Cortona Vacation Packages 2026 from $969

Cortona flight + hotel vacation packages

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

Hotel La Scaletta Al Ponte Vecchio

Historic Centre of Florence

$969

per person

Nov 9 - Nov 14

found 6 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

This hotel features a restaurant, a rooftop terrace, and a bar/lounge. WiFi in public areas is free. A coffee shop, a terrace, and dry cleaning are also on offer.

Hotel degli Orafi

Historic Centre of Florence

$1,199

per person

Oct 28 - Nov 1

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) 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.

Eden Rock Resort

$1,479

per person

Oct 9 - Oct 12

found 22 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

This residence features a restaurant, an outdoor pool, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. There's a poolside bar on site, and a 24-hour front desk and laundry facilities are also provided.

Villa Cora

Oltrarno

Save 100% on your flight

$4,632

per person

Oct 9 - Oct 12

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

A full-service spa, an outdoor pool, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and airport shuttle. Enjoy the gym and perks like free self parking and a free area shuttle.

Donati Luxury Tower Suites

Historic Centre of Florence

$1,741

per person

Nov 8 - Nov 14

found 17 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Florence (FLR)

This hotel features free WiFi in public areas, concierge services, and valet parking. A computer station, dry cleaning, and luggage storage are also on offer.

Top Cortona hotels deals

Villa di Piazzano - Small Luxury Hotel of the World

Localita Piazzano, C.P. 6 Cortona AR

$654 nightly

$728 total

Sep 12 - Sep 13

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

Monastero di Cortona Hotel & Spa

Via del Salvatore Cortona AR

Free Cancellation

Reserve now, pay when you stay

$355 nightly

$400 total

Sep 20 - Sep 21

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

Il Falconiere - Relais e Chateaux

Localita San Martino 370 Cortona AR

$539 nightly

$602 total

Sep 29 - Sep 30

Total with taxes and fees

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 Luca

Piazza Garibaldi 1 Cortona AR

Free Cancellation

Reserve now, pay when you stay

$87 nightly

$105 total

Oct 2 - Oct 3

Total with taxes and fees

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

Relais Villa Baldelli

San Pietro A Cegliolo 420 Cortona AR

Free Cancellation

Reserve now, pay when you stay

$119 nightly

$140 total

Oct 5 - Oct 6

Total with taxes and fees

This hotel features a bar/lounge, a poolside bar, and a seasonal outdoor pool. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Pool

Breakfast included

Hotel San Michele

Via Guelfa 15 Cortona AR

Free Cancellation

Reserve now, pay when you stay

$149 nightly

$173 total

Sep 6 - Sep 7

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

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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.

Stay near popular Cortona attractions

Villa Bramasole

9.2/10 (20 reviews)

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

See properties

Frequently asked questions

How much are vacation packages to Cortona?

You might be pleasantly surprised — you can vacation in Cortona for a paltry $969. 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.