Cortona Vacation Packages 2025/2026 from $839

Cortona flight + hotel vacation packages

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

Aurum Firenze

Historic Centre of Florence

Save 100% on your flight

$839

per person

Oct 16 - Oct 21

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

Free WiFi in public areas and a safe deposit box are available at this hotel. Enjoy the free buffet breakfast each morning. Staff at the 24-hour front desk can provide around-the-clock assistance.

Aurum Uffizi

Historic Centre of Florence

Save 100% on your flight

$885

per person

Oct 16 - Oct 21

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

Free WiFi in public areas, a terrace, and a garden are available at this hotel. Enjoy the free buffet breakfast each morning. A snack bar/deli and a safe deposit box are also provided.

The Moon Boutique Hotel & Spa

Historic Centre of Florence

Save 100% on your flight

$964

per person

Oct 16 - Oct 21

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

This hotel features a full-service spa and a bar/lounge. WiFi in public areas is free. Self parking, a snack bar/deli, and express check-out are also offered.

LHP River Club

Santa Croce

Save 100% on your flight

$890

per person

Oct 16 - Oct 21

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

An outdoor pool, valet parking, and concierge services are featured at this hotel. WiFi in public areas is free. A communal living room and luggage storage are also provided.

Hotel degli Orafi

Historic Centre of Florence

Save 100% on your flight

$1,297

per person

Oct 22 - Oct 26

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Florence (FLR)

This hotel features a rooftop terrace and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A terrace, a garden, and a snack bar/deli are also on offer.

Top Cortona hotels deals

Monastero di Cortona Hotel & Spa

Via del Salvatore, Cortona, AR

Free Cancellation

Reserve now, pay when you stay

$336 nightly

$379 total

Sep 1 - Sep 2

Total with taxes and fees

A full-service spa and an indoor pool are featured at this luxury hotel. Enjoy the hot tub and free perks like full breakfast and WiFi in public areas. You'll appreciate the sauna, bar/lounge, and snack bar/deli.

Pool

Hot Tub

Villa di Piazzano - Small Luxury Hotel of the World

Localita Piazzano, C.P. 6, Cortona, AR

Free Cancellation

Reserve now, pay when you stay

$639 nightly

$713 total

Aug 31 - Sep 1

Total with taxes and fees

This hotel features an outdoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and airport shuttle. Relax with a drink at the bar/lounge and enjoy perks like free self parking.

Pool

Parking included

Il Falconiere - Relais e Chateaux

Localita San Martino 370, Cortona, AR

Get rates

An attached winery, a full-service spa, and 2 outdoor pools are all featured at this luxury hotel. Families will appreciate kid-friendly dining and in-room childcare, along with hiking/biking trails. Enjoy the seasonal outdoor pool and free perks like buffet breakfast and free self parking.

Pool

Hot Tub

Hotel San Michele

Via Guelfa 15, Cortona, AR

Free Cancellation

$198 nightly

$227 total

Aug 30 - Aug 31

Total with taxes and fees

An area shuttle and a shopping center shuttle are featured at this hotel, along with a bar/lounge. WiFi in public areas is free. Traveling on business? Take advantage of the express check-in, express check-out, and airport shuttle.

Pet friendly

Free WiFi

Hotel Villa Marsili

Viale Cesare Battisti 13, Cortona, AR

Free Cancellation

Reserve now, pay when you stay

Get rates

This hotel features a bar/lounge, free WiFi in public areas, and a garden. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. A lobby fireplace, express check-out, and dry cleaning are also on offer.

Pet friendly

Free WiFi

Hotel San Luca

Piazza Garibaldi 1, Cortona, AR

Free Cancellation

Reserve now, pay when you stay

Get rates

This hotel features a restaurant, a gym, and a bar/lounge. WiFi in public areas is free. Self parking, a hair salon, and dry cleaning are also offered.

Pet friendly

Free WiFi

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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.

Popular places to visit

Piazza della Repubblica

Find out about the history of Cortona with a stop at Piazza della Repubblica. Make time to visit the cathedral and monuments while you're in the area.

Villa Bramasole

You can learn about the history of Cortona with a trip to Villa Bramasole. You can enjoy the wineries while in the area.

Cortona Cathedral

Find out about the history of Cortona with a stop at Cortona Cathedral. Make time to visit the cathedral and monuments while you're in the area.

Frequently asked questions

How much are vacation packages to Cortona?

You might be pleasantly surprised — you can vacation in Cortona for a paltry $839. Allow Travelocity to save you money and stress with our vacation packages. With flights, hotels and tours all ready to be snapped up, what's stopping you?

How long should my Cortona vacation be?

Around 3 nights is the average time frame travelers spend in Cortona. But the perfect trip length all depends on how many treasured memories you want to make. Why not stay a couple of extra days and uncover some hidden gems?

Where can I get the best vacation package deals for Cortona?

There's no need to look any further than Travelocity. With 400 air carriers and 1,000,000 worldwide properties, it's a breeze to find a Cortona package deal that satisfies your wanderlust.

Why should I purchase my Cortona vacation package via Travelocity?

By booking your hotel, flights, activities and car rental altogether, you'll save time and money. We offer a professional customer service support team available round-the-clock, and you'll know that you'll always be getting the best deal in town with our Price Match Guarantee. So, what are you waiting for? Book the getaway of your dreams today and get packing!

Can I save money on my Cortona car rental if I book it with my hotel or flight?

Sure can — bundle your hotel, car and flight into a Cortona vacation package and you can save tons. With so much to see in Cortona, that rental car will make it easy to explore. Once you're behind the wheel, put the stereo on and head to St. Peter's Basilica, a renowned attraction approximately 100 mi from Cortona.

Which airport is best for Cortona?

Many vacationers arrive at Peretola Airport (FLR). Once you've disembarked and picked up your bags, set off 55 mi southeast to reach central Cortona. Federico Fellini Intl. Airport (RMI) is the other option available, 60 mi from the city center.

What is there to do in Cortona?

Cortona is brimming with sights to discover, like Villa Bramasole and Piazza della Repubblica. These two fantastic attractions are at the top of most visitors' travel itineraries.

Where should I stay when visiting Cortona?

The Hotel Italia is recommended by many visitors. Book as soon as possible to avoid missing out.

Where to stay in Cortona: Best areas for travelers

Cortona Old Town: With its artistic vibe, this destination attracts creative types like bees to a honey pot. Find some inspiration at Museo Diocesano before hitting up the rest of what this leading neighborhood has to offer. The Hotel San Luca, the Hotel Villa Marsili, BW Signature Collection and the Monastero di Cortona Hotel & Spa are some options if you want to stay here.
San Pietro a Cegliolo: For a comfy place to stay, many travelers recommend the Relais Il Falconiere or the Holiday Apartment Agriturismo Borgo Elena. If you've got a bit of extra time, spend a few hours exploring the local sights.