Monticchiello Vacations from $1,002

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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 $1,572, price is now $1,002 per person
$1,002
per person
Sep 1 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.6/10 Good! (1,025 reviews)
The location is excellent. Close to the train station, shops and restaurants. Room was very clean. Breakfast was included. all good.

Reviewed on Jun 19, 2026

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was $1,995, price is now $1,280 per person
$1,280
per person
Sep 3 - Sep 8
found 1 day 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 Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
Price was $1,738, price is now $1,167 per person
$1,167
per person
Aug 23 - Aug 29
found 10 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.6/10 Exceptional! (566 reviews)
Absolutely fantastic hotel, we couldn’t believe how good it was. Exactly like the photos. The hotel was built only in 2018 and the facilities are constantly kept in perfect condition and spotlessly clean. In a quiet part of town easily walkable into the main attractions and close to a bus and a tram stop, a perfect sanctuary to rest at night time. All of the staff are so kind and polite, especially Francois who looked after us very well at breakfast time. The hotel would be worth the price tag just for the comfortable rooms and location, but it has the added bonus of a free breakfast (with tons of choices and free mimosas), free luxury spa facilities and free home made lemonade and biscuits available at all times. We can’t recommend this hotel enough as a boutique stay perfect for adults wanting a luxury escape.

Reviewed on Jun 8, 2026

Bernini Palace

Bernini Palace

5 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $2,329, price is now $1,568 per person
$1,568
per person
Aug 23 - Aug 29
found 10 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.8/10 Exceptional! (1,000 reviews)
The staff. The breakfast. The bar. All perfect. We really really loved our stay here. Planning on staying every year!

Reviewed on Jun 18, 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 $3,256, price is now $2,232 per person
$2,232
per person
Aug 24 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
10/10 Exceptional! (20 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

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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
$552 nightly
The price is $614 total per night from Jul 11 to Jul 12
$614 total
Jul 11 - Jul 12
Total with taxes and fees
9.6/10 Exceptional! (146 reviews)
"It’s a beautiful property, but be aware that it is secluded and that the restaurant menu is quite limited and after a couple of days, we were happy to go elsewhere. The waiting staff was attentive and nice, front desk not as much (maybe the la guard barrier?)"

Reviewed on Jun 19, 2026

Precise Tale Poggio Alla Sala
Nuovo Etruria Resort

Nuovo Etruria Resort

Via di S. Martino snc Montepulciano SI
Fully refundable
$104 nightly
The price is $119 total per night from Jul 3 to Jul 4
$119 total
Jul 3 - Jul 4
Total with taxes and fees
9.4/10 Exceptional! (96 reviews)
"Very friendly staff. Beautiful property."

Reviewed on Jun 19, 2026

Nuovo Etruria Resort
See all 4,176 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 $1,002 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.