Pentolina Holidays

    deals illustration
    Better together
    Save up to S$134 when you book a flight and hotel together*
    stays illustration
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    luggage illustration
    Rest easy
    Plan, book, and manage your trip all in one place

Top hotels in Pentolina

Hotel Athena
Hotel Athena
4 out of 5
P Mascagni 55, Siena, SI
Fully refundable
The price is S$211 per night from 16 Jul to 17 Jul
S$211
16 Jul - 17 Jul
includes taxes & fees
9.2/10 Wonderful! (1,002 reviews)
"From the moment we arrived for our two night stay Matteo and Tomasso were kind helpful and informative - We wanted a bigger room and were immediately accommodated - room was clean and comfortable and the hotel was in walking distance to all activities"

Reviewed on 21 Jun, 2025

Hotel Athena
Hotel Executive
Hotel Executive
4 out of 5
Via Nazareno Orlandi 32, Siena, SI
Fully refundableReserve now, pay when you stay
8.2/10 Very Good! (480 reviews)
"Really comfortable hotel , only stayed one night . A great nights sleep . All the staff without exception were friendly, helpful and could not do enough for us. Breakfast selection was in abundance but unfortunately the quality of the food was not great . Maybe less selection with better quality ..."

Reviewed on 2 Oct, 2024

Get rates
Hotel Executive
Hotel Italia
Hotel Italia
3 out of 5
Viale Camillo Benso Conte di Cavour, 67, Siena, SI
Fully refundableReserve now, pay when you stay
9/10 Wonderful! (987 reviews)
"Camas, area y staff muy buenos."

Reviewed on 22 Jun, 2025

Get rates
Hotel Italia
See all 3,472 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.

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.

What to do in Pentolina

From Florence: Siena & San Gimignano Day Trip with Lunch & Wine Tasting

From Florence: Siena & San Gimignano Day Trip with Lunch & Wine Tasting

S$124
per adult
90% of travellers recommend
From Florence: Siena & San Gimignano Day Trip with Lunch & Wine Tasting
From Siena: Chianti and Castles Tour with Wine Tastings

From Siena: Chianti and Castles Tour with Wine Tastings

S$125
per adult
From Siena: Chianti and Castles Tour with Wine Tastings
Siena: Horseback Adventure in the Tuscan Countryside

Siena: Horseback Adventure in the Tuscan Countryside

S$103
per adult
Siena: Horseback Adventure in the Tuscan Countryside
See all activities in Pentolina

* 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.