Ossaia Holidays from £443

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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!

Top Ossaia Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was £904, price is now £443 per person
£443
per person
6 Oct - 10 Oct
found 1 day ago
Return direct flight included
Birmingham (BHX) to Florence (FLR)
7.8/10 Good! (1,005 reviews)
The room that we used for 5 nights was filthy.and dusty. The shower was very small, barely squeeze in. The interior was outdated with only one point to recharge phones and the cupboards were broken. The door to the room required force to open and close. Location is convenient close to transport.

Reviewed on 23 Aug 2025

Giovanni Rooms Manarola

Giovanni Rooms Manarola

1 out of 5
Price was £1,210, price is now £489 per person
£489
per person
30 Sept - 6 Oct
found 4 hours ago
Return flight included
London (LON) to Pisa (PSA)
8/10 Very Good! (86 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
Price was £1,060, price is now £508 per person
£508
per person
14 Nov - 21 Nov
found 1 day ago
Return direct flight included
Birmingham (BHX) to Florence (FLR)
9.6/10 Exceptional! (469 reviews)
The hotel is located a 25 min walk away from the heart of Florence so very easy to access the main attractions within the city. The hotel itself is immaculate and the staff are extremely helpful with dealing with any questions you may have. Being able to access the spa everyday for 1 and 30 minutes is an excellent perk as the facilities are well worth a visit, you are also able to book massages for an extra fee. The breakfast also gives a variety of options to start each day and the room itself is spacious, with the shower particularly being very comfortable.

Reviewed on 13 Aug 2025

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was £974, price is now £469 per person
£469
per person
6 Oct - 10 Oct
found 1 day ago
Return direct flight included
Birmingham (BHX) to Florence (FLR)
7.8/10 Good! (1,005 reviews)
Our stay was lovely, very comfortable, small but good choice of breakfast. Beds were comfy and room was clean when we arrived and cleaned everyday. I would only suggest maybe for a shower curtains as when we had a shower the bathroom floor would be all wet, but easily to clean. And just a note on how to use the phone if we need to call reception but overall the hotel facilities and the staff were brilliant if i could give more then 5 stars i would.

Reviewed on 19 Aug 2025

Palazzo Firenze by Baglioni Hotels & Resorts

Palazzo Firenze by Baglioni Hotels & Resorts

5 out of 5
Historic Centre of Florence
Price was £9,669, price is now £5,144 per person
£5,144
per person
6 Oct - 10 Oct
found 6 hours ago
Return direct flight included
Birmingham (BHX) to Florence (FLR)
9.4/10 Exceptional! (230 reviews)
Gorgeous boutique hotel, like museum Beautiful rooms!!! Thank you Giovanni for all ur help and knowledge organizing everything for us, and breakfast waiters were great!!!

Reviewed on 21 Aug 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

Top hotels in Ossaia

A Point Arezzo Park Hotel

A Point Arezzo Park Hotel

4 out of 5
Loc. Battifolle, 36/T, A1 exit Arezzo, Arezzo, AR
Fully refundableReserve now, pay when you stay
7.6/10 Good! (141 reviews)
"It is very close to autostrada,which is good if you have car. The Breakfast was excellant,with a wonderful hostess. This lady is a big bonus to this hotel.The air-conditioning is building controlled,which would not suit everyone.The cleaner for our area had poor attention to detail. The lead cleaner ..."

Reviewed on 24 Sep 2024

Get rates
A Point Arezzo Park Hotel
Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

5 out of 5
Via del Salvatore, Cortona, AR
Fully refundableReserve now, pay when you stay
The price is £293 per night from 27 Aug to 28 Aug
£293
27 Aug - 28 Aug
includes taxes & fees
9.8/10 Exceptional! (230 reviews)
"Beautiful property, magical, great friendly staff, fantastic breakfast. Everything was perfect"

Reviewed on 7 Aug 2025

Monastero di Cortona Hotel & Spa
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
Fully refundableReserve now, pay when you stay
The price is £530 per night from 31 Aug to 1 Sept
£530
31 Aug - 1 Sept
includes taxes & fees
9.8/10 Exceptional! (220 reviews)
"Este hotel es excepcionalmente bello, unico y perfecto para unas vacaciones en la Toscana. La propiedad esta impecable al igual que las habitaciones, super limpias, cómodas y A/C super fuerte (no muy comunes en Europa) Staff fue muy amable y la cena espectacular. Es un deleite caminar la propiedad. ..."

Reviewed on 20 Aug 2025

Villa di Piazzano - Small Luxury Hotel of the World
See all 5,306 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.
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Popular places to visit

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

What to do in Ossaia

For your personal cooking class in Tuscany

Amazing four courses cooking class in Tuscany

£190
per adult
Amazing four courses cooking class in Tuscany
3 Regions in 1 Day from Rome with Tuscany Wine Tasting & Lunch

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

£77
per adult
100% of travellers recommend
From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
Montepulciano: Wine Tour and tasting

Montepulciano: Wine Tour and tasting

£45
per adult
100% of travellers recommend
Montepulciano: Wine Tour and tasting
See all activities in Ossaia

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 £443. 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.