Cortona Vacation Packages 2026 from $1,636

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Your Cortona Vacation

With plenty of highlights as well as hidden gems, this city is best experienced with a Cortona vacation package. Find a place to stay in Contrada Castello, which is good for dining, views and culture. Ready to explore? Villa Bramasole, Piazza della Repubblica and Cathedral of Cortona are just a few of the top-rated places to visit during your trip to Cortona. Whoever you're going away with and whatever the size of your budget, your ultimate Cortona vacation is only clicks away with Expedia.

The Latest Cortona vacation packages

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

Grand Hotel Cavour

Historic Centre of Florence

Save 100% on your flight

$1,636

per person

Oct 23 - Oct 28

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

9.2/10 Wonderful! (1,001 reviews)

Great location There is a lady at the front desk that was so very helpful and kind For sure coming back to this hotel

Reviewed on Aug 11, 2026

Palazzo Leopoldo Dimora Storica & Spa

$1,716

per person

Oct 23 - Oct 30

found 20 hours ago

Roundtrip flight included

New York (NYC) to Florence (FLR)

9.2/10 Wonderful! (294 reviews)

Wonderful old building with character and charm. Set right in the middle of Radda. Be aware you can drive into the restricted zone if you’re staying at the hotel, for 20 mins. I advise calling the hotel before you arrive.

Reviewed on Aug 6, 2026

Fonteverde Thermal Spa Resort Tuscany

Save 100% on your flight

$2,233

per person

Oct 23 - Oct 30

found 20 hours ago

Roundtrip flight included

New York (NYC) to Florence (FLR)

9.4/10 Exceptional! (208 reviews)

Wonderful place, great service and very good restaurant

Reviewed on Aug 11, 2026

Albergo Le Terme

$2,004

per person

Oct 23 - Oct 30

found 20 hours ago

Roundtrip flight included

New York (NYC) to Florence (FLR)

9.2/10 Wonderful! (78 reviews)

Upon checking we were greeted by a lovely lady that gave great instructions on parking and use of the spa. Our room was very clean and the bed was comfortable. The thermal spa was very nice as we arrived after 10 pm after a long drive from Sorrento. We were able to relax and enjoy the water until midnight. The next morning the breakfast as absolutely superb. We walked around the town until checkout but are going back to the hotel after our stay in north Italy this week. Also it was nice that they had a dedicated parking lot. Our auto was very safe. Checkout was simple as we were in our way to cinque terre. Very Much a 5 star stay.

Reviewed on Jul 28, 2026

Eden Rock Resort

Save 100% on your flight

$1,935

per person

Sep 21 - Sep 26

found 7 hours ago

Roundtrip non-stop flight included

New York (NYC) to Florence (FLR)

9.8/10 Exceptional! (109 reviews)

This was a beautiful property about 10 mins away from Florence. You get the beauty of Tuscany without having to go too far. The hotel only has 12 rooms and everyone knows you by name. We traveled with 2 kids and the rooms were very spacious. Staff are wonderful, Onsite restaurant was great. Views were breathtaking. We didn't have a car, and the hotel was able to help us with cabs easily. Service was excellent and we would highly recommend this hotel!

Reviewed on Jul 18, 2026

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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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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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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. Savor authentic Tuscan cuisine at outdoor cafés while absorbing panoramic countryside views.

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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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Santa Maria Nuova

8.8/10 (5 reviews)

This Renaissance masterpiece by Giorgio Vasari features a striking central dome and Greek cross plan just outside Cortona's walls. Enjoy the serene atmosphere while taking in panoramic views of the Tuscan countryside.

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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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Signorelli Theatre

9.2/10 (14 reviews)

You can make plans for a show at Signorelli Theatre during your stay in Cortona. Discover the area's countryside and monuments.

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Casali Palace

8.6/10 (7 reviews)

This Renaissance palace anchors Cortona's historic center with its distinctive stone façade. Wander through the surrounding cobblestone streets to discover authentic Tuscan charm in this hillside town.

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What to do in Cortona

Tasting Tour in One of The Most Beautiful Cellars in the World

$38

per adult

100% of travellers recommend

Montepulciano Wine Tasting in the Tuscan Countryside

$28

per adult

Montepulciano: Winery Tour and Tasting

$40

per adult

100% of travellers recommend

See all activities in Cortona

Cortona Hotel Deals

Villa di Piazzano - Small Luxury Hotel of the World

Localita Piazzano, C.P. 6 Cortona AR

$622 nightly

$694 total

Aug 23 - Aug 24

Total with taxes and fees

Monastero di Cortona Hotel & Spa

Via del Salvatore Cortona AR

Fully refundableReserve now, pay when you stay

$283 nightly

$320 total

Aug 23 - Aug 24

Total with taxes and fees

10/10 Exceptional! (304 reviews)

"Everything was absolutely perfect and we would happily go back."

Reviewed on Aug 6, 2026

Il Falconiere - Relais e Chateaux

Localita San Martino 370 Cortona AR

$468 nightly

$524 total

Aug 26 - Aug 27

Total with taxes and fees

See all 1,173 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.

Find the Best Cortona Vacation Packages

Things to do in and around Cortona

Cortona is perfect for a romantic getaway, offering stunning outdoor scenery and a range of activities. Visitors can indulge in spa treatments, enjoy theatrical performances, and embark on memorable day trips. Don't miss the chance to explore local art, take a private tour of the charming town, and visit nearby attractions like Orvieto and Pienza for a taste of Tuscany's rich culture and beauty.

Shopping

Cortona offers charming shopping experiences with local boutiques and artisan shops. For a wider selection, visit Valdichiana Outlet Village, located 10 miles away, featuring various brands and family-friendly amenities. If you're up for a drive, check out RI Crea RE and Maioliche Nulli, 21 and 29 miles away, respectively.

Recreation

Experience the charm of the Signorelli Theatre, where culture and romance meet in vibrant performances. Unwind at the Tennis Club Castiglionese, enjoying luxury amidst scenic views. For outdoor enthusiasts, the Golf Club Valdichiana offers a perfect blend of sport and nature, just a short drive from Cortona.

Adventure

Embark on Hannibal's Journey, a thrilling 5-mile hiking trail near Cortona that offers breathtaking scenery and outdoor adventure. For adrenaline junkies, the Magione Racetrack, 16 miles away, provides high-speed motor racing excitement. Lastly, enjoy family fun at Tavernelle Aquatic Park, located 20 miles from Cortona, with exhilarating water attractions.

Nightlife

Cortona's nightlife offers a charming blend of rustic bars and vibrant taverns. Enjoy local wines at Enoteca Vigna del Sole or dance to live music at Bar L'Incontro. For a cozy atmosphere, visit Caffè degli Artisti, where you can unwind with friends after a day of exploring.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in and around Cortona

Cortona offers a perfect blend of romance and outdoor beauty, making it an ideal vacation spot. Explore the charming churches, lively piazzas, and captivating museums that showcase the town's rich culture and history. Whether you're seeking a cultural experience, scenic views, or a taste of city life, Cortona has something for every traveler looking to immerse themselves in the heart of Tuscany.

Lake Trasimeno: Experience the serene beauty of Lake Trasimeno, located 11 miles from Cortona. Enjoy its picturesque beaches and breathtaking scenery, perfect for outdoor activities or a romantic day by the water.
Villa Bramasole: Explore the historic Villa Bramasole, nestled in Cortona. This charming site offers a glimpse into the rich culture of the area and is famously known for its stunning architecture and connection to the book Under the Tuscan Sun.
Piazza della Repubblica: Immerse yourself in the vibrant atmosphere of Piazza della Repubblica, a cultural hub in Cortona. Enjoy the lively ambiance, local shops, and exquisite architecture that reflect the city's history and charm.

Best time to go to Cortona

The best time to visit Cortona is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is sunny with no rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly cloudy with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	39.2°F (4.0°C)	Light Rain	Mostly Cloudy	Slightly Low	Slightly Low
February	41.2°F (5.1°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
March	46.0°F (7.8°C)	Light Rain	Mostly Sunny	Average	Slightly Low
April	52.7°F (11.5°C)	Light Rain	Mostly Sunny	Slightly High	Average
May	59.5°F (15.3°C)	Light Rain	Mostly Sunny	Average	Average
June	69.1°F (20.6°C)	Light Rain	Mostly Sunny	Average	Slightly High
July	74.8°F (23.8°C)	No Rain	Sunny	Slightly High	Slightly High
August	74.5°F (23.6°C)	No Rain	Sunny	Slightly High	Slightly High
September	65.7°F (18.7°C)	Light Rain	Mostly Sunny	Average	Average
October	56.8°F (13.8°C)	Light Rain	Mostly Sunny	Average	Average
November	48.6°F (9.2°C)	Light Rain	Mostly Sunny	Average	Average
December	41.7°F (5.4°C)	Light Rain	Mostly Sunny	Slightly Low	Average

Tips to save on your trip to Cortona

Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Cortona.
Consider traveling during the off-peak season (typically January to March) for more affordable package holidays to Cortona.
Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Cortona Essential Information

Language	Italian
Currency	Euros
Local Welcome	Ciao
Local Goodbye	Ciao
Population	2,200
Max Temp Winter	45ºF
Max Temp Summer	80ºF
Top Sights	Signorelli Theatre, Cathedral of Cortona and San Luciano Winery

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Frequently asked questions

How much does a Cortona vacation package cost?

You'll find cheap prices from $1,636 on Expedia for your Cortona break. However, factors like the season, length of stay and your choice of hotel will influence how much your vacation to Cortona costs.

What are the cheapest months to go to Cortona?

October, November and December are the best times to search for cheap Cortona vacation packages. Traveling in less busy months means you can typically find lower prices on hotels and flights.

How many days is enough for Cortona?

Cortona vacations come in many shapes and sizes, but to really sink your teeth into this destination, we'd suggest 3 days is a good ballpark. In this timeframe, you can fit in headline attractions like Palazzo Comunale and Museum of the Etruscan Academy and track down some hidden gems. Don't skip neighborhoods such as Cortona Old Town and Sodo either. If you're smart with your time, you can even allow for a day trip outside of Cortona too.

Is it worth booking a vacation package to Cortona?

Whether you want to visit major attractions like Villa Bramasole and Cathedral of Cortona on your Cortona vacation, or coming for its excellent nature, views and dining, there's something for everyone here. With so much to experience, you'll soon find out why so many travelers think Cortona is a good vacation destination.

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 vacation as a package?

An Expedia vacation package could save you hundreds of dollars when compared to arranging flights and stays individually. Better still, you can customize 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 vacation package to Cortona?

If you're considering an impromptu Cortona vacation, 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?

Pick the best time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to go to Cortona.
Set your budget: Factor in costs such as flights, meals and transportation when working out how much to set aside for your trip to Cortona. Then, pick a property that fits your budget, whether that's a low-cost option or a deluxe getaway.
Discover Cortona with our trip planning tool: Gain insights into the most popular attractions and best properties for your trip to Cortona. You can also save your must-visit places, collaborate with your group and arrange all your plans in one place.
Work out your trip length: Consider how much time you want to spend discovering Cortona. Plan your days so you can get to all the attractions and activities you're interested in at a comfortable pace.
Combine your airfare and accommodations: After you've settled on your travel dates and duration, lock in the ideal Cortona vacation package for you.
Book any activities or excursions: Now to the fun part — locking in everything you want to see and do. Check out some of the exciting things to do in Cortona and reserve your tickets in advance to save time (and maybe some dollars too!).

Does Expedia offer Book Now, Pay Later Cortona vacation packages?

Your Cortona getaway should be an escape from your daily routine, not a reason for money-related stress. So to allow you a little more flexibility, we've partnered with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there are no late payment fees or hidden costs to worry about.

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Cortona Vacation Rentals

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

Cortona Vacations from $1,636

Book a Hotel + Flight or Car together to unlock savings

Plan, book, travel with confidence

Better together

Find the right fit

Rest easy

Your Cortona Vacation

The Latest Cortona vacation packages

Grand Hotel Cavour

Palazzo Leopoldo Dimora Storica & Spa

Fonteverde Thermal Spa Resort Tuscany

Albergo Le Terme

Eden Rock Resort

Stay near popular Cortona attractions

Villa Bramasole

Cortona Cathedral

Piazza della Repubblica

Santa Margherita Basilica

Santa Maria Nuova

Eremo Le Celle

Signorelli Theatre

Casali Palace

What to do in Cortona

Tasting Tour in One of The Most Beautiful Cellars in the World

Montepulciano Wine Tasting in the Tuscan Countryside

Montepulciano: Winery Tour and Tasting

Cortona Hotel Deals

Villa di Piazzano - Small Luxury Hotel of the World

Monastero di Cortona Hotel & Spa

Il Falconiere - Relais e Chateaux

Find the Best Cortona Vacation Packages

Things to do in and around Cortona

Find the best attractions in and around Cortona

Best time to go to Cortona

Tips to save on your trip to Cortona

Cortona Essential Information

More vacations you might like

Frequently asked questions

Explore a world of travel with Expedia

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