Cortona Old Town Vacations from $818

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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.
The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
Price was $1,097, price is now $818 per person
$818
per person
Feb 13 - Feb 17
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
19.2/10 Exceptional! (495 reviews)
Everything—the breakfast, the staff, and the cleanliness—was perfect. The room was quiet and supremely comfortable. Highly recommend!

Reviewed on Nov 17, 2025

Relais Uffizi, Tailor made Hotel

Relais Uffizi, Tailor made Hotel

4 out of 5
Historic Centre of Florence
Price was $3,388, price is now $2,529 per person
$2,529
per person
Dec 29 - Jan 3
found 1 hour ago
Roundtrip flight included
New York (JFK) to Florence (FLR)
9.4/10 Exceptional! (118 reviews)
Phenomenal location!

Reviewed on Oct 18, 2025

Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Price was $1,248, price is now $877 per person
$877
per person
Jan 3 - Jan 9
found 6 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
15.2/10 Exceptional! (1,002 reviews)
Convenient location to fast food and train station

Reviewed on Nov 7, 2025

Arte' Boutique Hotel

Arte' Boutique Hotel

4 out of 5
Historic Centre of Florence
Price was $2,083, price is now $1,502 per person
$1,502
per person
Jan 3 - Jan 9
found 19 hours ago
Roundtrip flight included
Los Angeles (LAX) to Florence (FLR)
19.6/10 Exceptional! (293 reviews)
Good location and nice hotel

Reviewed on Nov 16, 2025

Via Roma 33 Tuscany Boutique Hotel & Spa - Adults Only

Via Roma 33 Tuscany Boutique Hotel & Spa - Adults Only

4 out of 5
Price was $1,627, price is now $1,233 per person
$1,233
per person
Jan 3 - Jan 9
found 19 hours ago
Roundtrip flight included
Los Angeles (LAX) to Florence (FLR)
19.2/10 Exceptional! (31 reviews)
Overall a lovely stay. The staff is very welcoming and accommodating. Rooms are very clean. Pool too cold to swim in even though they said that it was heated. Wirlpool/hot-tub was on the cool side too. Couldn’t get sauna to work properly -however, I should have asked. Restaurant food was very good.

Reviewed on May 12, 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
$292 nightly
The price is $326 total per night from Nov 30 to Dec 1
$326 total
Nov 30 - Dec 1
Total with taxes and fees
9.8/10 Exceptional! (250 reviews)
What a unique place. Near the top of the hill. Staff service and amenities were all great. Not an easy place to drive to. The taxis drive-in backwards the last eighth of a mile.

Reviewed on Nov 4, 2025

Monastero di Cortona Hotel & Spa
Hotel San Michele

Hotel San Michele

4 out of 5
Via Guelfa 15 Cortona AR
9/10 Wonderful! (270 reviews)
Very friendly and helpful staff. Nice rooms

Reviewed on Sep 7, 2025

Get rates
Hotel San Michele
Hotel Italia

Hotel Italia

3 out of 5
Via Ghibellina 5/7 Cortona AR
Fully refundableReserve now, pay when you stay
$102 nightly
The price is $119 total per night from Dec 15 to Dec 16
$119 total
Dec 15 - Dec 16
Total with taxes and fees
9/10 Wonderful! (277 reviews)
The personnel were warm and accommodating. The breakfast was amazing! The views were wonderful!

Reviewed on Nov 14, 2025

Hotel Italia
See all 5,161 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

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

Fortress of Girifalco

You can find out about the history of Cortona when you stop by Fortress of Girifalco. You can enjoy the wineries while in the area.

Fortress of Girifalco

Things to do

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

$256
per adult
Amazing four courses cooking class in Tuscany
Tuscany: Sanctuary of La Verna Day Tour Private Tour

Tuscany: Sanctuary of La Verna Day Tour Private Tour

$546
per traveler
Tuscany: Sanctuary of La Verna Day Tour Private Tour
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.