Contrada Castello Vacations
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- Better togetherSave up to ￥109,000 when you book a flight and hotel together*
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Contrada Castello Hotel Deals
Villa di Piazzano - Small Luxury Hotel of the World
Localita Piazzano, C.P. 6 Cortona AR
￥101,761
￥113,421 total
Sep 2 - Sep 3
includes taxes & fees
9.8/10 Exceptional! (245 reviews)
"Staff was helpful , and the room was clean. The Antica Casina di Caccia dining with wine pairing was absolutely amazing. Also took some great pictures in the garden. The breakfast was nice too."
Reviewed on Aug 17, 2026
Precise Tale Poggio Alla Sala
Via Poggio alla Sala 10 Montepulciano SI
Fully refundableReserve now, pay when you stay
￥93,963
￥104,472 total
Sep 30 - Oct 1
includes taxes & fees
9.6/10 Exceptional! (165 reviews)
"Fantastic stay!"
Reviewed on Aug 30, 2026
Monastero di Cortona Hotel & Spa
Via del Salvatore Cortona AR
Fully refundableReserve now, pay when you stay
￥56,420
￥63,546 total
Sep 13 - Sep 14
includes taxes & fees
10/10 Exceptional! (318 reviews)
"Before I share, I will say that the staff helping with breakfast and at the bar (by the pool) were great. However, the front desk employees were pretty cold in each of my interactions with them. When I first inquired about reserving time slots at the spa, I asked about the remaining available slots ..."
Reviewed on Aug 29, 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.
Frequently asked questions
How much does a Contrada Castello vacation package cost?
From as little as . Yes, you read that right. Our Contrada Castello packages are a simple way to make your budget go further. Bundle your flights, hotels and rental car and discover this lively destination.
How do I get a cheap travel package to Contrada Castello?
Combining your flight and hotel with Expedia won't just save precious time — it'll save you a nice amount too. A Contrada Castello vacation package makes it simple to organize the perfect trip. With more than 550 airlines all over the world to select from, finding flights that suit your busy schedule won't be a hassle. In addition to that, we have over 1,000,000 hotels globally to select from. Now that's what we call choice. Whatever your budget, Expedia can show you the world.
Where should I stay in Contrada Castello?
A trip to Contrada Castello isn't complete without paying a visit to Rocca del Leone. Why not stay close to this interesting tourist attraction?
What are the top hotels in Contrada Castello?
Get your trip off to an excellent start by locking in a room at B&B Antica Gabella. It's one of most popular properties in Contrada Castello. Another top option is Hotel Boutique Castiglione del Lago.
How far in advance should I book my Contrada Castello vacation?
It's difficult to pick the perfect time for airfares, but we usually say the earlier, the better. Most international flights on Expedia become available up to a year in advance. If you can't book early, don't fret. Cheap prices occasionally appear within a few weeks of departure dates.
What does an Expedia Contrada Castello travel package include?
It all depends on what type of getaway you're planning. Contrada Castello travel deals can include car rentals, hotels and flights. You can mix and match to find the travel package that suits you. You can also add on activities and experiences after you've booked to land even bigger discounts.
What should I know before booking a Contrada Castello travel package?
You can save a tidy sum by combining your airfares, hotels and rental cars. Once you've made your booking, add on fun stuff like activities or tours. Your next unforgettable vacation is only a couple of clicks away.
Can I choose my airline with a Contrada Castello Expedia vacation package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines all over the world. Our vacation packages give you the flexibility to pick from available flight, hotel or activity options that fit your needs.
If I'm not able to travel, can I cancel my Contrada Castello vacation package?
Don't worry if you're rethinking your Contrada Castello vacation package — it's possible to cancel or amend your booking. And if you've booked it within the last 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur charges from your hotel, airline or car rental company. We totally understand life can sometimes throw you a curveball, so make your way to our Customer Service Portal if that occurs. When you're ready to make changes, we'll take care of it.
Stay near popular Contrada Castello attractions
Rocca del Leone
9.4/10 (10 reviews)
You can learn about the history of Castiglione del Lago when you stop by Rocca del Leone. Stroll along the area's lakeside or simply enjoy its wineries.
Palazzo della Corgna
9.0/10 (12 reviews)
You can study the exhibits at Palazzo della Corgna, a museum with a storied past, during your trip to Castiglione del Lago. Stroll along the area's lakeside or simply enjoy its wineries.
Things to do
Enjoy a meal with wine tasting in the vineyard of Podere Casanova
￥18,219
per adult
Montepulciano: Tuscan Winery Tour with Wine Tasting & Meal
￥18,219
per adult
100% of travellers recommend
Montepulciano: Winery Tour, Tasting, and Vineyard Picnic
￥16,379
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.