Ossaia Holidays from £248

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Your Ossaia Holiday

Say farewell to the stress of planning and hello to a Ossaia holiday package. With the finer details organised before you go, you can focus on discovering this city, starting with Contrada Castello, which is good for dining, views and culture. A trip to Ossaia is a great opportunity to take in the sights. Check out well-known attractions like Villa Bramasole, Piazza della Repubblica and Cathedral of Cortona. Expedia has what you need to escape your routine. Tailor your holiday to Ossaia to suit your travel style, whatever that may be!

The Latest Ossaia Holiday Deals

Price found within the past 48 hours. Click for updated prices.
JOIVY Together Florence Secret Nest

JOIVY Together Florence Secret Nest

3 out of 5
Oltrarno
per person
27 Aug - 1 Sept
found 1 day ago
Return flight included
London (LON) to Florence (FLR)
9.2/10 Wonderful! (455 reviews)
Very nice hotel to stay in Florence, breakfast was excellent, clean and quite, transportation was around the corner, would stay again here for sure.

Reviewed on 19 May 2025

Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
per person
11 Aug - 18 Aug
found 1 day ago
Return flight included
Birmingham (BHX) to Florence (FLR)
7.6/10 Good! (1,000 reviews)
If one is not there for a fancy hotel room, but for sightseeing, this is a great, clean, bare bones room. It is close to the train station. We were on the 5th floor and had a great view! Breakfast was also on the 5th floor. Close proximity to all the museums and Duomo, 20 minute walk or less to everything. We walked everywhere!

Reviewed on 21 Jun 2025

Hotel Bencista

Hotel Bencista

3 out of 5
per person
27 Aug - 1 Sept
found 1 day ago
Return flight included
London (LON) to Florence (FLR)
7.2/10 Good! (11 reviews)
Giovanni Rooms Manarola

Giovanni Rooms Manarola

1 out of 5
per person
15 Sept - 19 Sept
found 1 day ago
Return flight included
London (LON) to Pisa (PSA)
8.2/10 Very Good! (85 reviews)
This property is in the centre of Manarola. A lovely, well-looked-after place. If you want to experience waking up in this amazing part of the world, we recommend this location.

Reviewed on 26 Apr 2025

The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
14 Sept - 20 Sept
found 1 day ago
Return direct flight included
Birmingham (BHX) to Florence (FLR)
9.6/10 Exceptional! (462 reviews)
Hands down the best place we have stayed. They accommodated to go breakfasts for our tours, arranged taxis, made cappuccino when we were heading out the door. Wonderful experience

Reviewed on 6 Jun 2025

Vernazza Sea View

Vernazza Sea View

1 out of 5
Save 100% on your flight
per person
15 Sept - 19 Sept
found 1 day ago
Return flight included
London (LON) to Pisa (PSA)
8/10 Very Good! (43 reviews)
The location was very convenient. Staff were nice…they let us check in early. However, when we reported no wifi service they said it was fixed but it never worked.

Reviewed on 18 Jun 2025

Ossaia Essential Information

Language
Italian
Currency
Euros
Local Welcome
Ciao
Local Goodbye
Ciao
Population
230
Max Temp Winter
7ºC
Max Temp Summer
27ºC
Top Sights
Cathedral of Cortona, Signorelli Theatre and Palazzo Comunale

Our pick of the best Ossaia Hotel Deals

Precise Tale Poggio Alla Sala
Precise Tale Poggio Alla Sala
5 out of 5
Via Poggio alla Sala 10, Montepulciano, SI
Stay at this 5-star luxury hotel in Montepulciano. Enjoy free breakfast, free Wi-Fi and an outdoor pool. Our guests praise the helpful staff in their reviews. ...
9.2/10 Wonderful! (94 reviews)
"This place is absolutely stunning and tranquil, with many amenities to enjoy. The spa area is fantastic, and the room was spotless. The staff provided excellent service, and breakfast was simply amazing. I wish I had stayed longer. If I return to Tuscany someday, I would definitely choose to stay ..."

Reviewed on 21 Jun 2025

Precise Tale Poggio Alla Sala
Nuovo Etruria Resort
Nuovo Etruria Resort
Via di S. Martino snc, Montepulciano, SI
Stay at this hotel in Montepulciano. Enjoy an outdoor pool, breakfast (surcharge) and daily housekeeping. Popular attractions Church of St. Agnes and Colonna ...
9/10 Wonderful! (12 reviews)
"The room was very clean. The view from the room is stunning! It is very quiet and relaxing. The resort is facing Montepulciano! The staff is very nice and friendly. I highly recommend it."

Reviewed on 14 Jun 2025

Nuovo Etruria Resort
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
Stay at this 5-star luxury hotel in Cortona. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff in their reviews. ...
9.6/10 Exceptional! (209 reviews)
"The service was excellent."

Reviewed on 7 Jun 2025

Villa di Piazzano - Small Luxury Hotel of the World
See all 5,234 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.

All Inclusive Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

How much does an Ossaia travel package cost?
We make it simple to see the world, with Ossaia packages starting from as little as £248. You'll have the flexibility to bundle your preferred hotels, airlines and car rental. For the ultimate getaway, why not add a couple of tours and experiences to your itinerary?
If I'm not able to travel, can I cancel my Ossaia travel package?
We get that life can throw you the odd curveball. If you've locked in an Ossaia travel package and need to amend or cancel it, we're here to help. It's always worth browsing our Customer Service Portal first for information. But in general, if you've booked your package within 24 hours, you may be able to change your itinerary at no cost. If it's been more than 24 hours, your hotel, airline or car rental company may impose a charge.
How do I get a cheap travel package to Ossaia?
Bundling your flight and hotel with Expedia won't just save precious time --- it'll save you a nice amount too. An Ossaia travel package makes it a cinch to put together the perfect trip. With more than 550 airlines across the world to choose from, finding flights that suit your schedule won't be an issue. In addition to that, we have over 1,000,000 hotels globally to select from. Talk about choice! No matter who you are, Expedia brings the world within your reach.
Does Expedia offer Book Now, Pay Later Ossaia holidays?
Good news! We do. Expedia has teamed up with online lender Klarna to help you easily pay for your holiday in instalments. Simply click on the payment plan that suits you best during checkout and take away the stress of budgeting for your trip. Make sure you bundle your accommodation, flights and car hire with Expedia to get the biggest bang for your buck. Browse our flexible payment options below:
  • Pay monthly holidays: Make your holiday dreams a reality sooner with Klarna's manageable monthly instalment plans. If making bite-sized repayments each month sounds right for you, choose this option during the checkout process.
  • Pay in instalments holidays: Into the idea of paying for your holiday in multiple transactions? Then select this Book Now, Pay Later option from Klarna.
  • Low deposit holidays: When you want to jump on an awesome deal but your budget doesn't quite go that far, Klarna's low deposit holiday plan will help you lock in your escape.

Where should I stay in Ossaia?
With fascinating attractions such as Cathedral of Cortona and Piazza della Repubblica in this area, see if you can find a hotel near either one. Fortress of Girifalco is another Ossaia hot spot that people flock to.
What are the top hotels in Ossaia?
Hotel Italia and Relais Villa Petrischio are a couple of the most sought-after hotels in Ossaia. Why not take a look at the amenities and facilities at each and then decide?
How far in advance should I book my Ossaia holiday?
To land cheap prices, book as early as you can. Airlines usually release flights, along with some of the lowest fares, nearly 12 months in advance. Hotels, activities and car rental should also be booked well in advance to avoid disappointment. If you're in need of a last-minute getaway to Ossaia, there are always lots of great bargains to be had on Expedia. Book your escape today!
What does an Expedia Ossaia travel package include?
With Expedia, you can select a combination of hotels, car rentals and flights to build your perfect Ossaia package. Once you've made your booking, you can add on the fun stuff like day tours and activities. Remember, the more you bundle, the bigger the savings!
What should I know before booking an Ossaia travel package?
Bundling your bookings into an Ossaia travel package is the easiest way to organise your trip. Not only that, you'll get great discounts just for combining your flights, hotels and car rentals. Once you've booked, why not add on an activity or a tour?
Can I choose my airline with an Ossaia Expedia travel package?
With a travel package, you're the one in charge. Whether you'd like to fly to Ossaia in first class or coach, simply choose from the available airline options. Expedia has access to over 550 airline partners worldwide.

Discover the most popular places to visit in Ossaia

Villa Bramasole

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

Villa Bramasole

Palazzo Comunale

Palazzo Comunale 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 theatre.

Palazzo Comunale

San Domenico Church

You can learn about the history of Cortona with a stop at San Domenico Church. Experience the area's museums and musical theatre.

San Domenico Church

Unmissable things to do in Ossaia

For your personal cooking class in Tuscany

Amazing four courses cooking class in Tuscany

£223
per adult
Amazing four courses cooking class in Tuscany
Tuscany: Sanctuary of La Verna Day Tour Private Tour

Tuscany: Sanctuary of La Verna Day Tour Private Tour

£395
per traveller
Tuscany: Sanctuary of La Verna Day Tour Private Tour
Cortona

Cortona Private Guided Tour

£219
per traveller
Cortona Private Guided Tour
See all activities in Ossaia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.