Title: Visit Ossaia: Best of Ossaia Tourism | Expedia Travel Guide - Expedia.ca

[Hotels in Ossaia](https://expedia.ca/Ossaia-Hotels.d6361235.Travel-Guide-Hotels)[Vacation Rentals in Ossaia](https://expedia.ca/Ossaia-Vacation-Rentals.d6361235.Travel-Guide-VacationRentals)[Ossaia Car Rentals](https://expedia.ca/Car-Rentals-In-Ossaia.d6361235.Car-Rental-Guide)[Ossaia Vacation Packages](https://expedia.ca/Ossaia.d6361235.Destination-Travel-Guides)

# Ossaia

## Travel Guide

## Visit Ossaia

Things to do

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

The Annual Vacation Sale 

Members save up to 40% on hotels and homes. Plan this year’s big trip and save. 

[Book now](https://expedia.ca/deals?rfrr=DX_SPRING_PROMO_6361235)

- Ossaia Hotel Deals
- Vacation Rentals in Ossaia

![Relais Villa Grazianella - UNA Esperienze](https://images.trvl-media.com/lodging/5000000/4320000/4310500/4310479/8b3fbbcc_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Relais Villa Grazianella - UNA Esperienze

Via Grazianella 5 Montepulciano SI

CA $269

CA $303 total

Mar 1 - Mar 2

includes taxes & fees

Book a stay at this business-friendly country house in Montepulciano. Enjoy free WiFi, free parking, and an attached winery. Our guests praise the helpful staff ...

9.8/10 Exceptional! (279 reviews)

Everything was perfect. Warm welcome, comfortable and spacious rooms, great breakfast. The staff was very kind and friendly. I also recommend the wine tasting experience. Highly recommended!

Reviewed on Dec 5, 2025

[](https://expedia.ca/Hotel-Search?startDate=01%2F03%2F2026&endDate=02%2F03%2F2026&selected=4310479&PinnedHotelID=4310479&HadPinnedHotel=true&regionId=6361235)

![Precise Tale Poggio Alla Sala](https://images.trvl-media.com/lodging/91000000/90890000/90888700/90888666/8fbdd5cc_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Precise Tale Poggio Alla Sala

Via 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. ...

9.4/10 Exceptional! (123 reviews)

Perfect escape

Fantastic hotel in an incredible setting. Staff were extremely helpful, attentive and understanding. The perfect location for a relaxing break and a centre for exploring Tuscany

Reviewed on Oct 27, 2025

[Get rates](https://expedia.ca/Hotel-Search?startDate=12%2F03%2F2026&endDate=13%2F03%2F2026&selected=90888666&PinnedHotelID=90888666&HadPinnedHotel=true&regionId=6361235)

[](https://expedia.ca/Hotel-Search?startDate=12%2F03%2F2026&endDate=13%2F03%2F2026&selected=90888666&PinnedHotelID=90888666&HadPinnedHotel=true&regionId=6361235)

![Villa di Piazzano - Small Luxury Hotel of the World](https://images.trvl-media.com/lodging/1000000/980000/972000/971985/473f66a9_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Villa di Piazzano - Small Luxury Hotel of the World

Localita Piazzano, C.P. 6 Cortona AR

CA $963

CA $1,065 total

Mar 28 - Mar 29

includes taxes & fees

Book a stay at this luxury hotel in Cortona. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular ...

9.8/10 Exceptional! (228 reviews)

Room was wonderful, bathroom spacious and well appointed. Staff amazing and so friendly

Reviewed on Nov 6, 2025

[](https://expedia.ca/Hotel-Search?startDate=28%2F03%2F2026&endDate=29%2F03%2F2026&selected=971985&PinnedHotelID=971985&HadPinnedHotel=true&regionId=6361235)

[See all 5,032 properties in Ossaia](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=27%2F02%2F2026&endDate=28%2F02%2F2026&regionId=6361235)

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](https://images.trvl-media.com/lodging/11000000/10660000/10653000/10652908/80de574a_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Abbadia Sicille Relais

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 Monastery of Sant'Anna ...

8.8/10 Excellent! (168 reviews)

Room was beyond expectations. Helpful staff and overall great experience.

Reviewed on Dec 7, 2025

[](https://expedia.ca/Trequanda-Hotels-Abbadia-Sicille.h10652908.Hotel-Information)

![Residenza Fabroni](https://images.trvl-media.com/lodging/9000000/8210000/8204400/8204306/093ed3b4_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

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! (96 reviews)

The parking states “on site”, as if there was a parking lot easy and close to get to and from, especially with luggage. The parking lot is a maze to get to and quite difficult to navigate to through the tiny streets. Other then that, place was clean, staff was great Very old school italy Also the ...

Reviewed on Jan 19, 2026

[](https://expedia.ca/Montepulciano-Hotels-Residenza-Fabroni.h8204306.Hotel-Information)

![Il Tosco](https://images.trvl-media.com/lodging/7000000/6310000/6309600/6309554/3e489ee1_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

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! (116 reviews)

Best stay of my life!

Reviewed on Dec 31, 2025

[](https://expedia.ca/Montepulciano-Hotels-Il-Tosco.h6309554.Hotel-Information)

[See all properties in Ossaia](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&regionId=6361235&sort=VACATION_RENTAL)

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.

## Check Ossaia hotel availability

[Tonight

](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=6361235&startDate=2026-02-26&endDate=2026-02-27)[Feb 26 - Feb 27](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=6361235&startDate=2026-02-26&endDate=2026-02-27)

[Tomorrow night

](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=6361235&startDate=2026-02-27&endDate=2026-02-28)[Feb 27 - Feb 28](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=6361235&startDate=2026-02-27&endDate=2026-02-28)

[This weekend

](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=6361235&startDate=27%2F02%2F2026&endDate=01%2F03%2F2026)[Feb 27 - Mar 1](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=6361235&startDate=27%2F02%2F2026&endDate=01%2F03%2F2026)

[Next weekend

](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=6361235&startDate=06%2F03%2F2026&endDate=08%2F03%2F2026)[Mar 6 - Mar 8](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=6361235&startDate=06%2F03%2F2026&endDate=08%2F03%2F2026)

### Popular places to visit

#### Villa Bramasole

You can learn about the history of Cortona with a trip to Villa Bramasole. You can enjoy the wineries while in the area. 

[](https://expedia.ca/Villa-Bramasole-Cortona.d553248635931712561.Vacation-Attraction)

#### Piazza della Repubblica

Find out about the history of Cortona with a stop at Piazza della Repubblica. Make time to visit the cathedral and monuments while you're in the area. 

[](https://expedia.ca/Piazza-Della-Repubblica-Cortona-Old-Town.d6102854.Vacation-Attraction)

#### Cortona Cathedral

Cortona Cathedral is just one of the places to see in Cortona, so why not enjoy the other things to explore during your travels? Experience the area's museums and musical theater. 

[](https://expedia.ca/Cathedral-Of-Cortona-Cortona-Old-Town.d6102846.Vacation-Attraction)

#### Giuseppe Garibaldi Memorial

You can learn about the history of Cortona when you stop by Giuseppe Garibaldi Memorial. Experience the area's museums and musical theater. 

[](https://expedia.ca/Belvedere-Cortona-Old-Town.d553248621533000990.Vacation-Attraction)

#### Signorelli Theatre

You can make plans for a show at Signorelli Theatre during your stay in Cortona. Discover the area's countryside and monuments. 

[](https://expedia.ca/Signorelli-Theatre-Cortona-Old-Town.d645383631929692160.Vacation-Attraction)

#### Farneta Abbey

Find out about the history of Farneta with a stop at Farneta Abbey. While you're here, you can savor the wineries. 

[](https://expedia.ca/Farneta-Abbey-Cortona.d553248622493475500.Vacation-Attraction)

### Things to do

![3 Regions in 1 Day from Rome with Tuscany Wine Tasting & Lunch](https://mediaim.expedia.com/localexpert/47282553/e14b5a73-0ff4-428f-a567-234540a94e59.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch

CA $115

per adult

**100%** of travellers recommend

[](https://expedia.ca/things-to-do/from-rome-bagnoregio-orvieto-day-trip-with-tuscany-wine-tasting-lunch.a47282553.activity-details)

![Oil museum and oil mill in Tuscany: tour and tasting](https://mediaim.expedia.com/localexpert/47137603/cba72fc6-87d4-4e36-971f-bc6dc0d28c6e.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Oil museum and oil mill in Tuscany: tour and tasting

CA $32

per adult

[](https://expedia.ca/things-to-do/oil-museum-and-oil-mill-in-tuscany-tour-and-tasting.a47137603.activity-details)

![Montepulciano Wine Tasting in the Tuscan Countryside](https://mediaim.expedia.com/localexpert/50286653/77c79a76-70f1-4375-9739-0f0f71d7da02.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Montepulciano Wine Tasting in the Tuscan Countryside

CA $40

per adult

[](https://expedia.ca/things-to-do/montepulciano-wine-tasting-in-the-tuscan-countryside.a50286653.activity-details)

![Bottaia](https://mediaim.expedia.com/localexpert/1175608/3e83d505-5c45-4a2c-b4f4-b2f1bc743f59.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

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

CA $53

per adult

**100%** of travellers recommend

[](https://expedia.ca/things-to-do/tasting-tour-in-one-of-the-most-beautiful-cellars-in-the-world.a1175608.activity-details)

![Montepulciano: Artisan Heroic Wine Tasting at the Terrace](https://mediaim.expedia.com/localexpert/49091559/d297e68c-49c4-42f7-bfe7-536b2a0686ce.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Montepulciano: Artisan Heroic Wine Tasting at the Terrace

CA $81

per adult

[](https://expedia.ca/things-to-do/montepulciano-artisan-heroic-wine-tasting-at-the-terrace.a49091559.activity-details)

![Chianciano Terme: Sensory Spa Admission Ticket](https://mediaim.expedia.com/localexpert/4515069/fea86ca0-c797-4cc2-a946-10b8adcb80b1.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Chianciano Terme: Sensory Spa Admission Ticket

CA $89

per adult

[](https://expedia.ca/things-to-do/chianciano-terme-sensory-spa-admission-ticket.a4515069.activity-details)

[See all activities in Ossaia](https://expedia.ca/Things-To-Do-In-Ossaia.d6361235.Travel-Guide-Activities)

## Cities near Ossaia

![Cortona showing a city and farmland](https://images.trvl-media.com/place/601360/f4054673-52dd-4f97-8d57-389d1f349940.jpg?impolicy=fcrop&w=512&h=288&q=medium)

### Cortona

## Explore a world of travel with Expedia

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- [5 Star Hotels in Cortona ](https://www.expedia.ca/5Star-Cortona-Hotels.s50-0-d601360.Travel-Guide-Filter-Hotels)
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- [Visit Amorosa ](https://www.expedia.ca/Amorosa.dx3000438909)
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- [Visit Potassa ](https://www.expedia.ca/Potassa.dx6361322)
- [Visit Province of Arezzo ](https://www.expedia.ca/Province-Of-Arezzo.dx6047262)
- [Visit Rigutino ](https://www.expedia.ca/Rigutino.dx6361226)
- [Visit San Pietro a Cegliolo ](https://www.expedia.ca/San-Pietro-A-Cegliolo.dx6130155)
- [Visit Sinalunga ](https://www.expedia.ca/Sinalunga.dx603293)
- [Visit Tegoleto ](https://www.expedia.ca/Tegoleto.dx3000708346)
- [Visit Terontola ](https://www.expedia.ca/Terontola.dx6025579)
- [Visit Tregozzano ](https://www.expedia.ca/Tregozzano.dx6361232)

- [Avis Rental Cars in Cortona ](https://www.expedia.ca/Avis-Car-Rentals-In-Cortona.d601360-c41.Car-Rental-Guide-Suppliers)
- [Car rentals near Cortona Old Town ](https://www.expedia.ca/Car-Rentals-In-Cortona-Old-Town.d553248633938945259.Car-Rental-Guide)
- [Car rental Cortona ](https://www.expedia.ca/Car-Rentals-In-Cortona.d601360.Car-Rental-Guide)
- [Car rental Mercatale di Cortona ](https://www.expedia.ca/Car-Rentals-In-Mercatale-Di-Cortona.d601101.Car-Rental-Guide)
- [Car rental Terontola ](https://www.expedia.ca/Car-Rentals-In-Terontola.d6025579.Car-Rental-Guide)
- [Enterprise Rental Cars in Cortona ](https://www.expedia.ca/Enterprise-Car-Rentals-In-Cortona.d601360-c15.Car-Rental-Guide-Suppliers)
- [Europcar Rental Cars in Cortona ](https://www.expedia.ca/Europcar-Car-Rentals-In-Cortona.d601360-c14.Car-Rental-Guide-Suppliers)
- [Hertz Rental Cars in Cortona ](https://www.expedia.ca/Hertz-Car-Rentals-In-Cortona.d601360-c40.Car-Rental-Guide-Suppliers)
- [Sixt Rental Cars in Cortona ](https://www.expedia.ca/Sixt-Car-Rentals-In-Cortona.d601360-c35.Car-Rental-Guide-Suppliers)

- [Cortona Vacation Rentals ](https://www.expedia.ca/Cortona-Vacation-Rentals.d601360.Travel-Guide-VacationRentals)

- [Things to do in Cortona ](https://www.expedia.ca/Things-To-Do-In-Cortona.d601360.Travel-Guide-Activities)
- [Things to do in Terontola ](https://www.expedia.ca/Things-To-Do-In-Terontola.d6025579.Travel-Guide-Activities)

- Cities near Ossaia
- Places of interest

[Cortona](https://expedia.ca/Cortona.dx601360)

- [Lake Trasimeno ](https://expedia.ca/Lake-Trasimeno-Umbria.d6055082.Vacation-Attraction)
- [Tiber River ](https://expedia.ca/Tiber-River-Marcigliana.d553248621532500472.Vacation-Attraction)
- [Piazza Grande ](https://expedia.ca/Piazza-Grande-Arezzo-Centro-Storico.d6104294.Vacation-Attraction)
- [Terme di Montepulciano Spa ](https://expedia.ca/Terme-Di-Montepulciano-Spa-Montepulciano.d6169786.Vacation-Attraction)
- [Piscine Termali Theia ](https://expedia.ca/Piscine-Termali-Theia-Chianciano-Terme.d553248621555471462.Vacation-Attraction)
- [San Donato Hospital ](https://expedia.ca/San-Donato-Hospital-Arezzo.d553248621583444251.Vacation-Attraction)
- [Palazzo Ricci ](https://expedia.ca/Palazzo-Ricci-Montepulciano.d553248621532500182.Vacation-Attraction)

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