Monticchiello Vacations from $886

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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.
Villa Tolomei Hotel & Resort

Villa Tolomei Hotel & Resort

5 out of 5
Oltrarno
Price was $1,161, price is now $886 per person
$886
per person
Jan 23 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Florence (FLR)
8.8/10 Excellent! (445 reviews)
Beautiful hotel! We didn't realize the pool would be closed when we were there, but otherwise excellent stay.

Reviewed on Oct 13, 2026

The Place Firenze

The Place Firenze

5 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $2,686, price is now $1,942 per person
$1,942
per person
Dec 3 - Dec 8
found 18 hours ago
Roundtrip non-stop flight included
New York (NYC) to Florence (FLR)
9.8/10 Exceptional! (203 reviews)

Portrait Firenze - Lungarno Collection

Portrait Firenze - Lungarno Collection

5 out of 5
Historic Centre of Florence
Price was $2,573, price is now $1,942 per person
$1,942
per person
Jan 23 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Florence (FLR)
9.8/10 Exceptional! (320 reviews)
Nice location, clean room, feel like home

Reviewed on Oct 27, 2026

Hotel Lungarno - Lungarno Collection

Hotel Lungarno - Lungarno Collection

5 out of 5
Historic Centre of Florence
Price was $1,970, price is now $1,506 per person
$1,506
per person
Jan 26 - Jan 30
found 1 day ago
Roundtrip flight included
New York (JFK) to Florence (FLR)
9.6/10 Exceptional! (644 reviews)
Beautiful hotel, beautiful rooms, fantastic location, amazing service and staff.

Reviewed on Nov 1, 2026

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

5 out of 5
Cortona Old Town
Price was $1,468, price is now $1,169 per person
$1,169
per person
Dec 3 - Dec 8
found 14 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
10/10 Exceptional! (357 reviews)

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Stay near popular Monticchiello attractions

Art Studio di Adelina Quadri

You can spend an afternoon browsing the exhibits at Art Studio di Adelina Quadri during your travels in Monticchiello. While you're here, you can savor the wineries.
See properties

What to do in Monticchiello

Montepulciano Wine Tasting in the Tuscan Countryside

Montepulciano Wine Tasting in the Tuscan Countryside

$28
per adult
Montepulciano Wine Tasting in the Tuscan Countryside
Montalcino: Guided Winery Tour and Wine Tasting

Montalcino: Guided Winery Tour and Wine Tasting

$51
per adult
Montalcino: Guided Winery Tour and Wine Tasting
Montepulciano: Winery Tour and Tasting

Montepulciano: Winery Tour and Tasting

$39
per adult
100% of travellers recommend
Montepulciano: Winery Tour and Tasting
See all activities in Monticchiello

Monticchiello Hotel Deals

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Via Di Poggio Alla Sala, 10 Montepulciano SI
Get rates
Precise Tale Poggio Alla Sala
Nuovo Etruria Resort

Nuovo Etruria Resort

4 out of 5
Via di S. Martino snc Montepulciano SI
$119 nightly
The price is $136 total per night from Nov 6 to Nov 7
$136 total
Nov 6 - Nov 7
Total with taxes and fees
9.2/10 Wonderful! (151 reviews)
"Beautiful and perfect stay in Montepulciano!"

Reviewed on Oct 27, 2026

Nuovo Etruria Resort
Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel

5 out of 5
Localita Castiglion del Bosco Montalcino SI
Fully refundableReserve now, pay when you stay
$904 nightly
The price is $1,005 total per night from Dec 3 to Dec 4
$1,005 total
Dec 3 - Dec 4
Total with taxes and fees
10/10 Exceptional! (87 reviews)
"Unique property well maintained and quite Serene , great staff"

Reviewed on Oct 30, 2026

Castiglion del Bosco, A Rosewood Hotel
See all 4,060 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

What's included in a Monticchiello vacation package?
A Monticchiello vacation package lets you combine round-trip flights, a hotel stay, and a rental car, offering flexibility to explore the scenic Tuscan countryside. Most hotels in this charming region offer complimentary breakfast, providing a delightful start to your day. Additionally, around 1 in 3 hotels provide airport shuttle service, which can be convenient for transfers from Florence Airport (FLR).

Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.
How can I save money on a Monticchiello vacation package?
When you bundle, you can save up to 30%*. To save money on a Monticchiello package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.
What are the top things to do in Monticchiello?
Monticchiello, an outdoor and nature destination, offers a blend of cultural sites and scenic beauty for your Monticchiello vacation:

These activities enhance any Monticchiello vacation. Browse and book things to do in Monticchiello on Expedia.
Do you need to rent a car in Monticchiello, or is public transport enough?
For Monticchiello vacation packages with flights, a rental car is highly recommended for exploring this outdoor and nature destination. Monticchiello and its surrounding Tuscan countryside are best navigated by car, as many cultural attractions and scenic spots are spread out. A car provides the flexibility to visit the Historic Centre of Pienza, about 5 miles away, or enjoy wine tastings at the Consorzio del Vino Nobile di Montepulciano, about 7 miles from central Monticchiello. While public transport options are available between larger towns, a rental car offers the convenience and direct access needed for a comprehensive Monticchiello vacation package experience. You can pick up a rental car at major airports like Rome (FCO-Fiumicino - Leonardo da Vinci Intl.) or Florence (FLR-Peretola).
Can I change or cancel my Monticchiello vacation package if my plans change?
Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.
Do One Key members get extra savings when booking Monticchiello vacation packages?
Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.
Does Expedia offer Book Now, Pay Later Monticchiello vacation packages?
Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Monticchiello vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.
How do I find last-minute vacation packages to Monticchiello?
To find last-minute vacation packages to Monticchiello, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.
How does free cancellation work on Monticchiello vacation packages?
Free cancellation on a Monticchiello vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.
Is it cheaper to book a Monticchiello vacation as a package or separately?
Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Monticchiello getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
Why should I book my Monticchiello vacation package with Expedia?
Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

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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.