Cortona Holidays

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Cortona Holiday

Our pick of the best Cortona Hotel Deals

Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World

Localita Piazzano, C.P. 6 Cortona AR
NZ$1,260
12 Oct - 13 Oct
includes taxes & fees
9.8/10 Exceptional! (251 reviews)
"Stunning little hotel with the most beautiful setting, gardens and pool. The room was exceptionally appointed clean. The best part of the stay was the restaurant. The best meals we had on our entire trip. Definitely recommend hiring e-bikes and riding up to Cortona!"

Reviewed on 20 Sept 2026

Villa di Piazzano - Small Luxury Hotel of the World
Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

Via del Salvatore Cortona AR
Fully refundableReserve now, pay when you stay
NZ$506
25 Oct - 26 Oct
includes taxes & fees
10/10 Exceptional! (343 reviews)
"5 star treatment, indoor pool is a charge to use and parking is rough. Overall excellent experience. Staff is great."

Reviewed on 4 Oct 2026

Monastero di Cortona Hotel & Spa
Il Falconiere - Relais e Chateaux

Il Falconiere - Relais e Chateaux

Localita San Martino 370 Cortona AR
NZ$763
2 Nov - 3 Nov
includes taxes & fees
Il Falconiere - Relais e Chateaux
See all 1,175 properties in Cortona
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.

Stay near popular Cortona attractions

Villa Bramasole

9.2/10 (20 reviews)
Made famous by "Under the Tuscan Sun," Villa Bramasole showcases classic Tuscan architecture. Admire this private residence from the road during a scenic walk through Cortona's charming countryside.
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Piazza della Repubblica

9.4/10 (95 reviews)
Piazza della Repubblica pulses as Cortona's medieval heart, framed by the Palazzo Comunale and its clock tower. Savour authentic Tuscan cuisine at outdoor cafés while absorbing panoramic countryside views.
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Cortona Cathedral

9.4/10 (77 reviews)
This Romanesque-Renaissance cathedral stands on ancient Roman temple remains, showcasing elegant portals and slender columns. Inside, experience serenity while admiring panoramic views of the Tuscan countryside.
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Fortress of Girifalco

8.8/10 (25 reviews)
You can find out about the history of Cortona with a trip to Fortress of Girifalco. You can enjoy the wineries while in the area.
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Santa Margherita Basilica

9.2/10 (30 reviews)
Perched high above Cortona, this Gothic-Baroque basilica houses Saint Margaret's remains, the town's patron saint. Visitors can admire the silver urn and enjoy sweeping Tuscan countryside views.
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San Domenico Church

9.0/10 (9 reviews)
After visiting San Domenico Church, make a plan to see the other sights and activities in Cortona. Make time to visit the cathedral and monuments while you're in the area.
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Palazzo Comunale

9.2/10 (44 reviews)
Palazzo Comunale 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 theatre.
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Eremo Le Celle

9.4/10 (12 reviews)
St. Francis of Assisi founded this rustic stone hermitage in 1211, offering a glimpse into Franciscan monastic life. Wander the peaceful cells and chapels amid the serene woodland setting.
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What to do in Cortona

Montepulciano Wine Tasting in the Tuscan Countryside

Montepulciano Wine Tasting in the Tuscan Countryside

NZ$50
per adult
Montepulciano Wine Tasting in the Tuscan Countryside
Montepulciano: Tuscan Cooking Class with Fresh Pasta & Wine

Montepulciano: Tuscan Cooking Class with Fresh Pasta & Wine

NZ$161
per adult
Montepulciano: Tuscan Cooking Class with Fresh Pasta & Wine
Montepulciano: Winery Tour and Tasting

Montepulciano: Winery Tour and Tasting

NZ$70
per adult
100% of travellers recommend
Montepulciano: Winery Tour and Tasting
See all activities in Cortona

Frequently asked questions

How much does a Cortona holiday package cost?
You'll find cheap prices on Expedia for your Cortona break. However, factors like the season, length of stay and your choice of hotel will influence how much your holiday to Cortona costs.
What are the cheapest months to go to Cortona?
If you'd like to snag a cheap Cortona holiday package, consider travelling in December, January and February. You're likely to find better prices on airfares and hotels during these months — perfect for travellers wishing to save money.
How many days is enough for Cortona?
With around 3 days, you'll have enough time to enjoy popular neighbourhoods like Cortona Old Town and Sodo during your Cortona holiday. Be sure to also add Palazzo Comunale and Museum of the Etruscan Academy to your must-see list. Searching for more adventures? Consider exploring outside of Cortona on tours and day trips.
Is it worth booking a holiday package to Cortona?
Popular for its views, dining and walking trails, a Cortona holiday is a hit with all kinds of visitors. Be sure to check out top sights like Villa Bramasole and Piazza della Repubblica, and consider renting a set of wheels for day trips to discover even more.
How to find the best Cortona package deals?
Start your search for a Cortona package deal by entering your preferred trip dates and destination under our "Packages" tab. Then apply a few filters, like "Property type" and "Popular locations," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect Cortona package deal straight away, simply switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Cortona escape underway.
Is it cheaper to book a Cortona holiday as a package?
An Expedia holiday package could save you hundreds of dollars when compared to arranging flights and stays individually. Better still, you can customise your Cortona trip to match your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a holiday package to Cortona?
If you're considering an impromptu Cortona holiday, browse our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can land terrific deals on your flights and hotels by booking well in advance.
How to plan a trip to Cortona?
  1. Choose when to go: Check your calendar and get packing. Your favourite season and the type of activities available will also help you decide when to escape to Cortona.
  2. Budget wisely: Besides the price of your stay, you'll need to factor in other expenses too. These include food, transportation and flights. Also, set aside some extra funds for unexpected costs that could crop up during your trip to Cortona.
  3. Work out your trip length: Think about how much time you'd like to spend discovering Cortona. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a leisurely pace.
  4. Bundle your accommodation and airfare: Once you've nailed down your dates and duration, book the right Cortona holiday package for you.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.