Pentolina Holidays

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Pentolina Holiday

Our pick of the best Pentolina Hotel Deals

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
The price is NZ$962 per night from 14 July to 15 July
NZ$962
14 July - 15 July
includes taxes & fees
9.4/10 Exceptional! (209 reviews)
"This hotel is the definition of La Dolce Vita! Starting from the beginning, when first arrived to the hotel, they picked up our bags, showed us around the property and responded any questions that we had. Elisa was amazing! She showed us around the property, he gave us recommendations of where to ..."

Reviewed on 1 July 2026

Borgo Scopeto Wine & Country Relais
Hotel Athena

Hotel Athena

4 out of 5
P Mascagni 55 Siena SI
Fully refundableReserve now, pay when you stay
The price is NZ$326 per night from 2 Aug to 3 Aug
NZ$326
2 Aug - 3 Aug
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
"El hotel está bien localizado. La propiedad está en buenas condiciones y el personal es muy atento. La comunicación del personal conmigo fue muy buena. Me hicieron buenas recomendaciones de restaurantes y se esmeraron en hacerme pasar unos hermosos dias. Lo recomiendo 100%."

Reviewed on 5 July 2026

Hotel Athena
Hotel Executive

Hotel Executive

4 out of 5
Via Nazareno Orlandi 32 Siena SI
Fully refundableReserve now, pay when you stay
The price is NZ$203 per night from 13 July to 14 July
NZ$203
13 July - 14 July
includes taxes & fees
8.4/10 Very good! (542 reviews)
"Nice clean hotel. Breakfast ok. Good parking"

Reviewed on 6 July 2026

Hotel Executive
See all 3,524 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

Florence: San Gimignano, Siena, Monteriggioni, Chianti & Lunch with Wine

Florence: San Gimignano, Siena, Monteriggioni, Chianti & Lunch with Wine

NZ$156
per adult
88% of travellers recommend
Florence: San Gimignano, Siena, Monteriggioni, Chianti & Lunch with Wine
Siena, San Gimignano, Monteriggioni & Chianti from Florence

Siena, San Gimignano, Monteriggioni & Chianti from Florence

NZ$128
per adult
86% of travellers recommend
Siena, San Gimignano, Monteriggioni & Chianti from Florence
Medieval Centre

Skip the Line: Siena Duomo and City Walking Tour

NZ$79
per adult
100% of travellers recommend
Skip the Line: Siena Duomo and City Walking Tour
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.

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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.