Cortona Old Town Holidays from £249

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Your Cortona Old Town Holiday

Take the hassle out of planning your next break by booking a Cortona Old Town holiday package. Soak in the sounds and sights of this enticing neighbourhood and experience what it has to offer. Eager to do some sightseeing during your trip to Cortona Old Town? Make sure you stop by nearby attractions such as Villa Bramasole, Piazza della Repubblica and Signorelli Theatre. Stop daydreaming and start doing. When you're ready to book your next holiday to Cortona Old Town, Expedia will help get you there.

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

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was £443, price is now £249 per person
£249
per person
6 Sept - 8 Sept
found 1 day ago
Return flight included
Edinburgh (EDI) to Florence (FLR)
7.6/10 Good! (1,004 reviews)
Highly recommended

Reviewed on 30 Jun 2026

Hotel Bencista

Hotel Bencista

3 out of 5
Price was £1,181, price is now £622 per person
£622
per person
23 Aug - 29 Aug
found 1 day ago
Return flight included
London (LON) to Florence (FLR)
6.8/10 (28 reviews)
Terribile. Esperienza da incubo, ci hanno rovinato la serata. Arriviamo alle 18:00 per il check-in e non c’è nessuno. Nessun messaggio, nessuna email, nessun preavviso con il codice di accesso. Nulla. Siamo costrette a chiamare un numero, restando fuori con tutte le valigie, mentre una persona al telefono ci chiede i documenti prima ancora di darci il codice. Situazione già assurda. Entriamo finalmente in stanza e la televisione non funziona. Zero canali, completamente inutilizzabile. Richiamiamo il numero del check-in e la signorina ci passa un altro numero, dicendo che “ci avrebbero aiutato loro”. Chiamiamo e risponde una persona estremamente scortese e cafona, che invece di scusarsi per il disagio esordisce con: “Innanzitutto chi vi ha dato questo numero? Io non sono nel mio orario lavorativo, prenderò provvedimenti” e subito dopo: “Io non sono un tecnico della televisione”. Nessuna scusa. Nessuna disponibilità. Trattate come se i loro problemi aziendali fossero colpa nostra. A quel punto chiedo il rimborso per poter andare in un’altra struttura. Mi viene risposto che “non hanno potere decisionale” e che la manager mi avrebbe contattata il giorno dopo. Mai sentiti. Spariti. Zero professionalità, zero assistenza, zero rispetto per il cliente. State lontani mille miglia.

Reviewed on 27 Feb 2026

The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was £1,728, price is now £933 per person
£933
per person
11 Sept - 18 Sept
found 1 day ago
Return direct flight included
Birmingham (BHX) to Florence (FLR)
9.6/10 Exceptional! (568 reviews)
Very nice and friendly staff, good breakfast, nice and clean hotel

Reviewed on 18 Jun 2026

Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was £462, price is now £256 per person
£256
per person
6 Sept - 8 Sept
found 1 day ago
Return flight included
Edinburgh (EDI) to Florence (FLR)
7.4/10 Good! (1,014 reviews)
Room was clean, breakfast was decent. In general, it was a good stay. Would likely consider staying again.

Reviewed on 30 Jun 2026

Eurostars Florence Boutique

Eurostars Florence Boutique

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was £1,649, price is now £929 per person
£929
per person
11 Sept - 18 Sept
found 1 day ago
Return direct flight included
Birmingham (BHX) to Florence (FLR)
8.6/10 Excellent! (490 reviews)
Very good location. Clean hotel. Our ac was broken but they handled us a new room inmediately. The hotel is confortable and size of the rooms are decent. Bigger than average in the area.

Reviewed on 26 Jun 2026

Top hotels in Cortona Old Town

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
The price is £322 per night from 26 Jul to 27 Jul
£322
26 Jul - 27 Jul
includes taxes & fees
10/10 Exceptional! (290 reviews)
"This is an excellent hotel, great staff, great location and great food. The breakfast is a really nice experience and the courtyard swimming pool is so peaceful."

Reviewed on 29 Jun 2026

Monastero di Cortona Hotel & Spa
Hotel San Michele

Hotel San Michele

4 out of 5
Via Guelfa 15 Cortona AR
Fully refundableReserve now, pay when you stay
The price is £122 per night from 20 Jul to 21 Jul
£122
20 Jul - 21 Jul
includes taxes & fees
Hotel San Michele
Hotel San Luca

Hotel San Luca

4 out of 5
Piazza Garibaldi 1 Cortona AR
The price is £74 per night from 27 Jul to 28 Jul
£74
27 Jul - 28 Jul
includes taxes & fees
8.6/10 Excellent! (433 reviews)
"Wonderful hotel with great view for Tuscany, good breakfast, perfect location to visit Cortona"

Reviewed on 30 Jun 2026

Hotel San Luca
See all 5,123 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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Frequently asked questions

How much does a Cortona Old Town travel package cost?
From just £249. Yes, you read that right. Our Cortona Old Town travel packages are the best way to make your dollar go further. Combine your flights, hotels and rental car and discover this lively destination.
If I'm not able to travel, can I cancel my Cortona Old Town travel package?
It's difficult to predict what tomorrow might bring, so it's comforting to know that you can cancel or change your Cortona Old Town travel package. If your booking was made in the last 24 hours, you may be eligible for a refund. If your booking is older, your hotel, airline or car rental company may charge a fee. Check our Customer Service Portal for further details.
How do I get a cheap travel package to Cortona Old Town?
Bundle your flights and hotels with Expedia to save big bucks on your next big adventure. With over 550 air carriers and 1,000,000 hotels around the globe, your Cortona Old Town travel package can be tailored exactly to suit your budget. With all those extra dollars, why not include a few awesome experiences and tours? It's an easy way to unlock even more bargains. That dream holiday to Cortona Old Town is much closer than you thought!
Does Expedia offer Book Now, Pay Later Cortona Old Town holidays?
Your bank balance shouldn't get in the way of escaping on holiday, so Expedia has devised a solution to help. Now that we've partnered with online lender Klarna, it's easier than ever to book a dream getaway without making a dent in your savings. Klarna offers flexible payment options during the checkout process that take the worry out of budgeting for your escape. Check out these flexible payment options:

  • Pay monthly holidays: Klarna has manageable monthly payment plans that work for all budgets, so you can have that well-deserved holiday now.
  • Pay in instalments holidays: If you'd like to pay off your getaway in multiple transactions, holidays paid in instalments might be the right choice for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: Clicking the "book now" button is easier with this plan. Just put down a small deposit on your holiday and then start packing your suitcase.

Where should I stay in Cortona Old Town?
A getaway to Cortona Old Town isn't complete without checking out Cathedral of Cortona, Piazza della Repubblica and Fortress of Girifalco. Spend your nights close to these popular sights and make sightseeing simple.
What are the top hotels in Cortona Old Town?
Hotel Italia and Relais Villa Petrischio are a couple of the most sought-after hotels in Cortona Old Town. Why not check out the amenities and facilities at each and then decide?
How far in advance should I book my Cortona Old Town holiday?
It can be difficult to know exactly when is the perfect time to book your Cortona Old Town holiday. But usually the earlier you book, the more affordable the prices. In some cases, you can reserve your flights and hotels up to a year before your departure date. If you're thinking of a last-minute getaway, no need to fret! There are fabulous deals featured on Expedia all the time.
What does an Expedia Cortona Old Town travel package include?
It comes down to what sort of getaway you have in mind. Cortona Old Town holiday deals can include hotels, car rentals and flights. You can mix and match to find the travel package that suits your budget and style. You can also add on experiences and activities after you've booked to pick up even bigger discounts.
What should I know before booking a Cortona Old Town travel package?
A travel package can be customized for your budget and is an easy way to make your budget go further. How much you include is totally up to you. Hotels, rental cars and flights — come up with a combination that suits your plans.
Can I choose my airline with a Cortona Old Town Expedia travel package?
The choice is all yours! We have access to over 550 airlines throughout the world, so you can design your Cortona Old Town escape according to your travel needs.

Stay near popular Cortona Old Town attractions

Piazza della Repubblica

9.4/10 (95 reviews)
Find out about the history of Cortona when you take a trip to Piazza della Repubblica. Make time to visit the cathedral and monuments while you're in the area.
See properties

Things to do

Cortona: Tagliatelle, Ravioli, and Tiramisu Cooking Class

Cortona: Tagliatelle, Ravioli, and Tiramisu Cooking Class

£125
per adult
Cortona: Tagliatelle, Ravioli, and Tiramisu Cooking Class
Pasta or Pizza cooking class in Cortona, vegetarian and vegan

Pasta or Pizza cooking class in Cortona, vegetarian and vegan

£104
per adult
Pasta or Pizza cooking class in Cortona, vegetarian and vegan
Castiglion Fiorentino: Tuscan Guided E-Bike Tour

Castiglion Fiorentino: Tuscan Guided E-Bike Tour

£128
per adult
Castiglion Fiorentino: Tuscan Guided E-Bike 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. Flight-inclusive packages are ATOL protected.