Cortona Holiday Homes from £61: Search Holiday Homes in Cortona

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

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Our top choices for Cortona holiday homes

A park with picnic tables, a playground, and a gravel path.

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

Cortona

includes taxes & fees

25 Sept - 26 Sept

2. Montecchio di Cortona

Montecchio

Monica S.

includes taxes & fees

22 Oct - 23 Oct

A hot tub in a grassy outdoor area with a mountain view.

3. Farmhouse with mountain views hot tub

Cortona

includes taxes & fees

27 Sept - 28 Sept

A building with a stone facade, multiple windows, and a balcony.

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

Cortona

includes taxes & fees

4 Oct - 5 Oct

A kitchen with white cabinets, a microwave, a sink, and a window with lace curtains.

5. Happy Nest Tuscany Between Florence and Rome

Castiglion Fiorentino

includes taxes & fees

25 Sept - 26 Sept

A brick building with a large sliding glass door, a brown door, and a small potted plant.

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

Foiano della Chiana

includes taxes & fees

25 Sept - 26 Sept

A person sitting at an outdoor table with a drink, a bowl of bread, and a glass of juice.

7. Dolce Casa 2 by Tiny Away

Rigutino

includes taxes & fees

27 Sept - 28 Sept

8. Dolce Casa 1 by Tiny Away

Rigutino

includes taxes & fees

28 Sept - 29 Sept

A narrow street with buildings on either side, stone walls, and a clear blue sky.

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

Arezzo Centro Storico

Maria Gemma

includes taxes & fees

1 Oct - 2 Oct

A neatly made bed with a dark patterned bedspread, two bedside tables with lamps, and two framed pictures on the wall.

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

Toscana

includes taxes & fees

22 Oct - 23 Oct

A cozy living room with a wooden ceiling, a sofa, a dining table with chairs, a bookshelf, and a view through a window.

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

Castel Rigone

John L.

includes taxes & fees

1 Oct - 2 Oct

A thatched-roof pavilion overlooking a calm lake with distant mountains.

12. Gorgeously restored tranquil farmhouse

Castiglione Del Lago PG

John C.

includes taxes & fees

2 Oct - 3 Oct

A stone building with a balcony, a wooden table with chairs, and a large umbrella.

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

Lisciano Niccone

includes taxes & fees

8 Oct - 9 Oct

A rustic kitchen with stone walls, a wooden ceiling, a green sofa with cushions, and a view through a large arched window.

14. Vacation Home 'La Limonaia' with Pool, Private Terrace & Wi-Fi

Monte San Savino

"My husband and I booked this place and were unable to stay due to lack of communication regarding check-in procedure. The listing states the host will make contact 3 days before which didn’t happen. We sent several messages the day of check-in and didn’t hear from the host until well after the check-in time (4pm). Given the remote location and time of day, we were worried we wouldn’t have anywhere to stay for the night so we booked a hotel in Arezzo which we were lucky to get on a holiday...

Anonymous traveller

includes taxes & fees

26 Sept - 27 Sept

A kitchen counter with a coffee maker, a paper towel holder, and a window with a view of greenery.

15. Holiday Home 'La Casina All'angolo'

Civitella in Val di Chiana

includes taxes & fees

30 Sept - 1 Oct

A kitchen with a tiled backsplash and three hanging utensils.

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

Castiglione del Lago

Bin L.

includes taxes & fees

27 Sept - 28 Sept

17. Casale I Tre Cipressi

Arezzo

A narrow stone pathway leading through an old stone building with arched doorways and potted plants.

18. Romantic farm in the Sienese hills

Trequanda, Siena

"Zum positiven: Kommunikation mit dem Gastgeber war sehr gut und informativ. Check in war gut, Antonio der die Übergabe der Schlüssel und die Erläuterung zum Appartement machte sprach leider nur italienisch, aber er war sehr freundlich und mit Händen und Füßen funktionierte es gut. Das Apartment war wirklich sehr schön und mit Liebe zum Detail eingerichtet. Die Location war wirklich sehr schön.Nun zum negativen: An allen Fenstern der Unterkunft waren keine Fliegengitter angebracht was es...

Harald B.

includes taxes & fees

25 Sept - 26 Sept

A stone building with a balcony, outdoor seating, and a stone staircase.

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

lisciano niccone

Anonymous traveller

includes taxes & fees

25 Sept - 26 Sept

A narrow street lined with stone buildings, some with wooden shutters, and potted plants.

20. Oasi del Borgo Montefollonico

Montefollonico

includes taxes & fees

26 Sept - 27 Sept

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Top Cortona Hotel Reviews

Monastero di Cortona Hotel & Spa

10/10 Excellent

"Service was top notch and Claudio at the bar made the best cocktails"

Hotel San Michele

8/10 Good

"This is a charming hotel housed in a 15th century palazzo as close as you can get to the center of Cortona. The staff was pleasant and helpful. Plus you can pull your car up for luggage drop off - a real convenience in a town center where cars are otherwise restricted. Just note this hotel is in an old building. Not all rooms are serviced by elevator - some stairs required. And like any historic property the facilities have charming quirks - rooms but not all public facilities have A/C, lighting is low and there are no amenities on site other than a lovely buffet breakfast you can enjoy inside or in a garden setting. However its location steps from Cortona’s Piazza Republica, restaurants and shops make up for any shortcomings!"

Villa di Piazzano - Small Luxury Hotel of the World

10/10 Excellent

"Stunning little hotel with the most beautiful setting, gardens and pool. The room was exceptionally appointed clean. The best part of the stay was the restaurant. The best meals we had on our entire trip. Definitely recommend hiring e-bikes and riding up to Cortona!"

Find out more about Cortona

Cortona Holiday Homes information

Number of reviews	20
Accommodation	207 Holiday Homes
Lowest Price	£61
Highest Price	£2,769

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Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Cortona holiday 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. Exclusive Private Villa for Groups with Panoramic Pool and Large Common Room – Between Tuscany and Umbria

14. Vacation Home 'La Limonaia' with Pool, Private Terrace & Wi-Fi

15. Holiday Home 'La Casina All'angolo'

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

17. Casale I Tre Cipressi

18. Romantic farm in the Sienese hills

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

20. Oasi del Borgo Montefollonico

Find holiday rentals that suit your style

Top Cortona Hotel Reviews

Monastero di Cortona Hotel & Spa

Hotel San Michele

Villa Borgo San Pietro

Villa di Piazzano - Small Luxury Hotel of the World

Locanda agli Amici

Hotel San Luca

Il Falconiere - Relais e Chateaux

B&B San Francesco

Relais Villa Baldelli

Find out more about Cortona

Cortona Holiday Homes information

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