Monticchiello Vacations from $562

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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.
Castello di Bossi

Castello di Bossi

2 out of 5
Price was $685, price is now $562 per person
$562
per person
Dec 9 - Dec 13
found 12 hours ago
Roundtrip flight included
Tel Aviv (TLV) to Florence (FLR)
7.8/10 Good! (8 reviews)

The Place Firenze

The Place Firenze

5 out of 5
Historic Centre of Florence
Price was $2,138, price is now $1,616 per person
$1,616
per person
Dec 9 - Dec 13
found 1 hour ago
Roundtrip non-stop flight included
Tel Aviv (TLV) to Florence (FLR)
9.8/10 Exceptional! (203 reviews)

Dimora Palanca Boutique & SPA

Dimora Palanca Boutique & SPA

5 out of 5
Historic Centre of Florence
Price was $1,075, price is now $860 per person
$860
per person
Dec 9 - Dec 13
found 4 hours ago
Roundtrip non-stop flight included
Tel Aviv (TLV) to Florence (FLR)
9.2/10 Wonderful! (78 reviews)
All

Reviewed on Oct 31, 2026

The Hoxton, Florence

The Hoxton, Florence

4 out of 5
Historic Centre of Florence
Price was $1,067, price is now $853 per person
$853
per person
Jan 16 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
9.4/10 Exceptional! (370 reviews)
Very nice staff, clean rooms and great room service and nice furniture ! Close to the main touristy places in the city, maximum of 30 minutes walk radius from everything that I wanted to visit!

Reviewed on Nov 2, 2026

Donati Luxury Tower Suites

Donati Luxury Tower Suites

5 out of 5
Historic Centre of Florence
Price was $1,476, price is now $1,198 per person
$1,198
per person
Dec 9 - Dec 13
found 4 hours ago
Roundtrip non-stop flight included
Tel Aviv (TLV) to Florence (FLR)
9.8/10 Exceptional! (82 reviews)
Great location. Historical building. Rooms were stunning. Lovely breakfast box delivered daily. Nice staff. The only negative is the roof is €250 per 2 hour booking, which I didn't expect, and would have been a reason for booking. Hence 4/5.

Reviewed on Oct 19, 2026

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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
Fully refundable
$118 nightly
The price is $135 total per night from Nov 13 to Nov 14
$135 total
Nov 13 - Nov 14
Total with taxes and fees
9.2/10 Wonderful! (152 reviews)
"Property was a little hard to find but just needs better signage. Once we got there, the property is beautiful, staff was excellent, price was reasonable, city center was walkable distance. Would definitely stay there again and would recommend it to others."

Reviewed on Nov 2, 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
$907 nightly
The price is $1,009 total per night from Dec 4 to Dec 5
$1,009 total
Dec 4 - Dec 5
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.