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Check prices for these dates

In two weeks
13 Mar - 15 Mar
In two months
24 Apr - 26 Apr
In three months
22 May - 24 May
In four months
19 Jun - 21 Jun

Our top choices for Ossaia holiday rentals

Bar (on property)

La Piccola Locanda

La Piccola Locanda
Chiusi
8.6 out of 10, Excellent, (9 reviews)
"This was a great place to stay for two nights in late October and to take out and back day trips by train to Siena and Florence on back-to-back days. Very close to the train station - very convenient. Breakfast in the restaurant in the morning was small, but good. Highly recommend this location! It's small, but serviced and supported very well by the staff at the restaurant. "
United States
Jeffery
La Piccola Locanda
Exterior

Luxury resort in the Tuscan countryside

Luxury resort in the Tuscan countryside
Trequanda
Luxury resort in the Tuscan countryside
Panoramic Cottage, 1 Bedroom | Exterior

Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (51 reviews)
"This property has a lovely view, great garden, attentive staff with good breakfast. Stayed in the cottage and the patio was very sunny and relaxing. "
United States
Lenise
Affitacamere Maria Gabriella
Terrace/patio

Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (168 reviews)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is 2.392.190 ₫
2.723.686 ₫ total
includes taxes & fees
17 Mar - 18 Mar
Abbadia Sicille Relais
Lunch and dinner served, local cuisine

Castello di Gargonza

Castello di Gargonza
3.0 star property
Monte San Savino
9.2 out of 10, Wonderful, (39 reviews)
"Beautiful area and friendly staff. We stayed here several years ago and were so excited to return."
United States
David
Castello di Gargonza
Free daily buffet breakfast

Relais La Saracina

Relais La Saracina
Pienza
Relais La Saracina
Property entrance

Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (96 reviews)
"gorgeous historical property, very attentive host, great location"
United States
Sarah
The price is 2.166.167 ₫
2.505.902 ₫ total
includes taxes & fees
4 Mar - 5 Mar
Residenza Fabroni
Suite Aria | Terrace/patio

Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (35 reviews)
"Wonderful "
United States
Rocio Q
The price is 4.717.840 ₫
5.312.742 ₫ total
includes taxes & fees
2 Mar - 3 Mar
Delcorto Suites
Food court

La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (133 reviews)
"Spotless, clean. Staff were friendly. Location and view was spectacular"
Australia
Kim
The price is 4.057.365 ₫
4.586.219 ₫ total
includes taxes & fees
4 Mar - 5 Mar
La Locanda di San Francesco
Interior

Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.8 out of 10, Exceptional, (88 reviews)
"Staff is great and many good restaurants in short walking distance."
United States
Mark
Meublé Il Riccio
Exterior

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 2.938.052 ₫
3.354.975 ₫ total
includes taxes & fees
2 Mar - 3 Mar
San Michele al Borgo
Exterior

L'Antica Sosta

L'Antica Sosta
Corciano
9.4 out of 10, Exceptional, (3 reviews)
"Molto accoglienti e gentili "
Italy
Valentina
The price is 1.645.477 ₫
1.810.025 ₫ total
includes taxes & fees
3 Mar - 4 Mar
L'Antica Sosta
Property entrance

Il Tosco

Il Tosco
Montepulciano
10.0 out of 10, Exceptional, (116 reviews)
"Best stay of my life!"
United States
MARTA F
The price is 8.884.669 ₫
9.896.254 ₫ total
includes taxes & fees
18 Mar - 19 Mar
Il Tosco
Deluxe Apartment, Hill View | Living area

IL GIARDINO DELLE NINFE

IL GIARDINO DELLE NINFE
Vernazzano Basso
The price is 6.799.365 ₫
7.479.301 ₫ total
includes taxes & fees
2 Mar - 3 Mar
IL GIARDINO DELLE NINFE
Exterior

Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (129 reviews)
"Great hosts, central location "
United States
Alexander
Bed & Breakfast Vicolo dell'Oste
Lobby

B&B Piccolo Hotel

B&B Piccolo Hotel
Cortona Old Town
9.4 out of 10, Exceptional, (20 reviews)
"This is such an amazing hotel in such an amazing place! "
United States
mansoor
B&B Piccolo Hotel
Exterior

Borgo Dolciano

Borgo Dolciano
Chiusi
9.0 out of 10, Wonderful, (25 reviews)
"Lovely restored Tuscan villa and farmhouse. Very comfortable stay. Felt that the people who run it do so with a lot of heart and style. Great value too. "
Canada
Carla
The price is 3.851.758 ₫
4.298.370 ₫ total
includes taxes & fees
7 Mar - 8 Mar
Borgo Dolciano
Breakfast area

Locanda Antico Borgo

Locanda Antico Borgo
Civitella in Val di Chiana
9.2 out of 10, Wonderful, (20 reviews)
"What an absolutely beautiful stay, in a stunning place. Our host was attentive and kind, and the food was wonderful. The hotel and rooms were spotlessly clean, and particularly for my needs on a road trip with my 18 year old son, the accommodation offering two adjoining bedrooms was perfect, and we could park outside. Also very good value in my opinion. I would definitely return, it’s also ideal for couples and I would love to bring my wife here. "
United Kingdom
Mr Andy
The price is 3.161.903 ₫
3.478.093 ₫ total
includes taxes & fees
2 Mar - 3 Mar
Locanda Antico Borgo
Romantic Double Room, 1 Queen Bed, Hot Tub, Ground Floor | Private spa tub

DormiVeglia B&B

DormiVeglia B&B
Monte San Savino
10.0 out of 10, Exceptional, (27 reviews)
"Amazing, warm, sweet, lovely, such a gem of a place!"
American Samoa
Melissa Hyun Joo
DormiVeglia B&B
Exterior

Artisti del Cavallo Tourism

Artisti del Cavallo Tourism
Foiano della Chiana
8.4 out of 10, Very good, (24 reviews)
"Good house for one night. "
Germany
Heiner
The price is 2.232.919 ₫
2.517.770 ₫ total
includes taxes & fees
2 Mar - 3 Mar
Artisti del Cavallo Tourism
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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Top Ossaia Hotel Reviews

Albergo San Biagio

Albergo San Biagio

10/10 Excellent
"Muy amable "
Arturo 3-night trip
Posted 1 month ago
Albergo San Biagio

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 Giuseppe Garibaldi Memorial and Villa Bramasole.

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.