Title: Visit Montecchio: 2026 Travel Guide for Montecchio, Castiglion Fiorentino | Expedia.com [Hotels in Montecchio](https://expedia.com/Montecchio-Hotels.d6361207.Travel-Guide-Hotels)[Vacation Rentals in Montecchio](https://expedia.com/Montecchio-Vacation-Rentals.d6361207.Travel-Guide-VacationRentals)[Car Rentals in Montecchio](https://expedia.com/Car-Rentals-In-Montecchio.d6361207.Car-Rental-Guide)[Montecchio Vacation Packages](https://expedia.com/Montecchio.d6361207.Destination-Travel-Guides) # Montecchio ## Travel Guide ![The Castle of Montecchio Vesponi is a walled, castle with turrets and battlements, which occupies the top of a hill (Montecchio), overlooking the Val di Chiana, named and drawn on a well-documented survey map by Leonardo da Vinci in 1503. Many cultural events have taken place within its walls, including art exhibitions (the last being one of works of Manzù), concerts, folklore festivals, re- enactments and events in the local dialect. Famous visitors to the Castle have included the late Queen Elizabeth, The Queen Mother (of England) who came to learn Documentary Moviesmore about the castle and the area and owned in 1384 by another Englishman, Sir John Hawkwood (known in Italian as Giovanni Acuto). Hawkwood appears in the world famous fresco by Paolo Uccello in the Cathedral of Santa Maria del Fiore, The Duomo of Florence. #Tuscany #Castle #Montecchio #Vesponi #Valdichiana #Castiglion Fiorentino](https://images.trvl-media.com/place/6047858/23b55128-2d48-4cca-8748-3abb573248a4.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ## Visit Montecchio Things to do - Montecchio Hotel Deals - Vacation Rentals in Montecchio ![Villa di Piazzano - Small Luxury Hotel of the World](https://images.trvl-media.com/lodging/1000000/980000/972000/971985/c358cc6c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Villa di Piazzano - Small Luxury Hotel of the World Localita Piazzano, C.P. 6 Cortona AR $649 nightly $719 total Mar 30 - Mar 31 Total with taxes and fees Book a stay at this luxury hotel in Cortona. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular ... 9.8/10 Exceptional! (228 reviews) Room was wonderful, bathroom spacious and well appointed. Staff amazing and so friendly Reviewed on Nov 6, 2025 [](https://expedia.com/Hotel-Search?startDate=3%2F30%2F2026&endDate=3%2F31%2F2026&selected=971985&PinnedHotelID=971985&HadPinnedHotel=true®ionId=6361207) ![Monastero di Cortona Hotel & Spa](https://images.trvl-media.com/lodging/24000000/23270000/23264500/23264410/b2055c17_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Monastero di Cortona Hotel & Spa Via del Salvatore Cortona AR $266 nightly $297 total Mar 29 - Mar 30 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 ... [](https://expedia.com/Hotel-Search?startDate=3%2F29%2F2026&endDate=3%2F30%2F2026&selected=23264410&PinnedHotelID=23264410&HadPinnedHotel=true®ionId=6361207) ![Hotel Minerva](https://images.trvl-media.com/lodging/2000000/1190000/1183500/1183404/27963802_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hotel Minerva Via Fiorentina, 4 Arezzo AR $90 nightly $106 total Apr 12 - Apr 13 Total with taxes and fees Book a stay at this business-friendly hotel in Arezzo. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular ... [](https://expedia.com/Hotel-Search?startDate=4%2F12%2F2026&endDate=4%2F13%2F2026&selected=1183404&PinnedHotelID=1183404&HadPinnedHotel=true®ionId=6361207) [See all 5,232 properties in Montecchio](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=3%2F20%2F2026&endDate=3%2F21%2F2026®ionId=6361207) 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](https://images.trvl-media.com/lodging/11000000/10660000/10653000/10652908/39e29e99_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### 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! (168 reviews) Room was beyond expectations. Helpful staff and overall great experience. Reviewed on Dec 7, 2025 [](https://expedia.com/Trequanda-Hotels-Abbadia-Sicille.h10652908.Hotel-Information) ![Residenza Fabroni](https://images.trvl-media.com/lodging/9000000/8210000/8204400/8204306/124b8b86_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### 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! (96 reviews) The parking states “on site”, as if there was a parking lot easy and close to get to and from, especially with luggage. The parking lot is a maze to get to and quite difficult to navigate to through the tiny streets. Other then that, place was clean, staff was great Very old school italy Also the ... Reviewed on Jan 19, 2026 [](https://expedia.com/Montepulciano-Hotels-Residenza-Fabroni.h8204306.Hotel-Information) ![Il Tosco](https://images.trvl-media.com/lodging/7000000/6310000/6309600/6309554/3e489ee1_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Il Tosco Via del Poliziano 13 Montepulciano SI Book a stay at this luxury residence in Montepulciano. Enjoy free WiFi, free parking, and room service. Popular attractions Medici Fortress and Torre del Pulcinella ... 10/10 Exceptional! (116 reviews) Best stay of my life! Reviewed on Dec 31, 2025 [](https://expedia.com/Montepulciano-Hotels-Il-Tosco.h6309554.Hotel-Information) [See all properties in Montecchio](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience®ionId=6361207&sort=VACATION_RENTAL) 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. ## Check Montecchio hotel availability [Tonight ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6361207&startDate=2026-03-19&endDate=2026-03-20)[Mar 19 - Mar 20](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6361207&startDate=2026-03-19&endDate=2026-03-20) [Tomorrow night ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6361207&startDate=2026-03-20&endDate=2026-03-21)[Mar 20 - Mar 21](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6361207&startDate=2026-03-20&endDate=2026-03-21) [This weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6361207&startDate=3%2F20%2F2026&endDate=3%2F22%2F2026)[Mar 20 - Mar 22](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6361207&startDate=3%2F20%2F2026&endDate=3%2F22%2F2026) [Next weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6361207&startDate=3%2F27%2F2026&endDate=3%2F29%2F2026)[Mar 27 - Mar 29](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6361207&startDate=3%2F27%2F2026&endDate=3%2F29%2F2026) ### 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. [](https://expedia.com/Tennis-Club-Castiglionese-Castiglion-Fiorentino.d553248621580159024.Vacation-Attraction) #### 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. [](https://expedia.com/Agricola-Buccelletti-Winery-Castiglion-Fiorentino.d553248621580159025.Vacation-Attraction) #### 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. [](https://expedia.com/Archaeological-Museum-Castiglion-Fiorentino.d553248621580159022.Vacation-Attraction) #### 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. [](https://expedia.com/Cassero-Tower-Castiglion-Fiorentino.d553248621580159023.Vacation-Attraction) #### 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. [](https://expedia.com/Vasari-Loggia-Castiglion-Fiorentino.d553248621580159026.Vacation-Attraction) #### 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. [](https://expedia.com/Municipal-Art-Gallery-Castiglion-Fiorentino.d553248621533001056.Vacation-Attraction) ### Things to do ![Montepulciano Wine Tasting in the Tuscan Countryside](https://mediaim.expedia.com/localexpert/50286653/77c79a76-70f1-4375-9739-0f0f71d7da02.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Montepulciano Wine Tasting in the Tuscan Countryside $29 per adult [](https://expedia.com/things-to-do/montepulciano-wine-tasting-in-the-tuscan-countryside.a50286653.activity-details) ![Montepulciano Wine Tasting with typical Tuscan Cold Cuts](https://mediaim.expedia.com/localexpert/50050116/b42fdd72-c9bb-49c8-8b4d-78b4f50de384.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Montepulciano Wine Tasting with typical Tuscan Cold Cuts $53 per adult [](https://expedia.com/things-to-do/montepulciano-wine-tasting-with-typical-tuscan-cold-cuts.a50050116.activity-details) [See all activities in Montecchio](https://expedia.com/Things-To-Do-In-Montecchio.d6361207.Travel-Guide-Activities) ## Cities near Montecchio ![Cortona featuring a city and farmland](https://images.trvl-media.com/place/601360/f4054673-52dd-4f97-8d57-389d1f349940.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Cortona ![Looking out the window on a fast train ride to Florence from Rome...](https://images.trvl-media.com/place/6047858/aaab608c-e23c-4d48-acbe-896e0882191d.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Castiglion Fiorentino - Cities near Montecchio - Places of interest [Cortona](https://expedia.com/Cortona.dx601360)[Castiglion Fiorentino](https://expedia.com/Castiglion-Fiorentino.dx6047858)[Il Borgo](https://expedia.com/Il-Borgo.dx6361285)[Poggiolo](https://expedia.com/Poggiolo.dx6361313)[Casa del Re](https://expedia.com/Casa-Del-Re.dx6361319) - [Lake Trasimeno ](https://expedia.com/Lake-Trasimeno-Umbria.d6055082.Vacation-Attraction) - [Arno River ](https://expedia.com/Arno-River-Tuscany.d553248621532501484.Vacation-Attraction) - [Tiber River ](https://expedia.com/Tiber-River-Marcigliana.d553248621532500472.Vacation-Attraction) - [Piazza Grande ](https://expedia.com/Piazza-Grande-Arezzo-Centro-Storico.d6104294.Vacation-Attraction) - [Arezzo Equestrian Centre ](https://expedia.com/Arezzo-Equestrian-Centre-Arezzo.d6312910.Vacation-Attraction) - [Piazza Grande ](https://expedia.com/Piazza-Grande-Montepulciano.d553248621533000912.Vacation-Attraction) - [Terme di Chianciano ](https://expedia.com/Terme-Di-Chianciano-Chianciano-Terme.d553248621555471461.Vacation-Attraction) - [Dome of Montepulciano ](https://expedia.com/Dome-Of-Montepulciano-Montepulciano.d553248621532500181.Vacation-Attraction) - [San Giovanni Terme Rapolano ](https://expedia.com/San-Giovanni-Terme-Rapolano-Rapolano-Terme.d553248621532500193.Vacation-Attraction) - [Tuscan Surgical Center ](https://expedia.com/Tuscan-Surgical-Center-Arezzo.d553248632870974319.Vacation-Attraction) - [Val di Chiana ](https://expedia.com/Val-Di-Chiana-Tuscany.d6049003.Vacation-Attraction) - [Terme di Montepulciano Spa ](https://expedia.com/Terme-Di-Montepulciano-Spa-Montepulciano.d6169786.Vacation-Attraction) - [San Donato Hospital ](https://expedia.com/San-Donato-Hospital-Arezzo.d553248621583444251.Vacation-Attraction) - [Terme Antica Querciolaia ](https://expedia.com/Terme-Antica-Querciolaia-Rapolano-Terme.d553248621532500215.Vacation-Attraction) - [Piscine Termali Theia ](https://expedia.com/Piscine-Termali-Theia-Chianciano-Terme.d553248621555471462.Vacation-Attraction) - [Villa Bramasole ](https://expedia.com/Villa-Bramasole-Cortona.d553248635931712561.Vacation-Attraction) - [Cathedral of Saints Peter and Donato ](https://expedia.com/Cathedral-Of-Saints-Peter-And-Donato-Arezzo-Centro-Storico.d6104274.Vacation-Attraction) - [Valdichiana Outlet Village ](https://expedia.com/Valdichiana-Outlet-Village-Foiano-della-Chiana.d6153160.Vacation-Attraction) - [Palazzo Avignonesi ](https://expedia.com/Palazzo-Avignonesi-Montepulciano.d553248621533000914.Vacation-Attraction) - [Villa a Sesta Polo Club ](https://expedia.com/Villa-A-Sesta-Polo-Club-Bucine.d553248622945495059.Vacation-Attraction) - [Piazza Guido Monaco ](https://expedia.com/Piazza-Guido-Monaco-Arezzo-Centro-Storico.d553248635975742732.Vacation-Attraction) - [Anghiari Historic Town Center ](https://expedia.com/Anghiari-Historic-Town-Center-Anghiari.d553248634983625076.Vacation-Attraction) - [Palazzo Ricci ](https://expedia.com/Palazzo-Ricci-Montepulciano.d553248621532500182.Vacation-Attraction) - [Consorzio del Vino Nobile di Montepulciano ](https://expedia.com/Consorzio-Del-Vino-Nobile-Di-Montepulciano-Montepulciano.d6105000.Vacation-Attraction) - [Isola Maggiore ](https://expedia.com/Isola-Maggiore-Tuoro-sul-Trasimeno.d3000404297.Vacation-Attraction) - [Cortona Cathedral ](https://expedia.com/Cortona-Cathedral-Cortona-Old-Town.d6102846.Vacation-Attraction) - [Piazza della Repubblica ](https://expedia.com/Piazza-Della-Repubblica-Cortona-Old-Town.d6102854.Vacation-Attraction) - [Basilica of San Francesco ](https://expedia.com/Basilica-Of-San-Francesco-Arezzo-Centro-Storico.d6104276.Vacation-Attraction) - [Fishing Museum of Magione ](https://expedia.com/Fishing-Museum-Of-Magione-Magione.d553248621532500670.Vacation-Attraction) - [Cantina Contucci ](https://expedia.com/Cantina-Contucci-Montepulciano.d6105002.Vacation-Attraction)