Monticchiello Vacations from $677

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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
Save 100% on your flight
per person
Sep 11 - Sep 15
found 7 hours ago
Roundtrip flight included
New York (NYC) to Florence (FLR)
7.8/10 Good! (1,000 reviews)
Excellent Location, friendly staff and good standard room

Reviewed on Jul 1, 2025

Tenuta di Artimino Member of Meliá Collection

Tenuta di Artimino Member of Meliá Collection

4 out of 5
Save 100% on your flight
per person
Sep 25 - Sep 30
found 23 hours ago
Roundtrip flight included
New York (NYC) to Florence (FLR)
9.4/10 Exceptional! (116 reviews)
One of the most amazing hotels I’ve ever stayed.

Reviewed on Jun 23, 2025

Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World

5 out of 5
Save 100% on your flight
per person
Aug 23 - Aug 29
found 1 day ago
Roundtrip flight included
New York (NYC) to Florence (FLR)
9.8/10 Exceptional! (210 reviews)
Our recent 4 night stay at Villa di Piazzano was truly perfect in every way! Celebrating our 40th wedding anniversary could not have been more enjoyed! Having booked our stay 6 mos in advance - I communicated many times via email during that time, seeking itinerary advice from the Conceirge. I always received very fast responses with creative ideas for our schedule that ended up proving most enjoyable. Cortona is a short, 10 minute drive away. Our arrival day was a dream, as we drove up the cypress lined drive which gave the feeling of arriving a royal residence! We were warmly greeted and instantly felt that our arrival was anticipated by the staff. We bonded very quickly with several of the team during our stay and experienced their excellent and warm hospitality. Our room, Luna Piena, proved to be absolutely perfect! Spotlessly clean and most roomy. We especially loved the bath area and roomy shower. Our room was accurately historical with every modern convenience. We enjoyed opening the windows each cool morning and loved listening to the birds sing. The property grounds were stunning! So much detail and care! The maintenance/gardening crew should be awarded! Amazing! We enjoyed wandering around the gardens and admiring all the flowers and plants! The swimming pool was crystal clear and the perfect temperature! Restaurant food was OUTSTANDING! I’m not sure how another resort hotel ANYWHERE in Tuscany region could top the experience we enjoyed at Villa di Piazzano!

Reviewed on Jun 24, 2025

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Save 100% on your flight
per person
Aug 23 - Aug 29
found 1 day ago
Roundtrip flight included
New York (NYC) to Florence (FLR)
9.4/10 Exceptional! (94 reviews)
Beautiful property. Excellent staff. Everyone was professional and friendly.

Reviewed on Jun 29, 2025

Villa Cora

Villa Cora

5 out of 5
Oltrarno
Save 100% on your flight
per person
Sep 19 - Sep 26
just found
Roundtrip flight included
New York (NYC) to Florence (FLR)
9.8/10 Exceptional! (448 reviews)
lovely and a short walk to the center of town.....

Reviewed on Jun 30, 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

Val D'Orcia Dreaming!!

Val D'Orcia Dreaming!!

$226
per adult
Val D'Orcia Dreaming!!
Brunello Wine Tour and Val D'Orcia Landscape

Brunello Wine Tour and Val D'Orcia Landscape

$254
per adult
Brunello Wine Tour and Val D'Orcia Landscape
Pienza & Montepulciano Small Group Tour from Siena

Pienza & Montepulciano Small Group Tour from Siena

$207
per adult
Pienza & Montepulciano Small Group Tour from Siena
See all activities in Monticchiello

Monticchiello Hotel Deals

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
$433 nightly
The price is $483 total per night from Jul 10 to Jul 11
$483 total
Jul 10 - Jul 11
Total includes taxes and fees
9.2/10 Wonderful! (96 reviews)
"Beautiful property. Excellent staff. Everyone was professional and friendly."

Reviewed on Jun 29, 2025

Precise Tale Poggio Alla Sala
Nuovo Etruria Resort
Nuovo Etruria Resort
Via di S. Martino snc, Montepulciano, SI
Fully refundableReserve now, pay when you stay
$114 nightly
The price is $131 total per night from Jul 9 to Jul 10
$131 total
Jul 9 - Jul 10
Total includes taxes and fees
9/10 Wonderful! (13 reviews)
"The room was very clean. The view from the room is stunning! It is very quiet and relaxing. The resort is facing Montepulciano! The staff is very nice and friendly. I highly recommend it."

Reviewed on Jun 14, 2025

Nuovo Etruria Resort
Hotel Relais II Chiostro di Pienza
Hotel Relais II Chiostro di Pienza
4 out of 5
Corso Rossellino 26, Pienza, SI
Fully refundableReserve now, pay when you stay
$173 nightly
The price is $197 total per night from Jul 6 to Jul 7
$197 total
Jul 6 - Jul 7
Total includes taxes and fees
8.6/10 Excellent! (568 reviews)
Great Town, not so great hotel
"The hotel it's ok It's a former Franciscan Convent dating back to 13th century! Depending of the room.it will be room size. The best views you will get from the outside terrace where breakfast it's served Amazing views of Toscana The hotel it's located right in the middle of the town Pienza right ..."

Reviewed on Jun 29, 2025

Hotel Relais II Chiostro di Pienza
See all 4,145 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 $677 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.