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Our top choices for Ossaia hotels

Albergo San Biagio

Albergo San Biagio
3.0 star property
Montepulciano
8.6 out of 10, Excellent, (206 reviews)
"Great place to stay"
Canada
Robert
The price is CA $77
CA $91 total
includes taxes & fees
Apr 29 - Apr 30
Albergo San Biagio

Hotel La Darsena

Hotel La Darsena
3.0 star property
Passignano sul Trasimeno
8.0 out of 10, Very good, (52 reviews)
"Great rest stop on our way to Rome. There is no direct access to the lake (it's about a 2 km walk/drive from the hotel), but the hotel is clean and nice. Staff were extremely helpful and friendly, and the free continental breakfast was wonderful! Great selection of pastries, and two very excellent coffee/cappuccino machines. Overall, a great place to rest, in a quiet, peaceful area."
United States
Jose
The price is CA $93
CA $107 total
includes taxes & fees
Apr 7 - Apr 8
Hotel La Darsena

Hotel Villa Ricci

Hotel Villa Ricci
3.0 star property
Chianciano Terme
8.2 out of 10, Very good, (225 reviews)
"Hotel villa ricci was a lovely relaxing stay and a great central place to stay "
United Kingdom
Kirsty
The price is CA $89
CA $103 total
includes taxes & fees
Apr 8 - Apr 9
Hotel Villa Ricci

Palazzo Brandano

Palazzo Brandano
Trequanda
9.6 out of 10, Exceptional, (78 reviews)
"Room and breakfast is great but a 20 minute drive to Pienza very cute area"
United States
Suzanne
The price is CA $108
CA $124 total
includes taxes & fees
Apr 9 - Apr 10
Palazzo Brandano

Casa Bellavista

Casa Bellavista
Cortona
10.0 out of 10, Exceptional, (20 reviews)
"Beautiful villa and property in the Tuscan hills. Gorgeous view of Cortona. Simonetta was a wonderful host and had wonderful breakfast each morning and cooking classes in afternoon. We really enjoyed our stay. "
United States
Gina
The price is CA $268
CA $301 total
includes taxes & fees
Apr 8 - Apr 9
Casa Bellavista

Fondaco del Moro

Fondaco del Moro
Civitella in Val di Chiana
9.6 out of 10, Exceptional, (37 reviews)
"Excellent breakfast, clean, quiet room. "
United States
Sheily
The price is CA $98
CA $108 total
includes taxes & fees
Apr 8 - Apr 9
Fondaco del Moro

Villa Tiberini Wine Relais

Villa Tiberini Wine Relais
Torrita di Siena
The price is CA $242
CA $270 total
includes taxes & fees
Apr 1 - Apr 2
Villa Tiberini Wine Relais

Il Monte

Il Monte
3.0 star property
Monte San Savino
8.6 out of 10, Excellent, (39 reviews)
"Ottimo hotel"
Italy
Tommaso
The price is CA $89
CA $144 total
includes taxes & fees
Apr 15 - Apr 16
Il Monte

Palazzo Carletti

Palazzo Carletti
Montepulciano
9.8 out of 10, Exceptional, (241 reviews)
"Beautiful hotel in a beautiful little town. Staff was very nice and helpful; breakfast was excellent and check in communication was top notch."
United States
Margaret
The price is CA $330
CA $370 total
includes taxes & fees
Apr 30 - May 1
Palazzo Carletti

Borgo Sant'Ambrogio Resort

Borgo Sant'Ambrogio Resort
5.0 star property
Trequanda
9.8 out of 10, Exceptional, (101 reviews)
"It was very clean, excellent service and communication with every staff member was great, location was incredible, and overall a very pleasant stay. If you have the opportunity, the stay is great!"
United States
Juan Carlos
The price is CA $242
CA $271 total
includes taxes & fees
Apr 6 - Apr 7
Borgo Sant'Ambrogio Resort

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 CA $208
CA $236 total
includes taxes & fees
Apr 21 - Apr 22
La Locanda di San Francesco

Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.8 out of 10, Exceptional, (91 reviews)
"Staff is great and many good restaurants in short walking distance."
United States
Mark
The price is CA $223
CA $252 total
includes taxes & fees
Apr 4 - Apr 5
Meublé Il Riccio

Il Gentiluomo Hotel & SPA

Il Gentiluomo Hotel & SPA
4.0 star property
Arezzo
8.6 out of 10, Excellent, (154 reviews)
"3 star hotel only"
Canada
David Joseph
The price is CA $81
CA $99 total
includes taxes & fees
Apr 27 - Apr 28
Il Gentiluomo Hotel & SPA

Hotel La Terrazza di Montepulciano

Hotel La Terrazza di Montepulciano
2.0 star property
Montepulciano
9.4 out of 10, Exceptional, (203 reviews)
"Very clean and the owner was very delightful "
Canada
Chad
The price is CA $160
CA $182 total
includes taxes & fees
Apr 10 - Apr 11
Hotel La Terrazza di Montepulciano

Santa Caterina Hotel & Bike

Santa Caterina Hotel & Bike
3.0 star property
Chianciano Terme
9.6 out of 10, Exceptional, (96 reviews)
"Used as an overnight stop to S Italy, this hotel was very convenient for the A1 and excellent value for money. The owner/manager is welcoming, helpful and speaks good English. Generous breakfast with delicious fresh pasties made by the owners brother."
United Kingdom
M Roderick
The price is CA $99
CA $114 total
includes taxes & fees
Apr 8 - Apr 9
Santa Caterina Hotel & Bike

Hotel Villa Paradiso

Hotel Villa Paradiso
4.0 star property
Passignano sul Trasimeno
7.6 out of 10, Good, (91 reviews)
"Stayed for 3 Nights really nice little place slightly expensive on the drinks though, the staff were lovely, it’s a shame they don’t have WI-Fi in the Bedrooms something the hotel should consider "
United Kingdom
Serena
The price is CA $109
CA $127 total
includes taxes & fees
Apr 7 - Apr 8
Hotel Villa Paradiso

Hotel Forum

Hotel Forum
4.0 star property
Foiano della Chiana
8.2 out of 10, Very good, (72 reviews)
"Great pool"
United States
Hassan
The price is CA $165
CA $187 total
includes taxes & fees
Apr 4 - Apr 5
Hotel Forum

Relais Villa Grazianella - UNA Esperienze

Relais Villa Grazianella - UNA Esperienze
Montepulciano
9.8 out of 10, Exceptional, (284 reviews)
"Absolutely breathtaking property. The staff was extremely welcoming and helpful. Truly such a beautiful experience. Highly recommend to anyone "
United States
Lisbet
The price is CA $346
CA $387 total
includes taxes & fees
Apr 28 - Apr 29
Relais Villa Grazianella - UNA Esperienze

Relais Villa Baldelli

Relais Villa Baldelli
4.0 star property
Cortona
9.2 out of 10, Wonderful, (130 reviews)
"Beautiful place. Fantastic staff and breakfast. Close to Corrona, Assisi Arezzo. And a great cooking class. You will be glad you stayed here. "
United States
Michael
The price is CA $172
CA $202 total
includes taxes & fees
Apr 24 - Apr 25
Relais Villa Baldelli

B&B Hotel Arezzo

B&B Hotel Arezzo
3.0 star property
Arezzo
8.4 out of 10, Very good, (354 reviews)
"great hotel"
Italy
Marco
The price is CA $82
CA $100 total
includes taxes & fees
Apr 23 - Apr 24
B&B Hotel Arezzo
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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Frequently asked questions

What is the best area to stay in Ossaia?
The best area to stay in Ossaia is the area immediately surrounding the main piazza, as this is where you'll find the heart of the village.

This central part of Ossaia is compact and easily walkable, with the piazza serving as a focal point for village life. You'll find a few local shops and eateries here, and it's where residents gather. The historic church is also located just off the piazza, adding to the village's character.

For couples looking for a romantic escape, staying in a converted farmhouse or villa just outside the village centre offers a truly authentic Tuscan experience. These properties often provide stunning views of the rolling hills and olive groves, and many come with private pools, allowing for a secluded and relaxing retreat.
When is the best time to go to Ossaia?
The best time to visit Ossaia, and Tuscany generally, is during the spring (April to June) and autumn (September to October) months. These periods offer pleasant weather and a less crowded experience.

For those planning a romantic getaway or a relaxed trip, spring is particularly lovely. The countryside is lush and green, wildflowers are in bloom, and the temperatures are comfortably warm without being too hot. This is a great time for leisurely drives through the vineyards, enjoying al fresco dining, and visiting local markets.

Couples looking for a culinary focus might prefer autumn. This season brings the grape harvest, truffle hunting season, and olive oil production, offering unique gastronomic experiences.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Ossaia.
How can I save on a Ossaia hotel booking with Expedia?
Members always get our best prices. Find our best Ossaia hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings.
How much is the nightly rate at a Ossaia hotel?
Prices for hotels in Ossaia often vary, but you can find a great deal from CA $107 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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