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Our top choices for Ossaia hotels

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa
5.0 star property
Cortona Old Town
10.0 out of 10, Exceptional, (260 reviews)
"Excellent hotel Staff very knowledgeable and friendly Loved everything about our stay and will return. "
Canada
Florence and Robert
The price is CA $394
CA $440 total
includes taxes & fees
Mar 15 - Mar 16
Monastero di Cortona Hotel & Spa

Cento Passi Dal Duomo

Cento Passi Dal Duomo
Arezzo Centro Storico
9.2 out of 10, Wonderful, (37 reviews)
"Very well located to visit the town"
United States
Miguel
Cento Passi Dal Duomo

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 $211
CA $239 total
includes taxes & fees
Feb 16 - Feb 17
La Locanda di San Francesco

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 CA $103
CA $119 total
includes taxes & fees
Feb 17 - Feb 18
Residenza Fabroni

Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (167 reviews)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is CA $114
CA $131 total
includes taxes & fees
Feb 26 - Feb 27
Abbadia Sicille Relais

Meublè Evoè

Meublè Evoè
Montepulciano
9.4 out of 10, Exceptional, (52 reviews)
"Hosts are amazing, great location and the breakfast was excellent."
United States
luis
Meublè Evoè

Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (128 reviews)
"Great hosts, central location "
United States
Alexander
The price is CA $136
CA $157 total
includes taxes & fees
Feb 15 - Feb 16
Bed & Breakfast Vicolo dell'Oste

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
The price is CA $152
CA $208 total
includes taxes & fees
Feb 19 - Feb 20
Affitacamere Maria Gabriella

Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.8 out of 10, Exceptional, (87 reviews)
"Amazing room staff atmoshpehere, there is no other hotel my wife will stay at in the heart of the town."
United States
Michael.
Meublé Il Riccio

Hotel La Terrazza di Montepulciano

Hotel La Terrazza di Montepulciano
2.0 star property
Montepulciano
9.2 out of 10, Wonderful, (200 reviews)
"Great family owned hotel in the centre of the town "
United Kingdom
Jonathan
The price is CA $161
CA $184 total
includes taxes & fees
Feb 15 - Feb 16
Hotel La Terrazza di Montepulciano

I Capricci di Merion Resort & Spa

I Capricci di Merion Resort & Spa
Tuoro sul Trasimeno
9.8 out of 10, Exceptional, (46 reviews)
"This property is so beautiful and the food at the resturant was fantastic. Our only complaint was the spa, the sauna was great, but the hottub was lukewarm and there was so much chlorine it made our eyes burn and we had to get out almost immediately. Otherwise a perfect experience!"
United States
Bliss
The price is CA $223
CA $245 total
includes taxes & fees
Feb 26 - Feb 27
I Capricci di Merion Resort & Spa

Palazzo Nobile di San Donato

Palazzo Nobile di San Donato
Montepulciano
9.4 out of 10, Exceptional, (72 reviews)
"Simply amazing!"
United States
Todd
The price is CA $218
CA $246 total
includes taxes & fees
Mar 5 - Mar 6
Palazzo Nobile di San Donato

Albergo San Biagio

Albergo San Biagio
3.0 star property
Montepulciano
8.6 out of 10, Excellent, (203 reviews)
"Great place to stay"
Canada
Robert
Albergo San Biagio

Agriturismo Antica Corte

Agriturismo Antica Corte
Montepulciano
9.8 out of 10, Exceptional, (33 reviews)
"Such an amazing and unique experience. Lovely property, exceeded our expectations and will definitely be one we recommend to all our friends and family!"
United Kingdom
Farah
The price is CA $175
CA $203 total
includes taxes & fees
Feb 15 - Feb 16
Agriturismo Antica Corte

Agriturismo Sanguineto

Agriturismo Sanguineto
Montepulciano
9.2 out of 10, Wonderful, (105 reviews)
"This hotel is beautiful I would 100% be recommending this beautiful place to everyone I know. Staff was super nice and helpful the food was delicious. Definitely coming back "
United States
Susana
The price is CA $180
CA $204 total
includes taxes & fees
Feb 17 - Feb 18
Agriturismo Sanguineto

Antico Sipario Boutique Hotel, BW Signature Collection

Antico Sipario Boutique Hotel, BW Signature Collection
Paciano
10.0 out of 10, Exceptional, (13 reviews)
"The hotel was incredible, would highly recommend it. The town is so cute. The host was great, their breakfast was homemade and so delicious. We will be back! "
United States
Natalya
The price is CA $140
CA $157 total
includes taxes & fees
Feb 15 - Feb 16
Antico Sipario Boutique Hotel, BW Signature Collection

Hotel Boutique Castiglione del Lago

Hotel Boutique Castiglione del Lago
4.0 star property
Contrada Castello
9.8 out of 10, Exceptional, (45 reviews)
"It was a great place to stay, modern, clean, friendly local staff."
Germany
Jamie
The price is CA $158
CA $182 total
includes taxes & fees
Feb 20 - Feb 21
Hotel Boutique Castiglione del Lago

EcoResort Il Cantico della Natura

EcoResort Il Cantico della Natura
Magione
9.0 out of 10, Wonderful, (60 reviews)
"Beautiful peaceful place!!!"
United States
Meg
The price is CA $126
CA $145 total
includes taxes & fees
Feb 23 - Feb 24
EcoResort Il Cantico della Natura

Locanda Vesuna

Locanda Vesuna
3.0 star property
Trequanda
9.4 out of 10, Exceptional, (52 reviews)
"Such a quiet and beautiful property, the hosts provided everything that was needed, and the location was great for visiting local Cantinas and Vineyards "
United States
Justin
The price is CA $120
CA $137 total
includes taxes & fees
Feb 17 - Feb 18
Locanda Vesuna

La Corte Medicea

La Corte Medicea
Montepulciano
9.0 out of 10, Wonderful, (37 reviews)
"We loved our stay."
United States
Donna
The price is CA $169
CA $193 total
includes taxes & fees
Feb 15 - Feb 16
La Corte Medicea
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

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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 $103 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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