Cortona Vacation Homes from ￥11,938

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

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Our top choices for Cortona vacation homes

1. Holiday home with panoramic terrace ideal for families and couples

Cortona

￥14,432 total

includes taxes & fees

Sep 16 - Sep 17

2. Montecchio di Cortona

Montecchio

Monica S.

￥19,065 total

includes taxes & fees

Sep 18 - Sep 19

3. Farmhouse with mountain views hot tub

Cortona

￥70,751 total

includes taxes & fees

Sep 17 - Sep 18

4. Apartment 'Vencaglia Casa del Nonno Bingheri' with Private Terrace & Wi-Fi

Cortona

￥72,600 total

includes taxes & fees

Sep 30 - Oct 1

5. Happy Nest Tuscany Between Florence and Rome

Castiglion Fiorentino

￥11,938 total

includes taxes & fees

Sep 16 - Sep 17

6. Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning

Foiano della Chiana

￥14,403 total

includes taxes & fees

Sep 16 - Sep 17

7. Dolce Casa 2 by Tiny Away

Rigutino

￥19,013 total

includes taxes & fees

Sep 17 - Sep 18

8. Dolce Casa 1 by Tiny Away

Rigutino

￥20,138 total

includes taxes & fees

Sep 17 - Sep 18

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Top Cortona Hotel Reviews

B&B San Francesco

10/10 Excellent

"Welcoming and helpful host - thank you."

Monastero di Cortona Hotel & Spa

10/10 Excellent

"I never write hotel reviews, but this hotel was so exceptional that I had to share my experience. The room was beautiful, spotless, and incredibly comfortable, with thoughtful turn-down service every evening. The staff were truly the most attentive and welcoming I’ve ever experienced. They helped arrange pickup from the train station, made restaurant reservations, and went above and beyond in so many little ways. Those small details made me feel genuinely cared for. The breakfast was lovely and served in such a beautiful setting — the perfect way to start the day. I absolutely loved my stay here and would come back to Cortona for this hotel alone. A truly special place with exceptional hospitality. Highly recommend!"

Il Falconiere - Relais e Chateaux

10/10 Excellent

"Il Falconiere treats you as a true guest. Welcoming, courteous and professional were all staff members. Food truly excellent and with the Michelin star, you will enjoy a sumptuous meal, ample portions, amuse bouche at meal's start with a surprise dessert tray with little bites. All staff you interact with are well trained and genuinely friendly and still professional. Our room was in the origjnal residence and had a modern bathroom, lovely size bedroom, anti room with a second desk. In the salon, upon entering the suite, you will find "gifts" left for guests with seating if wishing to entertain. Our group, 4 persons, were very impressed with accommodations, meals and courteous staff. Of course, owner and chef, Silvia Baracchi, too was gracious coming to tables in the evening, welcoming guests and if passed anyone during day, always smiled a buon giorno to one and all. A delightful experience and wonderful to share with good friends."

Find out more about Cortona

Cortona Vacation Homes information

Number of reviews	16
Accommodation	221 Vacation Homes
Lowest Price	￥11,938
Highest Price	￥469,708

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Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Cortona vacation homes

1. Holiday home with panoramic terrace ideal for families and couples

2. Montecchio di Cortona

3. Farmhouse with mountain views hot tub

4. Apartment 'Vencaglia Casa del Nonno Bingheri' with Private Terrace & Wi-Fi

5. Happy Nest Tuscany Between Florence and Rome

6. Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning

7. Dolce Casa 2 by Tiny Away

8. Dolce Casa 1 by Tiny Away

9. Tolletta 10 e Lode - One Bedroom House, Sleeps 4

10. Double room with private bathroom in the countryside 5 minutes from Montepulciano

11. Vacation Home La Perla del Lago-All the comfort of your own home with a lake view!

12. Gorgeously restored tranquil farmhouse

13. Holiday Home 'La Casina All'angolo'

14. Casale I Tre Cipressi

15. Exclusive Private Villa for Groups with Panoramic Pool and Large Common Room – Between Tuscany and Umbria

16. Palazzo Cofani Brizzolari – Historic Residence with Tower in the Heart of Arezzo

17. Casa Roda – Your Home by Lake Trasimeno, Between Umbria and Tuscany

18. Apartment "Pugnano Alto - Tartufo" with Shared Pool and Wi-Fi

19. Vacation Home "Casa Belvedere" with Private Garden, Private Pool & Wi-Fi

20. LANDLORD ALBACHIARA

Find vacation rentals that suit your style

Top Cortona Hotel Reviews

B&B San Francesco

Relais Villa Baldelli

Monastero di Cortona Hotel & Spa

Locanda del Molino

Il Falconiere - Relais e Chateaux

Hotel San Luca

"Villa Stefania" Old Tuscan Farmhouse - Great View on Cortona

Villa Borgo San Pietro

Villa di Piazzano - Small Luxury Hotel of the World

Find out more about Cortona

Cortona Vacation Homes information

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Search Vacation Homes in Cortona

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Cortona vacation homes

1. Holiday home with panoramic terrace ideal for families and couples

2. Montecchio di Cortona

3. Farmhouse with mountain views hot tub

4. Apartment 'Vencaglia Casa del Nonno Bingheri' with Private Terrace & Wi-Fi

5. Happy Nest Tuscany Between Florence and Rome

6. Holiday Home 'Stanza Azzurra' with Wi-Fi and Air Conditioning

7. Dolce Casa 2 by Tiny Away

8. Dolce Casa 1 by Tiny Away

9. Tolletta 10 e Lode - One Bedroom House, Sleeps 4

10. Double room with private bathroom in the countryside 5 minutes from Montepulciano

11. Vacation Home La Perla del Lago-All the comfort of your own home with a lake view!

12. Gorgeously restored tranquil farmhouse

13. Holiday Home 'La Casina All'angolo'

14. Casale I Tre Cipressi

15. Exclusive Private Villa for Groups with Panoramic Pool and Large Common Room – Between Tuscany and Umbria

16. Palazzo Cofani Brizzolari – Historic Residence with Tower in the Heart of Arezzo

17. Casa Roda – Your Home by Lake Trasimeno, Between Umbria and Tuscany

18. Apartment "Pugnano Alto - Tartufo" with Shared Pool and Wi-Fi

19. Vacation Home "Casa Belvedere" with Private Garden, Private Pool & Wi-Fi

20. LANDLORD ALBACHIARA

Find vacation rentals that suit your style

Top Cortona Hotel Reviews

B&B San Francesco

Find out more about Cortona

Cortona Vacation Homes information

Explore a world of travel with Expedia