Ossaia Holidays from £210

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £750 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Packages 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.
  • 7 Jan - 10 Jan

    Hotel Palazzo San niccolò & Spa + Flight

    Radda in Chianti
    3 nights
    4.0 star property
    9.2/10 - Wonderful (198 reviews)
    "Great stay!"
    Reviewed September 4, 2026
    Return • London (LON) - Florence (FLR)
    LGW - FLR • Direct FLR - LGW • Direct
    £297
    £210
    per traveller
    found 5 hours ago
    Hotel Palazzo San niccolò & Spa
  • 7 Jan - 10 Jan

    Villa Tolomei Hotel & Resort + Flight

    Oltrarno
    3 nights
    5.0 star property
    8.8/10 - Excellent (448 reviews)
    Return • London (LON) - Florence (FLR)
    LGW - FLR • Direct FLR - LGW • Direct
    £457
    £302
    per traveller
    found 4 hours ago
    Villa Tolomei Hotel & Resort
  • 19 Dec - 24 Dec

    The Place Firenze + Flight

    Historic Centre of Florence
    5 nights
    5.0 star property
    9.8/10 - Exceptional (203 reviews)
    Return • London (LON) - Florence (FLR)
    LHR - FLR • Direct FLR - LHR • Direct
    £1,900
    £1,267
    per traveller
    found 1 day ago
    The Place Firenze
  • 19 Dec - 24 Dec

    Il Rivalta - Place of Charme + Flight

    Historic Centre of Florence
    5 nights
    4.0 star property
    9.4/10 - Exceptional (647 reviews)
    Return • London (LON) - Florence (FLR)
    LHR - FLR • Direct FLR - LHR • Direct
    £770
    £539
    per traveller
    found 1 day ago
    Il Rivalta - Place of Charme
  • 7 Jan - 10 Jan

    Dimora Palanca Boutique & SPA + Flight

    Historic Centre of Florence
    3 nights
    5.0 star property
    9.2/10 - Wonderful (79 reviews)
    "All"
    Reviewed October 31, 2026
    Return • London (LON) - Florence (FLR)
    LGW - FLR • Direct FLR - LGW • Direct
    £466
    £334
    per traveller
    found 4 hours ago
    Dimora Palanca Boutique & SPA

Ossaia Hotel Deals

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.

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 £210. 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.