Monticchiello Vacations from $1,084

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Your Monticchiello Vacation

Simplify your travel planning by booking a Monticchiello vacation package. One of the best neighborhoods 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 vacation to Monticchiello today.

The Latest Monticchiello vacation packages

Price found within the past 48 hours. Click for updated prices.
Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Price was $1,687, price is now $1,084 per person
$1,084
per person
Aug 16 - Aug 22
found 21 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.6/10 Good! (1,025 reviews)
Good enough for stay in and out of the room . T

Reviewed on Jun 13, 2026

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Save 100% on your flight
Price was $3,808, price is now $2,623 per person
$2,623
per person
Jul 29 - Aug 5
just found
Roundtrip non-stop flight included
New York (NYC) to Florence (FLR)
9.6/10 Exceptional! (141 reviews)
What a nice place to stay and enjoying Tuscany region!! Lovely place and atmosphere!! We definitely love to come back and stay more time for next visit!!

Reviewed on Jun 13, 2026

Donati Luxury Tower Suites

Donati Luxury Tower Suites

5 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $4,933, price is now $3,126 per person
$3,126
per person
Jul 16 - Jul 22
found 22 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Florence (FLR)
9.8/10 Exceptional! (66 reviews)
Agradable estancia. Excelente servicio. La habitación la mantenían siempre limpia. Todo queda cerca del área. Muy recomendable

Reviewed on May 23, 2026

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was $1,703, price is now $1,089 per person
$1,089
per person
Aug 16 - Aug 22
found 21 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.6/10 Good! (1,011 reviews)
The hotel was conveniently located, and the service was good. Overall, it was a pleasant stay. However, I hope the hotel improves its Wi-Fi coverage, as the connection can become unstable when multiple guests are accessing the network.

Reviewed on Jun 5, 2026

The James Suite Hotel Firenze 1564 - Small Luxury Hotels of the World

The James Suite Hotel Firenze 1564 - Small Luxury Hotels of the World

5 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $4,720, price is now $3,141 per person
$3,141
per person
Jul 16 - Jul 22
found 22 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Florence (FLR)
10/10 Exceptional! (18 reviews)
Lovely stay. Highly recommend it!

Reviewed on Jun 11, 2026

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Discover the most popular places to visit in Monticchiello

Pienza Cathedral

Pienza Cathedral

5/5(136 reviews)

Admire the arresting Renaissance façade and the interior Gothic décor of this 15th-century cathedral commissioned by Pope Pius II.

Pienza Cathedral

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.

Piazza Pio II

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.

Pieve di Corsignano

What to do in Monticchiello

Montalcino: Guided Winery Tour and Wine Tasting

Montalcino: Guided Winery Tour and Wine Tasting

$52
per adult
Montalcino: Guided Winery Tour and Wine Tasting
Montepulciano Wine Tasting in the Tuscan Countryside

Montepulciano Wine Tasting in the Tuscan Countryside

$29
per adult
Montepulciano Wine Tasting in the Tuscan Countryside
Montalcino: Renowned Tuscan Olive Oil Mill Tour & Tasting

Montalcino: Renowned Tuscan Olive Oil Mill Tour & Tasting

$81
per adult
Montalcino: Renowned Tuscan Olive Oil Mill Tour & Tasting
See all activities in Monticchiello

Monticchiello Hotel Deals

Affitacamere Maria Gabriella

Affitacamere Maria Gabriella

Via Marino Cappelli, 6 Pienza SI
9.8/10 Exceptional! (62 reviews)
"A fantastic stay in such a beautiful part of Tuscany. Hosts were friendly and went out of their way to help. Breakfast was lovely and the room was clean and comfortable. Would highly recommend!"

Reviewed on Jun 15, 2026

Get rates
Affitacamere Maria Gabriella
Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Via Poggio alla Sala 10 Montepulciano SI
Fully refundableReserve now, pay when you stay
$399 nightly
The price is $446 total per night from Jun 23 to Jun 24
$446 total
Jun 23 - Jun 24
Total with taxes and fees
9.6/10 Exceptional! (144 reviews)
"What a nice place to stay and enjoying Tuscany region!! Lovely place and atmosphere!! We definitely love to come back and stay more time for next visit!!"

Reviewed on Jun 13, 2026

Precise Tale Poggio Alla Sala
Nuovo Etruria Resort

Nuovo Etruria Resort

Via di S. Martino snc Montepulciano SI
Fully refundable
$106 nightly
The price is $121 total per night from Jun 17 to Jun 18
$121 total
Jun 17 - Jun 18
Total with taxes and fees
9.2/10 Wonderful! (92 reviews)
"Clean room and the staff was very helpful"

Reviewed on Jun 5, 2026

Nuovo Etruria Resort
See all 4,066 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.

Find the Best Monticchiello Vacation Packages

Monticchiello Essential Information

Language
Italian
Currency
Euros
Local Welcome
Ciao
Local Goodbye
Ciao
Population
200
Max Temp Winter
50ºF
Max Temp Summer
85ºF
Top Sights
Pienza Cathedral, Palazzo Piccolomini and Enoteca Di Ghino

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Frequently asked questions

How much does a Monticchiello vacation package cost?
You'll find cheap prices from $1,084 on Expedia for your Monticchiello break. However, factors like the season, choice of hotel and length of stay will determine how much your vacation to Monticchiello costs.
What are the cheapest months to go to Monticchiello?
If you'd like to book a cheap Monticchiello vacation package, consider visiting in March, November and December. You'll typically find better rates on flights and hotels during these months — ideal for budget-conscious travelers.
How many days is enough for Monticchiello?
With a well-organized itinerary, you can easily hit the top Monticchiello sights in a few days. But if you want to discover hidden spots or go on day tours, consider booking your Monticchiello vacation for longer.
How to find the best Monticchiello package deals?
Use Expedia's handy filters to find some terrific Monticchiello package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your break for midweek, or browse for Monticchiello package deals in the low season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package well in advance.
Is it cheaper to book a Monticchiello vacation as a package?
You can enjoy significant savings on your Monticchiello escape by booking a tailored vacation package. Click on the "Package" heading, then select your travel dates and destination to view some great hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Monticchiello?
If you have your Monticchiello vacation dates locked in, book as early as you can to score some terrific deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spur-of-the-moment getaways? Our last-minute deals are perfect for jetting off on a whim.
Does Expedia offer Book Now, Pay Later Monticchiello vacation packages?
Your Monticchiello break should be an escape from your daily routine, not a source of money worries. So to allow you a bit more flexibility, we've teamed up with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there are no late payment fees or hidden costs to worry about.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.