Ossaia Holiday Rentals, Cortona: Private House Rentals

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Go beyond your typical stay in Ossaia

Pet friendly

Apartment

Pool

Condo

Spa

Hot tub

Family friendly

Farm

Waterpark

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Ossaia hotels

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

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

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

A multi-story building with a rooftop terrace featuring outdoor seating and umbrellas.

1. Villa Santa Margherita

Cortona Old Town

George F

3.027.199 ₫

3.477.915 ₫ total

includes taxes & fees

28 Sept - 29 Sept

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

A bedroom with a large bed, wooden ceiling beams, a window with a view of greenery, and a small table with a bowl.

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.

2. Relais Villa Baldelli

Cortona

Peter

3.705.291 ₫

4.312.614 ₫ total

includes taxes & fees

15 Oct - 16 Oct

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

A large estate with a swimming pool, surrounded by lush greenery and hills.

3. 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

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

A bedroom with a wooden headboard, two beds with pink and white bedding, a bedside table with a lamp, a small table with a bottle and glasses, and a window with a view of buildings.

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

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

4. B&B San Francesco

Cortona Old Town

Esther

2.131.148 ₫

2.906.649 ₫ total

includes taxes & fees

19 Oct - 20 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 historic stone building with arched doorways and a courtyard at twilight.

5. Relais La Corte dei Papi

Cortona

Frithjof

10.906.768 ₫

12.234.239 ₫ total

includes taxes & fees

7 Oct - 8 Oct

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

A bedside table with a vase of flowers, a book, and a drawer.

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

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.

6. Locanda agli Amici

Cortona

David

2.609.801 ₫

3.109.014 ₫ total

includes taxes & fees

7 Oct - 8 Oct

A stone building with outdoor seating and a fountain.

A rectangular swimming pool with clear blue water, surrounded by white lounge chairs and umbrellas, set against a backdrop of trees and a clear sky.

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

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

7. Villa Borgo San Pietro

Cortona

Olga

3.048.024 ₫

3.591.059 ₫ total

includes taxes & fees

4 Oct - 5 Oct

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

A bathroom with a bathtub, a table with a vase of flowers, and a view of the countryside through a window.

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

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

8. Hotel San Michele

Cortona Old Town

Tala

4.005.225 ₫

4.642.541 ₫ total

includes taxes & fees

21 Oct - 22 Oct

A swimming pool with lounge chairs and umbrellas, surrounded by a building with multiple windows and a staircase.

A hotel with a tiled patio, potted plants, and multiple flags.

A reception area with a clock, a wooden shelf with keys, a potted plant, and a lamp.

A street with palm trees, a building with a tiled roof, and a clear blue sky.

9. Trasimeno

Contrada Fontivegge

Marilyn

2.268.249 ₫

2.613.470 ₫ total

includes taxes & fees

8 Oct - 9 Oct

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

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

A pool surrounded by neatly trimmed hedges and a row of sun loungers.

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

10. Borgo Tre Rose

Montepulciano

Nathan

1.934.985 ₫

2.246.881 ₫ total

includes taxes & fees

24 Oct - 25 Oct

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

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

A narrow hallway with a stone wall and a clock.

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

11. Monastero di Cortona Hotel & Spa

Cortona Old Town

Alexander

6.512.205 ₫

7.400.220 ₫ total

includes taxes & fees

25 Oct - 26 Oct

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

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

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

12. Hotel Italia

Cortona Old Town

Frances

3.425.443 ₫

3.915.983 ₫ total

includes taxes & fees

24 Oct - 25 Oct

An outdoor dining area with tables and chairs under canopies, surrounded by greenery and a building with a tiled roof.

A conference room with a long table, black chairs, a red curtain backdrop, and wall-mounted lighting.

A large outdoor swimming pool with multiple lanes and a surrounding deck area.

A hotel room with a bed, bedside table, and a desk with a chair.

13. Hotel Apogeo

Sinalunga

Jason

2.615.392 ₫

2.936.249 ₫ total

includes taxes & fees

25 Sept - 26 Sept

An outdoor dining area with round tables, white chairs, and a variety of dishes and drinks.

A modern kitchen with a coffee machine, a refrigerator, and a dining area with two round tables and wicker chairs.

A two-story building with a flat roof and a covered front porch. There are two visible windows on the upper floor and a door on the ground floor.

A rectangular swimming pool with a stone border, surrounded by a grassy lawn and trees.

14. Park Hotel Montigeto

Passignano sul Trasimeno

"We used this Hotel as a stop over for one night on our travels around Europe. We are British, they spoke perfect English and made us feel welcome. The rooms and en suits were large with a safe, hairdryer etc everything that top hotels offer. Reserved us a table at the best restaurant on the lake which was some of the best food and wine ever tasted. The breakfast was great at the hotel so all together one of our best stops. It’s worth taking a swimming cap if you choose to use the pool and be...

Helen

2.287.136 ₫

2.604.736 ₫ total

includes taxes & fees

27 Sept - 28 Sept

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

A swimming pool with a stone wall and potted plants, surrounded by greenery and a clear sky.

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

A stone building with green shutters, a cobblestone courtyard, and a signboard.

15. Locanda del Molino

Cortona

Rochelle

2.220.687 ₫

2.680.988 ₫ total

includes taxes & fees

1 Oct - 2 Oct

A large, two-story building with a symmetrical facade, a central entrance, and evenly spaced windows.

A restaurant interior with tables set for dining, a kitchen area, and a wine display.

An outdoor dining area with tables set for breakfast, including pastries, fruit, and beverages.

A nighttime swimming pool with a clear reflection, surrounded by trees and lounge chairs.

16. Hotel Le Capanne

Arezzo

Robert

3.063.524 ₫

3.547.473 ₫ total

includes taxes & fees

25 Sept - 26 Sept

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

A table set for a tea service with a tiered tray of pastries, a teapot, and various cups and saucers.

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.

17. Hotel Villa Marsili

Cortona Old Town

fares

5.230.999 ₫

5.990.893 ₫ total

includes taxes & fees

21 Oct - 22 Oct

A narrow street with a yellow building on the left, a wooden structure in the background, and a row of white and pink flowers along the edge.

A bicycle with potted plants attached to it, parked against a textured wall.

A building entrance with the name "ALBERGO LA TERRAZZA" above a wooden door.

A hallway with arched ceilings, framed pictures on the walls, and a staircase leading to another room.

18. Hotel La Terrazza di Montepulciano

Montepulciano

Kevin

2.959.927 ₫

3.374.317 ₫ total

includes taxes & fees

30 Sept - 1 Oct

An outdoor patio with tables and chairs, overlooking a body of water.

A building with a green roof, large windows, and a garden with potted plants.

A breakfast buffet with various breads, pastries, and a cake, set in a room with large windows and a ceiling with a geometric pattern.

A beachside seating area with white chairs and a green umbrella, overlooking a calm sea and distant mountains.

19. Hotel Kursaal - Umbria

Passignano sul Trasimeno

Charles

2.571.721 ₫

2.918.349 ₫ total

includes taxes & fees

28 Sept - 29 Sept

A bedroom with a bed, a nightstand, a wall-mounted shelf, and a wall mural of a lake.

A bar area with stools, a refrigerator, and shelves with bottles.

A modern hotel room with a large bed, a nightstand with a lamp, a view of the outdoors through a sliding door, and a painting on the wall.

A swimming pool with a palm tree, a lounge chair, and a clear blue sky.

20. Hotel La Darsena

Passignano sul Trasimeno

Arto

1.860.988 ₫

2.135.885 ₫ total

includes taxes & fees

19 Oct - 20 Oct

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Top Ossaia Hotel Reviews

Nuovo Etruria Resort

8/10 Good

"The staff was very attentive and helpful specially Alfredo. He is terrific! My only complaint was a persistent low level hum that was noticeable at night, I figured that our room was above the kitchen area and that it was the industrial size refrigerator below. The view of the town up the hill from our room was spectacular. Decent breakfast. The pool was wonderful."

Villa Tiberini Wine Relais

10/10 Excellent

"Property was a bit remote, accessible by a 1K dirt driveway, but definitely worth the trip, and really not far from town and Montepulciano. Beautiful views, rooms were spacious and clean, and owners Nunzia and her husband Luca were helpful and gracious. We were able to spend several hours with Luca walking us through the wine making process, from picking the grapes to tracking the fermenting in oak barrels. Be sure to taste the wine, it is excellent. If you’re looking for a reasonably priced authentic experience in a wonderful location, this is it."

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."

Hotel Panoramic Montepulciano

10/10 Excellent

"buenas vistas panorámicas , es un hotel demasiado tranquilo , pero es muy bonito"

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!"

Relais Villa Grazianella - UNA Esperienze

10/10 Excellent

"We loved this hotel. We were lucky to have a two bedroom apartment. It’s not connected to the hotel, so be prepared to drive 10 minutes each way. The prepared breakfast was wonderful and the staff was always very pleasant."

Agriturismo La Sovana

10/10 Excellent

"We absolutely loved our stay at La Sovana! The grounds are impeccably manicured and maintained! The pool was lovely after a long day of sight seeing and we had an incredible time enjoying the dinner one evening. The stay were incredible throughout our stay and so helpful and kind. The owner was on site quite a bit and I think that added to the charm. He introduced himself at the dinner and danced with some guests. It gave it a beautiful family run feel and you could tell he took a lot of pride in his hotel. My husband and I loved the complimentary breakfast buffet. It gave us a great start to the our day of sight seeing in the area. Would return in a heartbeat!"

Il Gentiluomo Hotel & SPA

10/10 Excellent

"Everything was OK. Clean room, helpfull staff. Excellent breakfast."

More cheap stays in Ossaia

Hotel La Terrazza di Montepulciano

Via Pié al Sasso 16 Montepulciano SI

2.959.927 ₫

3.374.317 ₫ total

30 Sept - 1 Oct

includes taxes & fees

9.4/10 Exceptional! (211 reviews)

Locanda Granducato

località paccianese 48 Chiusi SI

3.620.529 ₫

4.041.781 ₫ total

7 Oct - 8 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

Get rates

Agriturismo Godiolo

VIA DI MARTIENA 24 Montepulciano SI

Get rates

Hotels in Ossaia with star rating

Frequently asked questions

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.

Explore a world of travel with Expedia

More ways to book

Book Hotels in Ossaia on Expedia.it

Find hotels in Ossaia from 2.589.830 ₫

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. Villa Santa Margherita

2. Relais Villa Baldelli

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

4. B&B San Francesco

5. Relais La Corte dei Papi

6. Locanda agli Amici

7. Villa Borgo San Pietro

8. Hotel San Michele

9. Trasimeno

10. Borgo Tre Rose

11. Monastero di Cortona Hotel & Spa

12. Hotel Italia

13. Hotel Apogeo

14. Park Hotel Montigeto

15. Locanda del Molino

16. Hotel Le Capanne

17. Hotel Villa Marsili

18. Hotel La Terrazza di Montepulciano

19. Hotel Kursaal - Umbria

20. Hotel La Darsena

Top Ossaia Hotel Reviews

Nuovo Etruria Resort

Villa Tiberini Wine Relais

Monastero di Cortona Hotel & Spa

Precise Tale Poggio Alla Sala

Hotel Panoramic Montepulciano

Il Falconiere - Relais e Chateaux

Relais Villa Grazianella - UNA Esperienze

Agriturismo La Sovana

Il Gentiluomo Hotel & SPA

More cheap stays in Ossaia

Hotel La Terrazza di Montepulciano

Locanda Granducato

La Locanda di Casalmustia

Hotel Sangallo

Residence Peloni

Agriturismo Godiolo

Hotels in Ossaia with star rating

Frequently asked questions

Explore a world of travel with Expedia

Go further with the Expedia app