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Ossaia flight + hotel packages

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Hotel Plaza e de Russie

Hotel Plaza e de Russie

5 out of 5
per person
Jun. 16 - Jun. 23
Roundtrip flight included
Toronto (YYZ) to Florence (FLR)
Stay at this 5-star luxury hotel in Viareggio. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the property condition in our reviews. Popular attractions Viareggio Beach and Piazza Shelley are located nearby.
The Sense Experience Resort

The Sense Experience Resort

4 out of 5
per person
Jun. 16 - Jun. 23
Roundtrip flight included
Toronto (YYZ) to Florence (FLR)
Stay at this 4-star beach hotel in Follonica. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ex Tony's and Libera di Torre Mozza Beach are located nearby.
TH Capoliveri - Grand Hotel Elba International

TH Capoliveri - Grand Hotel Elba International

4 out of 5
per person
Jun. 16 - Jun. 23
Roundtrip flight included
Toronto (YYZ) to Pisa (PSA)
Stay at this 4-star beach hotel in Capoliveri. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Naregno Beach and La Pionatta Beach are located nearby.
Hotel Capri & Residence

Hotel Capri & Residence

3 out of 5
per person
Jun. 16 - Jun. 23
Roundtrip flight included
Toronto (YYZ) to Florence (FLR)
Stay at this 3-star family-friendly hotel in Camaiore. Enjoy free WiFi, a rooftop terrace, and room service. Popular attractions Viareggio Beach and Forte dei Marmi Beach are located nearby.
Resort Hotel Tamerici

Resort Hotel Tamerici

4 out of 5
per person
Jun. 16 - Jun. 23
Roundtrip flight included
Toronto (YYZ) to Pisa (PSA)
Stay at this 4-star hotel in Marciana Marina. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Marciana Marina Beach and Spiaggia La Fenicia are located nearby.

Top Ossaia hotels deals

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
Free cancellation
Reserve now, pay when you stay
The price is CA $684 per night
CA $684
per night
May 13 - May 14
Stay at this 5-star luxury hotel in Cortona. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Hannibal's Journey and Villa Bramasole are located nearby.
Pool
Breakfast available
Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

5 out of 5
Via del Salvatore, Cortona
Free cancellation
Reserve now, pay when you stay
The price is CA $468 per night
CA $468
per night
May 24 - May 25
Stay at this 5-star luxury hotel in Cortona. Enjoy free breakfast, free WiFi, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Signorelli Theatre and Museum of the Etruscan Academy are located nearby.
Hot tub
Spa
Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Via Poggio alla Sala 10, Montepulciano, Provincia di Siena
Free cancellation
Reserve now, pay when you stay
The price is CA $741 per night
CA $741
per night
May 17 - May 18
Stay at this 5-star luxury hotel in Montepulciano. Enjoy free breakfast, free WiFi, and a full-service spa. Popular attractions Archaeological Civic Museum and Terme Sant'Elena are located nearby.
Spa
Pool
Hotel Villa Ricci

Hotel Villa Ricci

3 out of 5
Viale Giuseppe di Vittorio 51, Chianciano Terme, SI
Free cancellation
Reserve now, pay when you stay
The price is CA $92 per night
CA $92
per night
May 12 - May 13
Stay at this 3-star spa hotel in Chianciano Terme. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Terme Sant'Elena and Chianciano Art Museum are located nearby.
Pet-friendly
Spa
Hotel San Michele

Hotel San Michele

4 out of 5
Via Guelfa 15, Cortona, AR
Free cancellation
Reserve now, pay when you stay
The price is CA $151 per night
CA $151
per night
May 28 - May 29
Stay at this 4-star business-friendly hotel in Cortona. Enjoy free WiFi, 24-hour room service, and valet parking (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Piazza della Repubblica and Palazzo Comunale are located nearby.
Borgo Il Melone

Borgo Il Melone

4 out of 5
Case Sparse, 38, Localita Il Sodo, Cortona, AR
Free cancellation
Reserve now, pay when you stay
The price is CA $109 per night
CA $109
per night
May 21 - May 22
Stay at this 4-star business-friendly hotel in Cortona. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Cathedral of Cortona and Museo Diocesano are located nearby.
Pet-friendly
Pool
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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.

Popular places to visit

Image for Piazza della Repubblica

Piazza della Repubblica

5/5(1 review)

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.

Piazza della Repubblica
Image for Villa Bramasole

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.

Villa Bramasole
Image for Signorelli Theatre

Signorelli Theatre

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

Signorelli Theatre

Ossaia Vacations

Have more fun, stress less and wander wisely in Ossaia! Get your journey off to a sensational start by learning a little about this appealing destination.

Ossaia is a neighborhood in Cortona. You'll find it 3 miles (5 kilometers) south of the downtown area.

Travelers to Cortona will be rubbing shoulders with approximately 2,000 locals.

Places to visit in Ossaia

Whether you're looking to unwind with a few beers or seek out some hair-raising activities, Travelocity will help you. All you have to do is show up!

Where do you fly into for Ossaia?

Are you landing at Sant Egidio Airport (PEG)? Ossaia is only 25 miles (40 kilometers) away. Grab a cup of coffee, jump in a cab and you'll arrive in no time!

Frequently asked questions

How much are vacation packages to Ossaia?
Splash out on an unforgettable travel experience in Ossaia with a vacation package starting at just CA $1,795. Locking in your flights and hotels through Travelocity is so easy. On top of that, our vacation deals will leave you with extra cash for fun activities.
Where can I get the best vacation package deals for Ossaia?
Head straight to Travelocity. With access to 400 air carriers and a whopping 665,000 hotels around the world, selecting the perfect Ossaia package deal couldn’t be simpler.
Why should I book my Ossaia vacation bundle via Travelocity?
With our Price Match Guarantee, we’ll match any better price you find. Add on our 24/7 support and top-quality service and the vacation you’ve been dreaming of is closer than ever before.
Will I save money on my Ossaia car rental if I bundle it with my hotel or flight?
You certainly can — and booking one of our Ossaia vacation packages is the simplest way to do this. Bundle any combination of a hotel, flight, car and tour and score great discounts. The more you bundle, the more you save. There are plenty of exciting sights in and around Ossaia that are worth a road trip, including St. Peter’s Basilica (150 kilometersfrom Ossaia). Nothing tops exploring places like this with the freedom of your own set of wheels.
What is the best time of year to go to Ossaia?
You’ll land the cheapest hotel prices in and pay more during . It’s generally more relaxed in , while you’ll find more fellow visitors to hang out with in the months of . It comes down to how much you’re willing to spend, the weather conditions and how you handle crowds.
Where should I stay when visiting Ossaia?
If you’re looking for a base in Ossaia, the Villa il Trebbio is a good place to start. Many visitors lay their heads at this popular option.
Can I go on vacation to Ossaia at this time?
Get all the info you should know about quarantine policies and travel restrictions ahead of your journey to Ossaia. Our Covid-19 Travel Advisor is full of advice to help make your trip as hassle-free as possible.