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San Gimignano Vacation Packages

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A historic square with stone buildings, a prominent tower, and outdoor seating areas.

San Gimignano
Tuscany
Italy
Europe
Hotwire.com

San Gimignano Flight + Hotel Packages

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

Eurostars Florence Boutique

4 out of 5

Price was $1,515, price is now $1,111 per person

$1,111

per person

Oct 29 - Nov 3

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) to Florence (FLR)

Book a stay at this boutique hotel in Florence. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Popular attractions Piazza della Signoria and Piazza del Duomo are located nearby.

Reviewed on Aug 10, 2026

Aurum Uffizi

4 out of 5

Price was $1,889, price is now $1,220 per person

$1,220

per person

Oct 29 - Nov 5

found 1 day 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 Ponte Vecchio and Cathedral of Santa Maria del Fiore are located nearby.

Clean room, convenient location. has AC and lift. Breakfast was ok. Would stay again

Reviewed on Aug 12, 2026

Aurum Firenze

4 out of 5

Price was $1,768, price is now $1,162 per person

$1,162

per person

Oct 29 - Nov 5

found 1 day 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 Piazza del Duomo are located nearby.

Room is very small

Reviewed on Aug 21, 2026

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 2 hours 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

IQ Hotel Firenze

4 out of 5

Price was $2,073, price is now $1,528 per person

$1,528

per person

Oct 13 - Oct 17

found 11 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

Book a stay at this spa hotel in Florence. Enjoy free WiFi, an outdoor pool, and a full-service spa. Our guests praise the breakfast and the pool in our reviews. Popular attractions Piazza del Duomo and Cathedral of Santa Maria del Fiore are located nearby.

Rooms were clean and nicely laid out. Excellent showers. The in-room refrigerator was kept stocked and was *free*! The included breakfast had lots of tasty options. I would definitely stay there again. Walkable to all the touristy stuff and also very close to the tram line.

Reviewed on Aug 22, 2026

Giovanni Rooms Manarola

1 out of 5

Price was $1,608, price is now $1,195 per person

$1,195

per person

Oct 12 - Oct 17

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Pisa (PSA)

Stay at this affittacamere in Riomaggiore. Enjoy free WiFi, an airport shuttle (surcharge), and dry cleaning or laundry services. Popular attractions Cinque Terre Marine Protected Area and Vernazza Beach are located nearby.

Property was as describe, view was perfect, easy to find. Very clean AC wasn’t the best, however, we visited from the US so our AC is very cold. We never saw the owners, they left check-in instructions. They were semi- responsive già whatsapp. Bed is a very firm mattess.

Reviewed on Sep 24, 2025

Villa Tolomei Hotel & Resort

5 out of 5

Price was $1,507, price is now $1,120 per person

$1,120

per person

Oct 29 - Nov 3

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) to Florence (FLR)

Book a stay at this luxury hotel in Florence. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Ponte Vecchio and Piazza della Signoria are located nearby.

Wonderful property, amazing hosts. 20 minutes outside of Florence center-easy to get a taxi. My family loved everything about our stay here!

Reviewed on Jul 7, 2026

The James Suite Hotel Firenze 1564 - Small Luxury Hotels of the World

5 out of 5

Save 100% on your flight

Price was $4,157, price is now $3,126 per person

$3,126

per person

Nov 4 - Nov 9

found 14 hours ago

Roundtrip flight included

New York (JFK) to Florence (FLR)

Book a stay at this luxury hotel in Florence. Enjoy free breakfast, free WiFi, and room service. Popular attractions Piazza del Duomo and Ponte Vecchio are located nearby.

San Gimignano Vacation Packages 3-4 Night Stays

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

Aurum Uffizi

4 out of 5

Historic Centre of Florence

Price was $1,429, price is now $1,099 per person

$1,099

per person

Oct 17 - Oct 20

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

IQ Hotel Firenze

4 out of 5

Historic Centre of Florence

Price was $1,837, price is now $1,382 per person

$1,382

per person

Oct 14 - Oct 17

found 4 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

Hotel La Scaletta Al Ponte Vecchio

4 out of 5

Historic Centre of Florence

Price was $1,705, price is now $1,305 per person

$1,305

per person

Oct 11 - Oct 14

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

Relais Uffizi, Tailor made Hotel

4 out of 5

Historic Centre of Florence

Price was $2,389, price is now $1,842 per person

$1,842

per person

Oct 8 - Oct 11

found 1 day ago

Roundtrip non-stop flight included

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