Monticchiello Vacations from $511

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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 $703, price is now $511 per person
$511
per person
Jan 29 - Feb 1
found 5 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.6/10 Good! (1,002 reviews)
Close to train station and everything you need.

Reviewed on Nov 21, 2025

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $1,134, price is now $696 per person
$696
per person
Feb 21 - Feb 27
found 5 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,000 reviews)
Breakfast was good. Staff super friendly. Overall the expected quality for the paid price.

Reviewed on Nov 20, 2025

Art Atelier

Art Atelier

4 out of 5
Historic Centre of Florence
Price was $1,643, price is now $1,156 per person
$1,156
per person
Jan 14 - Jan 20
found 6 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Florence (FLR)
9.2/10 Wonderful! (1,001 reviews)
We loved how close everything is! The staff were quick to accommodate our needs and the complimentary breakfast was a nice addition to jumpstart our day.

Reviewed on Dec 4, 2025

The St. Regis Florence

The St. Regis Florence

5 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $2,847, price is now $2,097 per person
$2,097
per person
Jan 14 - Jan 20
found 6 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Florence (FLR)
9.6/10 Exceptional! (261 reviews)
Nice property in a great location.

Reviewed on Jun 29, 2025

Hotel Lungarno - Lungarno Collection

Hotel Lungarno - Lungarno Collection

5 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $1,817, price is now $1,343 per person
$1,343
per person
Jan 16 - Jan 20
found 2 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
9.6/10 Exceptional! (593 reviews)
Excellent location! Truly a 5 star hotel ! Great service, breakfast, and service . Bedrooms were clean! Bathrooms were excellent!

Reviewed on Nov 19, 2025

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Discover the most popular places to visit in Monticchiello

Cathedral of Pienza featuring heritage elements, a church or cathedral and religious elements

Pienza Cathedral

5/5(131 reviews)

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

Pienza Cathedral

Palazzo Piccolomini

5/5(80 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.

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

3 Regions in 1 Day from Rome with Tuscany Wine Tasting & Lunch

From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch

$103
per adult
100% of travellers recommend
From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
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
See all activities in Monticchiello

Monticchiello Hotel Deals

Relais Villa Grazianella - UNA Esperienze

Relais Villa Grazianella - UNA Esperienze

Via Grazianella 5 Montepulciano SI
Fully refundableReserve now, pay when you stay
$146 nightly
The price is $166 total per night from Dec 9 to Dec 10
$166 total
Dec 9 - Dec 10
Total with taxes and fees
9.6/10 Exceptional! (276 reviews)
Everything was perfect. Warm welcome, comfortable and spacious rooms, great breakfast. The staff was very kind and friendly. I also recommend the wine tasting experience. Highly recommended!

Reviewed on Dec 5, 2025

Relais Villa Grazianella - UNA Esperienze
Rosewood Castiglion del Bosco

Rosewood Castiglion del Bosco

5 out of 5
Localita Castiglion del Bosco Montalcino SI
Fully refundableReserve now, pay when you stay
$1,203 nightly
The price is $1,335 total per night from Jan 4 to Jan 5
$1,335 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
10/10 Exceptional! (69 reviews)
Wonderful stay

Reviewed on Nov 25, 2025

Rosewood Castiglion del Bosco
Grand Hotel Admiral Palace

Grand Hotel Admiral Palace

4 out of 5
Via Umbria 2 Chianciano Terme SI
Fully refundableReserve now, pay when you stay
$87 nightly
The price is $101 total per night from Dec 9 to Dec 10
$101 total
Dec 9 - Dec 10
Total with taxes and fees
8/10 Very Good! (303 reviews)
The staff was very helpful and nice. Safe neighborhood and quiet.

Reviewed on Jun 29, 2025

Grand Hotel Admiral Palace
See all 4,109 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 $511 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.