Contrada Castello Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Price found within the past 48 hours. Click for updated prices.
  • Front of property - evening/night
    Aug 6 - Aug 13

    TH Assisi - Hotel Cenacolo + Flight

    Assisi
    6 nights
    4.0 star property
    9.2/10 - Wonderful (667 reviews)
    Roundtrip • Québec City (YQB) - Rome (FCO)
    YQB - FCO • 1 stop FCO - YQB • 1 stop
    CA $1,605
    CA $1,431
    per traveller
    found 1 day ago
    TH Assisi - Hotel Cenacolo
  • Bar (on property)
    Aug 6 - Aug 13

    Posta Donini 1579 UNA Esperienze + Flight

    Perugia
    6 nights
    5.0 star property
    9.2/10 - Wonderful (255 reviews)
    Roundtrip • Québec City (YQB) - Rome (FCO)
    YQB - FCO • 1 stop FCO - YQB • 1 stop
    CA $2,385
    CA $1,897
    per traveller
    found 1 day ago
    Posta Donini 1579 UNA Esperienze
  • Exterior
    Aug 6 - Aug 13

    Hotel Sorella Luna + Flight

    Assisi Historic Center
    6 nights
    3.0 star property
    9.4/10 - Exceptional (274 reviews)
    "Exceptionally helpful staff!!"
    Reviewed May 26, 2026
    Roundtrip • Québec City (YQB) - Rome (FCO)
    YQB - FCO • 1 stop FCO - YQB • 1 stop
    CA $1,828
    CA $1,574
    per traveller
    found 1 day ago
    Hotel Sorella Luna
  • Indoor pool
    Aug 6 - Aug 13

    Sina Brufani + Flight

    Old Town Perugia
    6 nights
    5.0 star property
    9.2/10 - Wonderful (639 reviews)
    "Clean room, nice staff"
    Reviewed May 19, 2026
    Roundtrip • Québec City (YQB) - Rome (FCO)
    YQB - FCO • 1 stop FCO - YQB • 1 stop
    CA $2,013
    CA $1,797
    per traveller
    found 1 day ago
    Sina Brufani
  • Interior entrance
    Aug 6 - Aug 13

    Rosetta Hotel Perugia, Tapestry Collection by Hilton + Flight

    Old Town Perugia
    6 nights
    5.0 star property
    9.2/10 - Wonderful (9 reviews)
    "The hotel itself is lovely — well located, recently renovated, with nice décor that gives it a fresh feel. But what truly makes this place a gem is the people. Chiara at the front desk sets the tone from the moment you arrive. Marina and Yessenia in the breakfast restaurant are warm and attentive, and they make mornings genuinely enjoyable. And the bellboys keep everything running smoothly — special shout out to Vasile, one of the nicest guys you’ll meet. The property is solid, but the team is..."
    Reviewed May 21, 2026
    Roundtrip • Québec City (YQB) - Rome (FCO)
    YQB - FCO • 1 stop FCO - YQB • 1 stop
    CA $2,090
    CA $1,894
    per traveller
    found 1 day ago
    Rosetta Hotel Perugia, Tapestry Collection by Hilton

Contrada Castello 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
The price is CA $972 per night from Jun 19 to Jun 20
CA $972
CA $1,082 total
Jun 19 - Jun 20
includes taxes & fees
9.8/10 Exceptional! (235 reviews)
"The Hotel and grounds are beautiful and immaculately maintained. The entire staff really stands out. So friendly and welcoming. Those little gestures of respect and kindness are appreciated. Also it’s very convenient that they can speak English. There are several beautiful hotels in the area to experience, ..."

Reviewed on May 14, 2026

Villa di Piazzano - Small Luxury Hotel of the World
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
The price is CA $493 per night from Jun 28 to Jun 29
CA $493
CA $555 total
Jun 28 - Jun 29
includes taxes & fees
10/10 Exceptional! (282 reviews)
"We had an amazing stay at the monastero di Cortona. The property is absolutely beautiful and impeccably maintained. The pool area is lovely and the views are unbelievable. The staff was super helpful and attentive- gave us recommendations for restaurants (and made reservations for us) and helped ..."

Reviewed on May 26, 2026

Monastero di Cortona Hotel & Spa
Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Via Poggio alla Sala 10 Montepulciano SI
Fully refundableReserve now, pay when you stay
The price is CA $850 per night from Jun 18 to Jun 19
CA $850
CA $944 total
Jun 18 - Jun 19
includes taxes & fees
9.6/10 Exceptional! (140 reviews)
"Beautiful stay for our honeymoon. This is definitely a place to go and feel at peace in the Tuscan countryside. 15 min away from some wineries and 20 min away from Montepulciano. Great balance of feeling relaxed by the spa and pool with some quick getaways. Lastly, the restaurant was beyond excellent. ..."

Reviewed on May 23, 2026

Precise Tale Poggio Alla Sala
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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 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.

Things to do

Enjoy a meal with wine tasting in the vineyard of Podere Casanova

Enjoy a meal with wine tasting in the vineyard of Podere Casanova

CA $160
per adult
Enjoy a meal with wine tasting in the vineyard of Podere Casanova
Montepulciano: Wine Tour and tasting

Montepulciano: Wine Tour and tasting

CA $84
per traveller
Montepulciano: Wine Tour and tasting
Wine Tasting & Tour Premium

Wine Tasting & Tour Premium

CA $83
per adult
Wine Tasting & Tour Premium
See all activities in Castiglione del Lago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.