Pentolina Holidays

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Top hotels in Pentolina

Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

Banchi Di Sopra 85 Siena SI
Fully refundableReserve now, pay when you stay
S$473
26 Aug - 27 Aug
includes taxes & fees
Grand Hotel Continental Siena – Starhotels Collezione
Hotel Athena

Hotel Athena

P Mascagni 55 Siena SI
Fully refundableReserve now, pay when you stay
S$231
28 Aug - 29 Aug
includes taxes & fees
9.2/10 Wonderful! (1,006 reviews)
"Wonderful hotel in great location just a short walk from the centre but quiet and peaceful in the evening. Fabulous helpful staff. Breakfast always fresh and lots of choice. We used the terrace restaurant once and it was fabulous - what amazing views! Highly recommended for a short or longer ..."

Reviewed on 6 Aug, 2026

Hotel Athena
Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais

Strada Comunale 14 Siena - Vagliagli 18 Castelnuovo Berardenga SI
Fully refundableReserve now, pay when you stay
S$734
26 Aug - 27 Aug
includes taxes & fees
9.4/10 Exceptional! (219 reviews)
"We spent a wonderful week at Borgo Scopeto and thoroughly enjoyed every minute. It has everything you'd hope for from a luxury Tuscan retreat: beautiful historic buildings, immaculately kept grounds, and a peaceful atmosphere full of character. The staff were warm, attentive and genuinely welcoming ..."

Reviewed on 5 Aug, 2026

Borgo Scopeto Wine & Country Relais
See all 3,504 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

S$105
per adult
88% of travellers recommend
Florence: San Gimignano, Siena, Monteriggioni, Chianti & Lunch with Wine
Siena: Cathedral Complex Pass with Audio Guide

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

S$27
per adult
Siena: Cathedral Complex Pass with Audio Guide (OPA SI PASS)
From Florence: Siena & San Gimignano Day Trip with Lunch & Wine Tasting

Tuscany Day Trip to Siena & San Gimignano with Optional Wine Tasting

S$72
per adult
90% of travellers recommend
Tuscany Day Trip to Siena & San Gimignano with Optional Wine Tasting
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.

Explore a world of travel with Expedia

* 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.