Ossaia Holidays from £337
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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.
Residenza Florentia
Historic Centre of Florence
Save 100% on your flight
Price was £588, price is now £337 per person
£337
per person
14 Sept - 17 Sept
found 14 hours ago
Return flight included
London (LON) to Florence (FLR)
8.4/10 Very Good! (53 reviews)
Staff was helpful, the property was not very well maintained.
Reviewed on 1 Jun 2026
Aurum Firenze
Historic Centre of Florence
Save 100% on your flight
Price was £974, price is now £472 per person
£472
per person
3 Aug - 9 Aug
found 17 hours ago
Return direct flight included
Birmingham (BHX) to Florence (FLR)
7.6/10 Good! (1,025 reviews)
The location is excellent. Close to the train station, shops and restaurants. Room was very clean. Breakfast was included. all good.
Reviewed on 19 Jun 2026
Aurum Uffizi
Historic Centre of Florence
Save 100% on your flight
Price was £955, price is now £466 per person
£466
per person
3 Aug - 9 Aug
found 17 hours ago
Return direct flight included
Birmingham (BHX) to Florence (FLR)
7.6/10 Good! (1,011 reviews)
The hotel was conveniently located, and the service was good. Overall, it was a pleasant stay. However, I hope the hotel improves its Wi-Fi coverage, as the connection can become unstable when multiple guests are accessing the network.
Reviewed on 5 Jun 2026
Precise Tale Poggio Alla Sala
Price was £4,956, price is now £2,490 per person
£2,490
per person
6 Sept - 13 Sept
found 1 day ago
Return flight included
London (LGW) to Florence (FLR)
9.6/10 Exceptional! (144 reviews)
It’s a beautiful property, but be aware that it is secluded and that the restaurant menu is quite limited and after a couple of days, we were happy to go elsewhere. The waiting staff was attentive and nice, front desk not as much (maybe the la guard barrier?)
Reviewed on 19 Jun 2026
The Moon Boutique Hotel & Spa
Historic Centre of Florence
Save 100% on your flight
Price was £1,068, price is now £553 per person
£553
per person
14 Sept - 18 Sept
found 1 day ago
Return flight included
Birmingham (BHX) to Florence (FLR)
9.6/10 Exceptional! (566 reviews)
Absolutely fantastic hotel, we couldn’t believe how good it was. Exactly like the photos. The hotel was built only in 2018 and the facilities are constantly kept in perfect condition and spotlessly clean.
In a quiet part of town easily walkable into the main attractions and close to a bus and a tram stop, a perfect sanctuary to rest at night time. All of the staff are so kind and polite, especially Francois who looked after us very well at breakfast time.
The hotel would be worth the price tag just for the comfortable rooms and location, but it has the added bonus of a free breakfast (with tons of choices and free mimosas), free luxury spa facilities and free home made lemonade and biscuits available at all times.
We can’t recommend this hotel enough as a boutique stay perfect for adults wanting a luxury escape.
Reviewed on 8 Jun 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
The price is £552 per night from 26 Jun to 27 Jun
£552
26 Jun - 27 Jun
includes taxes & fees
9.6/10 Exceptional! (146 reviews)
"It’s a beautiful property, but be aware that it is secluded and that the restaurant menu is quite limited and after a couple of days, we were happy to go elsewhere. The waiting staff was attentive and nice, front desk not as much (maybe the la guard barrier?)"
Reviewed on 19 Jun 2026
Villa di Piazzano - Small Luxury Hotel of the World
Localita Piazzano, C.P. 6 Cortona AR
The price is £581 per night from 10 Jul to 11 Jul
£581
10 Jul - 11 Jul
includes taxes & fees
9.8/10 Exceptional! (237 reviews)
"The Villa is not only one of the most beautiful places on earth but also comfortable warm and inviting. The accommodations are gorgeous and the food is magnificent! The staff is a dream~ so kind and personable. I highly recommend as it will be a trip of a lifetime !!!!"
Reviewed on 9 Jun 2026
A Point Arezzo Park Hotel
Loc. Battifolle, 36/T Arezzo AR
Fully refundableReserve now, pay when you stay
The price is £67 per night from 1 Jul to 2 Jul
£67
1 Jul - 2 Jul
includes taxes & fees
7.6/10 Good! (165 reviews)
"Well, having travelled extensively for the past 13 years, this Hotel must be the coldest I have ever stayed in. It was December, but there was no heating on in the lobby area or the dining area so everyone had to wear coats or thick jumpers while eating their meals. The showers were not particularly ..."
Reviewed on 3 Dec 2025
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
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.
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.
San Domenico Church
After visiting San Domenico Church, make a plan to see the other sights and activities in Cortona. Make time to visit the cathedral and monuments while you're in the area.
What to do in Ossaia
Montepulciano: Winery Tour and Tasting
£30
per adult
100% of travellers recommend
Oil museum and oil mill in Tuscany: tour and tasting
£17
per adult
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* 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.
