Top 10 Hotels in Ossaia in 2026 (from $65)

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Where to stay in Ossaia?

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

1. Hotel Italia

Cortona Old Town

$114 total

includes taxes & fees

Nov 19 - Nov 20

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

2. Locanda del Molino

Cortona

$88 total

includes taxes & fees

Dec 13 - Dec 14

An outdoor seating area with tables and chairs, potted plants, and a view of the sea.

3. Villa Santa Margherita

Cortona Old Town

$136 total

includes taxes & fees

Nov 14 - Nov 15

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

4. Locanda agli Amici

Cortona

$101 total

includes taxes & fees

Nov 18 - Nov 19

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

5. Monastero di Cortona Hotel & Spa

Cortona Old Town

$262 total

includes taxes & fees

Nov 29 - Nov 30

A narrow stone-paved street flanked by historic buildings with wooden doors and shutters.

6. B&B San Francesco

Cortona Old Town

$109 total

includes taxes & fees

Dec 9 - Dec 10

An arched entrance with a wooden balcony, a tiled floor, and a door leading inside.

7. Hotel Boutique Castiglione del Lago

Contrada Castello

$100 total

includes taxes & fees

Nov 18 - Nov 19

A terraced garden with a stone staircase, outdoor seating, and a red statue.

8. Casa Kita

Cortona Old Town

$104 total

includes taxes & fees

Dec 1 - Dec 2

An outdoor café with tables and chairs, overlooking a body of water and a mountainous landscape.

9. Garden Palace Hotel

Contrada Castello

$206 total

includes taxes & fees

Dec 4 - Dec 5

10. Agriturismo Parco Fiorito

Tuoro sul Trasimeno

$169 total

includes taxes & fees

Nov 15 - Nov 16

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

11. Equo Suites

Castiglione del Lago

$123 total

includes taxes & fees

Nov 15 - Nov 16

A neatly made bed with a tray of breakfast items including tea, a flower, and a book.

12. Hotel La Darsena

Passignano sul Trasimeno

$75 total

includes taxes & fees

Nov 23 - Nov 24

A courtyard with a large tree, outdoor seating, and a building with shutters.

13. I Capricci di Merion Resort & Spa

Tuoro sul Trasimeno

$170 total

includes taxes & fees

Nov 15 - Nov 16

A buffet with various desserts and fruits, including pies, cakes, and pastries, arranged on tables with white tablecloths.

14. Cortona Resort Spa

Cortona

$171 total

includes taxes & fees

Nov 15 - Nov 16

A cozy lounge area with a blue sofa, multiple chairs, and tables, featuring a staircase and large windows with curtains.

15. Hotel Trasimeno

Passignano sul Trasimeno

$90 total

includes taxes & fees

Nov 25 - Nov 26

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

16. Relais La Corte dei Papi

Cortona

$320 total

includes taxes & fees

Nov 30 - Dec 1

A stone building with a courtyard, surrounded by greenery and a clear sky.

17. Casale l'Antico Carro

Cortona

$135 total

includes taxes & fees

Nov 14 - Nov 15

A waterfront hotel with a swimming pool, outdoor seating, and a view of the lake.

18. Hotel Lidò

Passignano sul Trasimeno

$114 total

includes taxes & fees

Nov 19 - Nov 20

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

19. Trasimeno

Contrada Fontivegge

$90 total

includes taxes & fees

Nov 24 - Nov 25

A spa area with a bathtub, towels, a bottle, and a candle.

20. Hotel Forum

Foiano della Chiana

$129 total

includes taxes & fees

Nov 28 - Nov 29

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Go beyond your typical stay in Ossaia

Check out reviews of Ossaia hotels guests love

Monastero di Cortona Hotel & Spa

Cortona Old Town

10/10 Exceptional

Eric

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

Il Falconiere - Relais e Chateaux

Cortona

10/10 Exceptional

This was the first hotel we visited in our two week Tuscany vacation. Coming out of Rome and getting on the highway north, it looked like the exit should be labeled for Cortona...but it wasn't and we wasted a lot of time getting lost (our fault). Once we found the hotel, it was a gem in the hills in the vineyards. Breakfast on the patio of the little glass Liminoere building was fabulous. Loved their boxer dog roamed around saying "hi". Owner/chef is on premises and she gives cooking lessons....

Barbara

Locanda agli Amici

Cortona

10/10 Exceptional

Staying here was amazing. We were in the heart of Cortona, which was so peaceful compared to busier areas of Italy. Very authentic. Sylvia made the entire stay wonderful. The hospitality here is unmatched. The food is delicious. The rooms are cute and the view...the view is stunning. I am so happy we decided to stay here!! I would 10/10 recommend. Taxis were hard to find, but Silvia drove us whenever we couldn't find a taxi. She is so friendly and welcoming. On top of that, we had a lovely...

Brittney

I Capricci di Merion Resort & Spa

Tuoro sul Trasimeno

10/10 Exceptional

Israel

Cortona Resort Spa

Cortona

10/10 Exceptional

Pro: gorgeous and spacious property, we were upgraded to a junior suite that was lovely, attentive staff, and incredible amenities. Pool was wonderful for tired bodies. Con: very few. The restaurant on site has pretty limited menu, toilet in room kept running all night long- informed staff on checkout (as it was troublesome to flush, and wasting water), fridge in room- housed in a cabinet that I feel caused it to overheat… and therefore was not very powerful enough to keep drinks cold. Loved...

Jeneva

Hotel Italia

Cortona Old Town

10/10 Exceptional

Eileen

Hotel Boutique Castiglione del Lago

Contrada Castello

10/10 Exceptional

Anonymous traveler

Equo Suites

Castiglione del Lago

10/10 Exceptional

Donald

Casa Kita

Cortona Old Town

10/10 Exceptional

Joy

A landscaped garden with a swimming pool, neatly trimmed hedges, and outdoor seating areas.

La Cantina Relais - Fattoria Il Cipresso

Arezzo

10/10 Exceptional

Steve

An aerial view of a property with a swimming pool, two buildings, and vineyard rows.

Podere La Rocca

Montepulciano

10/10 Exceptional

Our stay at Podere La Rocca was fabulous! The property is located in the rolling Tuscan hills just outside Montepulciano. The property is a working farm and vineyard with an onsite restaurant and pool. Our room was comfortable and clean. The bathroom was huge with a new jetted tub. We stayed on the second floor in a building with a large communal room with a fireplace. On the first floor of the same building was a rec room with a pool table. What made the stay was our experience at the...

A large brick building with a courtyard, surrounded by trees and a swimming pool.

Villa Svetoni Wine Resort

Montepulciano

10/10 Exceptional

Denise

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

Podere San Giuseppe

Castiglione del Lago

10/10 Exceptional

Timothy

A swimming pool surrounded by greenery, with a view of distant mountains and a clear sky.

Agriturismo La Terra

Montepulciano

10/10 Exceptional

Roe

A buffet with a variety of fruits and pastries.

Hotel Aganoor

Contrada Castello

10/10 Exceptional

Kevin

Frequently Asked Questions

What accommodations do travelers recommend in Ossaia?

Guests like Villa di Piazzano - Small Luxury Hotel of the World, Monastero di Cortona Hotel & Spa and Il Falconiere - Relais e Chateaux.

Can I book refundable accommodations in Ossaia?

If you're looking for the flexibility to change your travel plans to Ossaia, most properties offer refundable* rates you can book. You can see these accommodations by searching our site and using the "fully refundable" filter to narrow the results down.

Where can I stay in Ossaia if I want a vacation rental instead of a traditional hotel?

If you want to find a good alternative to a hotel, look over our selection of 7 vacation homes.

What will the weather in Ossaia be like during my vacation?

August and July are typically the warmest months in Ossaia when the average temp is 71°F. January and February are the coldest months when the average temperature is 42°F. November and October are the months with the most rain.

Why should I book my Ossaia hotel through Hotels.com?

There are lots of reasons to book your Ossaia trip with us: our free cancellations on selected hotels* gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™** on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.