Penna Holidays

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    Save up to S$134 when you book a flight and hotel together*
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Top hotels in Penna

Castello di Spaltenna- Small Luxury Hotels of the World
Castello di Spaltenna- Small Luxury Hotels of the World
5 out of 5
Via Spaltenna 13, Gaiole in Chianti, SI
Fully refundableReserve now, pay when you stay
9.4/10 Exceptional! (232 reviews)
"We stayed here as a family of six, including our two 3-year-olds, and it was by far our favorite place during our time in Italy! The kids absolutely loved swimming in the pools and running around the beautiful property. It felt peaceful, safe, and perfect. The breakfast was lovely each morning—fresh, ..."

Reviewed on 28 Jun, 2025

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Castello di Spaltenna- Small Luxury Hotels of the World
La Certosa di Pontignano
La Certosa di Pontignano
loc. Pontignano, 5, Castelnuovo Berardenga, SI
Fully refundableReserve now, pay when you stay
The price is S$106 per night from 17 Jul to 18 Jul
S$106
17 Jul - 18 Jul
includes taxes & fees
9.4/10 Exceptional! (428 reviews)
"It was a wonderful experience!! The room is extremely comfortable, and the whole hotel is so beautiful!!!! There is a garden that look it came out from a fairy tale! The staff is very friendly and welcoming! Recommend 100%"

Reviewed on 30 Jun, 2025

La Certosa di Pontignano
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! (177 reviews)
"Beautiful property, excellent service"

Reviewed on 31 May, 2025

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Borgo Scopeto Wine & Country Relais
See all 4,588 properties in Penna
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

Panoramic view of the Chianti Hills & Radda

Wine Experience In Chianti Hills from Florence

S$73
per adult
Wine Experience In Chianti Hills from Florence
Wine tasting in the historic Cantalici winery

Wine tasting in the historical Cantalici winery

S$22
per adult
100% of travellers recommend
Wine tasting in the historical Cantalici winery
Luxury Shopping Experience: Private Chauffeur to The Mall and Prada Outlet

Luxury Shopping Experience The Mall and Prada Outlet

S$328
per adult
Luxury Shopping Experience The Mall and Prada Outlet
See all activities in Penna

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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.