Penna Holidays

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    Save up to €185 when you book a flight and hotel together*
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Top Flight + Hotel Deals in Penna

Price found within the past 48 hours. Click for updated prices.
Hotel Villa Marsili

Hotel Villa Marsili

4 out of 5
Cortona Old Town
Save 100% on your flight
Price was €703, price is now €436 per person
€436
per person
25 Sept - 30 Sept
found 11 hours ago
Return flight included
Dublin (DUB) to Florence (FLR)
10/10 Exceptional! (305 reviews)
This hotel gets 5 stars in my book. The staff was welcoming as soon as we arrived and continued to be help throughout our stay. The rooms were old world elegant and so clean. The breakfast was world class, we have never had such large selections of food that were extremely delicious. They really go above and beyond to treat each of their guests like royalty.

Reviewed on 18 Aug 2025

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was €1,413, price is now €726 per person
€726
per person
25 Sept - 29 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
7.8/10 Good! (1,000 reviews)
In my particular case, I tink is a good hotel , I would like the breakfast has more options. Probably I comeback next time.

Reviewed on 18 Aug 2025

Hotel Bencista

Hotel Bencista

3 out of 5
Save 100% on your flight
Price was €1,014, price is now €530 per person
€530
per person
19 Sept - 26 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
7.4/10 Good! (13 reviews)
Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was €1,150, price is now €621 per person
€621
per person
25 Sept - 29 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
7.6/10 Good! (1,007 reviews)
Great location. Few minutes away from train station. Not so quiet. You could hear people from outside even the windows closed. If you are staying for a few days, it’s a great location.

Reviewed on 14 Aug 2025

LHP River Club

LHP River Club

5 out of 5
Santa Croce
Save 100% on your flight
Price was €1,020, price is now €658 per person
€658
per person
25 Sept - 29 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
10/10 Exceptional! (1 review)

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! (243 reviews)
"Beautiful hotal located in such a paradise location amazing view very good food. The staff was very nice. The service was amazing. I definitely recommend the place. It’s a beautiful relaxing, gorgeous."

Reviewed on 13 Aug 2025

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Castello di Spaltenna- Small Luxury Hotels of the World
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! (181 reviews)
"Beautiful property, excellent service"

Reviewed on 31 May 2025

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Borgo Scopeto Wine & Country Relais
A Point Arezzo Park Hotel

A Point Arezzo Park Hotel

4 out of 5
Loc. Battifolle, 36/T, A1 exit Arezzo, Arezzo, AR
Fully refundableReserve now, pay when you stay
7.6/10 Good! (141 reviews)
"It is very close to autostrada,which is good if you have car. The Breakfast was excellant,with a wonderful hostess. This lady is a big bonus to this hotel.The air-conditioning is building controlled,which would not suit everyone.The cleaner for our area had poor attention to detail. The lead cleaner ..."

Reviewed on 24 Sep 2024

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A Point Arezzo Park Hotel
See all 4,572 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

Private wine tour of Chianti or Montalcino

Private wine tour of Chianti

€675
per adult
Private wine tour of Chianti
AREZZO and CORTONA - Private Tour

AREZZO and CORTONA - Private Tour

€945
per adult
AREZZO and CORTONA - Private Tour
Private 10 Hour Tour to Arezzo from Rome

Private 10 Hour Tour to Arezzo from Rome

€995
per adult
Private 10 Hour Tour to Arezzo from Rome
See all activities in Penna

Frequently asked questions

How much does a Penna holiday package cost?
Offering excellent value package deals from €436 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.