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Our top choices for Ossaia hotels

Borgo Sant'Ambrogio Resort

Borgo Sant'Ambrogio Resort
5.0 star property
Trequanda
9.6 out of 10, Exceptional, (116 reviews)
"The hotel is stunning! Beautiful sunset and sunrise time. The restaurant is superb. I really enjoyed our time here. Will come back."
United States
Lu
The price is CA $336
CA $374 total
includes taxes & fees
Jul 16 - Jul 17
Borgo Sant'Ambrogio Resort

Locanda Vesuna

Locanda Vesuna
3.0 star property
Trequanda
9.2 out of 10, Wonderful, (59 reviews)
"A wonderful place to stay! So peaceful and relaxing, the property is beautiful! Oscar & Teresa are the greatest - so welcoming and made our trip special, they went above and beyond. The food was delicious, the room was great and I would highly recommend staying at this amazing inn if you are visiting the area!"
United States
Daryl
The price is CA $156
CA $176 total
includes taxes & fees
Jul 2 - Jul 3
Locanda Vesuna

Palazzo Brandano

Palazzo Brandano
Trequanda
9.4 out of 10, Exceptional, (91 reviews)
"Very charming medieval hotel Clean and comfortable Some rooms and the breakfast outdoor patio have a fantastic view. You really feel part of Tuscany After driving through some very narrow streets, you can park on their lot very close to the hotel"
Canada
Lucia
The price is CA $153
CA $173 total
includes taxes & fees
Jul 1 - Jul 2
Palazzo Brandano

Poggio Paradiso Resort & Spa

Poggio Paradiso Resort & Spa
Torrita di Siena
10.0 out of 10, Exceptional, (28 reviews)
"Excellent room and food. Great location!"
United States
Saurabh
The price is CA $486
CA $543 total
includes taxes & fees
Jul 14 - Jul 15
Poggio Paradiso Resort & Spa

Villa Svetoni Wine Resort

Villa Svetoni Wine Resort
Montepulciano
9.6 out of 10, Exceptional, (85 reviews)
"An absolutely perfect stay. The resort is intimate with beautiful rooms, a stunning pool where you can watch the sun set under the Tuscan hills. The gardens are fragrant and lovely. Our breakfast was the perfect start to the day. We also loved the wine tasting."
United States
Jennifer
The price is CA $416
CA $464 total
includes taxes & fees
Jul 12 - Jul 13
Villa Svetoni Wine Resort

Locanda del Molino

Locanda del Molino
4.0 star property
Cortona
9.6 out of 10, Exceptional, (37 reviews)
"family run business with great hospitality and excellent food"
United Kingdom
stefania
The price is CA $150
CA $178 total
includes taxes & fees
Jul 8 - Jul 9
Locanda del Molino

Agriturismo SOLE

Agriturismo SOLE
Trequanda
The price is CA $361
CA $401 total
includes taxes & fees
Jul 1 - Jul 2
Agriturismo SOLE

Fondaco del Moro

Fondaco del Moro
Civitella in Val di Chiana
9.6 out of 10, Exceptional, (51 reviews)
"Beautiful setting, felt like we were staying in a castle! The beds were comfortable and the property was amazing. Highly recommend this place."
Canada
Heather
The price is CA $99
CA $109 total
includes taxes & fees
Jul 1 - Jul 2
Fondaco del Moro

La Gustea Hotel & Cucina

La Gustea Hotel & Cucina
4.0 star property
Sarteano
9.0 out of 10, Wonderful, (39 reviews)
"Very nice and cozy hotel . The lady who checked us in and out was fantastic"
Canada
Tarek
The price is CA $169
CA $193 total
includes taxes & fees
Jul 1 - Jul 2
La Gustea Hotel & Cucina

Hotel I Due Cigni

Hotel I Due Cigni
3.0 star property
Montepulciano
9.4 out of 10, Exceptional, (441 reviews)
"This is very comfortable and well maintained hotel with a friendly staff, good breakfast, and is very convenient for visiting the Montepulciano area."
United States
Kevin
The price is CA $132
CA $152 total
includes taxes & fees
Jul 3 - Jul 4
Hotel I Due Cigni

La Torre ai Mari

La Torre ai Mari
3.0 star property
Sarteano
9.6 out of 10, Exceptional, (29 reviews)
"The owner is very nice, the place is clean and quiet. Small but nice pool, great for hot days. No aircon and need of a car to eat (restaurant is closed) are the only two minor items."
Spain
Marco
The price is CA $162
CA $185 total
includes taxes & fees
Jul 1 - Jul 2
La Torre ai Mari

Hotel Villa Paradiso

Hotel Villa Paradiso
4.0 star property
Passignano sul Trasimeno
7.8 out of 10, Good, (96 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 $140
CA $160 total
includes taxes & fees
Jul 7 - Jul 8
Hotel Villa Paradiso

Agriturismo Sanguineto

Agriturismo Sanguineto
Montepulciano
9.2 out of 10, Wonderful, (113 reviews)
"A beautiful well maintained property. Peaceful surroundings and close to Montepulciano and Pienza."
United States
anthony
The price is CA $157
CA $180 total
includes taxes & fees
Jul 3 - Jul 4
Agriturismo Sanguineto

Hotel Italia

Hotel Italia
3.0 star property
Cortona Old Town
9.0 out of 10, Wonderful, (294 reviews)
"The hotel was well located. Beautiful views. Excellent breakfast. Very personable staff."
United States
Frances
The price is CA $159
CA $183 total
includes taxes & fees
Jul 30 - Jul 31
Hotel Italia

Palazzo Nobile di San Donato

Palazzo Nobile di San Donato
Montepulciano
9.6 out of 10, Exceptional, (79 reviews)
"Location was excelente and Hostess was great . she did all the booking for VIP transportation, restaurants , vine yards and cooking classes Thank You Valentina"
United States
Ronald
The price is CA $173
CA $197 total
includes taxes & fees
Jul 21 - Jul 22
Palazzo Nobile di San Donato

Poggio Piglia

Poggio Piglia
Chiusi
9.8 out of 10, Exceptional, (57 reviews)
"Amazing stay — very clean, great rooms, and excellent service. "
United States
Marco
The price is CA $484
CA $532 total
includes taxes & fees
Jul 1 - Jul 2
Poggio Piglia

Residenza Dei Ricci Relais

Residenza Dei Ricci Relais
Chiusi
10.0 out of 10, Exceptional, (38 reviews)
"Very nice B&B"
United States
chi
The price is CA $232
CA $265 total
includes taxes & fees
Jul 28 - Jul 29
Residenza Dei Ricci Relais

Il Falconiere - Relais e Chateaux

Il Falconiere - Relais e Chateaux
5.0 star property
Cortona
9.4 out of 10, Exceptional, (131 reviews)
"Excellent staff and experiences! We had a wonderful time."
United States
Sam
The price is CA $547
CA $615 total
includes taxes & fees
Jul 17 - Jul 18
Il Falconiere - Relais e Chateaux

Hotel La Terrazza di Montepulciano

Hotel La Terrazza di Montepulciano
2.0 star property
Montepulciano
9.4 out of 10, Exceptional, (208 reviews)
"Very clean and the owner was very delightful "
Canada
Chad
The price is CA $162
CA $184 total
includes taxes & fees
Jul 12 - Jul 13
Hotel La Terrazza di Montepulciano

Albergo San Biagio

Albergo San Biagio
3.0 star property
Montepulciano
8.6 out of 10, Excellent, (228 reviews)
"Excellent stay!"
United States
Rodolfo
The price is CA $105
CA $122 total
includes taxes & fees
Jul 7 - Jul 8
Albergo San Biagio
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

More cheap stays in Ossaia

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 $134 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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