Find Romantic Hotels in Ossaia

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Check availability on Ossaia Romantic Hotels

Tonight
Dec 25 - Dec 26
Tomorrow
Dec 26 - Dec 27
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Ossaia romantic hotels

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)
"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
Outdoor wedding area
La Cantina Relais - Fattoria Il Cipresso

La Cantina Relais - Fattoria Il Cipresso

La Cantina Relais - Fattoria Il Cipresso
Arezzo
10.0 out of 10, Exceptional, (110)
"Stay was exceptional."
United States
Suzanne
La Cantina Relais - Fattoria Il Cipresso
Exterior
Locanda Vesuna

Locanda Vesuna

Locanda Vesuna
3.0 star property
Trequanda
9.4 out of 10, Exceptional, (52)
"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 ￥13,074
￥14,932 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Locanda Vesuna
Terrace/patio
Villa Svetoni Wine Resort

Villa Svetoni Wine Resort

Villa Svetoni Wine Resort
Montepulciano
9.6 out of 10, Exceptional, (73)
"Very nice place to go around from."
Canada
Raja
Villa Svetoni Wine Resort
Outdoor pool, sun loungers
Relais Villa Grazianella - UNA Esperienze

Relais Villa Grazianella - UNA Esperienze

Relais Villa Grazianella - UNA Esperienze
Montepulciano
9.8 out of 10, Exceptional, (279)
"Great room and service"
United States
ALFREDO
The price is ￥41,477
￥46,360 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Relais Villa Grazianella - UNA Esperienze
Couples treatment rooms, sauna, steam room, Turkish bath
Agriturismo Sanguineto

Agriturismo Sanguineto

Agriturismo Sanguineto
Montepulciano
9.0 out of 10, Wonderful, (104)
"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 ￥19,677
￥22,379 total
includes taxes & fees
Dec 29 - Dec 30
Agriturismo Sanguineto
Exterior
Grand Hotel Excelsior

Grand Hotel Excelsior

Grand Hotel Excelsior
4.0 star property
Chianciano Terme
8.4 out of 10, Very Good, (79)
"The front hotel staff was excellent! The hotel was nice and a great place to stay!"
United States
Colette
Grand Hotel Excelsior
Exterior
EcoResort Il Cantico della Natura

EcoResort Il Cantico della Natura

EcoResort Il Cantico della Natura
Magione
9.0 out of 10, Wonderful, (60)
"Beautiful peaceful place!!!"
United States
Meg
The price is ￥15,363
￥17,634 total
includes taxes & fees
Jan 8 - Jan 9, 2026
EcoResort Il Cantico della Natura
Lobby
Residenza Fabroni

Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (94)
"gorgeous historical property, very attentive host, great location"
United States
Sarah
The price is ￥13,703
￥15,809 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Residenza Fabroni
Seasonal outdoor pool, open 8:00 AM to 7:00 PM, pool umbrellas
Borgo Pulciano Agriturismo

Borgo Pulciano Agriturismo

Borgo Pulciano Agriturismo
Montone
8.6 out of 10, Excellent, (34)
"Great place & great staff. I would stay here again. "
United States
Steven
Borgo Pulciano Agriturismo
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

Abbadia Sicille Relais

Abbadia Sicille Relais

10/10 Excellent
"Room was beyond expectations. Helpful staff and overall great experience. "
Robert 1-night trip
Posted 3 weeks ago
Abbadia Sicille Relais

Frequently asked questions

Searching for romantic hotels in Ossaia?
If you and your partner need a romantic escape, we've got just the thing. If you want to get out and explore the larger area, you might head to Giuseppe Garibaldi Memorial, Villa Bramasole, or Piazza della Repubblica. If you're interested in staying near a certain attraction, you can sort properties by neighborhood or distance to top sights, so you and your partner will get to see everything on your list.
When is the best time of year for a romantic getaway to Ossaia?
If you're hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures 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.
What is there to do in Ossaia?
There's nothing better than wandering around a new place with your sweetheart, so consider taking time to discover all that Ossaia has to offer. There's plenty to see in the greater Cortona area, so you might plan to visit Giuseppe Garibaldi Memorial, Villa Bramasole, or Piazza della Repubblica.
What's the best way to get to Ossaia and around town during my romantic getaway?
These transportation options in Ossaia might help your romantic trip go off without a hitch: The closest major airport is Sant Egidio Airport (PEG), located 26.9 mi (43.3 km) from the city center. If you'd like to explore around the area, you may want a rental car for your journey.

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