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Dec 26 - Dec 27
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Dec 27 - Dec 28
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Dec 26 - Dec 28
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Jan 2 - Jan 4

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Our top choices for Ossaia hotels

Exterior
Palazzo Pio III

Palazzo Pio III

Palazzo Pio III
Sarteano
10.0 out of 10, Exceptional, (3)
Palazzo Pio III offers free WiFi and onsite spa services in this historic Italian town. After exploring nearby hiking trails, you're just minutes from Sarteano Castle and the Archaeological Museum. Mountain biking adventures await.
"Great stay at this hotel. Amazing breakfast and very warm welcome. I highly recommend Palazzo Pio III! Everything was perfect!"
Canada
Geneviève
Palazzo Pio III
Terrace/patio
La Gustea Hotel & Cucina

La Gustea Hotel & Cucina

La Gustea Hotel & Cucina
4.0 star property
Sarteano
9.0 out of 10, Wonderful, (37)
Mediterranean flavors await at this family-friendly retreat near Sarteano Castle. After enjoying the on-site restaurant and bar, explore nearby Archaeological Museum. With free breakfast, parking, and WiFi, plus garden views, this railway-accessible gem creates lasting memories.
"The staff was friendly and helpful"
United States
carol
La Gustea Hotel & Cucina
Front of property
Hotel Rosati

Hotel Rosati

Hotel Rosati
3.0 star property
Chiusi
8.4 out of 10, Very Good, (45)
Admire scenic views from the rooftop terrace of this Tuscan retreat near Cantina Olivi Le Buche. Enjoy local cuisine at Nonna Rosa, workout in the fitness center, or relax at the bar. With free WiFi and parking, exploration is effortless.
"Perfect. Perfect. "
Canada
Andrei
Hotel Rosati
Property grounds
Villa Hotel del Sole

Villa Hotel del Sole

Villa Hotel del Sole
3.0 star property
Chiusi
8.6 out of 10, Excellent, (28)
Discover the serene charm of this boutique hotel, where a rooftop terrace offers spectacular views of the Tuscan landscape. Located near Cantina Olivi Le Buche, guests enjoy free breakfast, WiFi, and parking while exploring Chiusi's treasures.
"Clean, great location off the highway and very friendly staff. "
Canada
Leonardo
The price is ￥13,358
￥15,060 total
includes taxes & fees
Jan 24 - Jan 25, 2026
Villa Hotel del Sole
Terrace/patio
Hotel Monica

Hotel Monica

Hotel Monica
3.0 star property
Chianciano Terme
7.8 out of 10, Good, (28)
Soak in panoramic views from the scenic rooftop terrace at this Italian retreat. Just a short drive from Terme di Chianciano and Piazza Italia, guests enjoy complimentary breakfast, WiFi, and parking plus an inviting bar and restaurant.
"Clean hotel. Area around is run down "
United States
ELVIRA
The price is ￥9,316
￥10,835 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Hotel Monica
Exterior
Palazzo Belvedere Chianciano Terme

Palazzo Belvedere Chianciano Terme

Palazzo Belvedere Chianciano Terme
Chianciano Terme
10.0 out of 10, Exceptional, (3)
Escape to a serene retreat in Chianciano Terme, just moments from Terme di Chianciano and Piscine Termali Theia. Enjoy complimentary breakfast at the café, sip drinks at the bar, or relax on the terrace after a day of wellness.
"La camera è un po' fredda, ma c'è il condizionatore che permette di regolare la temperatura. Il personale è cortese e disponibile. Ottima struttura."
Italy
Francesca
The price is ￥10,613
￥12,041 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Palazzo Belvedere Chianciano Terme
Garden
Grand Hotel Milano

Grand Hotel Milano

Grand Hotel Milano
4.0 star property
Chianciano Terme
8.0 out of 10, Very Good, (45)
Situated in charming Chianciano Terme near Piazza Italia and thermal attractions, this hotel offers massage services, a garden, and bar for relaxation. Free WiFi and parking make exploring the Italian countryside convenient and comfortable.
"."
Italy
Andrea
The price is ￥20,037
￥22,776 total
includes taxes & fees
Dec 27 - Dec 28
Grand Hotel Milano
Local cuisine
Grand Hotel Terme

Grand Hotel Terme

Grand Hotel Terme
4.0 star property
Chianciano Terme
8.0 out of 10, Very Good, (63)
Soak in wellness at this Chianciano Terme spa hotel with local cuisine at Bellevue restaurant. Unwind with massages and body treatments before exploring nearby Piscine Termali Theia. Free WiFi and parking enhance a rejuvenating Tuscan retreat.
"Old but maintained well. Quiet and easy"
United States
Amy
The price is ￥13,081
￥15,124 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Grand Hotel Terme
Breakfast, lunch, dinner served; Regional cuisine
Albergo Angiolino

Albergo Angiolino

Albergo Angiolino
3.0 star property
Chianciano Terme
8.8 out of 10, Excellent, (85)
Escape to this welcoming Italian hotel offering free breakfast, WiFi, and parking. Unwind with drinks at the bar or enjoy meals at the on-site restaurant. The peaceful garden and terrace provide perfect spots to relax after exploring nearby Piazza Italia and Terme di Chianciano.
"Breakfast was lovely with kind service. "
United States
Shay
The price is ￥14,399
￥16,427 total
includes taxes & fees
Jan 17 - Jan 18, 2026
Albergo Angiolino
Exterior
Grand Hotel Excelsior

Grand Hotel Excelsior

Grand Hotel Excelsior
4.0 star property
Chianciano Terme
8.4 out of 10, Very Good, (79)
Enjoy panoramic views from the rooftop terrace of this Art Deco hotel with an outdoor pool and sauna. Located near Piazza Italia and Terme di Chianciano, this retreat offers free breakfast, WiFi, and parking, plus a bar and deli for refreshments.
"The front hotel staff was excellent! The hotel was nice and a great place to stay!"
United States
Colette
Grand Hotel Excelsior
Couples treatment rooms, sauna, hot tub, steam room, Turkish bath
Grand Hotel Admiral Palace

Grand Hotel Admiral Palace

Grand Hotel Admiral Palace
4.0 star property
Chianciano Terme
8.2 out of 10, Very Good, (307)
Escape to this spa hotel in Chianciano Terme, just minutes from Piazza Italia and Terme di Chianciano. Enjoy rejuvenating massages and facials, dine at the restaurant, or unwind at the poolside bar after exploring the countryside. Free breakfast, WiFi, and parking included.
"The staff was very helpful and nice. Safe neighborhood and quiet."
United States
Anteneh
The price is ￥13,862
￥15,983 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Grand Hotel Admiral Palace
Property grounds
Residenza Dei Ricci Relais

Residenza Dei Ricci Relais

Residenza Dei Ricci Relais
Chiusi
10.0 out of 10, Exceptional, (36)
Wake up to the charm of Chiusi at this countryside relais. Enjoy the seasonal pool and garden after exploring nearby Etruscan museums. Free breakfast, WiFi and parking enhance your stay, while massages offer relaxation between sightseeing adventures.
"Great breakfast and very comfortable bed"
United States
Mitchell
Residenza Dei Ricci Relais
Reception
Hotel Montecarlo

Hotel Montecarlo

Hotel Montecarlo
3.0 star property
Chianciano Terme
8.6 out of 10, Excellent, (103)
Located near Chianciano Art Museum and Piazza Italia, this hotel offers a refreshing outdoor pool and restaurant serving local dishes. Relax with a drink at the bar or unwind on the terrace amid garden surroundings.
"Tutto bene "
Italy
Leonardo
The price is ￥21,641
￥24,393 total
includes taxes & fees
Dec 28 - Dec 29
Hotel Montecarlo
Lobby sitting area
Albergo Villa Gaia

Albergo Villa Gaia

Albergo Villa Gaia
Chianciano Terme
10.0 out of 10, Exceptional, (4)
Conveniently located near Chianciano Art Museum and Piazza Italia, this welcoming hotel offers free WiFi and daily housekeeping. Start each morning with a complimentary breakfast served from 8:00 AM in this picturesque Tuscan setting.
"Really enjoyed our stay here. "
United States
Benjamin
The price is ￥10,550
￥17,024 total
includes taxes & fees
Jan 14 - Jan 15, 2026
Albergo Villa Gaia
Property entrance
Hotel Perugina

Hotel Perugina

Hotel Perugina
3.0 star property
Chianciano Terme
8.2 out of 10, Very Good, (182)
Savor Italian hospitality near Chianciano Art Museum and Terme Sant'Elena. This cozy retreat offers convenient amenities including free WiFi, complimentary parking, room service, and a welcoming bar where you can unwind after exploring local attractions.
"The stay was good but you could hear people talking and laughing above , beside and below quite clearly."
Canada
Nicholas
The price is ￥7,289
￥8,606 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Hotel Perugina
Indoor pool
Hotel Villa Ricci

Hotel Villa Ricci

Hotel Villa Ricci
3.0 star property
Chianciano Terme
8.2 out of 10, Very Good, (223)
Soak in panoramic views from the rooftop terrace at this Chianciano Terme hotel. Relax with deep-tissue massages at the spa after a swim in the indoor pool. Enjoy free breakfast and WiFi, with easy access to Terme Sant'Elena.
"The hotel was nice. Clean rooms with a balcony where we saw a beautiful sunrise. Breakfast was really nice with lots of choice. Good parking and a nice area."
United States
Sushil
Hotel Villa Ricci
Seasonal outdoor pool, sun loungers
Al Giardino degli Etruschi

Al Giardino degli Etruschi

Al Giardino degli Etruschi
Chiusi
9.8 out of 10, Exceptional, (35)
"Beautiful place to visit. Wonderful attentive hosts Chickens very entertaining. Loved it here"
United States
Susan
Al Giardino degli Etruschi
Standard Double or Twin Room | Minibar, in-room safe, desk, blackout drapes
Hotel I Due Cigni

Hotel I Due Cigni

Hotel I Due Cigni
3.0 star property
Montepulciano
9.4 out of 10, Exceptional, (432)
Discover Italian hospitality at this Montepulciano gem with restaurant dining and a welcoming bar. Enjoy the tranquil garden terrace while staying close to popular thermal spas. Room service and free WiFi enhance your authentic Tuscan escape.
"Hotel was clean and owners were very friendly and helpful with getting around."
Canada
Douglas F.
Hotel I Due Cigni
Seasonal outdoor pool, pool umbrellas, sun loungers
Porsenna Resort

Porsenna Resort

Porsenna Resort
Castiglione del Lago
9.4 out of 10, Exceptional, (46)
Enjoy the relaxed countryside ambiance of this Castiglione del Lago retreat. The seasonal outdoor pool with poolside bar creates a perfect summer escape. Free perks include breakfast, WiFi and parking, while nearby attractions and a welcoming cafe round out your Italian getaway.
"Beautiful view and beautiful place to be out of town. "
United States
norma
The price is ￥19,185
￥21,398 total
includes taxes & fees
Dec 27 - Dec 28
Porsenna Resort
Indoor pool, open 9:00 AM to midnight, sun loungers
Albergo San Biagio

Albergo San Biagio

Albergo San Biagio
3.0 star property
Montepulciano
8.6 out of 10, Excellent, (201)
Relax in the Italian countryside at this hotel with an indoor pool and a children's pool. Enjoy Thai massages at the spa and Italian cuisine at Ristorante San Biagio. San Biagio and Torre del Pulcinella attractions are just minutes away.
"Great place to stay"
Canada
Robert
The price is ￥99,778
￥110,490 total
includes taxes & fees
Dec 31 - Jan 1, 2026
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

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

10/10 Excellent
"Everything was perfect! Would like to give this Property a 6 Star rating. The staff made you feel like royalty!!"
Sabrina 4-night trip
Posted 7 days ago
Monastero di Cortona Hotel & Spa

More cheap stays in Ossaia

Hotel La Terrazza di Montepulciano

Hotel La Terrazza di Montepulciano

Via Pié al Sasso 16 Montepulciano SI
The price is ￥18,367 per night from Dec 28 to Dec 29
￥18,367
￥20,939 total
Dec 28 - Dec 29
includes taxes & fees
9.2/10 Wonderful! (196 reviews)

Frequently asked questions

Where is the best place for a stay in Ossaia?
Located 18 mi (29 km) from the heart of Ossaia, A Point Arezzo Park Hotel is a top choice for your stay based on our traveler data. Other good choices for your visit to the area are Monastero di Cortona Hotel & Spa and Relais Villa Grazianella - UNA Esperienze. See all available top hotels, or vacation rentals in Ossaia.
What are some of the best vacation home rentals that Ossaia has to offer?
INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING: This vacation home near Ossaia is located in the city center and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a terrace, a garden, and a selection of books so you can immerse yourself in your vacation. See all vacation rentals in Ossaia.
If I need to cancel my hotel reservation in Ossaia, will I receive a refund?
Yes! You'll find that most hotel room reservations are fully refundable if cancelled before the accommodation's cancellation deadline, which is usually within 24-48 hours of check in. If your reservation is non-refundable, it might still be possible to cancel it and get a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Ossaia.
Where can I learn more about changing or cancelling my trip to Ossaia?
For additional details about rescheduling or cancelling your trip to Ossaia, click here.
What are some hotels with pools in Ossaia?
A Point Arezzo Park Hotel: Features 2 restaurants, a seasonal outdoor pool, and a full-service spa. Monastero di Cortona Hotel & Spa and Relais Villa Grazianella - UNA Esperienze are a couple of other choices that feature an onsite pool. View all hotels with pools in Ossaia.
What is the best hotel near Peretola Airport (FLR)?
Hotel Cosmopolitan is a popular 4-star hotel featuring free WiFi and a bar. It's located a short 0.7 mi (1.2 km) from Peretola Airport. Other good choices close to the airport are Best Western Plus CHC Florence and Hotel Mirage.
What is staying in Ossaia like?
Travelers to Ossaia will find plenty to explore and enjoy. In Ossaia, there are 15 hotels and other accommodations to choose from. Find out more about Ossaia.
What are the top places to visit in Ossaia?
Places to visit in the wider area include Giuseppe Garibaldi Memorial, Villa Bramasole, and Piazza della Repubblica. You'll also find Signorelli Theatre and La Braccesca Winery in the area. Check out what more to see and do in Expedia's Ossaia guide.
What's the weather like in Ossaia?
The hottest months are usually August and July with an average temp of 71°F, while the coldest months are January and February with an average of 42°F. Average annual precipitation for Ossaia is 36 inches.

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