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Check availability on Ossaia Romantic Hotels

Our top choices for Ossaia romantic hotels

Property grounds

Il Poggio dell'Eremita

Il Poggio dell'Eremita
Sinalunga
10.0 out of 10, Exceptional, (59 reviews)
"Fantastic place! Great location. "
Canada
Paul Q.
The price is ￥25,175
￥29,096 total
includes taxes & fees
Apr 19 - Apr 20
Il Poggio dell'Eremita
Property grounds

Romantic farm in the Sienese hills

Romantic farm in the Sienese hills
Trequanda, Siena
8.0 out of 10, Very Good, (1 review)
"Gemischt.Sehr gut: Zentrale Lage, viele Ausflugsmöglichkeiten (Siena, Cortona, Arezzo Pienza). Gepflegt, schöner Pool. Antonio ist die gute Seele des Hauses, freundlich, hilfsbereit und scheinbar immer fröhlich.Gut: Ausstattung des Hauses (wir haben im kleineren Poggiolino) gewohnt.Nicht gut: Zentrale Lage, direkt an einer wichtigen Regionalstraße. Also Ruhe in den Hügeln der Toskana hatten wir uns anders vorgestellt... Und:Im Schlafzimmer (UG) war es sehr warm (bei hohen Außentemperaturen)....
Germany
Heike K.
The price is ￥20,165
￥38,276 total
includes taxes & fees
Apr 15 - Apr 16
Romantic farm in the Sienese hills
Fridge, microwave, stovetop, dishwasher

"Il Focolare" Superior Apartment in Monticchiello

"Il Focolare" Superior Apartment in Monticchiello
Monticchiello
10.0 out of 10, Exceptional, (8 reviews)
"An wonderfully presented apartment in a beautiful town away from the tourist areas but close enough with a short drive. It’s a beautiful town and the apartment is a welcome retreat when you have enjoyed enough of the Tuscan sun. It’s clear the owner has attention to detail and that made our stay even better! "
Australia
Dan
The price is ￥17,738
￥21,846 total
includes taxes & fees
Apr 15 - Apr 16
"Il Focolare" Superior Apartment in Monticchiello
Pool

Zampugna Estate - Spigo's cottage

Zampugna Estate - Spigo's cottage
Torrita di Siena
10.0 out of 10, Exceptional, (1 review)
"This is a great place within a beautiful setting. The view of the Tuscan countryside is amazing. Our cottage was small, but neat and tidy. Perfect for 2 people while visiting southern Tuscany. Our host Ricardo was great and very helpful."
United States
Karen F.
The price is ￥44,812
￥61,430 total
includes taxes & fees
Apr 15 - Apr 16
Zampugna Estate - Spigo's cottage
Interior

Boutique Apartment Eleganza

Boutique Apartment Eleganza
Chiusi Scalo
9.6 out of 10, Exceptional, (5 reviews)
"Amazing apartment!So close to the train!"
United States
Ryan W.
The price is ￥14,683
￥17,913 total
includes taxes & fees
Apr 16 - Apr 17
Boutique Apartment Eleganza
2 bedrooms, desk, iron/ironing board, travel crib

The house in the village - Angelica apartment - Vald'Orcia

The house in the village - Angelica apartment - Vald'Orcia
Monticchiello
10.0 out of 10, Exceptional, (11 reviews)
"Marco was great to work with, was easily available for any of our questions and the stay was wonderful. The apartment is in a great location and had all we needed for our stay."
United States
Melissa B.
The price is ￥18,485
￥22,219 total
includes taxes & fees
May 10 - May 11
The house in the village - Angelica apartment - Vald'Orcia
Terrace/patio

Rosmarino - Estate Zampugna

Rosmarino - Estate Zampugna
Torrita di Siena
The price is ￥52,281
￥66,098 total
includes taxes & fees
Apr 19 - Apr 20
Rosmarino - Estate Zampugna
Interior

La Finestra sul Teatro

La Finestra sul Teatro
Cortona Old Town
9.8 out of 10, Exceptional, (36 reviews)
"This was perfectly clean. The host was perfect."
United States
Michelle H.
The price is ￥24,367
￥36,877 total
includes taxes & fees
Apr 19 - Apr 20
La Finestra sul Teatro
Interior

Elegant apartment in the heart of the historical area

Elegant apartment in the heart of the historical area
Arezzo Centro Storico
10.0 out of 10, Exceptional, (28 reviews)
"Excellent location to explore the town and surrounding areas"
United States
Marina
The price is ￥16,871
￥23,057 total
includes taxes & fees
Apr 20 - Apr 21
Elegant apartment in the heart of the historical area
Exterior

Luxury Tuscan Villa in Val d'Orcia, visit Montepulciano, Pienza and hot Springs!

Luxury Tuscan Villa in Val d'Orcia, visit Montepulciano, Pienza and hot Springs!
Chianciano Terme
9.4 out of 10, Exceptional, (10 reviews)
"What a lovely villa to call home for a few days! The villa itself is so big while also being cozy, the beds comfortable, the grounds beautiful, the view of the landscape breathtaking. We couldn't ask for a more helpful, lovey host who goes above and beyond to attend to her guests' needs. The venue has a hot tub that Fulvia offered to heat up for us if we were interested, and we enjoyed a glass of wine on the sunlit patio each evening. Be sure to bring layers if you visit Tuscany during...
United States
Laura M.
The price is ￥78,421
￥106,428 total
includes taxes & fees
Apr 15 - Apr 16
Luxury Tuscan Villa in Val d'Orcia, visit Montepulciano, Pienza and hot Springs!
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

Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World

10/10 Excellent
"We really enjoyed the hotel, very clean, good atmosphere!!! "
Anat 1-night trip
Posted 4 days ago
Villa di Piazzano - Small Luxury Hotel of the World
Grand Hotel Admiral Palace

Grand Hotel Admiral Palace

10/10 Excellent
"The staff was very helpful and nice. Safe neighborhood and quiet."
Anteneh 3-night trip
Posted 10 months ago
Grand Hotel Admiral Palace

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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