Visit Montecchio
Monastero di Cortona Hotel & Spa
Via del Salvatore Cortona AR
$271 nightly
The price is $308 total per night from Dec 14 to Dec 15
$308 total
Dec 14 - Dec 15
Total with taxes and fees
Book a stay at this luxury hotel in Cortona. Enjoy free breakfast, free WiFi, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ...
9.8/10 Exceptional! (254 reviews)
Our arrival experience was less than stellar for a warm welcome to property. Front desk associate was very cold and accusatory of the situation we encountered outside of the property. We have traveled extensively and I expected better arrival experience. It all changed for the better when we finally ...
Reviewed on Nov 23, 2025
Relais Villa Grazianella - UNA Esperienze
Via Grazianella 5 Montepulciano SI
$146 nightly
The price is $166 total per night from Dec 9 to Dec 10
$166 total
Dec 9 - Dec 10
Total with taxes and fees
Book a stay at this business-friendly country house in Montepulciano. Enjoy free WiFi, free parking, and an attached winery. Our guests praise the helpful staff ...
9.6/10 Exceptional! (276 reviews)
Everything was perfect. Warm welcome, comfortable and spacious rooms, great breakfast. The staff was very kind and friendly. I also recommend the wine tasting experience. Highly recommended!
Reviewed on Dec 5, 2025
Grand Hotel Admiral Palace
Via Umbria 2 Chianciano Terme SI
$87 nightly
The price is $101 total per night from Dec 11 to Dec 12
$101 total
Dec 11 - Dec 12
Total with taxes and fees
Book a stay at this spa hotel in Chianciano Terme. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Piazza Italia and Terme di Chianciano ...
8/10 Very Good! (303 reviews)
The staff was very helpful and nice. Safe neighborhood and quiet.
Reviewed on Jun 29, 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
Book a stay at this business-friendly residence in Trequanda. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Monastery of Sant'Anna ...
8.8/10 Excellent! (160 reviews)
In the middle of literally nowhere (for me) but so peaceful and serene! I love the history of this monastery. I must say as a solo traveler I was a little nervous at first because it’s very remote. I saw maybe 3 cars in the parking lot and two other guests. But it was safe! Checked in and got a restaurant ...
Reviewed on Dec 3, 2025
Farmhouse in the hills with panoramic view and swimming pool
Ristonchia Tuscany
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! (72 reviews)
Family vacation
Was wonderful and beautiful.
Reviewed on Nov 30, 2024
Il Poggio dell'Eremita
Sinalunga Tuscany
Stay at this villa in Sinalunga. Enjoy free WiFi, a garden, and patios. Popular attractions Torre Il Cassero and Piazza del Tribunal are located nearby.
10/10 Exceptional! (58 reviews)
The place was great! Everything as available and the host was extremely helpful and kind. Would definitely stay here again. The views of the small nearby towns are amazing. We loved it.
Reviewed on Nov 17, 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.
Popular places to visit
Tennis Club Castiglionese
Catch an event at Tennis Club Castiglionese during your trip 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.
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.
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.
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
Montepulciano Wine Tasting in the Tuscan Countryside
$29
per adult
Oil museum and oil mill in Tuscany: tour and tasting
$23
per adult
Montepulciano Wine Tasting with typical Tuscan Cold Cuts
$52
per adult
- Lake Trasimeno
- Piazza Grande
- Arno River
- Arezzo Equestrian Centre
- Valdichiana Outlet Village
- San Giovanni Terme Rapolano
- Tiber River
- Piscine Termali Theia
- Terme di Chianciano
- Terme di Montepulciano Spa
- San Donato Hospital
- Piazza Grande
- Centro Chirurgico Toscano
- Villa Bramasole
- Terme Antica Querciolaia
- Cathedral of Saints Peter and Donato
- Basilica of San Francesco
- Piazza della Repubblica
- Dome of Montepulciano
- Val di Chiana
- Piazza Guido Monaco
- Anghiari Historic Town Center
- Isola Maggiore
- Palazzo Avignonesi
- Palazzo Ricci
- Cantina Contucci
- Arezzo Exhibition Center
- Cantina del Redi
- Cortona Cathedral
- Villa a Sesta Polo Club
- Church of Santa Maria della Pieve