Monticchiello Vacations from $743

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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 Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $1,265, price is now $743 per person
$743
per person
Nov 3 - Nov 8
found 14 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,000 reviews)
Asking for extra towels was like asking for money. Amenities were limited such as a kettle. I got sick and needed warm water but their machine was turned off at night and no kettle available for the room. Less storage

Reviewed on Sep 17, 2025

Villa Cora

Villa Cora

5 out of 5
Oltrarno
Save 100% on your flight
Price was $2,054, price is now $1,219 per person
$1,219
per person
Dec 7 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
9.8/10 Exceptional! (458 reviews)
Villa Cora was delightful in every way. The only negative thing I have to say is that I am not currently still there. Alas, I would highly recommend Villa Cora as a jumping off point for your Tuscan or Firenze adventures.

Reviewed on Sep 6, 2025

The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $1,335, price is now $877 per person
$877
per person
Dec 7 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
9.6/10 Exceptional! (470 reviews)
Room as immaculately clean. Steam shower was amazing. A little annoyed about the A/C, it turns off when you leave the room, so it didn’t stay cool in our room when we were gonna all day. Spa access was a lil confusing, it wasn’t use as you wish, you had to reserve a slot in a 3hr window which was at dinner time. This resulted in us only using the spa once. Breakfast had a wide selection, with a small cook to order menu. Was delicious and quick. Bed was extremely comfortable. Tram station for the T2 line was right in front of the hotel, when coming from the airport you have change T1 line to T2 line, but very simple.

Reviewed on Sep 14, 2025

Collegio alla Querce - Auberge Collection

Collegio alla Querce - Auberge Collection

5 out of 5
Le Cure
Save 100% on your flight
Price was $2,829, price is now $1,878 per person
$1,878
per person
Nov 22 - Nov 25
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
10/10 Exceptional! (3 reviews)
Dimora Palanca Boutique & SPA

Dimora Palanca Boutique & SPA

5 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $1,476, price is now $1,038 per person
$1,038
per person
Dec 7 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
9.4/10 Exceptional! (48 reviews)
Property is beautiful and quiet. Would stay there again.

Reviewed on Sep 13, 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

Capturing the best version of yourself with beautiful professional pictures

Photography Guided Tour in the Heart of Val D'Orcia and Tuscany

$292
per traveler
Photography Guided Tour in the Heart of Val D'Orcia and Tuscany
Pienza: Private Walking Tour in the Heart of Tuscany

Pienza: Private Walking Tour in the Heart of Tuscany

$382
per traveler
Pienza: Private Walking Tour in the Heart of Tuscany
Pienza & Montepulciano Small Group Tour from Siena

Pienza & Montepulciano Small Group Tour from Siena

$210
per adult
Pienza & Montepulciano Small Group Tour from Siena
See all activities in Monticchiello

Monticchiello Hotel Deals

Hotel Relais II Chiostro di Pienza

Hotel Relais II Chiostro di Pienza

4 out of 5
Corso Rossellino 26, Pienza, SI
8.6/10 Excellent! (593 reviews)
Stunning setting - authentic italian
"The pictures do not do it justice - stunning setting and view, very nice hotel, very kind attentive staff. Would definitely recommend."

Reviewed on Aug 25, 2025

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Hotel Relais II Chiostro di Pienza
Hotel Panoramic

Hotel Panoramic

3 out of 5
Via di Villa Bianca, 8, Montepulciano, SI
$102 nightly
The price is $117 total per night from Oct 10 to Oct 11
$117 total
Oct 10 - Oct 11
Total with taxes and fees
8.6/10 Excellent! (248 reviews)
"Nice location. Staff was nice. The only issue is the room with no AC or plugs. When reviewing the property it appeared the property lists AC. You would assume the whole hotel has AC. Once I selected the room I should have looked closely at the AC availability. Rough night to sleep. Other than that ..."

Reviewed on Jul 26, 2025

Hotel Panoramic
Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Via Poggio alla Sala 10, Montepulciano, SI
$408 nightly
The price is $456 total per night from Oct 9 to Oct 10
$456 total
Oct 9 - Oct 10
Total with taxes and fees
9.2/10 Wonderful! (108 reviews)
"10/10, would definitely recommend!"

Reviewed on Aug 15, 2025

Precise Tale Poggio Alla Sala
See all 4,158 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.

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Frequently asked questions

How much does a Monticchiello vacation package cost?
You'll find cheap prices from $743 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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