Monsigliolo Vacations from $957
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Your Monsigliolo Vacation
Book a Monsigliolo vacation package and get ready to experience the best of this lively city. Consider staying in the neighborhood of Contrada Castello, which is great for dining, views and culture. Fill your itinerary with tours of Villa Bramasole, Piazza della Repubblica and Cathedral of Cortona, some of the top attractions you just have to see during your trip to Monsigliolo. Don't delay your visit to this city any longer. The ultimate Monsigliolo vacation is a couple of clicks away with Expedia.
The Latest Monsigliolo vacation packages
Price found within the past 48 hours. Click for updated prices.
Hotel Ginori al DUOMO
Historic Centre of Florence
$957
per person
Nov 17 - Nov 23
found 20 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
8.8/10 Excellent! (62 reviews)
Fantastic stay, thank you for the upgrade, spacious, cool rooms. Great location, walk to the station and across the road is a convenience store and great restaurants and gelato in the same street
Reviewed on Sep 4, 2026
Donati Luxury Tower Suites
Historic Centre of Florence
$1,980
per person
Dec 12 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.8/10 Exceptional! (73 reviews)
We loved this property. The room and view are beautiful. There are excellent restaurants and shopping around the corner.
Reviewed on Sep 21, 2026
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View all tripsWhat to do in Monsigliolo
Montepulciano Wine Tasting in the Tuscan Countryside
$29
per adult
Montepulciano: Winery Tour and Tasting
$40
per adult
100% of travellers recommend
Horseback riding through the vineyards in Montepulciano Tuscany
$92
per adult
Monsigliolo Hotel Deals
Villa di Piazzano - Small Luxury Hotel of the World
Localita Piazzano, C.P. 6 Cortona AR
$643 nightly
$716 total
Oct 14 - Oct 15
Total with taxes and fees
9.8/10 Exceptional! (251 reviews)
"Stunning little hotel with the most beautiful setting, gardens and pool. The room was exceptionally appointed clean. The best part of the stay was the restaurant. The best meals we had on our entire trip. Definitely recommend hiring e-bikes and riding up to Cortona!"
Reviewed on Sep 20, 2026
Nuovo Etruria Resort
Via di S. Martino snc Montepulciano SI
Fully refundable
$110 nightly
$125 total
Sep 29 - Sep 30
Total with taxes and fees
9.2/10 Wonderful! (133 reviews)
"very nice place to stay. wonderful view of Montepulciano. nice amenities and breakfast. The only issue was we stayed in the furthest building from the main house and Wi-Fi was limited. good location as a base to travel through Tuscany."
Reviewed on Sep 27, 2026
Precise Tale Poggio Alla Sala
Via Di Poggio Alla Sala, 10 Montepulciano SI
Fully refundableReserve now, pay when you stay
$531 nightly
$590 total
Oct 7 - Oct 8
Total with taxes and fees
9.6/10 Exceptional! (173 reviews)
"Great location, nice vineyards right out the door, lots of great restaurants nearby."
Reviewed on Sep 25, 2026
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 Monsigliolo Vacation Packages
Monsigliolo Essential Information
Language | Italian |
|---|---|
Currency | Euros |
Local Welcome | Ciao |
Local Goodbye | Ciao |
Max Temp Winter | 45ºF |
Max Temp Summer | 80ºF |
Top Sights | Signorelli Theatre, Cathedral of Cortona and Museum of the Etruscan Academy |
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Frequently asked questions
How much does a Monsigliolo vacation package cost?
You can pick up a vacation package to this top destination from $957 on Expedia. However, how much your vacation to Monsigliolo costs will depend on factors like your hotel choice, season and length of stay.
What are the cheapest months to go to Monsigliolo?
October, November and December are the best times to look for cheap Monsigliolo vacation packages. Traveling in less busy periods means you can generally find better prices on hotels and flights.
How many days is enough for Monsigliolo?
The ideal duration for your Monsigliolo vacation depends on what you'd like to do and see. Generally, a handful of days to a week will give you time to check out all the top attractions and explore some hidden treasures along the way.
How to find the best Monsigliolo package deals?
Use Expedia's handy filters to help you find some of the best Monsigliolo package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your break for midweek, or look for Monsigliolo package deals in the off-peak season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book a Monsigliolo vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll usually score a better deal than booking each component individually. And you'll still enjoy the flexibility to create a tailored Monsigliolo vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation package to Monsigliolo?
Land amazing discounts by reserving your flights early with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for a spur-of-the-moment Monsigliolo adventure.
Does Expedia offer Book Now, Pay Later Monsigliolo vacation packages?
Your Monsigliolo getaway is meant to be a relaxing escape from your busy life, not a source of money worries. So to give you that extra flexibility, we've joined up with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and spread the total cost over 3, 6 or 12 months. Plus, there are no late payment fees or hidden costs to worry about.
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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.
