Ossaia Hotel & Accommodation Deals 2026 from AU$131 - Compare prices by date

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

Villa

Condo

Spa

Pool

Spa pool

Cottage

Family friendly

Farm

Waterpark

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Ossaia hotels

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

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

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.

1. Borgo Tre Rose

Montepulciano

Nathan

AU$138

includes taxes & fees

22 Oct - 23 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.

2. Hotel San Luca

Cortona Old Town

Mariusz

AU$140

includes taxes & fees

25 Oct - 26 Oct

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

3. Relais Villa Baldelli

Cortona

Peter

AU$205

includes taxes & fees

8 Oct - 9 Oct

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

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

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

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

4. Villa Santa Margherita

Cortona Old Town

George F

AU$197

includes taxes & fees

31 Oct - 1 Nov

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

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

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

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

5. Hotel Villa Marsili

Cortona Old Town

fares

AU$303

includes taxes & fees

10 Oct - 11 Oct

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

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

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

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.

6. B&B San Francesco

Cortona Old Town

Esther

AU$150

includes taxes & fees

4 Oct - 5 Oct

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

A narrow hallway with a stone wall and a clock.

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

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

7. Monastero di Cortona Hotel & Spa

Cortona Old Town

Alexander

AU$440

includes taxes & fees

25 Oct - 26 Oct

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

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.

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.

8. Equo Suites

Castiglione del Lago

Alistair

AU$206

includes taxes & fees

6 Oct - 7 Oct

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

A restaurant with outdoor seating overlooking a historic town and the sea.

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.

9. Hotel Italia

Cortona Old Town

Frances

AU$199

includes taxes & fees

13 Oct - 14 Oct

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

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

10. Locanda del Molino

Cortona

Rochelle

AU$135

includes taxes & fees

27 Oct - 28 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.

11. Hotel San Michele

Cortona Old Town

Tala

AU$248

includes taxes & fees

31 Oct - 1 Nov

A stone building with outdoor seating and a fountain.

A stone building with multiple windows and a courtyard.

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.

12. Villa Borgo San Pietro

Cortona

Olga

AU$195

includes taxes & fees

12 Oct - 13 Oct

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

A waterfront restaurant with outdoor seating, a view of a river, and buildings 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 hotel with multiple balconies, a calm river, and a dock with boats.

13. Hotel Lidò

Passignano sul Trasimeno

Brian

AU$167

includes taxes & fees

2 Oct - 3 Oct

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

A spacious room with stone walls, wooden beams, and tiled flooring. There are several chairs and a table, along with potted plants.

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.

14. Hotel Villa Paradiso

Passignano sul Trasimeno

Maria

AU$131

includes taxes & fees

5 Oct - 6 Oct

A swimming pool with a brick wall and metal railings, surrounded by blooming flowers and a yellow building with a tiled roof.

A kitchen with wooden cabinets, a dining table with chairs, a window with curtains, and a radiator.

A hotel room with a bed, a desk, and a chair. There are two windows with views of greenery and a building.

A residential area with a swimming pool, a yellow building with a tiled roof, and a hill with a church in the background.

15. Villaggio Albergo Le Macerine

Contrada Fontivegge

ROBERT

AU$172

includes taxes & fees

7 Oct - 8 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.

16. Cortona Resort - Le Terre Dei Cavalieri

Cortona

Dana

AU$254

includes taxes & fees

1 Oct - 2 Oct

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

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

A hallway with a wooden door, a console table with a vase and a framed picture, and a red rug.

17. 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

AU$149

includes taxes & fees

5 Oct - 6 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 poolside area with lounge chairs and umbrellas, overlooking a scenic landscape.

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

18. Locanda agli Amici

Cortona

David

AU$169

includes taxes & fees

8 Oct - 9 Oct

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

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.

A dining area with a table set for a meal, surrounded by windows and a brick wall.

19. Locanda Poggioleone

Castiglione del Lago

Mary

AU$206

includes taxes & fees

15 Oct - 16 Oct

20. Agriturismo Parco Fiorito

Tuoro sul Trasimeno

Anonymous traveller

AU$248

includes taxes & fees

22 Oct - 23 Oct

View all properties

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

Top Ossaia Hotel Reviews

Recent Reviews in Ossaia

Nuovo Etruria Resort

10/10 Excellent

"Todo estuvo perfecto, el hotel muy muy lindo, la piscina extraordinaria, la habitación Muy cómoda, el servicio impecable, pero no funcionó el wifi en la habitación. No nos dieron un early check in ni guardaron las maletas, así que nos tuvimos que ir a Montslcino y ya no pudimos usar la piscina. Pero en general lo recomiendo mucho"

Villa Tiberini Wine Relais

10/10 Excellent

"It's great place for the large family."

Agriturismo La Sovana

10/10 Excellent

"We had a lovely 5 night stay at La Sovana in their apartment complex. We had a 2-bedroom, 2-bath with kitchen. It was the perfect set up for 2 couples to share. My only wish was that it included a washer/dryer set up. Laundry is available for a fee which we did use but it would be nice if there was washing capability in the apartment itself. The staff were super helpful, the property is clean and well maintained. The food in the restaurant is very good as well. We would definitely return to La Sovana."

Hotel Villa Ricci

10/10 Excellent

"Personal, muy amable y educado, muy cálida, recepción, lindo hotel. Lo aconsejo para quienes quieran visitar la toscana y sobretodo Montepulciano."

Relais Villa Grazianella - UNA Esperienze

10/10 Excellent

"In addition to the property being absolutely beautiful, the"

Precise Tale Poggio Alla Sala

10/10 Excellent

"Great location, nice vineyards right out the door, lots of great restaurants nearby."

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!"

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!"

More cheap accommodation in Ossaia

Hotel La Terrazza di Montepulciano

Via Pié al Sasso 16 Montepulciano SI

AU$185

5 Oct - 6 Oct

includes taxes & fees

9.4/10 Exceptional! (211 reviews)

Locanda Granducato

località paccianese 48 Chiusi SI

AU$206

13 Oct - 14 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

Frequently asked questions

What is the best area to stay in Ossaia?

The best area to stay in Ossaia is the area immediately surrounding the main piazza, as this is where you'll find the heart of the village.This central part of Ossaia is compact and easily walkable, with the piazza serving as a focal point for village life. You'll find a few local shops and eateries here, and it's where residents gather. The historic church is also located just off the piazza, adding to the village's character.For couples looking for a romantic escape, staying in a converted farmhouse or villa just outside the village centre offers a truly authentic Tuscan experience. These properties often provide stunning views of the rolling hills and olive groves, and many come with private pools, allowing for a secluded and relaxing retreat.

When is the best time to go to Ossaia?

The best time to visit Ossaia, and Tuscany generally, is during the spring (April to June) and autumn (September to October) months. These periods offer pleasant weather and a less crowded experience.For those planning a romantic getaway or a relaxed trip, spring is particularly lovely. The countryside is lush and green, wildflowers are in bloom, and the temperatures are comfortably warm without being too hot. This is a great time for leisurely drives through the vineyards, enjoying al fresco dining, and visiting local markets.Couples looking for a culinary focus might prefer autumn. This season brings the grape harvest, truffle hunting season, and olive oil production, offering unique gastronomic experiences.

Can I cancel my hotel reservation on Expedia?

You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if cancelled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Ossaia.

How can I save on a hotel booking in Ossaia with Expedia?

One Key™—Expedia's free travel rewards program—gives you instant access to discounts with Member Prices on Ossaia hotels. Plus, you'll earn OneKeyCash™* on eligible bookings to use on future trips. Booking an Expedia hotel and flight package is another great way to save, where bundling can result in significant savings. *Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

How much is the nightly rate for a hotel in Ossaia?

Prices for hotels in Ossaia often vary, but you can find a great deal from AU$131 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for our cheapest rates.

Explore a world of travel with Expedia

Arezzo Holiday Rentals

Book Hotels in Ossaia on Expedia.it

Search Ossaia hotels

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Ossaia

Check prices for these dates

Filter by

Property class

Guest rating

Our top choices for Ossaia hotels

1. Borgo Tre Rose

2. Hotel San Luca

3. Relais Villa Baldelli

4. Villa Santa Margherita

5. Hotel Villa Marsili

6. B&B San Francesco

7. Monastero di Cortona Hotel & Spa

8. Equo Suites

9. Hotel Italia

10. Locanda del Molino

11. Hotel San Michele

12. Villa Borgo San Pietro

13. Hotel Lidò

14. Hotel Villa Paradiso

15. Villaggio Albergo Le Macerine

16. Cortona Resort - Le Terre Dei Cavalieri

17. Park Hotel Montigeto

18. Locanda agli Amici

19. Locanda Poggioleone

20. Agriturismo Parco Fiorito

Top Ossaia Hotel Reviews

Recent Reviews in Ossaia

Nuovo Etruria Resort

Villa Tiberini Wine Relais

Agriturismo La Sovana

Hotel Villa Ricci

Relais Villa Grazianella - UNA Esperienze

Precise Tale Poggio Alla Sala

Villa di Piazzano - Small Luxury Hotel of the World

Hotel Panoramic Montepulciano

Il Falconiere - Relais e Chateaux

More cheap accommodation in Ossaia

Hotel La Terrazza di Montepulciano

Locanda Granducato

La Locanda di Casalmustia

Hotel Sangallo

Residence Peloni

Agriturismo Godiolo

Frequently asked questions

Explore a world of travel with Expedia

Go further with the Expedia app