Pentolina Holidays

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    Save up to S$134 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Top hotels in Pentolina

Hotel Athena

Hotel Athena

4 out of 5
P Mascagni 55, Siena, SI
Fully refundableReserve now, pay when you stay
The price is S$242 per night from 28 Aug to 29 Aug
S$242
28 Aug - 29 Aug
includes taxes & fees
Hotel Athena
Palazzo Ravizza

Palazzo Ravizza

4 out of 5
Pian dei Mantellini 34, Siena, SI
The price is S$201 per night from 31 Aug to 1 Sept
S$201
31 Aug - 1 Sept
includes taxes & fees
9.2/10 Wonderful! (689 reviews)
Just beautiful
"The building, the views, the staff, the food, everything was just incredible. It was so quiet we felt like we were the only people there until we went for breakfast and realised there were others in the hotel. The view from the our room at the back of the hotel over the Tuscan hills will live with ..."

Reviewed on 9 Aug, 2025

Palazzo Ravizza
Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais

5 out of 5
Strada Comunale 14 Siena - Vagliagli 18, Castelnuovo Berardenga, SI
Fully refundableReserve now, pay when you stay
9.2/10 Wonderful! (181 reviews)
"Beautiful property, excellent service"

Reviewed on 31 May, 2025

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Borgo Scopeto Wine & Country Relais
See all 3,518 properties in Pentolina
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.

What to do in Pentolina

Siena, San Gimignano, Monteriggioni & Chianti from Florence

Siena, San Gimignano, Monteriggioni & Chianti from Florence

S$97
per adult
88% of travellers recommend
Siena, San Gimignano, Monteriggioni & Chianti from Florence
Torre del Mangia

Siena and San Gimignano: Small-Group Tour with Lunch from Florence

S$190
per adult
100% of travellers recommend
Siena and San Gimignano: Small-Group Tour with Lunch from Florence
From Siena: Chianti and Castles Tour with Wine Tastings

From Siena: Chianti and Castles Tour with Wine Tastings

S$127
per adult
From Siena: Chianti and Castles Tour with Wine Tastings
See all activities in Pentolina

Frequently asked questions

How much does a Pentolina holiday package cost?
You'll find cheap prices on Expedia for your Pentolina getaway. However, factors like the length of stay, the season and your choice of hotel will influence how much your holiday to Pentolina costs.
What are the cheapest months to go to Pentolina?
January, February and November are the best times to search for cheap Pentolina holiday packages. Choosing to travel in quieter months means you can generally find lower prices on accommodation and flights.
How many days is enough for Pentolina?
The ideal duration of your Pentolina holiday depends on what you'd like to see. Usually, a few days to a week will give you time to visit all the top attractions and explore some hidden treasures along the way.
How to find the best Pentolina package deals?
Use Expedia's handy filters to help you find some of the best Pentolina package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or search for Pentolina package deals in the off-peak season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to book your holiday package as early as possible.
Is it cheaper to book a Pentolina holiday as a package?
An Expedia holiday package could land you significant savings when compared to arranging stays and flights separately. Better still, you can personalise your Pentolina escape to fit your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a holiday package to Pentolina?
Secure incredible bargains by booking your flights early with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for a spur-of-the-moment Pentolina trip.
How to plan a trip to Pentolina?

  1. Choose when to go: Check your schedule and get your bags packed. Your favourite time of year and the available activities will also help you decide when to escape to Pentolina.
  2. Budget wisely: On top of the cost of your stay, you'll need to consider other expenses too. These include food, transportation and flights. Also, set aside some extra funds for unexpected costs that may crop up during your trip to Pentolina.
  3. Decide how long to go for: Now that you're more familiar with Pentolina, you can work out the right length of your holiday. Create a rough itinerary and allocate enough time to get through everything on your must-do list.
  4. Bundle your airfare and accommodation: Once you've nailed down your trip dates and duration, lock in the right Pentolina holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.