Poggibonsi Vacations from $1,077

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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.
Hotel Fattoria degli Usignoli

Hotel Fattoria degli Usignoli

4 out of 5
Price was $1,722, price is now $1,077 per person
$1,077
per person
Apr 19 - Apr 22
found 13 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Florence (FLR)
8.2/10 Very Good! (162 reviews)
Absolutely beautiful property, quiet and peaceful!! Loved the experience!!

Reviewed on Oct 5, 2025

Hotel Palazzo San niccolò & Spa

Hotel Palazzo San niccolò & Spa

4 out of 5
Price was $1,770, price is now $1,130 per person
$1,130
per person
Apr 19 - Apr 22
found 13 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Florence (FLR)
9.2/10 Wonderful! (182 reviews)
The property is beautifully old but be careful how much luggage you bring as there is no elevator, Only stairs. Room is nice. Bathrooms nicely updated. No complaints!

Reviewed on Sep 30, 2025

Ultimo Mulino Wellness Country Hotel

Ultimo Mulino Wellness Country Hotel

4 out of 5
Price was $1,709, price is now $1,100 per person
$1,100
per person
Apr 19 - Apr 22
found 13 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Florence (FLR)
8.8/10 Excellent! (146 reviews)
The breakfast buffet was always well stocked and tasty. The staff were amazing, helpful and friendly. The food at the restaurant was delicious.

Reviewed on Oct 4, 2025

Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Price was $2,743, price is now $1,766 per person
$1,766
per person
Apr 15 - Apr 21
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
7.6/10 Good! (1,008 reviews)
Location is great, breakfast included and that is great but the coffee machine did not give hot chocolate. Staff ate friendly. Very close to the Terminal and Mercato Centrale and Duomo Florence👍👍

Reviewed on Mar 9, 2026

Delta Hotel

Delta Hotel

3 out of 5
Price was $1,674, price is now $1,079 per person
$1,079
per person
Apr 19 - Apr 22
found 13 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Florence (FLR)
8.4/10 Very Good! (159 reviews)
Very clean and staff were lovely

Reviewed on Sep 25, 2025

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Discover the most popular places to visit in Poggibonsi

The Rock of Staggia

Learn about the local history of Staggia with a stop at The Rock of Staggia. Discover the beautiful countryside in this culturally rich area, or enjoy its local tours.

The Rock of Staggia

Archeodromo di Poggibonsi

You can study the exhibits at Archeodromo di Poggibonsi, a museum with a story of its own, during your travels to Poggibonsi. Discover the beautiful countryside in this relaxing area, or enjoy its local tours.

Archeodromo di Poggibonsi

Poggio Imperiale Fortress

Learn about the local history of Poggibonsi when you take a trip to Poggio Imperiale Fortress. Discover the beautiful countryside and wineries in this quaint area.

Poggio Imperiale Fortress

What to do in Poggibonsi

Chianti Half Day Wine Tour from Florence

Chianti Half Day Wine Tour from Florence

$58
per adult
88% of travellers recommend
Chianti Half Day Wine Tour from Florence
Siena, San Gimignano, Monteriggioni & Chianti from Florence

Siena, San Gimignano, Monteriggioni & Chianti from Florence

$77
per adult
86% of travellers recommend
Siena, San Gimignano, Monteriggioni & Chianti from Florence
Florence Day Trip: Medieval Villages & Cooking Class

Florence Day Trip: Medieval Villages & Cooking Class

$164
per adult
86% of travellers recommend
Florence Day Trip: Medieval Villages & Cooking Class
See all activities in Poggibonsi

Poggibonsi Hotel Deals

Hotel Ristorante Alcide

Hotel Ristorante Alcide

4 out of 5
Viale Marconi, 67/A Poggibonsi SI
Fully refundableReserve now, pay when you stay
$46 nightly
The price is $58 total per night from Mar 29 to Mar 30
$58 total
Mar 29 - Mar 30
Total with taxes and fees
8/10 Very Good! (480 reviews)
I highly recommended

Reviewed on Oct 14, 2025

Hotel Ristorante Alcide
Hotel Toscana Ambassador

Hotel Toscana Ambassador

4 out of 5
Via Salceto, 11 Poggibonsi SI
Fully refundableReserve now, pay when you stay
$87 nightly
The price is $103 total per night from Mar 19 to Mar 20
$103 total
Mar 19 - Mar 20
Total with taxes and fees
8.2/10 Very Good! (326 reviews)
We recommend the Toscana Ambassador to everyone, as we had a great experience with its cleanliness, hospitality, friendliness, and an extraordinary breakfast, with excellent service from Ada & Julia and the rest of the crew, from the front desk to room service. If you ever visit Poggibonsi, Tuscany, ...

Reviewed on Nov 27, 2025

Hotel Toscana Ambassador
Podere il Pino

Podere il Pino

Localita Il Pino, n. 5 Poggibonsi SI
9.2/10 Wonderful! (17 reviews)
Beautiful place to stay. Great for kids and has an amazing view.

Reviewed on Jun 24, 2025

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Podere il Pino
See all 742 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

How much does a Poggibonsi vacation package cost?
You can snap up a vacation package to this top destination from $1,077 on Expedia. However, how much your vacation to Poggibonsi costs will depend on factors like the season, length of stay and hotel choice.
What are the cheapest months to go to Poggibonsi?
February, November and December are great times to search for cheap Poggibonsi vacation packages. Choosing to travel in quieter periods means you'll typically find lower prices on flights and hotels.
How many days is enough for Poggibonsi?
With around 3 days, you'll have plenty of time to experience popular neighborhoods such as San Gimignano City Centre and Casone during your Poggibonsi vacation. Make sure to also add Church of San Lorenzo and Poggio Imperiale Fortress to your must-see list. In the mood for more adventures? Consider exploring outside of Poggibonsi on day trips and tours.
Is it worth booking a vacation package to Poggibonsi?
Well known for its views, family-friendly attractions and history, a Poggibonsi vacation has something for everyone. Be sure to check out key sights like Church of San Lorenzo and Poggio Imperiale Fortress, and consider renting some wheels for day trips to experience even more.
How to find the best Poggibonsi package deals?
Start your search for a Poggibonsi package deal by entering your preferred trip dates and destination under our "Packages" tab. Then apply a few filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect Poggibonsi package deal right away, just change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Poggibonsi adventure underway.
Is it cheaper to book a Poggibonsi vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll usually land a better deal than booking each component separately. And you'll still have the freedom to create a tailored Poggibonsi vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Poggibonsi?
If you've got your Poggibonsi travel dates locked in, book as soon as you can to score some awesome deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are great for impromptu escapes.
How to plan a trip to Poggibonsi?

  1. Choose your travel dates: The things you want to do in Poggibonsi and your preferred season will help you decide when to travel.
  2. Calculate your budget: Ensure you have enough money to pay for everything from dining out and transportation to flights and activities. Your hotel will likely be the biggest expense during your trip to Poggibonsi.
  3. Use Expedia's trip planning tool to discover Poggibonsi: Research every aspect of your trip to Poggibonsi with this handy planner. Invite family or friends to collaborate on a group trip, search for stays or things to do and make bookings.
  4. Decide how long to go away for: Now that you're up to speed on Poggibonsi, you can work out the ideal length of your vacation. Put together a draft plan and give yourself enough time to get through everything on your must-do list.
  5. Combine your accommodations and airfare: After you've settled on your travel dates and duration, book the perfect Poggibonsi vacation package for you.
  6. Book any excursions or activities: Now to the fun part — organizing everything you want to see and do. Browse some of the incredible things to do in Poggibonsi and book your tickets in advance to save time (and maybe some money too!).

Does Expedia offer Book Now, Pay Later Poggibonsi vacation packages?
Your Poggibonsi getaway should be an escape from your busy life, not a source of money-related stress. So to give you a bit more flexibility, we've joined up with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.

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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.