Ossaia

Travel Guide

Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World

5 out of 5
Localita Piazzano, C.P. 6 Cortona AR
The price is $690 total per night from Oct 12 to Oct 13
$690 total
per night
Oct 12 - Oct 13
Book a stay at this luxury hotel in Cortona. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular attractions ...
9.8/10 Exceptional! (253 reviews)
"Stunning property; a real representation of Tuscany with the long driveway of tall trees; staff was amazing; food was excellent; gardens, picturesque! We would highly recommend! Overall amazing !!!"

Reviewed on Oct 5, 2026

Villa di Piazzano - Small Luxury Hotel of the World
Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Via Di Poggio Alla Sala, 10 Montepulciano SI
Book a stay at this luxury hotel in Montepulciano. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
9.6/10 Exceptional! (181 reviews)
"Great, peaceful place to stay. Gorgeous property with pools and spa. Could use another food option but otherwise excellent."

Reviewed on Oct 7, 2026

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Precise Tale Poggio Alla Sala
B&B Hotel Arezzo

B&B Hotel Arezzo

3 out of 5
Via Einstein, 4 Arezzo AR
The price is $75 total per night from Nov 8 to Nov 9
$75 total
per night
Nov 8 - Nov 9
Book a stay at this business-friendly hotel in Arezzo. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions UCI Cinemas Arezzo and Porta ...
B&B Hotel Arezzo
See all 5,078 properties in Ossaia
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Abbadia Sicille Relais

Abbadia Sicille Relais

4 out of 5
SP 14 Loc. Abbadia Sicille Trequanda SI
Book a stay at this business-friendly residence in Trequanda. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions San Giovanni d'Asso Station ...
Abbadia Sicille Relais
Il Tosco

Il Tosco

Via del Poliziano 13 Montepulciano SI
Book a stay at this luxury residence in Montepulciano. Enjoy free WiFi, free parking, and room service. Popular attractions Medici Fortress and Torre del Pulcinella ...
10/10 Exceptional! (135 reviews)
"Amazing property, fabulously appointed an upscale B&B experience. Complicated logistics are made easy through top notch communication and help. The food is exceptional and the host is amongst the best we have encountered! A do not miss! 10/10⭐️"

Reviewed on Oct 10, 2026

Il Tosco
Residenza Fabroni

Residenza Fabroni

Via di Gracciano nel Corso, 12 Montepulciano SI
Book a stay at this historic residence in Montepulciano. Enjoy free WiFi, an attached winery, and a rooftop terrace. Popular attractions Torre di Pulcinella ...
8.8/10 Excellent! (114 reviews)
"Great location. Amazing terrace. Would stay here again"

Reviewed on Sep 30, 2026

Residenza Fabroni
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Things to do

Montepulciano Wine Tasting in the Tuscan Countryside

Montepulciano Wine Tasting in the Tuscan Countryside

$29
per adult
Montepulciano Wine Tasting in the Tuscan Countryside
Montepulciano: Winery Tour and Tasting

Montepulciano: Winery Tour and Tasting

$40
per adult
100% of travellers recommend
Montepulciano: Winery Tour and Tasting
Horseback riding through the vineyards in Montepulciano Tuscany

Horseback riding through the vineyards in Montepulciano Tuscany

$92
per adult
Horseback riding through the vineyards in Montepulciano Tuscany
Montepulciano: Tuscan Cooking Class with Fresh Pasta & Wine

Montepulciano: Tuscan Cooking Class with Fresh Pasta & Wine

$92
per adult
Montepulciano: Tuscan Cooking Class with Fresh Pasta & Wine
Tasting Tour in One of The Most Beautiful Cellars in the World

Tasting Tour in One of The Most Beautiful Cellars in the World

$38
per adult
100% of travellers recommend
Tasting Tour in One of The Most Beautiful Cellars in the World
Montepulciano Gran Tour

Montepulciano Gran Tour

$17
per adult
Montepulciano Gran Tour
See all activities in Ossaia

Frequently asked questions

When is the best time to visit Ossaia?
The best time to visit Ossaia is from May through September, when the climate is generally most pleasant. For fewer crowds and better value, the quieter months of November through February are a good bet, offering a milder climate for travelers.
Can I book a refundable hotel in Ossaia?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Ossaia by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Ossaia with Expedia?
Expedia makes it easier to plan your Ossaia trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Ossaia?
The best choice depends on your travel style. Hotels in Ossaia can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Ossaia trip on Expedia?
Once you've booked your Ossaia trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Ossaia trip?
Expedia offers customer support before, during, and after your Ossaia trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Ossaia?
If it's your first trip to Ossaia, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Ossaia hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Ossaia hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

Cities near Ossaia

A hillside town with historic buildings, a church, and vineyards.

Cortona

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