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Our top choices for Ossaia hotels

Villa Svetoni Wine Resort

Villa Svetoni Wine Resort
Montepulciano
9.6 out of 10, Exceptional, (86 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 NZ$573
includes taxes & fees
12 July - 13 July
Villa Svetoni Wine Resort

Poggio Paradiso Resort & Spa

Poggio Paradiso Resort & Spa
Torrita di Siena
10.0 out of 10, Exceptional, (29 reviews)
"Excellent room and food. Great location!"
United States
Saurabh
The price is NZ$672
includes taxes & fees
21 July - 22 July
Poggio Paradiso Resort & Spa

Borgo Sant'Ambrogio Resort

Borgo Sant'Ambrogio Resort
5.0 star property
Trequanda
9.6 out of 10, Exceptional, (119 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 NZ$454
includes taxes & fees
16 July - 17 July
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 NZ$235
includes taxes & fees
5 July - 6 July
Locanda Vesuna

Borgo Dei Conti Resort Relais & Chateaux

Borgo Dei Conti Resort Relais & Chateaux
5.0 star property
Perugia
9.0 out of 10, Wonderful, (14 reviews)
"Great place to relax and heal"
United States
Dean
The price is NZ$1,556
includes taxes & fees
31 July - 1 Aug
Borgo Dei Conti Resort Relais & Chateaux

Agriturismo SOLE

Agriturismo SOLE
Trequanda
The price is NZ$638
includes taxes & fees
21 July - 22 July
Agriturismo SOLE

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 NZ$584
includes taxes & fees
7 July - 8 July
Poggio Piglia

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 NZ$251
includes taxes & fees
5 July - 6 July
La Torre ai Mari

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 NZ$163
includes taxes & fees
5 July - 6 July
Albergo San Biagio

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 NZ$209
includes taxes & fees
31 July - 1 Aug
Locanda del Molino

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 NZ$244
includes taxes & fees
5 July - 6 July
Palazzo Brandano

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 NZ$261
includes taxes & fees
22 July - 23 July
La Gustea Hotel & Cucina

Villa Hotel del Sole

Villa Hotel del Sole
3.0 star property
Chiusi
8.6 out of 10, Excellent, (29 reviews)
"Clean, great location off the highway and very friendly staff. "
Canada
Leonardo
The price is NZ$220
includes taxes & fees
10 July - 11 July
Villa Hotel del Sole

Lupaia

Lupaia
Torrita di Siena
10.0 out of 10, Exceptional, (73 reviews)
"One of the most special stays - from the service to the property - it was perfection! "
United States
Madeline
The price is NZ$1,522
includes taxes & fees
29 July - 30 July
Lupaia

Terra Antica Resort

Terra Antica Resort
Montepulciano
10.0 out of 10, Exceptional, (22 reviews)
"Great stay in Montepulciano "
United States
Jonathan
The price is NZ$1,023
includes taxes & fees
7 July - 8 July
Terra Antica Resort

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 NZ$285
includes taxes & fees
21 July - 22 July
Palazzo Nobile di San Donato

Hotel I Due Cigni

Hotel I Due Cigni
3.0 star property
Montepulciano
9.4 out of 10, Exceptional, (442 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 NZ$189
includes taxes & fees
5 July - 6 July
Hotel I Due Cigni

Villa Cicolina

Villa Cicolina
Montepulciano
9.6 out of 10, Exceptional, (92 reviews)
"Fantastic stay, beautiful setting and amazing food and service. One of the best hotels we've ever stayed at, will definitely be back!"
United Kingdom
Ben
The price is NZ$584
includes taxes & fees
8 July - 9 July
Villa Cicolina

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 NZ$335
includes taxes & fees
19 July - 20 July
Residenza Dei Ricci Relais

Nuovo Etruria Resort

Nuovo Etruria Resort
Montepulciano
9.2 out of 10, Wonderful, (102 reviews)
"Clean room and the staff was very helpful"
United States
Bianca
The price is NZ$208
includes taxes & fees
20 July - 21 July
Nuovo Etruria Resort
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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, although it depends on the cancellation policy of your booking. Most bookings are refundable if cancelled within 24 to 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 hotel booking in Ossaia with Expedia?
One Key™ – Expedia's free travel rewards programme – gives you instant access to perks and Member Prices on Ossaia hotels. Plus, you'll earn OneKeyCash™* on eligible bookings to use on future trips. Booking an Expedia hotel and flight package is another great way to save, where bundling can result in significant savings. *Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
How much is the nightly rate for a hotel in Ossaia?
Prices for hotels in Ossaia often vary, but you can find a great deal from NZ$202 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 our cheapest rates.

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