Monsigliolo Vacations from $748

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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.
The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
9.6/10 Exceptional! (462 reviews)
The hotel is located a 25 min walk away from the heart of Florence so very easy to access the main attractions within the city. The hotel itself is immaculate and the staff are extremely helpful with dealing with any questions you may have. Being able to access the spa everyday for 1 and 30 minutes is an excellent perk as the facilities are well worth a visit, you are also able to book massages for an extra fee. The breakfast also gives a variety of options to start each day and the room itself is spacious, with the shower particularly being very comfortable.

Reviewed on Aug 13, 2025

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Oct 9 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,000 reviews)
Great location and very clean

Reviewed on Aug 12, 2025

Palazzo Firenze by Baglioni Hotels & Resorts

Palazzo Firenze by Baglioni Hotels & Resorts

5 out of 5
Historic Centre of Florence
per person
Oct 9 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.4/10 Exceptional! (230 reviews)
I VERY MUCH ENJOYED THE STAY

Reviewed on Jul 18, 2025

Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World

5 out of 5
Save 100% on your flight
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
9.8/10 Exceptional! (218 reviews)
AMAZING! Gorgeous! I would recommend to everyone!

Reviewed on Jul 29, 2025

Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.6/10 Good! (1,007 reviews)
Great location. Few minutes away from train station. Not so quiet. You could hear people from outside even the windows closed. If you are staying for a few days, it’s a great location.

Reviewed on Aug 14, 2025

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Discover the most popular places to visit in Monsigliolo

Cortona featuring heritage architecture

Piazza della Repubblica

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

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

Cortona Cathedral

What to do in Monsigliolo

Cortona

Cortona Private Guided Tour

$305
per traveler
Cortona Private Guided Tour
For your personal cooking class in Tuscany

Amazing four courses cooking class in Tuscany

$311
per adult
Amazing four courses cooking class in Tuscany
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
See all activities in Monsigliolo

Monsigliolo Hotel Deals

A Point Arezzo Park Hotel

A Point Arezzo Park Hotel

4 out of 5
Loc. Battifolle, 36/T, A1 exit Arezzo, Arezzo, AR
Fully refundableReserve now, pay when you stay
$87 nightly
The price is $102 total per night from Aug 24 to Aug 25
$102 total
Aug 24 - Aug 25
Total includes taxes and fees
7.6/10 Good! (141 reviews)
"It is very close to autostrada,which is good if you have car. The Breakfast was excellant,with a wonderful hostess. This lady is a big bonus to this hotel.The air-conditioning is building controlled,which would not suit everyone.The cleaner for our area had poor attention to detail. The lead cleaner ..."

Reviewed on Sep 24, 2024

A Point Arezzo Park Hotel
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
$273 nightly
The price is $309 total per night from Aug 24 to Aug 25
$309 total
Aug 24 - Aug 25
Total includes taxes and fees
9.8/10 Exceptional! (228 reviews)
"Beautiful property, magical, great friendly staff, fantastic breakfast. Everything was perfect"

Reviewed on Aug 7, 2025

Monastero di Cortona Hotel & Spa
Il Casale Di Manuele 12, Emma Villas

Il Casale Di Manuele 12, Emma Villas

Montepulciano
10/10 Exceptional! (2 reviews)
Tuscany with Freinds
"We loved this home - everything was perfect and it was easy to find and enjoy. I highly recommend the next time you are wanting to stay in Tuscany!"

Reviewed on Jun 16, 2025

Get rates
Il Casale Di Manuele 12, Emma Villas
See all 5,332 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.

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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 $748 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.