The 10 Best 5 Star Hotels in Ossaia - 2026 Updated Prices

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Our top choices for Ossaia 5-star hotels

A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a stone building in the background.

A hallway with a checkered floor, arched windows, and a chandelier.

A buffet with various food items, a vase of flowers, and a mirror reflecting the room.

An outdoor dining area with tables set for a meal, surrounded by greenery and trees.

1. Villa di Piazzano - Small Luxury Hotel of the World

Cortona

Rushab

17.994.877 ₫

20.031.307 ₫ total

includes taxes & fees

12 Oct - 13 Oct

An aerial view of a large estate with multiple buildings, a swimming pool, and well-maintained gardens.

A large estate with multiple buildings, a swimming pool, and expansive green fields.

A cozy lounge area with a green sofa, a wooden coffee table, wicker chairs, and a view of a lush landscape through an arched doorway.

A spacious interior with a high arched ceiling, large windows, and a central seating area with chairs and tables.

2. Precise Tale Poggio Alla Sala

Montepulciano

Mark

14.549.533 ₫

16.182.083 ₫ total

includes taxes & fees

27 Sept - 28 Sept

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

A historic town with traditional architecture, a central courtyard with a swimming pool, and a view of distant mountains.

A pool area with lounge chairs, a hot tub, and a view of mountains.

A spacious lobby with a high ceiling, a grand chandelier, and a staircase leading to an upper level.

3. Monastero di Cortona Hotel & Spa

Cortona Old Town

Alexander

6.512.205 ₫

7.400.220 ₫ total

includes taxes & fees

25 Oct - 26 Oct

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

A person in a swimming pool with a view of trees and mountains through a window.

A person standing at the entrance of a building with a stone staircase leading up to a door.

A stone building with a red awning, potted plants, and a staircase leading to the entrance.

4. Il Falconiere - Relais e Chateaux

Cortona

Qingwen

11.442.809 ₫

12.823.884 ₫ total

includes taxes & fees

22 Oct - 23 Oct

A bathroom with two large white sinks, a mirror, and a view of a balcony with a railing.

A large, historic building with a swimming pool and lounge chairs.

An aerial view of a historic building complex with multiple structures, including a central building with a courtyard, surrounded by lush greenery and a winding road.

A modern lounge area with wicker furniture, a sofa, and a coffee table.

5. Borgo Dei Conti Resort Relais & Chateaux

Perugia

Carmel

22.387.705 ₫

24.833.671 ₫ total

includes taxes & fees

21 Oct - 22 Oct

A swimming pool with a view of a hilly landscape, surrounded by trees and grass.

A balcony with a view of a green landscape and a body of water.

A restaurant with brick arches, white tablecloths, and floral centerpieces.

6. Borgo Sant'Ambrogio Resort

Trequanda

María

4.781.304 ₫

5.348.233 ₫ total

includes taxes & fees

18 Oct - 19 Oct

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

A long banquet table with gold candelabras, white flowers, and gold tableware.

A historic stone building with arched doorways and a courtyard at twilight.

A large pool with a curved edge, surrounded by a courtyard with a building featuring arched windows and columns.

7. Relais La Corte dei Papi

Cortona

Frithjof

10.906.768 ₫

12.234.239 ₫ total

includes taxes & fees

7 Oct - 8 Oct

A stone villa with a swimming pool, outdoor seating, and a scenic sunset view.

An arched stone corridor leading to a room with a billiards table, a lamp, and a view of the outdoors.

A large, historic building with multiple wings and a courtyard.

A cozy living room with a fireplace, a clock, and a sofa.

8. Podere Cavalbianco

Monte San Savino

Edith

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Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Ossaia.

Hotel Continentale

Piazza Guido Monaco, 7 Arezzo AR

2.906.479 ₫

3.494.918 ₫ total

29 Sept - 30 Sept

includes taxes & fees

Il Gentiluomo Hotel & SPA

Via Raccordo Autostradale, 1/a Arezzo AR

1.913.189 ₫

2.282.103 ₫ total

28 Sept - 29 Sept

includes taxes & fees

8.6/10 Excellent! (173 reviews)

Grand Hotel Milano

Viale Roma, 46 Chianciano Terme SI

2.367.942 ₫

2.723.133 ₫ total

6 Oct - 7 Oct

includes taxes & fees

8/10 Very good! (55 reviews)

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Pool Spa Hot tub Breakfast included Waterpark

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.

Top Ossaia Hotel Reviews

Monastero di Cortona Hotel & Spa

10/10 Excellent

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

Precise Tale Poggio Alla Sala

10/10 Excellent

"We enjoyed this picturesque hotel for a night of R&R. We especially liked arranging for e bikes to be delivered and taking the back gravel roads to look around. The second day we ran the same route."

Il Falconiere - Relais e Chateaux

10/10 Excellent

"Amazing stay for our 25th anniversary. The property is breathtaking and every corner was like a Tuscan postcard! The room was beautiful, the pools were great and the food was exceptional. Would highly recommend and would go back in a second!"

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Change your mind

Treat yourself

Be picky

Check availability on Ossaia 5 Star Hotels

Our top choices for Ossaia 5-star hotels

1. Villa di Piazzano - Small Luxury Hotel of the World

2. Precise Tale Poggio Alla Sala

3. Monastero di Cortona Hotel & Spa

4. Il Falconiere - Relais e Chateaux

5. Borgo Dei Conti Resort Relais & Chateaux

6. Borgo Sant'Ambrogio Resort

7. Relais La Corte dei Papi

8. Podere Cavalbianco

Explore similar 4-star hotels

Hotel Continentale

Il Gentiluomo Hotel & SPA

Grand Hotel Milano

Top Ossaia Hotel Reviews

Monastero di Cortona Hotel & Spa

Precise Tale Poggio Alla Sala

Il Falconiere - Relais e Chateaux

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