A hillside town with historic buildings, a church, and vineyards.

Cortona Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Cortona vacation rentals

A hotel entrance with an arched doorway, a sign with the name 'Albergo I Michele', and a potted plant to the right.

1. B&B Piccolo Hotel

B&B Piccolo Hotel
Cortona Old Town
9.4 out of 10, Exceptional, (26 reviews)
"This is such an amazing hotel in such an amazing place! "
United States
mansoor
B&B Piccolo Hotel
A hotel room with a large bed, a desk, a chair, a small table, and a door leading to another room.

2. CASA AMBRA

CASA AMBRA
Cortona Old Town
$205 nightly
The price is $227
Nov 11 - Nov 12
Total with taxes and fees
CASA AMBRA
A building entrance with a number '10' sign, a potted plant with flowers, and a staircase leading to the entrance.

3. Vicolo Della Scala Rooms - Il Sole

Vicolo Della Scala Rooms - Il Sole
Cortona Old Town
$107 nightly
The price is $120
Nov 16 - Nov 17
Total with taxes and fees
Vicolo Della Scala Rooms - Il Sole
A building entrance with a number '10' sign, a potted plant with flowers, and a staircase leading to the entrance.

4. Vicolo Della Scala Rooms - La Luna

Vicolo Della Scala Rooms - La Luna
Cortona Old Town
$96 nightly
The price is $108
Nov 11 - Nov 12
Total with taxes and fees
Vicolo Della Scala Rooms - La Luna
A hotel room with a bed, a desk with a chair, a wardrobe, a television, and a window with curtains.

5. Limehome Arezzo Duomo

Limehome Arezzo Duomo
Arezzo Centro Storico
9.0 out of 10, Wonderful, (6 reviews)
"I really liked the brand new room. Nice design and super comfy bed. Plus free coffee is a nice addition to the experience there. Loved it. Plus my personal highlight were the nice views into the historical center of Arezzo."
Germany
Florian
$72 nightly
The price is $86
Nov 11 - Nov 12
Total with taxes and fees
Limehome Arezzo Duomo
A hotel room with a bed, a chair, a lamp, and a view of the outdoors.

6. La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (152 reviews)
"This place was great. Amazing view the room. Extremely friendly and helpful staff. This hotel made our trip - highly recommend"
Canada
Colin
$141 nightly
The price is $159
Nov 21 - Nov 22
Total with taxes and fees
La Locanda di San Francesco
A bedroom with a large bed, a chandelier, a mirror, and plants.

7. Bibi Boutique

Bibi Boutique
Arezzo Centro Storico
10.0 out of 10, Exceptional, (1 review)
"The BiBi was perfect for my needs. Its location is excellent, and the room had all the needed amenities. Fabio was a gracious host, orienting me to Arezzo and recommending a wonderful trattoria close by. I highly recommend and hope to return!"
United States
Carol
$78 nightly
The price is $93
Nov 11 - Nov 12
Total with taxes and fees
Bibi Boutique
A terrace with a table set for breakfast, overlooking a scenic landscape.

8. Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (50 reviews)
"Room, location, staff - it was perfection. We can not wait to return."
United States
Denise
$172 nightly
The price is $194
Nov 11 - Nov 12
Total with taxes and fees
Delcorto Suites
A breakfast setting with a fireplace, a table with plates, glasses, and a croissant.

9. San Michele al Borgo

San Michele al Borgo
Castiglion Fiorentino
9.8 out of 10, Exceptional, (9 reviews)
"Excellent staff and tasty breakfast!"
United States
Vern
$133 nightly
The price is $151
Nov 11 - Nov 12
Total with taxes and fees
San Michele al Borgo
A balcony with a view of a historic town, featuring terracotta-roofed buildings and a prominent church tower.

10. Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.8 out of 10, Exceptional, (122 reviews)
"The room was beautifully designed, clean and fresh with stunning views in a truly historic building. Family run and a special experience!!"
United States
Slimane
$137 nightly
The price is $155
Nov 12 - Nov 13
Total with taxes and fees
Meublé Il Riccio
A window with a view of a green landscape and hills.

11. Il Tosco

Il Tosco
Montepulciano
10.0 out of 10, Exceptional, (141 reviews)
"Excellent room, service and food. The best."
United States
Valerie
$227 nightly
The price is $255
Dec 10 - Dec 11
Total with taxes and fees
Il Tosco
A courtyard with a pool, stone benches, and a view of a hill.

12. TH Perugia - Castello di Monterone

TH Perugia - Castello di Monterone
Perugia
9.8 out of 10, Exceptional, (329 reviews)
"Beautiful garden, beautiful view, easy parking and tasty restaurant."
Canada
Sandro
$211 nightly
The price is $239
Nov 16 - Nov 17
Total with taxes and fees
TH Perugia - Castello di Monterone
A swimming pool with a water feature, surrounded by greenery and a table with chairs.

13. Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (171 reviews)
"Great location. Clean and quiet with good breakfast"
United States
Michael
$136 nightly
The price is $157
Nov 16 - Nov 17
Total with taxes and fees
Hotel San Gregorio
Pool

14. iConic Wellness Resort

iConic Wellness Resort
Arezzo
8.8 out of 10, Excellent, (45 reviews)
"It was wonderful!"
United States
Wade
$74 nightly
The price is $88
Dec 2 - Dec 3
Total with taxes and fees
iConic Wellness Resort
A hotel room with a large bed, a fireplace, and a brick ceiling.

15. DormiVeglia B&B

DormiVeglia B&B
Monte San Savino
10.0 out of 10, Exceptional, (30 reviews)
"Amazing, warm, sweet, lovely, such a gem of a place!"
American Samoa
Melissa Hyun Joo
$108 nightly
The price is $123
Nov 22 - Nov 23
Total with taxes and fees
DormiVeglia B&B
A covered corridor with brick columns, potted plants, and a view of a lush landscape.

16. Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (185 reviews)
"Great Historical location."
Canada
Robert
$61 nightly
The price is $71
Dec 10 - Dec 11
Total with taxes and fees
Abbadia Sicille Relais
A balcony with potted plants and a view of a cityscape.

17. Cameracaffè Centro

Cameracaffè Centro
Arezzo Centro Storico
8.6 out of 10, Excellent, (195 reviews)
"Very convenient and a beautifull terrasse to have breakfast with an amazing vue on Arezzo!"
France
Alexandre
$93 nightly
The price is $109
Nov 16 - Nov 17
Total with taxes and fees
Cameracaffè Centro
A courtyard with outdoor seating, a stone building with a tower, and a well-maintained garden.

18. Castello di Gargonza

Castello di Gargonza
3.0 star property
Monte San Savino
9.4 out of 10, Exceptional, (49 reviews)
"Roberto, his wife and his staff were all round great. Very friendly helpful and great service. We were very happy to find this authentic castle/village to stay in Tuscany."
Canada
Iain
$274 nightly
The price is $306
Nov 12 - Nov 13
Total with taxes and fees
Castello di Gargonza
A modern hotel room with large windows, a bed, a desk, and a chair.

19. B&B 52cento

B&B 52cento
Arezzo Centro Storico
8.2 out of 10, Very good, (85 reviews)
"Very accessible and easy accommodation. Very pleasant room and reasonable breakfast. Within walking distance of train station and city centre."
Australia
Tina
$77 nightly
The price is $91
Nov 11 - Nov 12
Total with taxes and fees
B&B 52cento
Terrace/patio

20. Casale dell'Assiolo

Casale dell'Assiolo
Castiglione del Lago
9.0 out of 10, Wonderful, (2 reviews)
"Super søde værter. Og rigtig fint værelse. Vi kommer igen"
Denmark
Emma
$111 nightly
The price is $126
Nov 14 - Nov 15
Total with taxes and fees
Casale dell'Assiolo
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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Top Cortona Hotel Reviews

Villa Santa Margherita

Villa Santa Margherita

10/10 Excellent
"Recommend do not arrive late at night into Cortona upon arrival. The roads are narrow and NOT like USA at all. GPS showed fastest route. However, part of the road are extremely narrow and hilly. There are no street signs at all. Local people are extremely helpful and friendly. We got lost and they showed us to the hotel."
THUHUONG 3-night trip
Posted 8 hours ago
Villa Santa Margherita

Find out more about Cortona

Everything you need to know about Cortona vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Cortona vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cortona vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Cortona vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cortona. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Cortona in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Cortona rentals

At Expedia, we put the best Cortona vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Cortona rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cortona vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cortona. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Cortona?

Yes, there are vacation rentals close to the most popular sights in Cortona, or you can go with a secluded option if you're looking for a relaxing stay. Cortona is known for its cathedral and monuments. Make sure you have time to check out the temples and musical theater during your trip.

What are some of the best vacation home rentals that Cortona has to offer?

Beautiful tuscan villa with pool, ideal for groups: This highly rated vacation home rental in Cortona is located in the mountains and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals are there in Cortona?

With 171 Expedia vacation rentals, you're sure to find just the right place for your Cortona stay.

What’s there to see and do in Cortona?

Cultural attractions include Museum of the Etruscan Academy and Signorelli Theatre, whereas Val di Chiana is one spot to enjoy nature. While here, Piazza della Repubblica and Villa Bramasole are other places worth a visit.

What’s a vacation rental in Cortona like?

A vacation rental is a private property where you can stay for a long or short time in Cortona. Vacation rentals provide amenities like kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about cleanliness, vacation rentals can offer a sense of privacy away from public hotel elevators and bustling concierge desks while still allowing you to travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great choice for a family trip.