Poggibonsi Vacations from $1,070

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Your Poggibonsi Vacation

When you book a vacation package to Poggibonsi, you can relax and enjoy your break knowing your travel plans have been made in advance. Uncover the wonders of this city from your base in a neighborhood like Mensanello, which is great for history. If your trip to Poggibonsi includes some sightseeing, don't miss well-known attractions like Collegiate Church of Santa Maria Assunta, Tenuta Torciano Winery and Piazza Duomo. Don't delay your visit to this city any longer. Your dream Poggibonsi vacation is only a few clicks away with Expedia.

The Latest Poggibonsi vacation packages

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

Eurostars Florence Boutique

Historic Centre of Florence
$1,070
per person
Dec 6 - Dec 13
found 8 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
8.6/10 Excellent! (503 reviews)
The bed was comfortable but low to the floor. The shower was very slippery and could have used a shower mat. The breakfast was great. The staff were very nice and helpful.

Reviewed on Oct 10, 2026

c-hotels Diplomat

c-hotels Diplomat

Historic Centre of Florence
$1,125
per person
Dec 6 - Dec 13
found 8 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
8.4/10 Very Good! (1,000 reviews)
Great location for early morning train travel! The hotel is quite nice. A little noisy from the street but we expected it due to the location so it wasn’t an issue.

Reviewed on Oct 11, 2026

Hotel Santa Maria Novella

Hotel Santa Maria Novella

Historic Centre of Florence
$2,194
per person
Dec 6 - Dec 13
found 8 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
9.6/10 Exceptional! (1,014 reviews)
Nice location easy to train station able to walk staff so sweet, breakfast delicious and so so clean luxury stay

Reviewed on Oct 21, 2026

Hotel L'Orologio Firenze

Hotel L'Orologio Firenze

Historic Centre of Florence
$1,991
per person
Dec 6 - Dec 13
found 8 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
9.6/10 Exceptional! (1,000 reviews)
It gave a old school elegant feel. The rooms was very spacious and the staff was friendly and informative.

Reviewed on Oct 23, 2026

Hotel Balestri

Hotel Balestri

Historic Centre of Florence
$1,694
per person
Dec 6 - Dec 13
found 8 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
9.4/10 Exceptional! (1,003 reviews)
Had a great room with access to a rooftop patio and a spectacular view

Reviewed on Oct 21, 2026

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Stay near popular Poggibonsi attractions

Church of San Lorenzo

9.0/10 (9 reviews)
This modest Romanesque church houses a remarkable 15th-century fresco by Pier Francesco Fiorentino. Combine your visit with a walk along the ancient Via Francigena pilgrimage route.
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Archeodromo di Poggibonsi

7.4/10 (3 reviews)
Step back in time at this full-scale reconstruction of a 9th-century Carolingian village. Watch costumed interpreters demonstrate medieval crafts and daily life in an authentic historical setting.
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Poggio Imperiale Fortress

7.6/10 (4 reviews)
This Renaissance military fortress, designed by Giuliano da Sangallo, offers panoramic views across Chianti and Val d'Elsa. Explore the archaeological park with its reconstructed Frankish village.
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San Lucchese Convent

8.6/10 (4 reviews)
This 13th-century Franciscan Gothic convent honors Saint Lucchese with remarkable medieval frescoes and serene architecture. Explore the tranquil cloister while enjoying views of the Tuscan countryside.
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Magione Castle

8.0/10 (5 reviews)
This medieval complex once served as a hospital for pilgrims on the Via Francigena route. Explore its Romanesque church and discover the fascinating legacy of the Knights Templar through guided tours.
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The Rock of Staggia

7.6/10 (5 reviews)
This medieval stronghold once guarded the strategic Via Francigena trade route between Florence and Siena. Explore its cylindrical towers and double walls on a guided tour through Tuscan history.
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Fountain of Fate

7.0/10 (8 reviews)
This 13th-century travertine fountain showcases medieval engineering with six double arches and pilasters. Explore its serene archaeological park setting, enhanced by Mimmo Paladino's contemporary art installations.
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Collegiata di Santa Maria Assunta Museum

You can spend an afternoon exploring the galleries in Collegiata di Santa Maria Assunta Museum in Poggibonsi. Discover the countryside while you're in the area.
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What to do in Poggibonsi

Siena: Cathedral Complex Pass with Audio Guide

Siena: Cathedral Complex Pass with Audio Guide (OPA SI PASS)

$22
per adult
Siena: Cathedral Complex Pass with Audio Guide (OPA SI PASS)
Chianti Wine and Food Safari

SMALL-GROUP Wine Safari: Tuscany Wine Tasting Tour from Florence

$146
per adult
100% of travellers recommend
SMALL-GROUP Wine Safari: Tuscany Wine Tasting Tour from Florence
Siena, San Gimignano, Monteriggioni & Chianti from Florence

Siena, San Gimignano, Monteriggioni & Chianti from Florence

$62
per adult
88% of travellers recommend
Siena, San Gimignano, Monteriggioni & Chianti from Florence
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Poggibonsi Hotel Deals

Hotel Toscana Ambassador

Hotel Toscana Ambassador

Via Salceto, 11 Poggibonsi SI
Fully refundableReserve now, pay when you stay
$68 nightly
$74 total
Nov 1 - Nov 2
Total with taxes and fees
Hotel Toscana Ambassador
Villa San Lucchese

Villa San Lucchese

Località San Lucchese, 5 Poggibonsi SI
$104 nightly
$121 total
Oct 28 - Oct 29
Total with taxes and fees
9.4/10 Exceptional! (360 reviews)
"The place itself is beautiful!!"

Reviewed on Oct 13, 2026

Villa San Lucchese
B&B Poggiobonizio

B&B Poggiobonizio

Via Montenero 37 Poggibonsi SI
$65 nightly
$71 total
Nov 23 - Nov 24
Total with taxes and fees
9.2/10 Wonderful! (77 reviews)
"Don't be fooled by outside entrance, it was.very nice inside.was very attentive and helpful. Room had everything and great shower room. Lovely breakfast and kitchen that allowed you to cook should you desire. Great stay Bob"

Reviewed on Aug 17, 2026

B&B Poggiobonizio
See all 746 properties in Poggibonsi
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.

Find the Best Poggibonsi Vacation Packages

Poggibonsi Essential Information

Language
Italian
Currency
Euros
Local Welcome
Ciao
Local Goodbye
Ciao
Closest Airport
Peretola Airport (FLR)
Population
21,700
Max Temp Winter
50ºF
Max Temp Summer
85ºF
Top Sights
Tenuta Torciano Winery, Monteriggioni Castle and Castello di Radda Winery

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Frequently asked questions

What's included in a Poggibonsi vacation package?
A Poggibonsi vacation package lets you combine round-trip flights, hotel stays, and rental cars for your trip to this central Italian destination. Most hotels in Poggibonsi offer airport shuttle service to and from Florence (FLR-Peretola) Airport, and most also include free breakfast, adding convenience and value to your stay.Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.
How can I save money on a Poggibonsi vacation package?
When you bundle, you can save up to 30%*. To save money on a Poggibonsi package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.
What's the best vacation package for Poggibonsi?
The best vacation packages in Poggibonsi for a romantic escape often center around luxurious stays. Consider a Poggibonsi vacation package with a stay at One Belvedere Tuscany, a 5-star property rated 9.6 out of 10. This hotel, available for around $620 per night, offers a spa and an outdoor pool, perfect for unwinding together amidst the Tuscan landscape.For families, a Poggibonsi vacation package built around Villa San Lucchese is a strong choice. This 4-star hotel, rated 9.3 out of 10 and available for around $180 per night, features family rooms and an outdoor pool. Travelers frequently praise the wonderful staff and lovely big rooms, making it a comfortable base for exploring the region.If you're seeking the best value, a Poggibonsi vacation package with a stay at B&B Poggiobonizio offers a great option. This 4-star property, rated 8.7 out of 10, is available for around $80 per night and includes free breakfast and free WiFi, providing a comfortable and affordable stay.*Package availability and prices may change depending on dates and demand.
Is Poggibonsi better suited for a beach vacation or a cultural trip?
Poggibonsi is primarily a cultural destination, known for its rich history and position within the Chianti Classico region. The area boasts a deep Etruscan-Roman heritage and played a significant role in medieval Tuscany, with sites like the historic Monteriggioni Castle and the Museo del Cristallo di Colle di Val d'Elsa offering insights into the past.Travelers on a Poggibonsi vacation can explore Renaissance-era architecture and numerous wineries, such as Antinori nel Chianti Classico, making it ideal for those seeking historical exploration and wine tasting. Your Poggibonsi vacation package can be customized around these cultural activities.
Is Poggibonsi a good choice for a family vacation package?
Poggibonsi can be a good choice for family vacation packages, especially for those interested in history and outdoor exploration within the Tuscan countryside. Several hotels cater to families, offering amenities like family rooms and outdoor pools.For example, Villa San Lucchese, a 4-star property rated 9.3 out of 10, provides family rooms and an outdoor pool. Similarly, Antico Podere Il Bugnolo, rated 8.9 out of 10, also features family rooms and an outdoor pool, making it a comfortable base for your family's Poggibonsi vacation package.Families can explore historical sites like Archeodromo di Poggibonsi, about 1 mile from central Poggibonsi, which offers an interactive look at the area's past. The impressive Monteriggioni Castle, about 12 miles from central Poggibonsi, also provides an engaging outing for all ages.
What are the top things to do in Poggibonsi?
A Poggibonsi vacation offers a range of historical sites and wineries for travelers to explore:Browse and book things to do in Poggibonsi on Expedia.
Do you need to rent a car in Poggibonsi, or is public transport enough?
For a Poggibonsi vacation package, a rental car offers the most flexibility for exploring the wider Tuscan region. While Poggibonsi itself is a central urban destination, many of the area's renowned attractions are spread out.For instance, wineries like Tenuta Torciano Winery are about 8 miles from central Poggibonsi, and historical sites such as Monteriggioni Castle are about 12 miles away. The famous Antinori nel Chianti Classico is even further, about 16 miles from the city center. A car allows you to visit these destinations at your own pace, making it easier to craft your ideal Poggibonsi vacation package with flights.
Are Poggibonsi vacation package hotels conveniently located?
Poggibonsi vacation package hotels offer various locations, with some close to the city center and others providing a more secluded experience in the surrounding Tuscan countryside.For stays near the heart of the city, Villa San Lucchese, a 4-star property rated 9.3 out of 10, is about 1 mile from central Poggibonsi, with travelers frequently praising the wonderful staff and lovely big rooms. Antico Podere Il Bugnolo, rated 8.9 out of 10, is also about 1 mile from central Poggibonsi. For options slightly further out, One Belvedere Tuscany, a 5-star hotel rated 9.6 out of 10, and Villa Lecchi Hotel Wellness, a 4-star hotel rated 9 out of 10, are both about 3 miles from central Poggibonsi.Consider your planned activities when choosing a hotel, as locations vary from urban proximity to countryside tranquility.
Can I change or cancel my Poggibonsi vacation package if my plans change?
Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.
Do One Key members get extra savings when booking Poggibonsi vacation packages?
Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.
Does Expedia offer Book Now, Pay Later Poggibonsi vacation packages?
Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Poggibonsi vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.
How do I find last-minute vacation packages to Poggibonsi?
To find last-minute vacation packages to Poggibonsi, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.
How does free cancellation work on Poggibonsi vacation packages?
Free cancellation on a Poggibonsi vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.
Is it cheaper to book a Poggibonsi vacation as a package or separately?
Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Poggibonsi getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
Why should I book my Poggibonsi vacation package with Expedia?
Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.