region Flight + Hotel Packages

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

Hotel La Scaletta Al Ponte Vecchio

4 out of 5

Price was $1,582, price is now $1,207 per person

$1,207

per person

Aug 23 - Aug 29

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 Uffizi Gallery are located nearby.

Great location

Reviewed on Jul 13, 2026

Donati Luxury Tower Suites

5 out of 5

Save 100% on your flight

Price was $3,149, price is now $2,249 per person

$2,249

per person

Aug 24 - Aug 29

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

Book a stay at this luxury hotel in Florence. Enjoy free WiFi, valet parking (surcharge), and train station pick-up service (surcharge). Popular attractions Cathedral of Santa Maria del Fiore and Piazza del Duomo are located nearby.

Perfect location. Unmanned reception at night.

Reviewed on Jul 5, 2026

Aurum Uffizi

4 out of 5

Price was $1,728, price is now $1,238 per person

$1,238

per person

Aug 24 - Aug 29

found 19 hours ago

Roundtrip non-stop flight included

Boston (BOS) 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 Uffizi Gallery and Ponte Vecchio are located nearby.

Very centrally located. We enjoyed our stay and would recommend it. Only issue was you could smell the drains in room 203. They tried to get rid of the smell but couldn’t. Avoid this room and you will be fine.

Reviewed on Jul 15, 2026

Residenza Florentia

1 out of 5

Price was $1,776, price is now $1,275 per person

$1,275

per person

Sep 28 - Oct 3

found 5 hours ago

Roundtrip non-stop flight included

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

Stay at this hotel in Florence. Enjoy free WiFi, daily housekeeping, and concierge services. Popular attractions Cathedral of Santa Maria del Fiore and Ponte Vecchio are located nearby.

Staff was helpful, the property was not very well maintained.

Reviewed on Jun 1, 2026

Bernini Palace

5 out of 5

Price was $2,504, price is now $1,805 per person

$1,805

per person

Aug 23 - Aug 29

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

Book a stay at this luxury hotel in Florence. Enjoy free breakfast, free WiFi, and a rooftop terrace. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Uffizi Gallery and Ponte Vecchio are located nearby.

Great hotel, we'll located at the heart of historic Florence. The staff is amazing, food is great, love it. Always stay here when I visit Florence. Thank you

Reviewed on Jul 15, 2026

Eurostars Florence Boutique

4 out of 5

Price was $2,348, price is now $1,696 per person

$1,696

per person

Sep 22 - Sep 26

found 1 hour ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

Book a stay at this boutique hotel in Florence. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Popular attractions Uffizi Gallery and Cathedral of Santa Maria del Fiore are located nearby.

Very good location. Clean hotel. Our ac was broken but they handled us a new room inmediately. The hotel is confortable and size of the rooms are decent. Bigger than average in the area.

Reviewed on Jun 26, 2026

Aurum Firenze

4 out of 5

Price was $1,691, price is now $1,222 per person

$1,222

per person

Aug 24 - Aug 29

found 19 hours ago

Roundtrip non-stop flight included

Boston (BOS) 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 Cathedral of Santa Maria del Fiore and Ponte Vecchio are located nearby.

Bathroom has odd smells.

Reviewed on Jul 16, 2026

Precise Tale Poggio Alla Sala

5 out of 5

Price was $3,940, price is now $3,007 per person

$3,007

per person

Aug 29 - Sep 3

found 18 hours ago

Roundtrip non-stop flight included

Boston (BOS) 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.