Pietraia Vacations from $1,095

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Your Pietraia Vacation

Book a customized Pietraia vacation package that has only the things you need and nothing you don't. Great for dining, views and culture, consider basing yourself in the neighborhood of Contrada Castello. Villa Bramasole, Piazza della Repubblica and Cathedral of Cortona are just some of the many sights you'll want to see during your trip to Pietraia. A few quick clicks is all it takes to craft a tailor-made Pietraia vacation on Expedia.

The Latest Pietraia vacation packages

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

Hotel Botticelli

4 out of 5
Historic Centre of Florence
Price was $1,460, price is now $1,095 per person
$1,095
per person
Dec 19 - Dec 23
found 8 hours ago
Roundtrip flight included
Boston (BOS) to Florence (FLR)
8.6/10 Excellent! (980 reviews)
Booked a room for 1 and it was quite small, not worth the price for me but good location

Reviewed on Sep 25, 2025

The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
Price was $1,749, price is now $1,186 per person
$1,186
per person
Dec 19 - Dec 23
found 8 hours ago
Roundtrip flight included
Boston (BOS) to Florence (FLR)
9.6/10 Exceptional! (477 reviews)
Superb hotel. Rooms magnificent, reflect the photos. Staff amazingly friendly and helpful.

Reviewed on Sep 27, 2025

Villa Cora

Villa Cora

5 out of 5
Oltrarno
Save 100% on your flight
Price was $2,025, price is now $1,389 per person
$1,389
per person
Nov 20 - Nov 25
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
9.8/10 Exceptional! (461 reviews)
The hotel is very beautiful, and the surrounding environment is also excellent.

Reviewed on Sep 26, 2025

Dimora Palanca Boutique & SPA

Dimora Palanca Boutique & SPA

5 out of 5
Historic Centre of Florence
Price was $1,731, price is now $1,275 per person
$1,275
per person
Nov 3 - Nov 8
found 15 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
9.4/10 Exceptional! (51 reviews)
Property is beautiful and quiet. Would stay there again.

Reviewed on Sep 13, 2025

Hotel Ville sull'Arno

Hotel Ville sull'Arno

5 out of 5
Campo di Marte
Price was $1,481, price is now $1,103 per person
$1,103
per person
Dec 19 - Dec 23
found 8 hours ago
Roundtrip flight included
Boston (BOS) to Florence (FLR)
9.6/10 Exceptional! (748 reviews)
Exceptional staff and breakfast.

Reviewed on Sep 23, 2025

Don't see what you're looking for?
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Discover the most popular places to visit in Pietraia

Cortona featuring heritage architecture

Piazza della Repubblica

Find out about the history of Cortona with a stop at Piazza della Repubblica. Make time to visit the cathedral and monuments while you're in the area.

Piazza della Repubblica

Villa Bramasole

You can learn about the history of Cortona with a trip to Villa Bramasole. You can enjoy the wineries while in the area.

Villa Bramasole

Cortona Cathedral

Cortona Cathedral is just one of the places to see in Cortona, so why not enjoy the other things to explore during your travels? Experience the area's museums and musical theater.

Cortona Cathedral

What to do in Pietraia

Montepulciano Wine Tasting in the Tuscan Countryside

Montepulciano Wine Tasting in the Tuscan Countryside

$30
per adult
Montepulciano Wine Tasting in the Tuscan Countryside
3 Regions in 1 Day from Rome with Tuscany Wine Tasting & Lunch

From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch

$105
per adult
100% of travellers recommend
From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
Oil museum and oil mill in Tuscany: tour and tasting

Oil museum and oil mill in Tuscany: tour and tasting

$24
per adult
Oil museum and oil mill in Tuscany: tour and tasting
See all activities in Pietraia

Pietraia Hotel Deals

Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World

5 out of 5
Localita Piazzano, C.P. 6, Cortona, AR
Fully refundableReserve now, pay when you stay
$498 nightly
The price is $558 total per night from Oct 21 to Oct 22
$558 total
Oct 21 - Oct 22
Total with taxes and fees
9.6/10 Exceptional! (223 reviews)
"I stayed at Villa di Piazzano for two nights and overall had a lovely experience. The check-in process was seamless, and the staff were warm, professional, and very attentive, which set a great tone from the start. The property itself is absolutely gorgeous, with beautiful grounds and a peaceful ..."

Reviewed on Sep 23, 2025

Villa di Piazzano - Small Luxury Hotel of the World
Hotel Relais II Chiostro di Pienza

Hotel Relais II Chiostro di Pienza

4 out of 5
Corso Rossellino 26, Pienza, SI
Fully refundableReserve now, pay when you stay
$77 nightly
The price is $92 total per night from Oct 13 to Oct 14
$92 total
Oct 13 - Oct 14
Total with taxes and fees
8.6/10 Excellent! (595 reviews)
Stunning setting - authentic italian
"The pictures do not do it justice - stunning setting and view, very nice hotel, very kind attentive staff. Would definitely recommend."

Reviewed on Aug 25, 2025

Hotel Relais II Chiostro di Pienza
Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

5 out of 5
Via del Salvatore, Cortona, AR
Fully refundableReserve now, pay when you stay
$322 nightly
The price is $364 total per night from Oct 28 to Oct 29
$364 total
Oct 28 - Oct 29
Total with taxes and fees
9.8/10 Exceptional! (239 reviews)
"Beautiful, unique property! Stunning views of the countryside. The staff were all very helpful and friendly. We will definitely recommend!"

Reviewed on Sep 27, 2025

Monastero di Cortona Hotel & Spa
See all 5,228 properties in Pietraia
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.

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Frequently asked questions

How much does a Pietraia vacation package cost?
You can grab a vacation package to this destination from $1,095 on Expedia. However, how much your vacation to Pietraia costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Pietraia?
You're likely to find reduced prices and better availability in October, November and December. Browse our cheap Pietraia vacation packages and you could get some great off-season deals.
How many days is enough for Pietraia?
The ideal duration for your Pietraia vacation depends on what you'd like to see. Generally, a few days to a week will give you enough time to hit all the leading sights and discover some hidden treasures along the way.
How to find the best Pietraia package deals?
Begin your search for a Pietraia package deal by entering your preferred travel dates and destination under our "Packages" tab. Then apply a few filters, like "Property type" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the ideal Pietraia package deal straight away, just play around with your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Pietraia adventure off to a flying start.
Is it cheaper to book a Pietraia vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll generally land a better deal than booking each component individually. And you'll still have the freedom to create a customized Pietraia vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Pietraia?
Land incredible bargains by reserving your flights early with Expedia. If being spontaneous is more your thing, take advantage of our last-minute deals for an impromptu Pietraia trip.
How to plan a trip to Pietraia?

  1. Choose the perfect time to travel: Your schedule, favorite season and the type of weather you like can all influence your decision on when to travel to Pietraia.
  2. Plan your budget wisely: As well as the cost of your stay, you should consider other expenses. These include food, flights and transportation. Also, put aside some extra funds for unexpected costs that could crop up during your trip to Pietraia.
  3. Discover Pietraia using Expedia's trip planning tool: Gain insights into the top attractions and best stays for your trip to Pietraia. You can also save your must-visit places, collaborate with friends and family and manage your plans in one place.
  4. Decide how long to go for: Now that you're more familiar with Pietraia, you can figure out the ideal length of your break. Put together a rough plan and allocate enough time to cover everything you want to see.
  5. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. Now all that's left is to choose a Pietraia vacation package that brings all your bookings together.
  6. Book experiences or activities in advance: Whether it's a ticket to a big attraction or a day trip in nature, you won't have to worry about missing out on Pietraia's best offerings. Find all the exciting things to do in Pietraia in Pietraia with our dedicated activity guide.

Does Expedia offer Book Now, Pay Later Pietraia vacation packages?
Secure your perfect trip to Pietraia with Expedia's Book Now, Pay Later vacations. No need to save like crazy or wait for payday — we've joined forces with online lender Affirm to offer you flexibility and choice. Our vacation packages with payment plans allow you to split the cost over 3, 6 or 12 months. With no late payment fees or extra charges, it's easy to budget for your trip and snap up bargains before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.