San Gimignano Vacation Packages 2026 from $1,242

San Gimignano flight + hotel vacation packages

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

Hotel Meridiana

Santissima Annunziata

$1,242

per person

Aug 11 - Aug 15

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Florence (FLR)

This hotel features a bar/lounge, a coffee shop, and free WiFi in public areas. A garden, luggage storage, and concierge services are also on offer.

Hotel San Luca

Cortona Old Town

$1,291

per person

Aug 11 - Aug 15

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Florence (FLR)

This hotel features a restaurant, a gym, and a bar/lounge. WiFi in public areas is free. Self parking, a hair salon, and dry cleaning are also offered.

Best Western Hotel San Marco

$1,316

per person

Aug 11 - Aug 15

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Florence (FLR)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Traveling on business? Take advantage of the business center, conference center, and conference space. There's a bar/lounge on site, and a 24-hour front desk and laundry facilities are also provided.

Hotel Europa

$1,278

per person

Aug 11 - Aug 15

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Florence (FLR)

A restaurant and a bar/lounge are featured at this hotel. Traveling for business? Take advantage of the free WiFi in public areas, express check-in, and conference space. Enjoy the free buffet breakfast each morning.

Hotel Villa Il Castagno

Santissima Annunziata

$1,280

per person

Aug 11 - Aug 15

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Florence (FLR)

A bar/lounge and a terrace are featured at this hotel, along with free self parking. WiFi in public areas is free. A garden, a snack bar/deli, and a hair salon are also on offer.

Top San Gimignano hotels deals

Mormoraia

Agriturismo San Gimignano San Gimignano SI

$264 nightly

$296 total

Jun 28 - Jun 29

Total with taxes and fees

This luxury farm stay features an attached winery, a full-service spa, and a restaurant. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi. A bar/lounge, a poolside bar, and a snack bar/deli are also provided.

Pool

Spa

Hotel Casolare Le Terre Rosse

Loc. San Donato San Gimignano SI

Free Cancellation

Reserve now, pay when you stay

$152 nightly

$173 total

Jul 17 - Jul 18

Total with taxes and fees

This hotel features a restaurant, a seasonal outdoor pool, and a bar/lounge. Families will appreciate the playground and onsite laundry facilities. There's no skimping on freebies - guests receive free WiFi, free self parking, and a free area shuttle.

Pool

Pet friendly

Cappuccina Country Resort

Loc La Cappuccina 46/a San Gimignano SI

Free Cancellation

Reserve now, pay when you stay

$169 nightly

$194 total

Jul 1 - Jul 2

Total with taxes and fees

This hotel features a restaurant, a seasonal outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the a rooftop terrace and free perks like cooked-to-order breakfast and free self parking.

Pool

Breakfast included

Poderi Arcangelo

Localita Capezzano San Gimignano SI

Free Cancellation

Reserve now, pay when you stay

$182 nightly

$205 total

Jun 27 - Jun 28

Total with taxes and fees

This Tuscan-style farm stay features an attached winery, 3 outdoor pools, and a restaurant. Families will appreciate the picnic area, kid-friendly dining, and babysitting. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi.

Pool

Parking included

Hotel Sovestro

Localita Sovestro 63 San Gimignano SI

Free Cancellation

Reserve now, pay when you stay

$191 nightly

$217 total

Jun 27 - Jun 28

Total with taxes and fees

This smoke-free hotel features an attached winery, 2 outdoor pools, and a restaurant. Business travelers can take advantage of the free WiFi in public areas. Enjoy the 24-hour gym and perks like free self parking and a free area shuttle.

Pool

Parking included

Hotel Leon Bianco

Piazza Della Cisterna 13 San Gimignano SI

$117 nightly

$135 total

Jul 5 - Jul 6

Total with taxes and fees

This hotel features a gym and a hot tub. Business travelers can take advantage of the free WiFi in public areas. There's a bar/lounge on site, and laundry facilities and concierge services are also provided.

Hot Tub

Free WiFi

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Popular places to visit

Piazza della Cisterna

4.5/5(53 reviews)

Find out about the history of San Gimignano when you spend time at Piazza della Cisterna. Discover the area's beautiful countryside and wineries.

Piazza Duomo

4.5/5(53 reviews)

Find out about the history of San Gimignano when you take a trip to Piazza Duomo. Discover the area's beautiful countryside, or seek out its local tours.

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San Gimignano Communal Palace

3/5(1 review)

You can browse the exhibits at San Gimignano Communal Palace, a museum with a storied past, during your trip to San Gimignano. Discover the area's beautiful countryside, or seek out its local tours.

Frequently asked questions

How much are vacation packages to San Gimignano?

With a Travelocity vacation package, you can experience the sights and sounds of San Gimignano for only $1,242. Hotels, flights and adventures — we have everything you need. You'll save tons just for bundling together your bookings. And with all that taken care of before you go, you can sit back, relax and enjoy the adventure.

How long should my San Gimignano vacation be?

Around 3 nights is the average time frame visitors spend in San Gimignano. But how long is right for you depends on how many magical memories you want to make. Why not stay a couple of extra days and discover some hidden gems?

Where can I get the best vacation package deals for San Gimignano?

Whatever your travel style, Travelocity can help you find an unbeatable San Gimignano package deal. The only thing you need to do is select a combination from our 400 air carriers and 1,000,000 properties worldwide.

Why should I book my San Gimignano vacation bundle with Travelocity?

With first-rate service, support available 24/7 and some of the most amazing getaways on offer, you'll never wander alone. And if you find a lower price, we'll match it. That's our Price Match Guarantee.

Will I save money on my San Gimignano car rental if I book it with my hotel or flight?

Bundling your hotel, flight and car into a San Gimignano vacation package is a great way to land the best deal. Plus, having your own car rental gives you absolute freedom to get to all those landmarks you'd like to see. Located 120 mi from San Gimignano, Aquarium of Genoa is one place that should be on your itinerary. Buckle up and make a day trip of it.

Which airport is best for San Gimignano?

The primary airport for San Gimignano is Peretola Airport (FLR). You'll find it 25 mi south of the downtown area.

What is there to do in San Gimignano?

San Gimignano has plenty of sights to explore, including Collegiate Church of Santa Maria Assunta and Medieval Criminal and Torture Museum. These well-known attractions are at the top of most travelers' to-do lists.

Where should I stay when visiting San Gimignano?

Many people choose to spend their nights at the Hotel Casolare Le Terre Rosse. It's an excellent base for your San Gimignano getaway.