Monsigliolo Vacations from $589

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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.
Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Price was $982, price is now $589 per person
$589
per person
Jan 10 - Jan 15
found 23 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.6/10 Good! (1,002 reviews)
Close to train station and everything you need.

Reviewed on Nov 21, 2025

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was $1,096, price is now $688 per person
$688
per person
Feb 9 - Feb 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,000 reviews)
Breakfast was good. Staff super friendly. Overall the expected quality for the paid price.

Reviewed on Nov 20, 2025

Hotel Regency

Hotel Regency

5 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $1,408, price is now $924 per person
$924
per person
Jan 10 - Jan 15
found 23 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.4/10 Exceptional! (439 reviews)
Loved it! Great place and very convenient

Reviewed on Jul 4, 2025

Villa Cora

Villa Cora

5 out of 5
Oltrarno
Price was $1,664, price is now $1,105 per person
$1,105
per person
Feb 14 - Feb 17
found 1 day ago
Roundtrip flight included
Indianapolis (IND) to Florence (FLR)
9.8/10 Exceptional! (467 reviews)
Nice property and staff.

Reviewed on Nov 13, 2025

Relais Uffizi, Tailor made Hotel

Relais Uffizi, Tailor made Hotel

4 out of 5
Historic Centre of Florence
Price was $1,255, price is now $845 per person
$845
per person
Feb 9 - Feb 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.4/10 Exceptional! (120 reviews)
Phenomenal location!

Reviewed on Oct 18, 2025

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See all available trips from Columbus to Monsigliolo
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Discover the most popular places to visit in Monsigliolo

Cortona featuring heritage architecture

Piazza della Repubblica

5/5(4 reviews)

Find out about the history of Cortona with a stop at Piazza della Repubblica. Make time to visit the cathedral and monuments while you're in the area.

Piazza della Repubblica

Villa Bramasole

You can learn about the history of Cortona with a trip to Villa Bramasole. You can enjoy the wineries while in the area.

Villa Bramasole

Cortona Cathedral

Cortona Cathedral is just one of the places to see in Cortona, so why not enjoy the other things to explore during your travels? Experience the area's museums and musical theater.

Cortona Cathedral

What to do in Monsigliolo

3 Regions in 1 Day from Rome with Tuscany Wine Tasting & Lunch

From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch

$103
per adult
100% of travellers recommend
From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
Montepulciano Wine Tasting in the Tuscan Countryside

Montepulciano Wine Tasting in the Tuscan Countryside

$29
per adult
Montepulciano Wine Tasting in the Tuscan Countryside
Oil museum and oil mill in Tuscany: tour and tasting

Oil museum and oil mill in Tuscany: tour and tasting

$23
per adult
Oil museum and oil mill in Tuscany: tour and tasting
See all activities in Monsigliolo

Monsigliolo Hotel Deals

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

5 out of 5
Via del Salvatore Cortona AR
Fully refundableReserve now, pay when you stay
$296 nightly
The price is $335 total per night from Dec 14 to Dec 15
$335 total
Dec 14 - Dec 15
Total with taxes and fees
9.8/10 Exceptional! (254 reviews)
Our arrival experience was less than stellar for a warm welcome to property. Front desk associate was very cold and accusatory of the situation we encountered outside of the property. We have traveled extensively and I expected better arrival experience. It all changed for the better when we finally ...

Reviewed on Nov 23, 2025

Monastero di Cortona Hotel & Spa
Hotel Continentale

Hotel Continentale

4 out of 5
Piazza Guido Monaco, 7 Arezzo AR
Fully refundableReserve now, pay when you stay
$128 nightly
The price is $152 total per night from Dec 16 to Dec 17
$152 total
Dec 16 - Dec 17
Total with taxes and fees
8.4/10 Very Good! (451 reviews)
We had a last-minute stay there due to the train strike, and it was a great evening after all… The hotel was right there in the main Square plus near the train station. The staff was lovely and they have the most beautiful rooftop patio and bar. you have to check out.

Reviewed on Oct 17, 2025

Hotel Continentale
Relais Villa Grazianella - UNA Esperienze

Relais Villa Grazianella - UNA Esperienze

Via Grazianella 5 Montepulciano SI
$113 nightly
The price is $129 total per night from Dec 14 to Dec 15
$129 total
Dec 14 - Dec 15
Total with taxes and fees
9.6/10 Exceptional! (275 reviews)
Great room and service

Reviewed on Nov 11, 2025

Relais Villa Grazianella - UNA Esperienze
See all 5,228 properties in Monsigliolo
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 $589 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.