Top Town Houses in Cortona in 2026

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

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Our top choices for Cortona town houses

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

1. B&B Piccolo Hotel

Cortona Old Town

mansoor

4.127.566 ₫ total

includes taxes & fees

2 Nov - 3 Nov

A narrow cobblestone street with a rustic stone building featuring a wooden door and arched window.

2. San Michele al Borgo

Castiglion Fiorentino

Vern

4.147.428 ₫ total

includes taxes & fees

19 Oct - 20 Oct

3. iConic Wellness Resort

Arezzo

Rheymarie

2.304.556 ₫ total

includes taxes & fees

25 Oct - 26 Oct

An outdoor seating area with a pergola, a fire pit, and a flower arrangement.

4. Fontelunga Hotel & Villas

Foiano della Chiana

Brian

8.531.347 ₫ total

includes taxes & fees

11 Oct - 12 Oct

5. Casale dell'Assiolo

Castiglione del Lago

3.906.341 ₫ total

includes taxes & fees

6 Oct - 7 Oct

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

6. DormiVeglia B&B

Monte San Savino

Melissa Hyun Joo

3.279.973 ₫ total

includes taxes & fees

12 Oct - 13 Oct

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

7. B&B 52cento

Arezzo Centro Storico

Tina

2.199.652 ₫ total

includes taxes & fees

18 Oct - 19 Oct

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

8. Meublé Il Riccio

Montepulciano

Christopher

4.695.064 ₫ total

includes taxes & fees

8 Oct - 9 Oct

A narrow alleyway with buildings on either side, string lights hanging above, and a sign reading "ROOMS".

9. Bed & Breakfast Vicolo dell'Oste

Montepulciano

Shelly

3.139.909 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

10. Cameracaffè Centro

Arezzo Centro Storico

Alexandre

2.716.273 ₫ total

includes taxes & fees

7 Oct - 8 Oct

A patio area with outdoor seating, potted plants, and a view of the landscape.

11. Affitacamere Maria Gabriella

Pienza

Janine und Thomas

3.842.213 ₫ total

includes taxes & fees

7 Oct - 8 Oct

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

12. La Locanda di San Francesco

Montepulciano

Colin

6.060.150 ₫ total

includes taxes & fees

12 Oct - 13 Oct

An arched stone bridge with a white building on the right, featuring a balcony with plants.

13. Locanda Antico Borgo

Civitella in Val di Chiana

"What an absolutely beautiful stay, in a stunning place. Our host was attentive and kind, and the food was wonderful. The hotel and rooms were spotlessly clean, and particularly for my needs on a road trip with my 18 year old son, the accommodation offering two adjoining bedrooms was perfect, and we could park outside. Also very good value in my opinion. I would definitely return, it’s also ideal for couples and I would love to bring my wife here. "

Mr Andy

3.300.418 ₫ total

includes taxes & fees

5 Oct - 6 Oct

A staircase with a wooden handrail, a potted plant, and a chair in a hallway.

14. Villa Fontis Rapolano

Rapolano Terme

Barbara

2.771.767 ₫ total

includes taxes & fees

4 Oct - 5 Oct

A bakery display with various pastries and desserts.

15. La Piccola Locanda

Chiusi

autumn

3.471.280 ₫ total

includes taxes & fees

3 Oct - 4 Oct

A corridor with wooden flooring, a white cushioned bench, and shelves on both sides displaying bottles.

16. Allegra Toscana - Affittacamere Guest house

Arezzo Centro Storico

Justin

4.262.416 ₫ total

includes taxes & fees

4 Oct - 5 Oct

A bedroom with a brick archway, a bed with white linens, a small table with a magazine, and a painting on the wall.

17. TuscanyLettings Studio&Room

Pienza

Lucas

2.640.255 ₫ total

includes taxes & fees

2 Nov - 3 Nov

A balcony with a metal railing, a small table with a chair, potted plants, and a view of the sea.

18. PienzaLettings Suites

Pienza

Pearlyn

2.434.156 ₫ total

includes taxes & fees

2 Nov - 3 Nov

A cozy outdoor seating area with stone walls and red foliage, featuring a table and chairs, and a door leading to a covered entrance.

19. L'Olmo

Pienza

Jennifer

12.968.016 ₫ total

includes taxes & fees

2 Nov - 3 Nov

A stone building with arched windows and a gravel driveway.

20. Villa La Ginestra

Subbiano

Philippe

3.242.005 ₫ total

includes taxes & fees

7 Oct - 8 Oct

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Top Cortona Hotel Reviews

Monastero di Cortona Hotel & Spa

8/10 Good

"Breakfast was amazing!! Property was not great, but nice!"

Locanda agli Amici

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 anyone visiting Cortona."

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 Town Houses information

Number of reviews	909
Accommodation	2 Town Houses
Lowest Price	2.199.652 ₫
Highest Price	12.968.016 ₫

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Change your mind

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Check prices for these dates

Our top choices for Cortona town houses

1. B&B Piccolo Hotel

2. San Michele al Borgo

3. iConic Wellness Resort

4. Fontelunga Hotel & Villas

5. Casale dell'Assiolo

6. DormiVeglia B&B

7. B&B 52cento

8. Meublé Il Riccio

9. Bed & Breakfast Vicolo dell'Oste

10. Cameracaffè Centro

11. Affitacamere Maria Gabriella

12. La Locanda di San Francesco

13. Locanda Antico Borgo

14. Villa Fontis Rapolano

15. La Piccola Locanda

16. Allegra Toscana - Affittacamere Guest house

17. TuscanyLettings Studio&Room

18. PienzaLettings Suites

19. L'Olmo

20. Villa La Ginestra

Top Cortona Hotel Reviews

Monastero di Cortona Hotel & Spa

Il Falconiere - Relais e Chateaux

Cortona Resort - Le Terre Dei Cavalieri

Villa Borgo San Pietro

Relais Villa Baldelli

Hotel San Luca

Locanda agli Amici

Hotel San Michele

Villa di Piazzano - Small Luxury Hotel of the World

Find out more about Cortona

Cortona Town Houses information

Explore a world of travel with Expedia

Search Town Houses in Cortona

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Cortona town houses

1. B&B Piccolo Hotel

2. San Michele al Borgo

3. iConic Wellness Resort

4. Fontelunga Hotel & Villas

5. Casale dell'Assiolo

6. DormiVeglia B&B

7. B&B 52cento

8. Meublé Il Riccio

9. Bed & Breakfast Vicolo dell'Oste

10. Cameracaffè Centro

11. Affitacamere Maria Gabriella

12. La Locanda di San Francesco

13. Locanda Antico Borgo

14. Villa Fontis Rapolano

15. La Piccola Locanda

16. Allegra Toscana - Affittacamere Guest house

17. TuscanyLettings Studio&Room

18. PienzaLettings Suites

19. L'Olmo

20. Villa La Ginestra

Top Cortona Hotel Reviews

Monastero di Cortona Hotel & Spa

Find out more about Cortona

Cortona Town Houses information

Explore a world of travel with Expedia