Top 10 Hotels in Ossaia (from $92) 2026 - Competitive Prices

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

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

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

1. Borgo Tre Rose

Montepulciano

Nathan

$84 nightly

$97 total

Oct 22 - Oct 23

Total with taxes and fees

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

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

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

A hotel room with a large bed, a bedside table with a lamp, a mirror, and a framed picture on the wall.

2. Hotel San Luca

Cortona Old Town

Mariusz

$81 nightly

$98 total

Oct 25 - Oct 26

Total with taxes and fees

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

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

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

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

3. Relais Villa Baldelli

Cortona

Peter

$128 nightly

$150 total

Oct 8 - Oct 9

Total with taxes and fees

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

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

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.

4. Hotel Villa Marsili

Cortona Old Town

fares

$152 nightly

$176 total

Oct 10 - Oct 11

Total with taxes and fees

A stone building with outdoor seating and a fountain.

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.

A stone building with multiple windows and a courtyard.

5. Villa Borgo San Pietro

Cortona

Olga

$108 nightly

$127 total

Oct 4 - Oct 5

Total with taxes and fees

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

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

6. Locanda del Molino

Cortona

Rochelle

$78 nightly

$95 total

Oct 27 - Oct 28

Total with taxes and fees

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

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

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

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

7. Villa Santa Margherita

Cortona Old Town

George F

$107 nightly

$123 total

Oct 2 - Oct 3

Total with taxes and fees

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 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.

8. B&B San Francesco

Cortona Old Town

Esther

$92 nightly

$106 total

Oct 8 - Oct 9

Total with taxes and fees

A window with a view of a body of water and distant land.

A terrace with sun loungers overlooking a body of water and a stone building.

A restaurant with multiple tables set for dining, a wine rack on the wall, and a rustic brick ceiling.

A bedroom with a large bed, a chair, a nightstand, and a view of a tree through an open door.

9. Hotel Aganoor

Contrada Castello

Alina

$108 nightly

$124 total

Oct 5 - Oct 6

Total with taxes and fees

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

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.

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

10. Hotel San Michele

Cortona Old Town

Tala

$153 nightly

$178 total

Oct 8 - Oct 9

Total with taxes and fees

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.

11. Hotel Italia

Cortona Old Town

Frances

$121 nightly

$139 total

Oct 13 - Oct 14

Total with taxes and fees

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

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.

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

12. Monastero di Cortona Hotel & Spa

Cortona Old Town

Alexander

$247 nightly

$281 total

Oct 25 - Oct 26

Total with taxes and fees

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

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

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

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

13. Villaggio Albergo Le Macerine

Contrada Fontivegge

ROBERT

$111 nightly

$127 total

Oct 7 - Oct 8

Total with taxes and fees

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

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

A large building with a tiled roof, surrounded by grapevines and a hay bale in a field.

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

14. Cortona Resort - Le Terre Dei Cavalieri

Cortona

Dana

$156 nightly

$178 total

Oct 1 - Oct 2

Total with taxes and fees

A cozy wooden cabin room with a bed, pillows, a TV, and a view of the outdoors.

A modern indoor pool area with wooden benches, a hot tub, and large windows offering views of the surrounding greenery.

A buffet with various food items and a mirror reflecting the room's architecture.

A stone-walled room with a stone bench, a bathtub with a pink light, and a window with a view.

15. I Capricci di Merion Resort & Spa

Tuoro sul Trasimeno

$161 nightly

$178 total

Oct 5 - Oct 6

Total with taxes and fees

16. Agriturismo Parco Fiorito

Tuoro sul Trasimeno

Anonymous traveler

$153 nightly

$170 total

Oct 22 - Oct 23

Total with taxes and fees

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

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

17. Locanda agli Amici

Cortona

David

$99 nightly

$118 total

Oct 25 - Oct 26

Total with taxes and fees

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

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.

A waterfront hotel with multiple balconies, a calm river, and a dock with boats.

18. Hotel Lidò

Passignano sul Trasimeno

Brian

$102 nightly

$117 total

Oct 2 - Oct 3

Total with taxes and fees

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

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

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

19. 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

$92 nightly

$105 total

Oct 1 - Oct 2

Total with taxes and fees

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.

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

20. Hotel Villa Paradiso

Passignano sul Trasimeno

Maria

$79 nightly

$92 total

Oct 4 - Oct 5

Total with taxes and fees

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Top Ossaia Hotel Reviews

Il Falconiere - Relais e Chateaux

10/10 Excellent

"There is nothing to fault here, it’s a perfect hotel. Staff are brilliant, and the buildings and grounds are really well looked after. Breakfast and lunch are ideal too."

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"

More cheap stays in Ossaia

Hotel La Terrazza di Montepulciano

Via Pié al Sasso 16 Montepulciano SI

$113 nightly

$129 total

Oct 5 - Oct 6

Total with taxes and fees

9.4/10 Exceptional! (211 reviews)

Locanda Granducato

località paccianese 48 Chiusi SI

$129 nightly

$144 total

Oct 5 - Oct 6

Total with taxes and fees

7/10 Good! (2 reviews)

La Locanda di Casalmustia

Piazza della Pieve 3 Trequanda SI

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8.6/10 Excellent! (44 reviews)

Hotel Sangallo

Via Dei Fiori 30 Montepulciano SI

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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

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Frequently asked questions

When is the best time to go to Ossaia?

The best time to go to Ossaia, Tuscany, is during the spring (April to June) and fall (September to October) months.Spring offers pleasant temperatures, ideal for exploring the Tuscan countryside, visiting vineyards, and enjoying outdoor activities without the heat of summer. The landscapes are lush and green, and wildflowers are in bloom, creating beautiful scenery. This period is particularly good for couples seeking a romantic getaway, with opportunities for leisurely drives and al fresco dining.Fall provides a similar experience with comfortable temperatures, and it's also harvest season, especially for grapes and olives. This means you can experience local festivals and enjoy fresh, seasonal produce.

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 canceled 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 much is the nightly rate at a Ossaia hotel?

Prices for hotels in Ossaia often vary, but you can find a great deal from $92 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 the cheapest rate.

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Find hotels in Ossaia from $92

Upfront pricing

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. Borgo Tre Rose

2. Hotel San Luca

3. Relais Villa Baldelli

4. Hotel Villa Marsili

5. Villa Borgo San Pietro

6. Locanda del Molino

7. Villa Santa Margherita

8. B&B San Francesco

9. Hotel Aganoor

10. Hotel San Michele

11. Hotel Italia

12. Monastero di Cortona Hotel & Spa

13. Villaggio Albergo Le Macerine

14. Cortona Resort - Le Terre Dei Cavalieri

15. I Capricci di Merion Resort & Spa

16. Agriturismo Parco Fiorito

17. Locanda agli Amici

18. Hotel Lidò

19. Park Hotel Montigeto

20. Hotel Villa Paradiso

Top Ossaia Hotel Reviews

Il Falconiere - Relais e Chateaux

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

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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