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
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Cortona vacation rentals

An upper floor view of a courtyard with stone walls, arched doorways, and seating areas with potted plants.

1. B&B Piccolo Hotel

B&B Piccolo Hotel
Cortona Old Town
9.2 out of 10, Wonderful, (25 reviews)
"This is such an amazing hotel in such an amazing place! "
United States
mansoor
The price is ₩190,132
₩212,147 total
includes taxes & fees
Nov 2 - Nov 3
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
The price is ₩307,058
₩340,016 total
includes taxes & fees
Nov 8 - Nov 9
CASA AMBRA
A narrow stone staircase leading up a hillside, flanked by buildings with wooden doors and windows, and hanging laundry.

3. Vicolo Della Scala Rooms - La Luna

Vicolo Della Scala Rooms - La Luna
Cortona Old Town
The price is ₩133,988
₩153,392 total
includes taxes & fees
Oct 15 - Oct 16
Vicolo Della Scala Rooms - La Luna
A narrow stone staircase leading up a hillside, flanked by buildings with wooden doors and windows, and hanging laundry.

4. Vicolo Della Scala Rooms - Il Sole

Vicolo Della Scala Rooms - Il Sole
Cortona Old Town
The price is ₩149,750
₩170,730 total
includes taxes & fees
Oct 23 - Oct 24
Vicolo Della Scala Rooms - Il Sole
A modern kitchen with wooden cabinets, a microwave, and a black countertop.

5. Limehome Arezzo Duomo

Limehome Arezzo Duomo
Arezzo Centro Storico
10.0 out of 10, Exceptional, (3 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
The price is ₩90,071
₩116,342 total
includes taxes & fees
Oct 13 - Oct 14
Limehome Arezzo Duomo
Room

6. Bibi Boutique

Bibi Boutique
Arezzo Centro Storico
The price is ₩110,547
₩130,609 total
includes taxes & fees
Oct 13 - Oct 14
Bibi Boutique
Pool

7. iConic Wellness Resort

iConic Wellness Resort
Arezzo
8.8 out of 10, Excellent, (41 reviews)
"Beautiful and peaceful resort! Hope to return soon❤️"
United States
Rheymarie
The price is ₩113,003
₩133,310 total
includes taxes & fees
Oct 25 - Oct 26
iConic Wellness Resort
A crowded restaurant with brick walls and multiple tables and chairs.

8. La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (150 reviews)
"This place was great. Amazing view the room. Extremely friendly and helpful staff. This hotel made our trip - highly recommend"
Canada
Colin
The price is ₩238,824
₩268,712 total
includes taxes & fees
Nov 3 - Nov 4
La Locanda di San Francesco
A narrow cobblestone street with a rustic stone building featuring a wooden door and arched window.

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
The price is ₩188,331
₩213,169 total
includes taxes & fees
Oct 14 - Oct 15
San Michele al Borgo
An outdoor seating area with a pergola, a fire pit, and a flower arrangement.

10. Fontelunga Hotel & Villas

Fontelunga Hotel & Villas
Foiano della Chiana
10.0 out of 10, Exceptional, (10 reviews)
"Wonderful stay!"
Canada
Brian
The price is ₩378,404
₩422,249 total
includes taxes & fees
Oct 13 - Oct 14
Fontelunga Hotel & Villas
A narrow cobblestone street flanked by historic stone buildings with arched doorways and windows.

11. Il Tosco

Il Tosco
Montepulciano
10.0 out of 10, Exceptional, (135 reviews)
"Beautiful hotel in the best location. We so enjoyed our stay, especially the amazing breakfast and sweets they had available all day long."
United States
Margaret
The price is ₩309,517
₩346,473 total
includes taxes & fees
Nov 2 - Nov 3
Il Tosco
A table set outdoors with breakfast items including bread, a cup, and a glass of juice.

12. Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (162 reviews)
"Great location, clean room and communal space. We were disappointed that we were given a room with jacuzzi but no shower and refrigerator was broken. Overall a nice experience"
United States
Julia
The price is ₩171,782
₩197,967 total
includes taxes & fees
Nov 8 - Nov 9
Hotel San Gregorio
An interior courtyard with stone columns, arches, and a mosaic.

13. Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.6 out of 10, Exceptional, (119 reviews)
"What a gem! Absolutely loved the hotel and enjoyed our stay. Staff very friendly and helpful, and our room was outstanding. The view from our balcony was breathtaking. Top of our list!"
United States
Christopher
The price is ₩213,919
₩241,316 total
includes taxes & fees
Oct 14 - Oct 15
Meublé Il Riccio
A spa area with a stone-walled arch, a hot tub, and a small window.

14. 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
The price is ₩147,799
₩168,584 total
includes taxes & fees
Nov 8 - Nov 9
DormiVeglia B&B
A bedroom with a bed, a chair, a small table, and a window with curtains.

15. Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (141 reviews)
"Wonderful place - clean, comfortable, quiet with excellent hosts. Perfect location near everything in town including the parking. Can’t wait to return!"
United States
Shelly
The price is ₩141,254
₩161,384 total
includes taxes & fees
Nov 1 - Nov 2
Bed & Breakfast Vicolo dell'Oste
A courtyard with a pool, stone benches, and a view of a hill.

16. TH Perugia - Castello di Monterone

TH Perugia - Castello di Monterone
Perugia
9.8 out of 10, Exceptional, (328 reviews)
"Beautiful garden, beautiful view, easy parking and tasty restaurant."
Canada
Sandro
The price is ₩299,692
₩340,169 total
includes taxes & fees
Oct 18 - Oct 19
TH Perugia - Castello di Monterone
A modern hotel room with large windows, a bed, a desk, and a chair.

17. B&B 52cento

B&B 52cento
Arezzo Centro Storico
8.0 out of 10, Very good, (82 reviews)
"Very accessible and easy accommodation. Very pleasant room and reasonable breakfast. Within walking distance of train station and city centre."
Australia
Tina
The price is ₩101,417
₩120,566 total
includes taxes & fees
Oct 19 - Oct 20
B&B 52cento
A terrace with a table set for breakfast, overlooking a scenic landscape.

18. Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (47 reviews)
"Room, location, staff - it was perfection. We can not wait to return."
United States
Denise
The price is ₩228,822
₩257,709 total
includes taxes & fees
Oct 13 - Oct 14
Delcorto Suites
An arched doorway leading to a building with a wooden door and a staircase.

19. Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (114 reviews)
"Staff was great, and they even scheduled transportation to and from the train station for us. Great location on the main strip of Montepluciano!"
United States
Nicholas
The price is ₩98,224
₩114,051 total
includes taxes & fees
Oct 13 - Oct 14
Residenza Fabroni
A patio area with outdoor seating, potted plants, and a view of the landscape.

20. Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (71 reviews)
"A very pleasant and homey place to stay"
Germany
Janine und Thomas
The price is ₩145,547
₩197,482 total
includes taxes & fees
Oct 13 - Oct 14
Affitacamere Maria Gabriella
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

Hotel San Michele

Hotel San Michele

10/10 Excellent
"Perfect location. Very friendly staff and spacious rooms. Right in the heart of Cortona!"
Asha 1-night trip
Posted 1 day ago
Hotel San Michele

Find out more about Cortona

Search for Vacation rentals in Cortona on Expedia.co.uk! You can easily find your home rentals, villas, Vacation apartments in Cortona using one of the methods below:

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Look no further and take a look at our great range of rental properties in Cortona!

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.

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.