Monticchiello Holidays from £196

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £750 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Packages with flights are ATOL protected

Your Monticchiello Holiday

Simplify your travel planning by booking a Monticchiello holiday package. One of the best neighbourhoods to stay in this fascinating city is Macciano, which is great for walking and a lot more. If your trip to Monticchiello includes a little sightseeing, don't miss much-loved attractions like Pienza Cathedral, Palazzo Piccolomini and Historic Centre of Pienza. Check out Expedia's extensive range of travel options and start planning your ultimate holiday to Monticchiello today.

Top Monticchiello Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Corte Guelfa

Corte Guelfa

3 out of 5
Historic Centre of Florence
Price was £327, price is now £196 per person
£196
per person
21 Jan - 24 Jan
found 10 hours ago
Return flight included
London (LON) to Florence (FLR)
9.6/10 Exceptional! (225 reviews)

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was £692, price is now £411 per person
£411
per person
1 Jan - 4 Jan
found 10 hours ago
Return flight included
London (LON) to Florence (FLR)
7.6/10 Good! (1,003 reviews)

Donati Luxury Tower Suites

Donati Luxury Tower Suites

5 out of 5
Historic Centre of Florence
Price was £821, price is now £498 per person
£498
per person
21 Jan - 24 Jan
found 10 hours ago
Return flight included
London (LON) to Florence (FLR)
9.8/10 Exceptional! (82 reviews)
Great boutique hotel with good size room and bathroom. Very clean and helpful staff. Would definitely stay here again.

Reviewed on 9 Nov 2026

Relais La Corte dei Papi

Relais La Corte dei Papi

5 out of 5
Save 100% on your flight
Price was £1,468, price is now £949 per person
£949
per person
27 Dec - 2 Jan
found 1 day ago
Return flight included
London (LON) to Florence (FLR)
9.6/10 Exceptional! (66 reviews)

Columbus Urban Resort

Columbus Urban Resort

5 out of 5
Campo di Marte
Price was £359, price is now £239 per person
£239
per person
21 Jan - 24 Jan
found 10 hours ago
Return flight included
London (LON) to Florence (FLR)
9.2/10 Wonderful! (37 reviews)

Monticchiello Essential Information

Language
Italian
Currency
Euros
Local Welcome
Ciao
Local Goodbye
Ciao
Population
200
Max Temp Winter
10ºC
Max Temp Summer
29ºC
Top Sights
Pienza Cathedral, Palazzo Piccolomini and Enoteca Di Ghino

Top hotels in Monticchiello

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Via Di Poggio Alla Sala, 10 Montepulciano SI
Get rates
Precise Tale Poggio Alla Sala
Nuovo Etruria Resort

Nuovo Etruria Resort

4 out of 5
Via di S. Martino snc Montepulciano SI
The price is £84 per night from 20 Nov to 21 Nov
£84
20 Nov - 21 Nov
includes taxes & fees
Nuovo Etruria Resort
Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel

5 out of 5
Localita Castiglion del Bosco Montalcino SI
Fully refundableReserve now, pay when you stay
The price is £752 per night from 2 Dec to 3 Dec
£752
2 Dec - 3 Dec
includes taxes & fees
10/10 Exceptional! (87 reviews)
"Unique property well maintained and quite Serene , great staff"

Reviewed on 30 Oct 2026

Castiglion del Bosco, A Rosewood Hotel
See all 3,982 properties in Monticchiello
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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Stay near popular Monticchiello attractions

Art Studio di Adelina Quadri

You can spend an afternoon exploring the galleries in Art Studio di Adelina Quadri during your travels in Monticchiello. While you're here, you can savour the wineries.
See properties

What to do in Monticchiello

Montepulciano: Winery Tour and Tasting

Montepulciano: Winery Tour and Tasting

£29
per adult
100% of travellers recommend
Montepulciano: Winery Tour and Tasting
Tasting Tour in One of The Most Beautiful Cellars in the World

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

£28
per adult
100% of travellers recommend
Tasting Tour in One of The Most Beautiful Cellars in the World
Montalcino: Guided Winery Tour and Wine Tasting

Montalcino: Guided Winery Tour and Wine Tasting

£38
per adult
Montalcino: Guided Winery Tour and Wine Tasting
See all activities in Monticchiello

Frequently asked questions

Why should I book my Monticchiello holiday with Expedia?
Expedia has you covered for every detail of your upcoming Monticchiello trip. You'll always get the best prices, but when you bundle your accommodation, flights and/or car hire into a holiday package, you'll get even more savings. Looking to really make the most of your stay? Add some awesome tours and activities to your package. Expedia offers flexible cancellation policies on most bookings, so you won't need to worry if your travel plans change. Head over to our Customer Service Portal link to find out more.
When is the best time of year to holiday in Monticchiello?
Monticchiello can get very busy in February, May and July, so if you want to escape the crowds, pack your bags for March, November and December. To give you an idea of what type of weather you can experience, the average daytime temperature in January, the coolest time of year in Monticchiello, is 4ºC. The warmest time here is July, when temperatures average 22ºC.
What is the top hotel for my holiday in Monticchiello?
Offering many of home's creature comforts, Hotel Relais II Chiostro di Pienza will make the perfect base for your Monticchiello holiday.
How do I get a cheap holiday to Monticchiello?
Bundle your hotels and flights with Expedia to save on your next trip. With more than 400 air carriers and 321,000 hotels across the globe, your Monticchiello holiday can be tailored exactly to suit your budget. With all that extra money, why not add one or two interesting tours and activities? It's an easy way to unlock even more bargains. The holiday you've always dreamed of in Monticchiello is closer than you thought! Learn more about how you can save money on your next holiday when you bundle your flight and hotel bookings with Expedia.
What should I do on my Monticchiello holiday?
There are so many things to do and see while on your holiday in Monticchiello. Pienza Cathedral, Palazzo Piccolomini, Historic Centre of Pienza and Piazza Pio II are just some of this city's best attractions.
What is the best area to stay in when on holiday in Monticchiello?
A holiday in Monticchiello isn't complete without checking out Art Studio di Adelina Quadri. Why not book a stay near this interesting attraction?
Do I need a visa for my Monticchiello holiday?
Official government websites will have all the information you need on visa requirements, application procedures and any supporting documentation. Your nationality and reason for visiting, whether it be for work or pleasure, will determine if you need a visa for Monticchiello. Also double-check that your passport is up to date and has at least six months validity remaining beyond your return date. Do all your travel planning ahead of time to avoid any nasty last-minute surprises.
What should I wear on my Monticchiello holiday?
First, consider the type of activities planned during your trip to Monticchiello and choose versatile pieces that you can mix and match. For fashion inspiration or even information on dress codes, browse style blogs or social media accounts. Pack your bags with confidence by monitoring the weather conditions in Monticchiello. July brings the warmest temperatures, with daily averages of 22ºC, while January days average 4ºC, making it the coolest month.
What does an Expedia Monticchiello holiday include?
Hotels, hire cars and flights — you'll discover them all here. With Expedia, you can create your Monticchiello package however you want. All you have to do is decide what you need. Once you've made your booking, why not add extras like experiences and activities? The more you bundle, the greater the savings! Apartments and villas are a couple of the most popular property types in Monticchiello. No matter your holiday style or group size, you can count on Expedia for the freedom to tailor your next escape.
Does Expedia offer Book Now, Pay Later Monticchiello holidays?
Expedia has teamed up with online lender Klarna to make your next getaway easier on your hip pocket. Paying by instalment means you can spread the costs of your next adventure, leaving you with more cash to splash while you're travelling. Klarna has several payment plans to choose from, so you're sure to find one that fits into your budget. Check out these flexible payment options:

  • Pay monthly holidays: Escape on that dream holiday sooner with Klarna's easy payment plans. If paying over multiple transactions works for you, choose this option during the checkout process.
  • No-deposit holidays: Pressing the "book now" button is much easier with this plan. With no deposit required for your getaway, you can Book Now, Pay Later and start packing your bags.

Can I choose my airline with a Monticchiello Expedia holiday?
Expedia offers access to more than 400 airline partners worldwide, so you definitely can. Just choose the airline you want and create the perfect Monticchiello holiday.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.