Contrada Castello Holidays

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  • Better together

    Save up to €900 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

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    Plan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
  • View from property
    Aug 16 - Aug 23

    Residenza Porta Guelfa + Flight

    Bevagna
    7 nights
    3.0 star property
    8.4/10 - Very good (47 reviews)
    "."
    Reviewed February 28, 2026
    Return • Cork (ORK) - Rome (FCO)
    ORK - FCO • 1 stop FCO - ORK • 1 stop
    €1,084
    €818
    per traveller
    found 1 day ago
    Residenza Porta Guelfa
  • View from property
    Aug 16 - Aug 23

    International Hotel & Suite + Flight

    San Benedetto del Tronto
    7 nights
    4.0 star property
    8.6/10 - Excellent (246 reviews)
    "."
    Reviewed September 22, 2025
    Return • Cork (ORK) - Rome (FCO)
    ORK - FCO • 1 stop FCO - ORK • 1 stop
    Save 100% on your flight
    €1,542
    €1,109
    per traveller
    found 1 day ago
    International Hotel & Suite
  • Indoor pool
    Aug 16 - Aug 23

    Sina Brufani + Flight

    Old Town Perugia
    7 nights
    5.0 star property
    9.2/10 - Wonderful (639 reviews)
    "Clean room, nice staff"
    Reviewed May 19, 2026
    Return • Cork (ORK) - Rome (FCO)
    ORK - FCO • 1 stop FCO - ORK • 1 stop
    €1,024
    €854
    per traveller
    found 1 day ago
    Sina Brufani

Top hotels in Contrada Castello

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 €671 per night from 1 Jul to 2 Jul
€671
1 Jul - 2 Jul
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 14 May 2026

Villa di Piazzano - Small Luxury Hotel of the World
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 €581 per night from 28 Jun to 29 Jun
€581
28 Jun - 29 Jun
includes taxes & fees
9.6/10 Exceptional! (142 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 23 May 2026

Precise Tale Poggio Alla Sala
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 €397 per night from 17 Jun to 18 Jun
€397
17 Jun - 18 Jun
includes taxes & fees
10/10 Exceptional! (283 reviews)
"Beautiful property - great location. Staff was wonderful. They organized transportation for us and the driver was fantastic - ask for Tony!"

Reviewed on 31 May 2026

Monastero di Cortona Hotel & Spa
See all 4,945 properties in Contrada Castello
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 holiday 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 holiday package makes it simple to organise 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 holiday?
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 holiday is only a couple of clicks away.
Can I choose my airline with a Contrada Castello Expedia holiday package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines all over the world. Our holiday 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 holiday package?
Don't worry if you're rethinking your Contrada Castello holiday 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.