Ossaia Holidays from £415
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to £750 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPackages with flights are ATOL protected
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!
Top Ossaia Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Dimora Palanca Boutique & SPA
Historic Centre of Florence
£415
per person
19 Oct - 22 Oct
found 1 day ago
Return flight included
London (LON) to Florence (FLR)
9.2/10 Wonderful! (68 reviews)
This hotel is definitely not 5*, no amenities provided, very poor breakfast, like at 3* hotel, room was full of dark black hair, and most important pay attention to the location , as it’s in central station area, and we felt unsafe to walk there in the evening
Reviewed on 27 Aug 2026
Eden Rock Resort
£693
per person
23 Oct - 27 Oct
found 21 hours ago
Return flight included
London (LHR) to Florence (FLR)
9.8/10 Exceptional! (109 reviews)
This was a beautiful property about 10 mins away from Florence. You get the beauty of Tuscany without having to go too far. The hotel only has 12 rooms and everyone knows you by name. We traveled with 2 kids and the rooms were very spacious. Staff are wonderful, Onsite restaurant was great. Views were breathtaking. We didn't have a car, and the hotel was able to help us with cabs easily. Service was excellent and we would highly recommend this hotel!
Reviewed on 18 Jul 2026
The Moon Boutique Hotel & Spa
Historic Centre of Florence
£551
per person
9 Nov - 15 Nov
found 1 day ago
Return direct flight included
Birmingham (BHX) to Florence (FLR)
9.6/10 Exceptional! (584 reviews)
All the staff were amazing and helpful! The kitchen staff for breakfast catered for all out needs. The spa was excellent too and I’d highly recommended this hotel to anyone. It’s in a Great location with good links to the airport and tourist spots across the city.
Reviewed on 29 Aug 2026
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 |
Top hotels in Ossaia
Precise Tale Poggio Alla Sala
Via Poggio alla Sala 10 Montepulciano SI
Fully refundableReserve now, pay when you stay
£482
30 Sept - 1 Oct
includes taxes & fees
Villa di Piazzano - Small Luxury Hotel of the World
Localita Piazzano, C.P. 6 Cortona AR
£579
7 Sept - 8 Sept
includes taxes & fees
9.8/10 Exceptional! (245 reviews)
"Staff was helpful , and the room was clean. The Antica Casina di Caccia dining with wine pairing was absolutely amazing. Also took some great pictures in the garden. The breakfast was nice too."
Reviewed on 17 Aug 2026
Monastero di Cortona Hotel & Spa
Via del Salvatore Cortona AR
Fully refundableReserve now, pay when you stay
£293
13 Sept - 14 Sept
includes taxes & fees
10/10 Exceptional! (318 reviews)
"Before I share, I will say that the staff helping with breakfast and at the bar (by the pool) were great. However, the front desk employees were pretty cold in each of my interactions with them. When I first inquired about reserving time slots at the spa, I asked about the remaining available slots ..."
Reviewed on 29 Aug 2026
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.
What to do in Ossaia
Tasting Tour in One of The Most Beautiful Cellars in the World
£28
per adult
100% of travellers recommend
Montepulciano: Winery Tour and Tasting
£30
per adult
100% of travellers recommend
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 £415. 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.
* 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.
