Cortona Old Town Vacations from $934

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Your Cortona Old Town Vacation

Reserving a Cortona Old Town vacation package is a good way to become acquainted with this unique neighborhood. From its well-known places to its lesser-known gems, there's a lot to delve into. Eager to sightsee during your trip to Cortona Old Town? Be sure to check out nearby attractions like Villa Bramasole, Cathedral of Cortona and Piazza della Repubblica. Expedia can help you turn your ideal Cortona Old Town vacation into reality, no matter your budget or travel plans.

The Latest Cortona Old Town Vacation Packages

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

Hotel Grifone

4 out of 5
Campo di Marte
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Florence (FLR)
8/10 Very Good! (120 reviews)
Friendly staff, convenient location, great room. Highly recommended!

Reviewed on Jul 19, 2025

Hotel Datini

Hotel Datini

4 out of 5
per person
Oct 20 - Oct 25
found 19 hours ago
Roundtrip flight included
Orlando (MCO) to Florence (FLR)
8/10 Very Good! (260 reviews)
The rooms are spacious and beds are comfy. Bathroom is awesome and has everything you need. You have breakfast included and it is amazing. Bus station is right behind the hotel and you can go anywhere from there. The staff are very kind.

Reviewed on Jun 16, 2024

Starhotels Vespucci

Starhotels Vespucci

4 out of 5
per person
Oct 20 - Oct 25
found 19 hours ago
Roundtrip flight included
Orlando (MCO) to Florence (FLR)
8.4/10 Very Good! (520 reviews)
We had a wonderful stay at Starhotels Vespucci. The rooms were clean, comfortable, and well-equipped. The staff was friendly and professional, always ready to help. Breakfast was delicious with a good variety. Convenient location for both business and leisure. Highly recommended!

Reviewed on May 21, 2025

Hotel President

Hotel President

4 out of 5
per person
Oct 20 - Oct 25
found 19 hours ago
Roundtrip flight included
Orlando (MCO) to Florence (FLR)
7.6/10 Good! (210 reviews)
No AC in April as they turn it ON from May onwards?

Reviewed on May 2, 2025

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Sep 20 - Sep 24
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Florence (FLR)
7.8/10 Good! (1,001 reviews)
Very well connected. Room size Good for Family of 4. AC was not very efficient in room, Kind of slow. Rest ok Even breakfast included which is good for wallet

Reviewed on Jul 25, 2025

Cortona Old Town Hotel Deals

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

5 out of 5
Via del Salvatore, Cortona, AR
Fully refundableReserve now, pay when you stay
$294 nightly
The price is $332 total per night from Aug 4 to Aug 5
$332 total
Aug 4 - Aug 5
Total includes taxes and fees
9.8/10 Exceptional! (223 reviews)
"Gorgeous hotel, very helpful and friendly staff, stunning pool and spa. Loved everything about this hotel! Just know that it’s an uphill walk to get there from the town center."

Reviewed on Jul 22, 2025

Monastero di Cortona Hotel & Spa
Hotel Villa Marsili

Hotel Villa Marsili

4 out of 5
Viale Cesare Battisti 13, Cortona, AR
Fully refundableReserve now, pay when you stay
9.8/10 Exceptional! (302 reviews)
Il migliore!!!
"No other hotel in Cortona will do!"

Reviewed on Jul 13, 2025

Get rates
Hotel Villa Marsili
Hotel San Michele

Hotel San Michele

4 out of 5
Via Guelfa 15, Cortona, AR
Fully refundable
$112 nightly
The price is $132 total per night from Aug 13 to Aug 14
$132 total
Aug 13 - Aug 14
Total includes taxes and fees
9/10 Wonderful! (265 reviews)
"Very conveniently located in the heart of Cortona."

Reviewed on May 20, 2025

Hotel San Michele
See all 5,242 properties in Cortona Old Town
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.
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Discover the most popular places to visit in Cortona Old Town

Cortona featuring heritage architecture

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.

Piazza della Repubblica

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.

Cortona Cathedral

Santa Margherita Basilica

You can learn about the history of Cortona when you stop by Santa Margherita Basilica. Discover the area's museums and cathedral.

Santa Margherita Basilica

Things to do

For your personal cooking class in Tuscany

Amazing four courses cooking class in Tuscany

$311
per adult
Amazing four courses cooking class in Tuscany
Cortona

Cortona Private Guided Tour

$305
per traveler
Cortona Private Guided Tour
Montepulciano: Wine Tour and tasting

Montepulciano: Wine Tour and tasting

$61
per adult
100% of travellers recommend
Montepulciano: Wine Tour and tasting
See all activities in Cortona
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.