Title: Visit Monticchiello: Best of Monticchiello Tourism | Expedia Travel Guide - Expedia.ca [Hotels in Monticchiello](https://expedia.ca/Monticchiello-Hotels.d6285816.Travel-Guide-Hotels)[Vacation Rentals in Monticchiello](https://expedia.ca/Monticchiello-Vacation-Rentals.d6285816.Travel-Guide-VacationRentals)[Monticchiello Car Rentals](https://expedia.ca/Car-Rentals-In-Monticchiello.d6285816.Car-Rental-Guide)[Monticchiello Vacation Packages](https://expedia.ca/Monticchiello.d6285816.Destination-Travel-Guides) # Monticchiello ## Travel Guide ![Monticchiello which includes a small town or village and heritage architecture as well as an individual female](https://images.trvl-media.com/place/6285816/de4d8af6-64b9-4df8-b83a-27b0de35e925.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Monticchiello which includes a small town or village and heritage architecture as well as an individual female](https://images.trvl-media.com/place/6285816/de4d8af6-64b9-4df8-b83a-27b0de35e925.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Monticchiello showing signage](https://images.trvl-media.com/place/6285816/099c853a-6dad-4dfb-8296-97ddf5b39e95.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Monticchiello featuring heritage architecture and flowers](https://images.trvl-media.com/place/6285816/6d7b6b4f-64c7-4e12-9a68-efae9578a423.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Monticchiello showing a small town or village as well as a couple](https://images.trvl-media.com/place/6285816/62a88ae8-faf3-43b5-a1f5-26686fb0ec00.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ## Visit Monticchiello Things to do #### Breathtaking natural landscapes, a storybook medieval quarter and community theatre productions await in this peaceful hilltop town above the Val d’Orcia. Monticchiello is one of the many towns with gorgeous scenery that you can visit while touring Tuscany’s Siena province. The town’s origins trace back to Roman times and it flourished as a medieval stronghold from the mid-1200s. Today, Monticchiello is recognized for its close-knit community spirit, summer theatre productions and agritourism. The town’s historic quarter is a compact, walled area that appears as though it has been plucked from a movie set. Spacious streets lead to brick-paved squares framed by stone houses with flower-filled balconies and shuttered windows. Punctuating the skyline are seven towers that have survived since the towns heyday. Two of them flank the main gateway, Porta Sant’Agata. One of the most important landmarks is Chiesa dei Santi Leonardo di Limoges e Cristoforo. This 13th-century Gothic church dominates the sleepy Piazza Commenda. Venture inside to admire frescoes created by artists of the Siense School. Pietro Lorenzetti and Pietruccio di Betto are among the painters whose works decorate the walls. A great time to visit is in July and August when the Teatro Povero puts on its annual show. Local residents write, direct, choreograph and perform every aspect of the shows, which bring to life social and political issues relevant to the town. Performances are open-air and run from Tuesday to Sunday. Monticchiello is a burgeoning agritourim destination. Farms in the immediate surroundings present opportunities to get up-close with Tuscany’s stunning countryside. Relax at the farms’ swimming pools, dine on locally sourced produce and explore the region on rented bike. Similarly, the green landscapes and terraced fields of nearby Riserva Naturale Lucciolabella and Riserva Naturale Pietraporciana are a photography- and nature-lover’s paradise. Monticchiello is just a 20-minute drive from [Pienza](https://www.expedia.ca/Pienza.d6023645.Destination-Travel-Guides) and [Montepulciano](https://www.expedia.ca/Montepulciano.d601351.Destination-Travel-Guides) and easy to visit on a daytrip from both towns. Parking is available at the entrance to the old town. Active visitors might want to get here on foot via the hilly country lanes of the Val d’Orcia. ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=DX_SPRING_PROMO_6285816) - Monticchiello Hotel Deals - Vacation Rentals in Monticchiello ![Affitacamere Maria Gabriella](https://images.trvl-media.com/lodging/23000000/22940000/22938800/22938763/ac017ccb_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Affitacamere Maria Gabriella Via Marino Cappelli, 6 Pienza SI Book a stay at this business-friendly affittacamere in Pienza. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Art Studio di Adelina Quadri ... 9.8/10 Exceptional! (51 reviews) This property has a lovely view, great garden, attentive staff with good breakfast. Stayed in the cottage and the patio was very sunny and relaxing. Reviewed on Nov 8, 2025 [Get rates](https://expedia.ca/Hotel-Search?startDate=20%2F03%2F2026&endDate=21%2F03%2F2026&selected=22938763&PinnedHotelID=22938763&HadPinnedHotel=true®ionId=6285816) [](https://expedia.ca/Hotel-Search?startDate=20%2F03%2F2026&endDate=21%2F03%2F2026&selected=22938763&PinnedHotelID=22938763&HadPinnedHotel=true®ionId=6285816) ![Relais Villa Grazianella - UNA Esperienze](https://images.trvl-media.com/lodging/5000000/4320000/4310500/4310479/cd1e0f87_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Relais Villa Grazianella - UNA Esperienze Via Grazianella 5 Montepulciano SI CA $265 CA $298 total Mar 9 - Mar 10 includes taxes & fees Book a stay at this luxury country house in Montepulciano. Enjoy free WiFi, free parking, and an attached winery. Our guests praise the helpful staff in our ... 9.8/10 Exceptional! (279 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 [](https://expedia.ca/Hotel-Search?startDate=09%2F03%2F2026&endDate=10%2F03%2F2026&selected=4310479&PinnedHotelID=4310479&HadPinnedHotel=true®ionId=6285816) ![Precise Tale Poggio Alla Sala](https://images.trvl-media.com/lodging/91000000/90890000/90888700/90888666/33c1dfc6_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Precise Tale Poggio Alla Sala Via Poggio alla Sala 10 Montepulciano SI CA $487 CA $546 total Mar 24 - Mar 25 includes taxes & fees Book a stay at this 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! (123 reviews) Perfect escape Fantastic hotel in an incredible setting. Staff were extremely helpful, attentive and understanding. The perfect location for a relaxing break and a centre for exploring Tuscany Reviewed on Oct 27, 2025 [](https://expedia.ca/Hotel-Search?startDate=24%2F03%2F2026&endDate=25%2F03%2F2026&selected=90888666&PinnedHotelID=90888666&HadPinnedHotel=true®ionId=6285816) [See all 4,083 properties in Monticchiello](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=07%2F03%2F2026&endDate=08%2F03%2F2026®ionId=6285816) 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. ![Hotel San Gregorio](https://images.trvl-media.com/lodging/3000000/2700000/2692200/2692135/0e5f89fd_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hotel San Gregorio Via Della Madonnina 4 Pienza SI Book a stay at this business-friendly residence in Pienza. Enjoy free WiFi, an outdoor pool, and room service. Popular attractions RI Crea RE and Enoteca Di ... 9.4/10 Exceptional! (134 reviews) Super convenient location steps to the historic center. Possibly the only hotel with its own dedicated secure / covered parking. Well decorated and breakfast was great! Reviewed on Oct 25, 2025 [](https://expedia.ca/Pienza-Hotels-Hotel-San-Gregorio.h2692135.Hotel-Information) ![Casanova - Panoramic Rooms and Suites](https://images.trvl-media.com/lodging/52000000/51830000/51829000/51828901/9867dcf1_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Casanova - Panoramic Rooms and Suites Strada Provinciale 146 di Chianciano San Quirico d'Orcia SI Stay at this residence in San Quirico d'Orcia. Enjoy free breakfast, free WiFi, and an outdoor pool. Popular attractions Horti Leonini and Chapel of our Lady ... [](https://expedia.ca/San-Quirico-DOrcia-Hotels-Resort-Casanova-Panoramic-Rooms-And-Suites.h51828901.Hotel-Information) ![Bosco della Spina](https://images.trvl-media.com/lodging/2000000/1210000/1206200/1206161/46c3ab32_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Bosco della Spina via della Tinaia 13 Murlo SI Book a stay at this luxury residence in Murlo. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Castello di Montepescini and La Porta ... 9.6/10 Exceptional! (169 reviews) Lovely stay! I would highly recommend this hotel. The indoor pool was just so enjoyable after a day out sightseeing. Reviewed on Oct 30, 2025 [](https://expedia.ca/Murlo-Hotels-Bosco-Della-Spina.h1206161.Hotel-Information) [See all properties in Monticchiello](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience®ionId=6285816&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 Monticchiello hotel availability [Tonight ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6285816&startDate=2026-03-06&endDate=2026-03-07)[Mar 6 - Mar 7](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6285816&startDate=2026-03-06&endDate=2026-03-07) [Tomorrow night ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6285816&startDate=2026-03-07&endDate=2026-03-08)[Mar 7 - Mar 8](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6285816&startDate=2026-03-07&endDate=2026-03-08) [This weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6285816&startDate=06%2F03%2F2026&endDate=08%2F03%2F2026)[Mar 6 - Mar 8](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6285816&startDate=06%2F03%2F2026&endDate=08%2F03%2F2026) ### Popular places to visit ![Cathedral of Pienza featuring religious elements, a church or cathedral and heritage elements](https://images.trvl-media.com/place/6105122/c1401c7d-833e-46b8-b745-83c1e9ce5dd9.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Pienza Cathedral 4.5/5(32 reviews) Admire the arresting Renaissance façade and the interior Gothic décor of this 15th-century cathedral commissioned by Pope Pius II. [](https://expedia.ca/Pienza-Cathedral-Pienza.d6105122.Vacation-Attraction) #### Historic Centre of Pienza Explore the great outdoors at Historic Centre of Pienza, a lovely green space in Pienza. Discover the countryside and churches in this quaint area. [](https://expedia.ca/Historic-Centre-Of-Pienza-Pienza.d623288508983611392.Vacation-Attraction) #### Piazza Pio II After visiting Piazza Pio II, make a plan to see the other sights and activities in Pienza. While you're here, you can savor the wineries. [](https://expedia.ca/Piazza-Pio-II-Pienza.d553248621533000907.Vacation-Attraction) #### Palazzo Piccolomini 4.5/5(15 reviews) You can study the exhibits at Palazzo Piccolomini, a museum with a storied past, during your trip to Pienza. While you're here, you can savor the wineries. [](https://expedia.ca/Palazzo-Piccolomini-Pienza.d6105120.Vacation-Attraction) #### Monastery of Sant'Anna in Camprena You can find out about the history of Pienza with a visit to Monastery of Sant'Anna in Camprena. Discover the countryside and churches in this quaint area. [](https://expedia.ca/Monastery-Of-SantAnna-In-Camprena-Pienza.d811545272430104576.Vacation-Attraction) #### Pieve di Corsignano You can find out about the history of Pienza with a trip to Pieve di Corsignano. While you're here, you can savor the wineries. [](https://expedia.ca/Pieve-Di-Corsignano-Pienza.d553248621533000906.Vacation-Attraction) ### Things to do ![3 Regions in 1 Day from Rome with Tuscany Wine Tasting & Lunch](https://mediaim.expedia.com/localexpert/47282553/e14b5a73-0ff4-428f-a567-234540a94e59.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch CA $127 per adult **100%** of travellers recommend [](https://expedia.ca/things-to-do/from-rome-bagnoregio-orvieto-day-trip-with-tuscany-wine-tasting-lunch.a47282553.activity-details) ![Seggiano: Guided Tour of the Olive Grove and Food Tasting](https://mediaim.expedia.com/localexpert/48314154/3c3e6332-4460-423d-8ee4-7953fc5d8637.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Seggiano: Guided Tour of the Olive Grove and Food Tasting CA $40 per adult [](https://expedia.ca/things-to-do/seggiano-guided-tour-of-the-olive-grove-and-food-tasting.a48314154.activity-details) ![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 CA $40 per adult [](https://expedia.ca/things-to-do/montepulciano-wine-tasting-in-the-tuscan-countryside.a50286653.activity-details) ![Montalcino: Guided Winery Tour and Wine Tasting](https://mediaim.expedia.com/localexpert/44628122/e1c18867-816c-4ff5-aaae-8b2f08187f9c.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Montalcino: Guided Winery Tour and Wine Tasting CA $73 per adult [](https://expedia.ca/things-to-do/montalcino-guided-winery-tour-and-wine-tasting.a44628122.activity-details) ![Bottaia](https://mediaim.expedia.com/localexpert/1175608/3e83d505-5c45-4a2c-b4f4-b2f1bc743f59.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Tasting Tour in One of The Most Beautiful Cellars in the World CA $53 per adult **100%** of travellers recommend [](https://expedia.ca/things-to-do/tasting-tour-in-one-of-the-most-beautiful-cellars-in-the-world.a1175608.activity-details) ![Montepulciano: Artisan Heroic Wine Tasting at the Terrace](https://mediaim.expedia.com/localexpert/49091559/d297e68c-49c4-42f7-bfe7-536b2a0686ce.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Montepulciano: Artisan Heroic Wine Tasting at the Terrace CA $81 per adult [](https://expedia.ca/things-to-do/montepulciano-artisan-heroic-wine-tasting-at-the-terrace.a49091559.activity-details) [See all activities in Monticchiello](https://expedia.ca/Things-To-Do-In-Monticchiello.d6285816.Travel-Guide-Activities) ## Cities near Monticchiello ![Pienza showing a monument, a square or plaza and heritage architecture](https://images.trvl-media.com/place/6023645/9d678ea5-9752-4000-8f7c-af307fb65e61.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Pienza - Cities near Monticchiello - Places of interest [Pienza](https://expedia.ca/Pienza.dx6023645) - [Art Studio di Adelina Quadri ](https://expedia.ca/Art-Studio-Di-Adelina-Quadri-Pienza.d553248621562145321.Vacation-Attraction) - [Lake Trasimeno ](https://expedia.ca/Lake-Trasimeno-Umbria.d6055082.Vacation-Attraction) - [Pienza Cathedral ](https://expedia.ca/Pienza-Cathedral-Pienza.d6105122.Vacation-Attraction) - [Tenuta Greppo Franco Biondi Santi ](https://expedia.ca/Tenuta-Greppo-Franco-Biondi-Santi-Montalcino.d6103260.Vacation-Attraction) - [Piscine Termali Theia ](https://expedia.ca/Piscine-Termali-Theia-Chianciano-Terme.d553248621555471462.Vacation-Attraction) - [Terme di Montepulciano Spa ](https://expedia.ca/Terme-Di-Montepulciano-Spa-Montepulciano.d6169786.Vacation-Attraction) - [Fortress of Montalcino ](https://expedia.ca/Fortress-Of-Montalcino-Montalcino.d553248621533000896.Vacation-Attraction) - [Palazzo Ricci ](https://expedia.ca/Palazzo-Ricci-Montepulciano.d553248621532500182.Vacation-Attraction) ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. 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