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San Gimignano Vacation Packages

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San Gimignano Flight + Hotel Packages

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

Grand Hotel Cavour

4 out of 5
Price was $1,304, price is now $1,020 per person
$1,020
per person
Dec 11 - Dec 16
found 1 day 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.

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

5 out of 5
Price was $1,819, price is now $1,471 per person
$1,471
per person
Dec 6 - Dec 13
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 Cortona. Enjoy free breakfast, free WiFi, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Signorelli Theatre and Museum of the Etruscan Academy are located nearby.
Frederico went above and beyond to transfer us to our villa and Giulio was a fantastic bartender

Reviewed on Oct 13, 2026

Aurum Uffizi

Aurum Uffizi

4 out of 5
Price was $1,491, price is now $1,109 per person
$1,109
per person
Nov 20 - Nov 25
found 2 days ago
Roundtrip 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 Piazza del Duomo are located nearby.
Breakfast and air conditioning

Reviewed on Oct 16, 2026

Aurum Firenze

Aurum Firenze

4 out of 5
Price was $1,406, price is now $1,074 per person
$1,074
per person
Nov 20 - Nov 25
found 2 days ago
Roundtrip 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 Piazza del Duomo and Ponte Vecchio are located nearby.

Hotel L'Orologio Firenze

Hotel L'Orologio Firenze

4 out of 5
Price was $1,646, price is now $1,272 per person
$1,272
per person
Jan 3 - Jan 8
found 20 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
Book a stay at this boutique hotel in Florence. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Piazza del Duomo and Ponte Vecchio are located nearby.

Hotel Number Nine

Hotel Number Nine

5 out of 5
Price was $3,418, price is now $2,663 per person
$2,663
per person
Dec 25 - Jan 1
found 21 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
Book a stay at this luxury hotel in Florence. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Piazza del Duomo and Ponte Vecchio are located nearby.

Hotel La Scaletta Al Ponte Vecchio

Hotel La Scaletta Al Ponte Vecchio

4 out of 5
Price was $1,553, price is now $1,223 per person
$1,223
per person
Nov 20 - Nov 25
found 2 days ago
Roundtrip 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.

Hotel Certosa Di Maggiano

Hotel Certosa Di Maggiano

5 out of 5
Price was $1,324, price is now $1,046 per person
$1,046
per person
Dec 10 - Dec 15
found 2 days ago
Roundtrip non-stop flight included
New York (NYC) 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.
Our stay for our honeymoon was amazing. We loved our room and we were upgraded to a suite because they had it available. All the staff were kind and helpful. They carried our luggage up two flights of stairs to our room, helped make reservations, called taxis for us, etc. The property was beautiful, maintained nicely, and was very quiet. Really have no complaints. To note it is outside of city Centre of Siena so you will need taxis back and forth to the city for meals etc. which can get quite pricey so just plan ahead. Our room could’ve been cleaned a little better in between each day but overall it was still very clean. We would definitely stay there again!!

Reviewed on Sep 28, 2026

San Gimignano Vacation Packages 3-4 Night Stays

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

Aurum Firenze

4 out of 5
Historic Centre of Florence
Price was $1,669, price is now $1,269 per person
$1,269
per person
Jan 1 - Jan 5
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
Hotel Balestri

Hotel Balestri

4 out of 5
Historic Centre of Florence
Price was $1,779, price is now $1,495 per person
$1,495
per person
Jan 1 - Jan 5
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
The Hoxton, Florence

The Hoxton, Florence

4 out of 5
Historic Centre of Florence
Price was $1,629, price is now $1,373 per person
$1,373
per person
Jan 1 - Jan 5
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
Il Rivalta - Place of Charme

Il Rivalta - Place of Charme

4 out of 5
Historic Centre of Florence
Price was $1,851, price is now $1,576 per person
$1,576
per person
Jan 1 - Jan 5
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)

San Gimignano Vacation Packages 5-7 Night Stays

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

Aurum Firenze

4 out of 5
Historic Centre of Florence
Price was $1,406, price is now $1,074 per person
$1,074
per person
Nov 20 - Nov 25
found 2 days ago
Roundtrip flight included
Boston (BOS) to Florence (FLR)
Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was $1,491, price is now $1,109 per person
$1,109
per person
Nov 20 - Nov 25
found 2 days ago
Roundtrip flight included
Boston (BOS) to Florence (FLR)
Hotel L'Orologio Firenze

Hotel L'Orologio Firenze

4 out of 5
Historic Centre of Florence
Price was $1,646, price is now $1,272 per person
$1,272
per person
Jan 3 - Jan 8
found 20 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
Hotel Number Nine

Hotel Number Nine

5 out of 5
Historic Centre of Florence
Price was $3,418, price is now $2,663 per person
$2,663
per person
Dec 25 - Jan 1
found 21 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Vueling Airlines
Fri, Dec 25 - Thu, Jan 14
BCN
Barcelona Intl.
FLR
Peretola
$102 Roundtrip, found 5 hours ago
$102
Roundtrip
found 5 hours ago
Select Vueling Airlines flight, departing Fri, Dec 25 from Barcelona Intl. to Peretola, returning Thu, Jan 14, priced at $102 found 5 hours ago
Air France
Wed, Nov 11 - Thu, Nov 19
CDG
Roissy-Charles de Gaulle
FLR
Peretola
$146 Roundtrip, just found
$146
Roundtrip
just found
Select Air France flight, departing Wed, Nov 11 from Roissy-Charles de Gaulle to Peretola, returning Thu, Nov 19, priced at $146 just found
Vueling Airlines
Thu, May 6 - Mon, May 10
LGW
Gatwick
FLR
Peretola
$219 Roundtrip, found 1 hour ago
$219
Roundtrip
found 1 hour ago
Select Vueling Airlines flight, departing Thu, May 6 from Gatwick to Peretola, returning Mon, May 10, priced at $219 found 1 hour ago
ITA Airways
Thu, May 6 - Mon, May 10
LHR
Heathrow
FLR
Peretola
$226 Roundtrip, just found
$226
Roundtrip
just found
Select ITA Airways flight, departing Thu, May 6 from Heathrow to Peretola, returning Mon, May 10, priced at $226 just found