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](https://images.trvl-media.com/place/6285816/de4d8af6-64b9-4df8-b83a-27b0de35e925.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)

![Monticchiello](https://images.trvl-media.com/place/6285816/099c853a-6dad-4dfb-8296-97ddf5b39e95.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)

![Monticchiello](https://images.trvl-media.com/place/6285816/6d7b6b4f-64c7-4e12-9a68-efae9578a423.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)

![Monticchiello](https://images.trvl-media.com/place/6285816/62a88ae8-faf3-43b5-a1f5-26686fb0ec00.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)

![Monticchiello](https://images.trvl-media.com/place/6285816/aedf3374-e869-472d-9ce5-a67ac8fa3ed5.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.

- Monticchiello Hotel Deals
- Vacation Rentals in Monticchiello

![Affitacamere Maria Gabriella](https://images.trvl-media.com/lodging/23000000/22940000/22938800/22938763/020483c6_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Affitacamere Maria Gabriella

Via Marino Cappelli, 6 Pienza SI

CA $150

CA $204 total

Apr 13 - Apr 14

includes taxes & fees

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

[](https://expedia.ca/Hotel-Search?startDate=13%2F04%2F2026&endDate=14%2F04%2F2026&selected=22938763&PinnedHotelID=22938763&HadPinnedHotel=true&regionId=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 $349

CA $390 total

Apr 19 - Apr 20

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! (284 reviews)

Absolutely breathtaking property. The staff was extremely welcoming and helpful. Truly such a beautiful experience. Highly recommend to anyone

Reviewed on Mar 21, 2026

[](https://expedia.ca/Hotel-Search?startDate=19%2F04%2F2026&endDate=20%2F04%2F2026&selected=4310479&PinnedHotelID=4310479&HadPinnedHotel=true&regionId=6285816)

![Fonteverde Lifestyle & Thermal Retreat](https://images.trvl-media.com/lodging/1000000/910000/909000/908918/f6fb188e_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Fonteverde Lifestyle & Thermal Retreat

Localita Terme, 1 San Casciano dei Bagni SI

CA $473

CA $527 total

Apr 19 - Apr 20

includes taxes & fees

Book a stay at this luxury hotel in San Casciano dei Bagni. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Fonteverde Terme and Pasticceria ...

9.4/10 Exceptional! (191 reviews)

Great place! Excellent service by everyone we encountered.

Reviewed on Feb 13, 2026

[](https://expedia.ca/Hotel-Search?startDate=19%2F04%2F2026&endDate=20%2F04%2F2026&selected=908918&PinnedHotelID=908918&HadPinnedHotel=true&regionId=6285816)

[See all 4,088 properties in Monticchiello](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=06%2F04%2F2026&endDate=07%2F04%2F2026&regionId=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! (140 reviews)

Room was large and very clean. Bed was king sized and comfortable. Check-in was easy with underground parking for a nominal fee. Hotel is right outside downtown area, making it super walkable. Breakfast was great with many options.

Reviewed on Apr 3, 2026

[](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! (170 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&regionId=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&regionId=6285816&startDate=2026-04-05&endDate=2026-04-06)[Apr 5 - Apr 6](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=6285816&startDate=2026-04-05&endDate=2026-04-06)

[Tomorrow night

](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=6285816&startDate=2026-04-06&endDate=2026-04-07)[Apr 6 - Apr 7](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=6285816&startDate=2026-04-06&endDate=2026-04-07)

[Next weekend

](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=6285816&startDate=10%2F04%2F2026&endDate=12%2F04%2F2026)[Apr 10 - Apr 12](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=6285816&startDate=10%2F04%2F2026&endDate=12%2F04%2F2026)

### Popular places to visit

![Pienza Cathedral](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)

#### 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)

#### 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)

#### 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 $124

per adult

**98%** 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 $39

per adult

[](https://expedia.ca/things-to-do/montepulciano-wine-tasting-in-the-tuscan-countryside.a50286653.activity-details)

![Tasting Tour in One of The Most Beautiful Cellars in the World](https://mediaim.expedia.com/localexpert/1175608/57fdcc57-4a4e-4904-bd65-7afb578cabbc.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Tasting Tour in One of The Most Beautiful Cellars in the World

CA $52

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)

![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 $71

per adult

[](https://expedia.ca/things-to-do/montalcino-guided-winery-tour-and-wine-tasting.a44628122.activity-details)

![Montalcino, Pienza & Montepulciano Wine & Food Tour](https://mediaim.expedia.com/localexpert/365312/f72c5d78-7220-4d3d-82b1-5eab5fac0378.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Tuscany Wine & Hills from Florence

CA $203

per adult

**84%** of travellers recommend

[](https://expedia.ca/things-to-do/tuscany-wine-hills-from-florence.a365312.activity-details)

[See all activities in Monticchiello](https://expedia.ca/Things-To-Do-In-Monticchiello.d6285816.Travel-Guide-Activities)

## Cities near Monticchiello

![Pienza](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)
- [Terme di Montepulciano Spa ](https://expedia.ca/Terme-Di-Montepulciano-Spa-Montepulciano.d6169786.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)
- [Fortress of Montalcino ](https://expedia.ca/Fortress-Of-Montalcino-Montalcino.d553248621533000896.Vacation-Attraction)
- [Consorzio del Vino Nobile di Montepulciano ](https://expedia.ca/Consorzio-Del-Vino-Nobile-Di-Montepulciano-Montepulciano.d6105000.Vacation-Attraction)

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