Ossaia Holiday Rentals, Cortona: Private House Rentals

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Family friendly

Farm

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Our top choices for Ossaia hotels

A rustic outdoor dining area with stone walls, a table, and wicker chairs.

A swimming pool with lounge chairs and umbrellas, surrounded by a brick pathway and greenery.

A stone building with a large arched doorway, surrounded by greenery and a hillside in the background.

A stone pathway leading through an arched stone structure, surrounded by greenery and a lamp post.

1. Relais Villa Baldelli

Cortona

Peter

฿3,924

฿4,616 total

includes taxes & fees

15 Oct - 16 Oct

A couple in a hot tub with a cityscape view through large windows.

A balcony with terracotta pots of flowers, a view of a rural landscape, and a stone building with a tiled roof.

A hotel entrance with an arched doorway, a sign with the name 'Albergo I Michele', and a potted plant to the right.

A room with a large window, a vase of red flowers, and a white umbrella outside.

2. Hotel San Michele

Cortona Old Town

฿4,027

฿4,579 total

includes taxes & fees

2 Nov - 3 Nov

A building with a stone pathway leading to an arched entrance, flanked by potted plants and lit by ground lights.

A spacious living room with a yellow sofa, a wooden coffee table, and a floral rug. There are two armchairs and a dining table with chairs. The room has a large window with curtains, a mirror, and wall-mounted lights.

A hotel room with a fireplace, two armchairs, a bed, and a dresser.

An outdoor dining area with tables and chairs, a garden with a lawn and potted plants, and a building with multiple windows and balconies.

3. Hotel Villa Marsili

Cortona Old Town

fares

฿7,737

฿8,810 total

includes taxes & fees

18 Oct - 19 Oct

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

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

4. Monastero di Cortona Hotel & Spa

Cortona Old Town

MICHELLE

฿8,882

฿10,071 total

includes taxes & fees

25 Oct - 26 Oct

A dining area with a table and chairs, large windows with curtains, and a view of a landscape.

A reception area with a wooden console table, two wall clocks, and a staircase leading to an upper level.

A window view of a town with buildings, trees, and parked cars.

A balcony with two lounge chairs, a small table with a drink, and a scenic view.

5. Hotel San Luca

Cortona Old Town

Mariusz

฿2,713

฿3,285 total

includes taxes & fees

26 Oct - 27 Oct

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

A lobby with a reception desk, a fireplace, and a large arched doorway leading outside.

A bedroom with a stone wall, a bed with a headboard, a desk with a computer, a chair, a window with a view, and a ceiling with exposed beams.

A historic stone building with a sign reading "Hotel Italia."

6. Hotel Italia

Cortona Old Town

Fernando

฿3,841

฿4,319 total

includes taxes & fees

3 Nov - 4 Nov

A building with multiple floors, a staircase leading to the entrance, and a small garden area with a palm tree and bushes.

A buffet table with various food items, including cookies, pastries, and dairy products, with labels indicating gluten-free options.

A spacious room with a fireplace, multiple seating areas, and large windows allowing natural light.

A balcony with potted plants and a view of the sea.

7. Villa Santa Margherita

Cortona Old Town

George F

฿3,592

฿4,702 total

includes taxes & fees

31 Oct - 1 Nov

A stone building with outdoor seating and a fountain.

A bedroom with a bed, a dining table, and a TV. There is a balcony with a view of greenery.

A stone building with multiple windows and a courtyard.

A stone building with a tiled roof, a small window, and a metal fence.

8. Villa Borgo San Pietro

Cortona

Olga

฿3,960

฿4,657 total

includes taxes & fees

16 Oct - 17 Oct

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

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.

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

9. Il Falconiere - Relais e Chateaux

Cortona

Qingwen

฿12,848

฿14,283 total

includes taxes & fees

2 Nov - 3 Nov

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

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

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

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

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

Cortona

lynda

฿21,173

฿23,591 total

includes taxes & fees

15 Oct - 16 Oct

A tranquil sunset over a calm body of water with a gazebo structure in the foreground.

A cozy bedroom with a large bed, two armchairs, a small table with a teapot, and a window with a view of trees.

A building with a rustic facade, a door with shutters, and a small outdoor seating area under a vine-covered archway.

An aerial view of a rural property with multiple buildings, a swimming pool, and surrounding agricultural fields.

11. Cortona Resort - Le Terre Dei Cavalieri

Cortona

Jinhee

฿5,002

฿5,690 total

includes taxes & fees

15 Oct - 16 Oct

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

A cobblestone street with terracotta planters and a sign indicating the location of the Chiesa di San Francesco.

A wooden staircase with a handrail on both sides, leading to an upper floor.

A view through a window of a courtyard with a stone building, a clock tower, and a garden with a geometric flower bed.

12. B&B San Francesco

Cortona Old Town

Esther

฿2,702

฿3,685 total

includes taxes & fees

25 Oct - 26 Oct

A historic building with a courtyard, surrounded by lush greenery and trees.

A cozy living room with a grey sofa, a green lamp, and a large mirror.

A well-maintained garden with tall cypress trees, a lawn, and a building with a tiled roof.

A living room with a sofa, two armchairs, a floor lamp, a radiator, a window with curtains, a cabinet, and framed pictures on the wall.

13. Equo Suites

Castiglione del Lago

฿3,942

฿4,487 total

includes taxes & fees

3 Nov - 4 Nov

An outdoor dining area with a table set with food and wine, surrounded by outdoor seating and a large house in the background.

A restaurant with round tables set for dining, large windows with curtains, and a view of the countryside.

A courtyard with a brick building, surrounded by well-maintained lawns and potted plants.

A poolside dining setup with tables and chairs, a pool, and a sunset in the background.

14. Borgo Tre Rose

Montepulciano

Jinhee

฿2,453

฿2,848 total

includes taxes & fees

2 Nov - 3 Nov

A waterfront hotel with a swimming pool, a boat dock, and a view of the water.

A marina with boats docked, a waterfront building, and a cityscape in the background.

A hotel room with a bed, a desk with a lamp, a TV, and a window with a view of the sea.

A waterfront restaurant with outdoor seating, a view of a river, and buildings in the background.

15. Hotel Lidò

Passignano sul Trasimeno

Brian

฿3,377

฿3,865 total

includes taxes & fees

16 Oct - 17 Oct

A stone building with a rustic charm, featuring a welcoming entrance and a small outdoor seating area.

A restaurant with a long communal table, wooden chairs, stone walls, and various kitchen utensils displayed on the walls.

A bedroom with a bed, a table with lemons, a window with curtains, and a radiator.

A cozy living room with a fireplace, a sofa, a dining table, and various decorative items.

16. Locanda del Molino

Cortona

Rochelle

฿2,568

฿3,125 total

includes taxes & fees

27 Oct - 28 Oct

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

A modern bathroom with a large freestanding bathtub, a glass shower enclosure, and ornate mirrors.

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

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

17. Relais La Corte dei Papi

Cortona

Frithjof

฿11,482

฿12,780 total

includes taxes & fees

9 Nov - 10 Nov

A person relaxing in a hot tub with a view of a pool and outdoor seating area.

A view from a window with a brick wall, overlooking a green landscape with trees and a clear sky.

An outdoor dining area with brick columns, metal chairs, and tables set for a meal.

An aerial view of a resort with a swimming pool, lounge chairs, and a bar area.

18. Locanda Poggioleone

Castiglione del Lago

Mary

฿3,361

฿3,847 total

includes taxes & fees

18 Oct - 19 Oct

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

A couple dining at a table with a scenic view of mountains and a lake.

A person seated at a table with a glass of white wine, in a room with tables and chairs, and a plant in the background.

A poolside area with lounge chairs and umbrellas, overlooking a scenic landscape.

19. Locanda agli Amici

Cortona

David

฿3,386

฿3,874 total

includes taxes & fees

4 Nov - 5 Nov

A nighttime swimming pool area with lounge chairs and umbrellas, surrounded by stone buildings and trees.

A neatly made bed with a headboard, two bedside tables, and a wall-mounted artwork.

A restaurant with wooden beams, large windows with white curtains, and multiple seating areas.

Villa Paradiso with a stone wall entrance, a metal gate, and a signboard.

20. Hotel Villa Paradiso

Passignano sul Trasimeno

"Nice hotel, rooms are a decent size and the bed was comfortable. Breakfast was very good, lots of choice Excellent pool area and ample seating/ sun loungers. Layout of hotel can be a little confusing at first, finding your way down stairs to dinning area but additional signage was put up indicating directions. Hotel appears to do a lot of its business accommodating large coach parties, certainly during our stay so lots of people at breakfast at same time before they go off on trips."

Keith

฿2,802

฿3,232 total

includes taxes & fees

18 Oct - 19 Oct

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Top Ossaia Hotel Reviews

Monastero di Cortona Hotel & Spa

10/10 Excellent

"Frederico went above and beyond to transfer us to our villa and Giulio was a fantastic bartender"

Albergo San Biagio

8/10 Good

"Not a happy greeting but checked in ok. Swimming was a €5 charge but you needed to wear a swim cap €2 if needed. The restaurant staff were fantastic and really helpful and asked about us and our trip. The town is bit of a hike - drive to is best."

Hotel Continentale

10/10 Excellent

"The location of this hotel is excellent!"

Precise Tale Poggio Alla Sala

10/10 Excellent

"Stunningly beautiful resort for a 3 day getaway with my parents to experience the best of Tuscany - everything was perfect and pictures worth a thousand words!"

Il Gentiluomo Hotel & SPA

10/10 Excellent

"It was perfect….the outside was a little run down but the inside was perfect. They had just moved and not cleaned up so that did not help the appearance."

Palazzo Brandano

10/10 Excellent

"Large rooms, helpful staff, delicious breakfast at a very reasonable price. There’s no water by the hotel, as seen in the picture. It’s located on a very old walled town… quite quaint."

Poggio Paradiso Resort & Spa

10/10 Excellent

"The hotel was beautiful and extremely clean. The food at the restaurant was some of the best food we’ve ever had. Exceptional service and hospitality. Highly recommend. Would love to come back."

Hotel Panoramic Montepulciano

8/10 Good

"Ok."

Agriturismo La Sovana

8/10 Good

"Wonderful"

More cheap stays in Ossaia

Hotel La Terrazza di Montepulciano

Via Pié al Sasso 16 Montepulciano SI

฿3,752

฿4,278 total

18 Oct - 19 Oct

includes taxes & fees

9.4/10 Exceptional! (215 reviews)

Locanda Granducato

località paccianese 48 Chiusi SI

฿4,590

฿5,124 total

15 Oct - 16 Oct

includes taxes & fees

7/10 Good! (2 reviews)

La Locanda di Casalmustia

Piazza della Pieve 3 Trequanda SI

Get rates

8.6/10 Excellent! (44 reviews)

Hotel Sangallo

Via Dei Fiori 30 Montepulciano SI

Get rates

8/10 Very good! (59 reviews)

Residence Peloni

Via Polidori 50 Arezzo AR

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Agriturismo Godiolo

VIA DI MARTIENA 24 Montepulciano SI

Get rates

Frequently asked questions

Where is the best place for a stay in Ossaia?

Located 2.1 mi (3.4 km) from the heart of Ossaia, Villa di Piazzano - Small Luxury Hotel of the World is a top choice for your stay, based on our traveller data. Two other choices for your trip to the area are Nuovo Etruria Resort and Precise Tale Poggio Alla Sala. See all available top hotels, or vacation rentals in Ossaia.

If I need to cancel my hotel reservation in Ossaia, will I receive a refund?

Yes! You'll find that most hotel reservations are fully refundable provided that you cancel before the accommodation's cancellation deadline, which is often 24 or 48 hours before your arrival date. If your reservation is non-refundable, you might be able to still cancel and be given a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Ossaia.

What are some hotels with pools in Ossaia?

Villa di Piazzano - Small Luxury Hotel of the World: Features a snack bar/deli, an outdoor pool and free self parking. Nuovo Etruria Resort and Precise Tale Poggio Alla Sala are a couple of other choices that offer an on-site pool. View all hotels with pools in Ossaia.

What is staying in Ossaia like?

Travellers to Ossaia will find plenty to explore and enjoy. In Ossaia, there are 13 hotels and other accommodation options to choose from. Find out more about Ossaia.

What should I see while I'm in Ossaia?

Places to visit in the wider area include Villa Bramasole, Piazza della Repubblica and Isola Maggiore. You'll also find Passignano sul Trasimeno Marina and Tennis Club Castiglionese in the area. Take a look at what more there is to see and do in Expedia's Ossaia guide.

What's the seasonal weather like in Ossaia?

The hottest months are usually August and July, with an average temperature of 22°C, while the coldest months are January and February, with an average of 6°C. Average annual precipitation for Ossaia is 906 mm.

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More ways to book

Book Hotels in Ossaia on Expedia.it

Find hotels in Ossaia from ฿2,848

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Ossaia

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Ossaia hotels

1. Relais Villa Baldelli

2. Hotel San Michele

3. Hotel Villa Marsili

4. Monastero di Cortona Hotel & Spa

5. Hotel San Luca

6. Hotel Italia

7. Villa Santa Margherita

8. Villa Borgo San Pietro

9. Il Falconiere - Relais e Chateaux

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

11. Cortona Resort - Le Terre Dei Cavalieri

12. B&B San Francesco

13. Equo Suites

14. Borgo Tre Rose

15. Hotel Lidò

16. Locanda del Molino

17. Relais La Corte dei Papi

18. Locanda Poggioleone

19. Locanda agli Amici

20. Hotel Villa Paradiso

Top Ossaia Hotel Reviews

Monastero di Cortona Hotel & Spa

Albergo San Biagio

Hotel Continentale

Precise Tale Poggio Alla Sala

Il Gentiluomo Hotel & SPA

Palazzo Brandano

Poggio Paradiso Resort & Spa

Hotel Panoramic Montepulciano

Agriturismo La Sovana

More cheap stays in Ossaia

Hotel La Terrazza di Montepulciano

Locanda Granducato

La Locanda di Casalmustia

Hotel Sangallo

Residence Peloni

Agriturismo Godiolo

Frequently asked questions

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