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

Cortona Vacation Rentals

Dates

November 2026

December 2026

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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

Cortona Old Town

mansoor

A hotel room with a large bed, a desk, a chair, a small table, and a door leading to another room.

2. CASA AMBRA

Cortona Old Town

₩310,369 total

includes taxes & fees

Nov 10 - Nov 11

A narrow stone staircase leading up a hillside, flanked by buildings with wooden doors and windows, and hanging laundry.

3. Vicolo Della Scala Rooms - Il Sole

Cortona Old Town

₩169,984 total

includes taxes & fees

Nov 11 - Nov 12

4. Vicolo Della Scala Rooms - La Luna

Cortona Old Town

₩152,413 total

includes taxes & fees

Nov 11 - Nov 12

A restaurant named 'SALUMERIA FOCACCE E VINI' with outdoor seating and a stone facade.

5. Limehome Arezzo Duomo

Arezzo Centro Storico

Florian

₩130,081 total

includes taxes & fees

Nov 17 - Nov 18

A crowded restaurant with brick walls and multiple tables and chairs.

6. La Locanda di San Francesco

Montepulciano

Colin

₩228,212 total

includes taxes & fees

Nov 25 - Nov 26

A bedroom with a large bed, a chandelier, a mirror, and plants.

7. Bibi Boutique

Arezzo Centro Storico

Carol

₩146,056 total

includes taxes & fees

Nov 10 - Nov 11

A terrace with a table set for breakfast, overlooking a scenic landscape.

8. Delcorto Suites

Montepulciano

Denise

₩261,177 total

includes taxes & fees

Nov 10 - Nov 11

9. San Michele al Borgo

Castiglion Fiorentino

Vern

₩205,539 total

includes taxes & fees

Nov 10 - Nov 11

An interior courtyard with stone columns, arches, and a mosaic.

10. Meublé Il Riccio

Montepulciano

Christopher

₩244,564 total

includes taxes & fees

Nov 10 - Nov 11

A narrow cobblestone street flanked by historic stone buildings with arched doorways and windows.

11. Il Tosco

Montepulciano

Valerie

₩351,135 total

includes taxes & fees

Nov 10 - Nov 11

A courtyard with a pool, stone benches, and a view of a hill.

12. TH Perugia - Castello di Monterone

Perugia

Sandro

₩344,746 total

includes taxes & fees

Nov 10 - Nov 11

A table set outdoors with breakfast items including bread, a cup, and a glass of juice.

13. Hotel San Gregorio

Pienza

Michael

₩214,009 total

includes taxes & fees

Nov 16 - Nov 17

14. iConic Wellness Resort

Arezzo

Wade

₩120,043 total

includes taxes & fees

Dec 2 - Dec 3

A spa area with a stone-walled arch, a hot tub, and a small window.

15. DormiVeglia B&B

Monte San Savino

Melissa Hyun Joo

₩170,852 total

includes taxes & fees

Nov 22 - Nov 23

A covered corridor with brick columns, potted plants, and a view of a lush landscape.

16. Abbadia Sicille Relais

Trequanda

Robert

₩101,780 total

includes taxes & fees

Nov 26 - Nov 27

A view of a historic town with prominent buildings and a church tower.

17. Cameracaffè Centro

Arezzo Centro Storico

Alexandre

₩149,323 total

includes taxes & fees

Nov 16 - Nov 17

A courtyard with outdoor seating, a stone building with a tower, and a well-maintained garden.

18. Castello di Gargonza

Monte San Savino

Iain

₩418,000 total

includes taxes & fees

Nov 12 - Nov 13

A modern hotel room with large windows, a bed, a desk, and a chair.

19. B&B 52cento

Arezzo Centro Storico

Tina

₩134,764 total

includes taxes & fees

Nov 11 - Nov 12

20. Casale dell'Assiolo

Castiglione del Lago

Emma

₩172,443 total

includes taxes & fees

Nov 14 - Nov 15

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Find vacation rentals that suit your style

Top Cortona Hotel Reviews

A terrace with sun loungers, stone walls, and potted plants.

Monastero di Cortona Hotel & Spa

Cortona Old Town

10/10 Excellent

Eric

A person in a white robe standing by a window with a view of mountains.

Locanda agli Amici

Cortona

10/10 Excellent

This was the perfect away from the city stay for us. Cortona was just a quick few day stay for us but the staff/sylvia were fantastic. Room was clean, the breakfast was delicious. A/c and water pressure from the shower was much needed and the location was perfect for us. It is a short walk from downtown Cortona (steep walk into the city and about 15 mins) but the views are unmatched. Sylvia went above and beyond for us picking us up and dropping us off at the bus station. Highly recommend to...

Kaylan

A grand banquet hall with ornate ceiling, long tables set for a formal event, and elaborate floral centerpieces.

Relais La Corte dei Papi

Cortona

10/10 Excellent

Traci

A rustic dining area with a brick fireplace, wooden table, and chairs.

Agriturismo Villa Augusto

Cortona

10/10 Excellent

Kristian

Two people seated at a round table outdoors, with a candle and food on the table, and a large tree in the background.

Cortona Resort Spa

Cortona

10/10 Excellent

Pro: gorgeous and spacious property, we were upgraded to a junior suite that was lovely, attentive staff, and incredible amenities. Pool was wonderful for tired bodies. Con: very few. The restaurant on site has pretty limited menu, toilet in room kept running all night long- informed staff on checkout (as it was troublesome to flush, and wasting water), fridge in room- housed in a cabinet that I feel caused it to overheat… and therefore was not very powerful enough to keep drinks cold. Loved...

Jeneva

A terraced garden with a stone staircase, outdoor seating, and a red statue.

Casa Kita

Cortona Old Town

10/10 Excellent

Joy

A gazebo with a glass enclosure, surrounded by potted plants and wicker furniture, overlooking a scenic landscape.

Il Falconiere - Relais e Chateaux

Cortona

10/10 Excellent

This was the first hotel we visited in our two week Tuscany vacation. Coming out of Rome and getting on the highway north, it looked like the exit should be labeled for Cortona...but it wasn't and we wasted a lot of time getting lost (our fault). Once we found the hotel, it was a gem in the hills in the vineyards. Breakfast on the patio of the little glass Liminoere building was fabulous. Loved their boxer dog roamed around saying "hi". Owner/chef is on premises and she gives cooking lessons....

Barbara

A view of a historic building with a green dome through a window, with candles and rolled towels on the windowsill.

Hotel Italia

Cortona Old Town

10/10 Excellent

Eileen

A courtyard with stone buildings, a gravel path, and potted plants.

B&B San Francesco

Cortona Old Town

10/10 Excellent

Martin

A courtyard with stone buildings, a wooden staircase, and a grassy area with stepping stones.

Casale l'Antico Carro

Cortona

10/10 Excellent

The Revd. Canon Dr. Michael

A stone-arched entrance to a building with a glass door, potted flowers, and wall-mounted lights.

LA CORTE DI AMBRA

Cortona Old Town

10/10 Excellent

Anna

A restaurant with glass walls, tables set with white tablecloths, and chairs.

La Cantina Relais - Fattoria Il Cipresso

Arezzo

10/10 Excellent

Steve

Terra Antica Resort

Montepulciano

10/10 Excellent

Nikhil

A large estate with multiple buildings, a well-maintained garden, and a vineyard in the background.

Lupaia

Torrita di Siena

10/10 Excellent

This was the most amazing place to stay! This was our favorite stop on a 30-day trip to Greece, Italy and Switzerland. The surrounding countryside is stunning. Our room had a Turkish Bath - what a fun experience. We were a couple of weeks in to our vacation, and we were ready for some down time. Having a private little garden, overlooking the Tuscan hillside was WONDERFUL. The dinner we had on site was one of the best of our entire trip. Breakfast in the morning was an incredible display...

KC Traveler

A wooden structure with a circular window, a wooden deck, and a view of trees and sky.

The Monteleone

Monteleone d'Orvieto

10/10 Excellent

Paul

Find out more about Cortona

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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.

Cortona Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Cortona vacation rentals

1. B&B Piccolo Hotel

2. CASA AMBRA

3. Vicolo Della Scala Rooms - Il Sole

4. Vicolo Della Scala Rooms - La Luna

5. Limehome Arezzo Duomo

6. La Locanda di San Francesco

7. Bibi Boutique

8. Delcorto Suites

9. San Michele al Borgo

10. Meublé Il Riccio

11. Il Tosco

12. TH Perugia - Castello di Monterone

13. Hotel San Gregorio

14. iConic Wellness Resort

15. DormiVeglia B&B

16. Abbadia Sicille Relais

17. Cameracaffè Centro

18. Castello di Gargonza

19. B&B 52cento

20. Casale dell'Assiolo

Find vacation rentals that suit your style

Top Cortona Hotel Reviews

Monastero di Cortona Hotel & Spa

10/10 Excellent

Find out more about Cortona

Frequently Asked Questions

Can I find vacation rentals in Cortona?

How many vacation rentals are there in Cortona?

What’s there to see and do in Cortona?

What’s a vacation rental in Cortona like?