Cortona Old Town Vacations from $620

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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.
Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was $912, price is now $620 per person
$620
per person
Nov 29 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,008 reviews)
Perfect accommodation.

Reviewed on Oct 2, 2025

The Club House

The Club House

5 out of 5
Price was $1,288, price is now $957 per person
$957
per person
Nov 2 - Nov 6
found 1 day ago
Roundtrip flight included
New York (NYC) to Florence (FLR)
10/10 Exceptional! (4 reviews)
We LOVED staying at The Clubhouse. The service was attentive, the facility was well kept. It felt like we were staying at a friends house but with AMAZING service. We would love to stay here again in the future. Thank you to all of the staff for making such a special experience for us.

Reviewed on Oct 1, 2025

The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
Price was $1,696, price is now $1,163 per person
$1,163
per person
Nov 4 - Nov 8
found 17 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.6/10 Exceptional! (477 reviews)
Everything was perfect

Reviewed on Oct 1, 2025

Villa Cora

Villa Cora

5 out of 5
Oltrarno
Save 100% on your flight
Price was $2,578, price is now $1,818 per person
$1,818
per person
Nov 3 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
9.8/10 Exceptional! (461 reviews)
The hotel is very beautiful, and the surrounding environment is also excellent.

Reviewed on Sep 26, 2025

Portrait Firenze - Lungarno Collection

Portrait Firenze - Lungarno Collection

5 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $3,142, price is now $2,260 per person
$2,260
per person
Nov 4 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
9.8/10 Exceptional! (296 reviews)
The hotel was very nice however there was construction below us. Additionally, the restaurant and bar were not open due to renovations.

Reviewed on Mar 5, 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
$265 nightly
The price is $296 total per night from Nov 2 to Nov 3
$296 total
Nov 2 - Nov 3
Total with taxes and fees
9.8/10 Exceptional! (239 reviews)
"Beautiful, unique property! Stunning views of the countryside. The staff were all very helpful and friendly. We will definitely recommend!"

Reviewed on Sep 27, 2025

Monastero di Cortona Hotel & Spa
Hotel San Michele

Hotel San Michele

4 out of 5
Via Guelfa 15, Cortona, AR
$124 nightly
The price is $146 total per night from Oct 30 to Oct 31
$146 total
Oct 30 - Oct 31
Total with taxes and fees
9/10 Wonderful! (267 reviews)
"Very friendly and helpful staff. Nice rooms"

Reviewed on Sep 7, 2025

Hotel San Michele
Hotel Villa Marsili

Hotel Villa Marsili

4 out of 5
Viale Cesare Battisti 13, Cortona, AR
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $171 total per night from Nov 3 to Nov 4
$171 total
Nov 3 - Nov 4
Total with taxes and fees
9.8/10 Exceptional! (310 reviews)
"I can't recommend the Marsili highly enough. The property is perfectly situated just on the outskirts of Cortona center. A 5 minute walk and you are exploring a fascinating, casual, friendly, safe and fun neighborhood. Every member of the staff went out of their way to meet our needs. We loved the ..."

Reviewed on Sep 14, 2025

Hotel Villa Marsili
See all 5,237 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

5/5(4 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.

Piazza della Repubblica

Cortona Cathedral

Cortona Cathedral is just one of the places to see in Cortona, so why not enjoy the other things to explore during your travels? Experience the area's museums and musical theater.

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

WELCOME!

Private visit to the House of Grand Duke Leopold of Tuscany with invitation

$47
per adult
Private visit to the House of Grand Duke Leopold of Tuscany with invitation
Montepulciano: Wine Tour and tasting

Montepulciano: Wine Tour and tasting

$61
per adult
100% of travellers recommend
Montepulciano: Wine Tour and tasting
For your personal cooking class in Tuscany

Amazing four courses cooking class in Tuscany

$260
per adult
Amazing four courses cooking class in Tuscany
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.