Monticchiello Vacations from $723

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to $1,045 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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.
The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Oct 30 - Nov 4
found 15 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.6/10 Exceptional! (462 reviews)
The hotel is located a 25 min walk away from the heart of Florence so very easy to access the main attractions within the city. The hotel itself is immaculate and the staff are extremely helpful with dealing with any questions you may have. Being able to access the spa everyday for 1 and 30 minutes is an excellent perk as the facilities are well worth a visit, you are also able to book massages for an extra fee. The breakfast also gives a variety of options to start each day and the room itself is spacious, with the shower particularly being very comfortable.

Reviewed on Aug 13, 2025

The Sense Experience Resort

The Sense Experience Resort

5 out of 5
per person
Sep 21 - Sep 27
found 21 hours ago
Roundtrip flight included
New York (JFK) to Florence (FLR)
9.2/10 Wonderful! (186 reviews)
Great rooms and great beach

Reviewed on Aug 3, 2025

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Sep 26 - Oct 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,000 reviews)
In my particular case, I tink is a good hotel , I would like the breakfast has more options. Probably I comeback next time.

Reviewed on Aug 18, 2025

Grand Hotel Cavour

Grand Hotel Cavour

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Sep 23 - Sep 29
found 20 hours ago
Roundtrip non-stop flight included
New York (NYC) to Florence (FLR)
9.2/10 Wonderful! (1,011 reviews)
Close to everywhere, great rooftop bar with amazing view

Reviewed on Aug 17, 2025

Palazzo Firenze by Baglioni Hotels & Resorts

Palazzo Firenze by Baglioni Hotels & Resorts

5 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Oct 30 - Nov 4
found 15 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.4/10 Exceptional! (230 reviews)
I VERY MUCH ENJOYED THE STAY

Reviewed on Jul 18, 2025

Don't see what you're looking for?
See all available trips from Columbus to Monticchiello
View all trips

Discover the most popular places to visit in Monticchiello

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

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

Pienza & Montepulciano Small Group Tour from Siena

Pienza & Montepulciano Small Group Tour from Siena

$209
per adult
Pienza & Montepulciano Small Group Tour from Siena
Capturing the best version of yourself with beautiful professional pictures

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

$290
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

$380
per traveler
Pienza: Private Walking Tour in the Heart of Tuscany
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
Fully refundableReserve now, pay when you stay
$120 nightly
The price is $139 total per night from Sep 14 to Sep 15
$139 total
Sep 14 - Sep 15
Total includes taxes and fees
8.6/10 Excellent! (582 reviews)
"Great experience"

Reviewed on Aug 13, 2025

Hotel Relais II Chiostro di Pienza
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
$388 nightly
The price is $434 total per night from Aug 24 to Aug 25
$434 total
Aug 24 - Aug 25
Total includes taxes and fees
9.4/10 Exceptional! (106 reviews)
"10/10, would definitely recommend!"

Reviewed on Aug 15, 2025

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, Castelnuovo dell'Abate, Montalcino, SI
Fully refundableReserve now, pay when you stay
$581 nightly
The price is $651 total per night from Aug 26 to Aug 27
$651 total
Aug 26 - Aug 27
Total includes taxes and fees
8.8/10 Excellent! (324 reviews)
"We stayed two nights midway through travelling around Tuscany. It was a lovely peaceful break for us. We felt very pampered by all of the staff who were superb. Dining by the pool area was lovely. A very happy couple of days."

Reviewed on Jul 29, 2025

Castello di Velona Resort Thermal SPA & Winery
See all 4,164 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.

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Monticchiello vacation package cost?
You'll find cheap prices from $723 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.