Monticchiello Vacations from $1,327

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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 $1,904, price is now $1,327 per person
$1,327
per person
Jul 7 - Jul 13
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
7.6/10 Good! (1,008 reviews)
Front desk staff are helpful. Breakfast room attendants are good. Food is average.

Reviewed on May 6, 2026

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was $1,948, price is now $1,340 per person
$1,340
per person
Jul 7 - Jul 13
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
7.6/10 Good! (1,001 reviews)
Excellent helpful staff let us store our bags in the lobby for a couple of hours after checkout- much appreciated- clean and quiet - central location was walkable to everywhere- and they were very nice to our 6 month old baby

Reviewed on May 2, 2026

Eurostars Florence Boutique

Eurostars Florence Boutique

4 out of 5
Historic Centre of Florence
Price was $2,548, price is now $1,790 per person
$1,790
per person
Jun 27 - Jul 3
found 12 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
8.6/10 Excellent! (485 reviews)
The room was clean and the staff very accommodating. The breakfast was quite sufficient and had a good variety. The location is great. It's a short walk from the square, shopping and from restaurants.

Reviewed on Dec 13, 2025

Hotel Villani

Hotel Villani

2 out of 5
Historic Centre of Florence
Price was $1,898, price is now $1,371 per person
$1,371
per person
Jul 21 - Jul 27
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Florence (FLR)
8.6/10 Excellent! (488 reviews)
The staff was amazing- friendly and helpful. The hotel has a bit of a retro vibe, which I really liked. My side of the bed wasn’t very comfortable, but my partners side was. Breakfast was so good that I almost asked for recipes. And the location cannot be beat!

Reviewed on May 2, 2026

Hotel La Scaletta Al Ponte Vecchio

Hotel La Scaletta Al Ponte Vecchio

4 out of 5
Historic Centre of Florence
Price was $2,350, price is now $1,722 per person
$1,722
per person
Jul 7 - Jul 13
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
8.8/10 Excellent! (993 reviews)
Loved the rooftop view! They upgraded my room and were very attentive. Amazing location!

Reviewed on May 1, 2026

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Discover the most popular places to visit in Monticchiello

Pienza Cathedral

Pienza Cathedral

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

Pienza Cathedral

Palazzo Piccolomini

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.

Palazzo Piccolomini

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

What to do in Monticchiello

Montalcino: Guided Winery Tour and Wine Tasting

Montalcino: Guided Winery Tour and Wine Tasting

$53
per adult
Montalcino: Guided Winery Tour and Wine Tasting
Montepulciano Wine Tasting in the Tuscan Countryside

Montepulciano Wine Tasting in the Tuscan Countryside

$30
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

$83
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! (55 reviews)
The staff was very accommodating and helpful. They helped us not only with a recommendation at a local restaurant, but with a reservation as well. The room was fantastic, with great views, air conditioning and heat, with a bathroom that was incredibly well designed. Parking was easy and the breakfast ...

Reviewed on May 1, 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
$444 nightly
The price is $496 total per night from May 7 to May 8
$496 total
May 7 - May 8
Total with taxes and fees
9.4/10 Exceptional! (131 reviews)
Absolutely amazing! We travel with small children and this accomodation was incredible. The accomodation and staff was 5 star

Reviewed on May 3, 2026

Precise Tale Poggio Alla Sala
Castello di Velona Resort Thermal SPA & Winery

Castello di Velona Resort Thermal SPA & Winery

5 out of 5
Località Velona Montalcino SI
Fully refundableReserve now, pay when you stay
$579 nightly
The price is $649 total per night from May 12 to May 13
$649 total
May 12 - May 13
Total with taxes and fees
9/10 Wonderful! (345 reviews)
There was no air conditioning in our room. It wasn’t too hot but not really pleasant sleep. Leaving the windows open at night in the country side up in a mountain is a little scary we could get bugs or else in the room. I am sorry, but A/C is a must for a hotel this level

Reviewed on May 6, 2026

Castello di Velona Resort Thermal SPA & Winery
See all 4,065 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 $1,327 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.