Poggiolo
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Precise Tale Poggio Alla Sala
Via Poggio alla Sala 10, Montepulciano, SI
Fully refundableReserve now, pay when you stay
$393 nightly
The price is $439 total per night from Jul 29 to Jul 30
$439 total
Jul 29 - Jul 30
Total includes taxes and fees
Stay at this 5-star luxury hotel in Montepulciano. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
9.4/10 Exceptional! (100 reviews)
"beautiful property. Emanates "tuscany" amid garden and vineyards. Great villa with excellent and well chosen art. Very comfortable and quiet. Nice amenities. Would stay here again. Much appreciated it for its character and charm and of course service."
Reviewed on Jul 7, 2025
Villa di Piazzano - Small Luxury Hotel of the World
Localita Piazzano, C.P. 6, Cortona, AR
$524 nightly
The price is $585 total per night from Jul 21 to Jul 22
$585 total
Jul 21 - Jul 22
Total includes taxes and fees
Stay at this 5-star luxury hotel in Cortona. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular ...
9.6/10 Exceptional! (212 reviews)
"Would definitely come back! The Italian garden at the property is beautiful."
Reviewed on Jul 9, 2025
Nuovo Etruria Resort
Via di S. Martino snc, Montepulciano, SI
$129 nightly
The price is $147 total per night from Jul 23 to Jul 24
$147 total
Jul 23 - Jul 24
Total includes taxes and fees
Stay at this hotel in Montepulciano. Enjoy an outdoor pool, breakfast (surcharge), and daily housekeeping. Popular attractions Church of St. Agnes and Colonna ...
9.2/10 Wonderful! (20 reviews)
"Near town, not walkable to town"
Reviewed on Jul 14, 2025
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.
Abbadia Sicille Relais
SP 14 Loc. Abbadia Sicille, Trequanda, SI
Stay at this 4-star business-friendly residence in Trequanda. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions The Saints Peter and Andrew ...
8.8/10 Excellent! (155 reviews)
An amazing find. Would love to return
"An amazing place with a luxury feel. Comfy, welcoming and peacefully relaxing"
Reviewed on Nov 30, 2024
Residenza Fabroni
Via di Gracciano nel Corso, 12, Montepulciano, SI
Book a stay at this historic residence in Montepulciano. Enjoy free WiFi, an attached winery, and a rooftop terrace. Popular attractions Torre di Pulcinella ...
8.8/10 Excellent! (86 reviews)
"Just awesome"
Reviewed on Jul 6, 2025
Farmhouse in the hills with panoramic view and swimming pool
Ristonchia
Book a stay at this family-friendly vacation home in Castiglion Fiorentino. Enjoy private pools, a garden, and laundry facilities. Popular attractions Tennis ...
9.4/10 Exceptional! (66 reviews)
Family vacation
"Was wonderful and beautiful."
Reviewed on Nov 30, 2024
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.
Popular places to visit
Tennis Club Castiglionese
You can take time to visit Tennis Club Castiglionese during your travels to Castiglion Fiorentino. You can enjoy the wineries while in the area.
Agricola Buccelletti Winery
You can enjoy a tasting or tour at Agricola Buccelletti Winery during your travels to La Strada-Santa Cristina. Discover the area's countryside and wineries.
Cassero Tower
Find out about the history of Castiglion Fiorentino when you spend time at Cassero Tower. You can enjoy the wineries while in the area.
Archaeological Museum
You can browse the exhibits at Archaeological Museum, a museum with a storied past, during your trip to Castiglion Fiorentino. You can enjoy the wineries while in the area.
Vasari Loggia
You can find out about the history of Castiglion Fiorentino with a trip to Vasari Loggia. You can enjoy the wineries while in the area.
Municipal Art Gallery
You can study the exhibits at Municipal Art Gallery, a museum with a storied past, during your trip to Castiglion Fiorentino. You can enjoy the wineries while in the area.
Things to do
Traditional Tuscan Cuisine Cooking Class, Castiglion Fiorentino near Cortona
$158
per adult
Montepulciano: Wine Tour and tasting
$61
per adult
100% of travellers recommend
Private visit to the House of Grand Duke Leopold of Tuscany with invitation
$47
per adult
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- Tennis Club Castiglionese
- Visit Castiglion Fiorentino
- Casa del Re Vacations
- Municipal Art Gallery
- Castiglion Fiorentino Vacations
- Cassero Tower
- Visit La Strada-Santa Cristina
- Il Borgo Vacations
- La Strada-Santa Cristina Vacations
- Visit San Pietro a Cegliolo
- Agricola Buccelletti Winery
- Visit Castroncello
- Visit Sodo
- Visit Polvano
- Eremo Le Celle
- Visit Cortona
- Santa Maria Nuova
- Signorelli Theatre
- Museum of the Etruscan Academy
- Casali Palace
- Palazzo Comunale
- Piazza della Repubblica
- Cortona Vacations
- Where to stay in Cortona
- Visit Cortona Old Town
- Santa Margherita Basilica
- Fortress of Girifalco
- Avis Rental Cars in Castiglion Fiorentino
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- Lake Trasimeno
- Arno River
- Valdichiana Outlet Village
- Arezzo Equestrian Centre
- Piazza Grande
- Piazza Grande
- San Giovanni Terme Rapolano
- Tiber River
- Dome of Montepulciano
- Terme Antica Querciolaia
- Val di Chiana
- Centro Chirurgico Toscano
- San Donato Hospital
- Cathedral of Saints Peter and Donato
- Villa Bramasole
- Isola Maggiore
- Palazzo Avignonesi
- Palazzo Ricci
- Piazza Guido Monaco
- Piazza della Repubblica
- Basilica of San Francesco
- Anghiari Historic Town Center
- Cantina Contucci
- Cantina del Redi
- Cortona Cathedral
- Church of Santa Maria della Pieve
- Consorzio del Vino Nobile di Montepulciano
- Church of St. Agnes
- Sualzo Beach
- Castello di Magione
- Rocca del Leone