Penna Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top hotels in Penna
La Certosa di Pontignano
loc. Pontignano, 5 Castelnuovo Berardenga SI
Fully refundableReserve now, pay when you stay
S$164
8 Sept - 9 Sept
includes taxes & fees
9.4/10 Exceptional! (560 reviews)
"Beautiful place, very quiet, in love with gardens"
Reviewed on 31 Aug, 2026
Villa Pitiana
Via Provinciale Per Tosi 7 Reggello FI
Fully refundableReserve now, pay when you stay
S$140
24 Sept - 25 Sept
includes taxes & fees
8.6/10 Excellent! (155 reviews)
"Lovely room and gorgeous location. Best to have a car when coming as it is far away from major areas. Lots of in-house facilities and walks. Good for a relaxing break. We enjoyed family holiday, with visits to the pool and easy drive to Florence."
Reviewed on 28 Aug, 2026
Borgo Scopeto Wine & Country Relais
Strada Comunale 14 Siena - Vagliagli 18 Castelnuovo Berardenga SI
Fully refundableReserve now, pay when you stay
S$878
7 Sept - 8 Sept
includes taxes & fees
9.4/10 Exceptional! (225 reviews)
"Such a beautiful and quiet property. The staff were so friendly and accommodating. The food and drinks were delicious and we enjoyed the spa as well!"
Reviewed on 1 Sept, 2026
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 Penna
Tuscan Brewery Guided Tour with beer and food tasting
S$37
per adult
Tasting with Private Walk in a Cellar in Tuscany
S$37
per adult
Frequently asked questions
How much does a Penna holiday package cost?
Offering excellent value package deals on Expedia, you'll be thrilled with how little a holiday to Penna costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Penna?
January, February and March are the best times to look for cheap Penna holiday packages. Choosing to travel in quieter months means you can generally find better prices on hotels and flights.
How many days is enough for Penna?
The ideal duration for your Penna holiday depends on what you'd like to do and see. Generally, a handful of days to a week will give you plenty of time to visit all the leading attractions and discover some hidden spots along the way.
How to find the best Penna package deals?
Finding a cheap Penna package deal is a breeze with Expedia. After you've entered your travel dates and destination under our "Packages" tab, set your budget range, apply some filters and see what's available. You can customise your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to discover the most economical Penna package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are usually lower.
Is it cheaper to book a Penna holiday as a package?
Expedia holiday packages are designed to give you more bang for your buck. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll generally snag a better deal than booking each component individually. And you'll still have the freedom to create a personalised Penna holiday by choosing your favourite airline, accommodation type and car class.
When to book a holiday package to Penna?
Enjoy fantastic discounts by booking your flights in advance with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Penna adventure.
How to plan a trip to Penna?
- Choose when to get away: Check your diary and get your bags packed. Your favourite season and the type of activities on offer will also help you decide when to visit Penna.
- Figure out your budget: Make sure you have enough money to pay for everything from dining out and transportation to flights and experiences. Your accommodation will probably be the biggest expense during your trip to Penna.
- Decide how long to go for: Now that you're more familiar with Penna, you can figure out the ideal length of your holiday. Create a draft itinerary and allocate enough time to get through everything on your must-do list.
- Bundle your bookings: With your travel dates in place, you can combine your car rental, flights, hotels and more into a personalised Penna holiday package.
* 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.
