Default HTG hotel image

Search Holiday Rentals in Ossaia

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Ossaia holiday rentals

An upper floor view of a courtyard with stone walls, arched doorways, and seating areas with potted plants.

1. B&B Piccolo Hotel

B&B Piccolo Hotel
Cortona Old Town
9.2 out of 10, Wonderful, (25 reviews)
"This is such an amazing hotel in such an amazing place! "
United States
mansoor
The price is 4.039.493 ₫
4.561.839 ₫ total
includes taxes & fees
22 Oct - 23 Oct
B&B Piccolo Hotel
A fountain with water cascading down a column, surrounded by greenery and a building in the background.

2. Residence al Lago

Residence al Lago
Contrada Fontivegge
8.6 out of 10, Excellent, (39 reviews)
"We stayed for one night, but the rooms are only good for night, it was very expensive for the room and location "
United States
Hananeh
The price is 2.443.238 ₫
2.806.678 ₫ total
includes taxes & fees
28 Sept - 29 Sept
Residence al Lago
A hotel room with a large bed, a desk, a chair, a small table, and a door leading to another room.

3. CASA AMBRA

CASA AMBRA
Cortona Old Town
The price is 8.476.106 ₫
9.412.515 ₫ total
includes taxes & fees
25 Oct - 26 Oct
CASA AMBRA
A narrow stone staircase leading up a hillside, flanked by buildings with wooden doors and windows, and hanging laundry.

4. Vicolo Della Scala Rooms - La Luna

Vicolo Della Scala Rooms - La Luna
Cortona Old Town
The price is 2.641.870 ₫
3.024.454 ₫ total
includes taxes & fees
5 Oct - 6 Oct
Vicolo Della Scala Rooms - La Luna
An outdoor seating area with a pergola, a fire pit, and a flower arrangement.

5. Fontelunga Hotel & Villas

Fontelunga Hotel & Villas
Foiano della Chiana
10.0 out of 10, Exceptional, (9 reviews)
"Wonderful stay!"
Canada
Brian
The price is 7.752.238 ₫
8.645.859 ₫ total
includes taxes & fees
12 Oct - 13 Oct
Fontelunga Hotel & Villas
A narrow cobblestone street with a rustic stone building featuring a wooden door and arched window.

6. San Michele al Borgo

San Michele al Borgo
Castiglion Fiorentino
9.8 out of 10, Exceptional, (9 reviews)
"Excellent staff and tasty breakfast!"
United States
Vern
The price is 3.713.363 ₫
4.203.096 ₫ total
includes taxes & fees
30 Sept - 1 Oct
San Michele al Borgo

7. Casale dell'Assiolo

Casale dell'Assiolo
Castiglione del Lago
The price is 3.486.564 ₫
3.954.336 ₫ total
includes taxes & fees
6 Oct - 7 Oct
Casale dell'Assiolo
An arched doorway leading to a building with a wooden door and a staircase.

8. Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (110 reviews)
"Staff was great, and they even scheduled transportation to and from the train station for us. Great location on the main strip of Montepluciano!"
United States
Nicholas
The price is 2.615.499 ₫
2.995.446 ₫ total
includes taxes & fees
13 Oct - 14 Oct
Residenza Fabroni
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Ossaia Hotel Reviews

Nuovo Etruria Resort

Nuovo Etruria Resort

8/10 Good
"The staff was very attentive and helpful specially Alfredo. He is terrific! My only complaint was a persistent low level hum that was noticeable at night, I figured that our room was above the kitchen area and that it was the industrial size refrigerator below. The view of the town up the hill from our room was spectacular. Decent breakfast. The pool was wonderful."
Robert 2-night trip
Posted 1 day ago
Nuovo Etruria Resort

Frequently asked questions

Are there holiday rentals in Ossaia?

Yes, there are holiday rentals close to the most popular sights in Ossaia, or you can select a more secluded option if you're looking for a relaxing stay.

How many holiday rentals are there in Ossaia?

With 7 Expedia holiday rentals, you're guaranteed to find just the right place for your Ossaia stay.

What’s there to see and do in Ossaia?

While exploring the area, visit family-friendly sights like Naturalistic Oasis La Valle, or get outside and enjoy nature at Isola Maggiore. In the wider area, you’ll find Villa Bramasole and Piazza della Repubblica.

What’s a holiday rental in Ossaia like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Ossaia. Holiday rentals offer extras such as hot tubs, fire pits and patios so you'll have all the conveniences of home. If you're concerned about cleanliness, holiday rentals can offer a sense of safety away from shared hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive option for family trips.