Monsigliolo Vacations from $995

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

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

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.
  • A hotel room with two beds, each with white linens and pillows, and a dark wood panel wall.
    Feb 4 - Feb 10

    Aurum Firenze + Flight

    Historic Centre of Florence
    5 nights
    4.0 star property
    7.4/10 - Good (1,001 reviews)
    "Nice place, good location"
    Reviewed November 11, 2026
    Roundtrip • New York (EWR) - Florence (FLR)
    EWR - FLR • 1 stop FLR - EWR • 1 stop
    $1,353
    $995
    per traveler
    found 1 day ago
    Aurum Firenze
  • A rooftop pool with a view of the Florence Cathedral and surrounding cityscape.
    Feb 4 - Feb 10

    Donati Luxury Tower Suites + Flight

    Historic Centre of Florence
    5 nights
    5.0 star property
    9.8/10 - Exceptional (83 reviews)
    "Great boutique hotel with good size room and bathroom. Very clean and helpful staff. Would definitely stay here again."
    Reviewed November 9, 2026
    Roundtrip • New York (EWR) - Florence (FLR)
    EWR - FLR • 1 stop FLR - EWR • 1 stop
    $2,754
    $1,916
    per traveler
    found 1 day ago
    Donati Luxury Tower Suites
  • A hotel room with a bed, a flat-screen TV mounted on the wall, a wooden wardrobe, and a mirror.
    Feb 4 - Feb 10

    Aurum Uffizi + Flight

    Historic Centre of Florence
    5 nights
    4.0 star property
    7.6/10 - Good (1,001 reviews)
    Roundtrip • New York (EWR) - Florence (FLR)
    EWR - FLR • 1 stop FLR - EWR • 1 stop
    $1,481
    $1,040
    per traveler
    found 1 day ago
    Aurum Uffizi
  • A view of the Florence Cathedral from a window, with a bottle of champagne and a bowl of strawberries on the table.
    Dec 27 - Jan 2

    Hotel Duomo Firenze + Flight

    Historic Centre of Florence
    5 nights
    3.0 star property
    9.2/10 - Wonderful (999 reviews)
    "Amazing location. So cool to be literally across from the Duomo. Easy walk to so many places to shop and eat. Free sparkling and still water was great. Snacks and free gelato! Staff was the most friendly and helpful. Highly recommend this place!"
    Reviewed November 3, 2026
    Roundtrip • Boston (BOS) - Florence (FLR)
    BOS - FLR • 1 stop FLR - BOS • 2 stops
    $4,413
    $3,148
    per traveler
    found 1 day ago
    Hotel Duomo Firenze
  • A table set for two with wine glasses, a candle, and cutlery, overlooking a river with buildings and a bridge in the background.
    Jan 22 - Jan 29

    Hotel Lungarno - Lungarno Collection + Flight

    Historic Centre of Florence
    4 nights
    5.0 star property
    9.6/10 - Exceptional (648 reviews)
    "Overall, the property is beautiful, very centrally, located and easy walking distance to every place. Our room was lovely very clean and the staff very helpful. I would definitely stay here again."
    Reviewed November 10, 2026
    Roundtrip • Boston (BOS) - Florence (FLR)
    BOS - FLR • 1 stop FLR - BOS • 1 stop
    $1,812
    $1,336
    per traveler
    found 1 day ago
    Hotel Lungarno - Lungarno Collection

Monsigliolo Hotel Deals

A view of a historic building with a green dome through a window, with candles and rolled towels on the windowsill.

Hotel Italia

Hotel Italia
3.0 star property
Cortona Old Town, 2.8 mi from Monsigliolo
9.0 out of 10, Wonderful, (301 reviews)
$102 nightly
The price is $115
Nov 15 - Nov 16
Total with taxes and fees
Hotel Italia
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.
See all properties in Monsigliolo

Frequently Asked Questions

How much does a Monsigliolo vacation package cost?

You can pick up a vacation package to this top destination from $995 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.