Deals on vacations and trips to Cortona Old Town

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Cortona Old Town flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Villa Tolomei Hotel & Resort

Villa Tolomei Hotel & Resort

5 out of 5
Oltrarno
Price was $2,124, price is now $1,419 per person
$1,419
per person
Jan 10 - Jan 15
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Florence (FLR)
This hotel features a restaurant, a gym, and a bar/lounge. Families will appreciate the onsite laundry facilities and babysitting. Enjoy the seasonal outdoor pool and free perks like buffet breakfast and free self parking.
Hotel Berchielli

Hotel Berchielli

4 out of 5
Historic Centre of Florence
Price was $3,046, price is now $1,909 per person
$1,909
per person
Jan 10 - Jan 15
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Florence (FLR)
This hotel doesn't skimp on freebies - guests receive free buffet breakfast and free WiFi. Traveling on business? Take advantage of the 24-hour business center, laundry service, and airport shuttle. There's a bar/lounge on site, and a 24-hour front desk and laundry facilities are also provided.
Hotel Roma

Hotel Roma

4 out of 5
Historic Centre of Florence
Price was $2,808, price is now $1,786 per person
$1,786
per person
Jan 10 - Jan 15
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Florence (FLR)
This hotel features a gym and a bar/lounge. WiFi in public areas is free. Valet parking, a coffee shop, and limo/town car service are also offered.
Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was $2,600, price is now $1,723 per person
$1,723
per person
Dec 29 - Jan 5
found 1 day ago
Roundtrip non-stop flight included
San Francisco (SFO) 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.
Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Price was $2,395, price is now $1,609 per person
$1,609
per person
Dec 29 - Jan 5
found 1 day ago
Roundtrip non-stop flight included
San Francisco (SFO) 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.

Top Cortona Old Town hotels deals

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

5 out of 5
Via del Salvatore Cortona AR
Free Cancellation
Reserve now, pay when you stay
$245 nightly
The price is $278 total per night
$278 total
Oct 25 - Oct 26
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.
Hotel San Michele

Hotel San Michele

4 out of 5
Via Guelfa 15 Cortona AR
Free Cancellation
Reserve now, pay when you stay
$121 nightly
The price is $137 total per night
$137 total
Nov 2 - Nov 3
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 San Luca

Hotel San Luca

4 out of 5
Piazza Garibaldi 1 Cortona AR
Free Cancellation
Reserve now, pay when you stay
$87 nightly
The price is $104 total per night
$104 total
Oct 25 - Oct 26
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
Hotel Italia

Hotel Italia

3 out of 5
Via Ghibellina 5/7 Cortona AR
Free Cancellation
Reserve now, pay when you stay
$103 nightly
The price is $116 total per night
$116 total
Nov 17 - Nov 18
Total with taxes and fees
Free WiFi in public areas, express check-in, and express check-out are available at this hotel. Enjoy the free buffet breakfast each morning. Luggage storage and a safe deposit box are also provided.
Hotel Villa Marsili

Hotel Villa Marsili

4 out of 5
Viale Cesare Battisti 13 Cortona AR
Free Cancellation
Reserve now, pay when you stay
$175 nightly
The price is $197 total per night
$197 total
Nov 3 - Nov 4
Total with taxes and fees
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.
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
$634 nightly
The price is $707 total per night
$707 total
Oct 19 - Oct 20
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
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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 Old Town attractions

Piazza della Repubblica

9.4/10 (95 reviews)
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.
See properties

Frequently asked questions

How much are vacation packages to Cortona Old Town?
With vacation packages on offer from just $1,419, there's no need to max out the credit card for your getaway to Cortona Old Town. Travelocity can help. Bundle experiences, hotels and flights into a convenient package and score excellent discounts. The more you book, the greater the savings.
Where can I get the best vacation package deals for Cortona Old Town?
With around 400 partner airlines and 1,000,000 properties around the world, it's tough to beat Travelocity. Make the most of our extensive range and grab an affordable Cortona Old Town vacation package. Doesn't it feel amazing when vacation planning is that easy?
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We offer round-the-clock support, exceptional service and a Price Match Guarantee. Life is all about the journey — and we have alluring destinations for you to journey to in all four corners of the globe. Explore with us and make your hip pocket happy.
Can I save on my Cortona Old Town car rental if I book it with a hotel or flight?
Sure can — and if you also add an activity or experience to your Cortona Old Town vacation package, you'll pick up even greater savings. With a package from Travelocity, you can find things to do in the area that suit you. Then, hop in your rental car and work your way through the list. St. Peter's Basilica is one must-see attraction to take a look at. You'll find it 100 mi from Cortona Old Town.
What is there to do in Cortona Old Town?
Piazza della Repubblica and Signorelli Theatre are loved by many travelers. Cross these popular attractions off your Cortona Old Town itinerary and discover what the buzz is about.

Photos of local treasures

Browse Cortona Old Town vacation photos for more inspiration

A historic town with medieval architecture, including a prominent tower and a church with a bell tower.
A historic square with cobblestone pavement, traditional buildings, and outdoor seating areas.
A panoramic view of a rural landscape with rolling hills, a clear blue sky, and a mix of agricultural fields and scattered buildings.
A church surrounded by a forest and clouds.
A bee on a sunflower.