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Aug 16 - Aug 17
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Aug 17 - Aug 18
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Aug 21 - Aug 23
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Aug 28 - Aug 30

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Our top choices for Ossaia hotels

1. Hotel Italia

Hotel Italia
Cortona Old Town
United States
Frances
CA $149
CA $172 total
includes taxes & fees
Aug 19 - Aug 20
Hotel Italia

2. Hotel San Luca

Hotel San Luca
Cortona Old Town
United States
Massimo
CA $125
CA $150 total
includes taxes & fees
Sep 13 - Sep 14
Hotel San Luca

3. Locanda del Molino

Locanda del Molino
Cortona
United Kingdom
Christopher
CA $141
CA $168 total
includes taxes & fees
Sep 9 - Sep 10
Locanda del Molino

4. Hotel Villa Marsili

Hotel Villa Marsili
Cortona Old Town
United States
fares
CA $244
CA $282 total
includes taxes & fees
Aug 17 - Aug 18
Hotel Villa Marsili

5. Hotel San Michele

Hotel San Michele
Cortona Old Town
United States
james
CA $193
CA $226 total
includes taxes & fees
Aug 20 - Aug 21
Hotel San Michele

6. Villa Santa Margherita

Villa Santa Margherita
Cortona Old Town
Canada
jean-paul
CA $144
CA $191 total
includes taxes & fees
Aug 22 - Aug 23
Villa Santa Margherita

7. Relais Villa Baldelli

Relais Villa Baldelli
Cortona
United States
Peter
CA $195
CA $228 total
includes taxes & fees
Sep 9 - Sep 10
Relais Villa Baldelli

8. Relais La Corte dei Papi

Relais La Corte dei Papi
Cortona
United Kingdom
Frithjof
CA $543
CA $610 total
includes taxes & fees
Aug 27 - Aug 28
Relais La Corte dei Papi

9. Villa Borgo San Pietro

Villa Borgo San Pietro
Cortona
United States
Stephen
CA $167
CA $197 total
includes taxes & fees
Aug 24 - Aug 25
Villa Borgo San Pietro

10. Locanda agli Amici

Locanda agli Amici
Cortona
Canada
Kimberly
CA $189
CA $221 total
includes taxes & fees
Sep 10 - Sep 11
Locanda agli Amici

11. Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa
Cortona Old Town
United Kingdom
Daniel
CA $414
CA $469 total
includes taxes & fees
Aug 23 - Aug 24
Monastero di Cortona Hotel & Spa

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

Villa di Piazzano - Small Luxury Hotel of the World
Cortona
United States
Niyome
CA $976
CA $1,086 total
includes taxes & fees
Sep 4 - Sep 5
Villa di Piazzano - Small Luxury Hotel of the World

13. Hotel Villa Paradiso

Hotel Villa Paradiso
Passignano sul Trasimeno
United States
Maria
CA $138
CA $159 total
includes taxes & fees
Sep 6 - Sep 7
Hotel Villa Paradiso

14. Villa Schiatti

Villa Schiatti
Castiglion Fiorentino
United States
Soudabeh
CA $207
CA $234 total
includes taxes & fees
Aug 26 - Aug 27
Villa Schiatti

15. Cortona Resort - Le Terre Dei Cavalieri

Cortona Resort - Le Terre Dei Cavalieri
Cortona
United States
Dana
CA $233
CA $264 total
includes taxes & fees
Aug 27 - Aug 28
Cortona Resort - Le Terre Dei Cavalieri

16. Equo Suites

Equo Suites
Castiglione del Lago
Australia
Alistair
CA $226
CA $256 total
includes taxes & fees
Sep 6 - Sep 7
Equo Suites

17. Borgo Tre Rose

Borgo Tre Rose
Montepulciano
United States
Nathan
CA $185
CA $210 total
includes taxes & fees
Aug 24 - Aug 25
Borgo Tre Rose

18. Park Hotel Montigeto

Park Hotel Montigeto
Passignano sul Trasimeno
United Kingdom
Helen
CA $136
CA $155 total
includes taxes & fees
Sep 14 - Sep 15
Park Hotel Montigeto

19. Hotel La Darsena

Hotel La Darsena
Passignano sul Trasimeno
Finland
Arto
CA $108
CA $124 total
includes taxes & fees
Sep 10 - Sep 11
Hotel La Darsena

20. Villa Svetoni Wine Resort

Villa Svetoni Wine Resort
Montepulciano
United States
Amanda
CA $340
CA $381 total
includes taxes & fees
Sep 3 - Sep 4
Villa Svetoni Wine Resort
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Top Ossaia Hotel Reviews

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

8/10 Good
"Great property, location and views.The staff is running a bit thin but helpful...Some training re. customer service attention could be improved, management is clearly not on top for oversight or direct feedback from guests (some supposedly G.M. women passed through the lobby on her way to her week end as we were checking in without bothering to take the opportunity to greet us...never to be seen again for the next 2 days !).The parking and directions are not very practical, the restaurant is too pretentious and lifeless compared to many great options 5 mn away in town).The landscaping and maintenance of pool area could be better for such a gorgeous architecture. All in all, I would recommend ownership to invest a little bit more and hire a more attentive and hands on leadership figure for day to day management to make this property deliver a true 5 stars experience as per global standards and surrounding luxury competitors...(the Nun Assisi provided us with a real Luxury service !)."
Douglas 2-night trip
Posted 20 hours ago
Monastero di Cortona Hotel & Spa
Il Falconiere - Relais e Chateaux

Il Falconiere - Relais e Chateaux

10/10 Excellent
"Beautiful property and location."
Gary 1-night trip
Posted 2 days ago
Il Falconiere - Relais e Chateaux
Relais Villa Grazianella - UNA Esperienze

Relais Villa Grazianella - UNA Esperienze

10/10 Excellent
"Magnifique hôtel, service exceptionnel, propreté impeccable et excellente nourriture. Nous y retournerons sans aucun doute."
Isabelle 3-night trip
Posted 3 days ago
Relais Villa Grazianella - UNA Esperienze
Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

8/10 Good
"Precise Tale Poggio Alla Sala is a beautiful, peaceful property in a stunning and remote location near Montepulciano. The rooms and entire establishment were exceptionally clean and well maintained. The staff were friendly and welcoming, and the property is especially family- and kid-friendly, making it a great choice for families looking for a relaxing stay. Breakfast was included and offered eggs, fresh fruit, a variety of breads, and cold cuts. The selection was good, but it was essentially the same every day with little variation. The breakfast staff were pleasant, although the service could have been more attentive. Unfortunately, the service at the pool and restaurant was the biggest weakness of our stay. There is a walk-up snack and drink bar, but empty glasses and plates were rarely collected. There was no real pool service, and water was not consistently refilled. At the restaurant, tables were often left with empty plates for extended periods, and wait staff rarely checked on guests after the food was served. For a property at this price point, we expected a more attentive level of service. The setting, cleanliness, and family-friendly atmosphere are excellent, but the lack of consistent service at the pool and restaurant took away from what could otherwise be an exceptional experience. Overall, this is a gorgeous and very clean property with friendly people, a peaceful atmosphere, and a great environment for families with children. The location and surroundings"
Luis 5-night trip
Posted 3 days ago
Precise Tale Poggio Alla Sala
Grand Hotel Admiral Palace

Grand Hotel Admiral Palace

10/10 Excellent
"Na"
Vivian 9-night trip
Posted 5 days ago
Grand Hotel Admiral Palace
Agriturismo La Sovana

Agriturismo La Sovana

10/10 Excellent
"Beautiful stay here. Restaurant was fantastic and they prepared special dishes to meet our vegetarian needs. Buffet breakfast with fresh cappuccinos was wonderful. Room was impeccably clean with daily cleaning service. This was our second time here and we are hoping to return to this authentic Tuscany resort. You will likely not find a better place to stay at in Tuscany."
Karen 4-night trip
Posted 7 days ago
Agriturismo La Sovana
Nuovo Etruria Resort

Nuovo Etruria Resort

10/10 Excellent
"Missed the entrance as it’s not very well sign posted. Amazing views, Pool was great, great staff. The room was very very hot upstairs, there was only an aircon downstairs, which meant the kids were fine, but we were baked by the morning. Other than that, faultless."
Ant 1-night trip
Posted 9 days ago
Nuovo Etruria Resort
Il Gentiluomo Hotel & SPA

Il Gentiluomo Hotel & SPA

10/10 Excellent
"Very clean and reasonably priced hotel close to Arezzo and the Autostrada."
Thomas Ezio 1-night trip
Posted 9 days ago
Il Gentiluomo Hotel & SPA
Hotel Minerva

Hotel Minerva

10/10 Excellent
"Very recommended"
John 1-night trip
Posted 2 weeks ago
Hotel Minerva

More cheap stays in Ossaia

Hotel La Terrazza di Montepulciano

Hotel La Terrazza di Montepulciano

Via Pié al Sasso 16 Montepulciano SI
CA $161
CA $183 total
Aug 17 - Aug 18
includes taxes & fees
9.4/10 Exceptional! (210 reviews)
Hotel La Terrazza di Montepulciano
Locanda Granducato

Locanda Granducato

località paccianese 48 Chiusi SI
Get ratesLocanda Granducato
La Locanda di Casalmustia

La Locanda di Casalmustia

Piazza della Pieve 3 Trequanda SI
Get rates
8.6/10 Excellent! (44 reviews)
La Locanda di Casalmustia
Hotel Sangallo

Hotel Sangallo

Via Dei Fiori 30 Montepulciano SI
Get rates
8/10 Very good! (59 reviews)
Hotel Sangallo
Agriturismo Godiolo

Agriturismo Godiolo

VIA DI MARTIENA 24 Montepulciano SI
Get ratesAgriturismo Godiolo
IL Molinaccio di Montepulciano

IL Molinaccio di Montepulciano

VIA ANTICA CHIUSINA 12 Montepulciano SI
Get ratesIL Molinaccio di Montepulciano

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 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 CA $124 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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