Monsigliolo Vacations from $617

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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 $898, price is now $617 per person
$617
per person
Nov 12 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,007 reviews)
Breakfast was excellent

Reviewed on Sep 29, 2025

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was $1,000, price is now $657 per person
$657
per person
Nov 12 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,008 reviews)
Great location! I loved my experience there. I would Definitely return.

Reviewed on Oct 8, 2025

Hotel Duomo Firenze

Hotel Duomo Firenze

3 out of 5
Historic Centre of Florence
Price was $1,420, price is now $983 per person
$983
per person
Nov 12 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9/10 Wonderful! (1,005 reviews)
The location and great staff

Reviewed on Oct 5, 2025

The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
Price was $1,304, price is now $903 per person
$903
per person
Nov 12 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.6/10 Exceptional! (477 reviews)
The front desk speaks multiple languages, and is very informative about the area around the hotel. The hotel is bright & clean, and they are the first hotel I stayed at in my time in Europe that didn't lock me out of the air conditioning setting. The spa was nice and relaxing and they make sure not too many people are there at the same time which is super nice. It was great after walking 20,000 steps in a day to sit in the turkish bath. They packed me a box breakfast the day I had to leave early to go on an excursion, and they offered one the day I went to the airport. Overall, amazing value for the price. The only complaint which isn't on them is that there are not many restaurant options immediately next to the hotel - just one. However, I spent most of my time in the city center so that was fine.

Reviewed on Oct 4, 2025

LHP River Club

LHP River Club

5 out of 5
Santa Croce
Price was $923, price is now $671 per person
$671
per person
Nov 11 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9/10 Wonderful! (8 reviews)
Beautiful room and comfortable bed. Clean. Nice pool area. There are no elevators but the stairs are not long. AC is not very strong but suffices. Area is full of hidden gems from bakeries to late night pizza. Parking can be a challenge but not more than other parts of the city. About a 20 min walk to the center and plenty of shops and restaurants along the way.

Reviewed on Sep 23, 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

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

Montepulciano Wine Tasting in the Tuscan Countryside

Montepulciano Wine Tasting in the Tuscan Countryside

$30
per adult
Montepulciano Wine Tasting in the Tuscan Countryside
3 Regions in 1 Day from Rome with Tuscany Wine Tasting & Lunch

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

$105
per adult
100% of travellers recommend
From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
Oil museum and oil mill in Tuscany: tour and tasting

Oil museum and oil mill in Tuscany: tour and tasting

$24
per adult
Oil museum and oil mill in Tuscany: tour and tasting
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
$97 nightly
The price is $114 total per night from Nov 2 to Nov 3
$114 total
Nov 2 - Nov 3
Total with taxes and fees
7.6/10 Good! (144 reviews)
Meh
"This hotel has so much potential, but many details are missing. From music to create a pleasant atmosphere in the communal areas, especially restaurant and breakfast space. (So awkward to hear everyone chew their food around you and the kitchen staff comments in the background) To electrical jobs ..."

Reviewed on Jul 3, 2025

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
$264 nightly
The price is $295 total per night from Nov 2 to Nov 3
$295 total
Nov 2 - Nov 3
Total with taxes and fees
9.8/10 Exceptional! (239 reviews)
"Beautiful, unique property! Stunning views of the countryside. The staff were all very helpful and friendly. We will definitely recommend!"

Reviewed on Sep 27, 2025

Monastero di Cortona Hotel & Spa
Hotel Relais II Chiostro di Pienza

Hotel Relais II Chiostro di Pienza

4 out of 5
Corso Rossellino 26, Pienza, SI
Fully refundableReserve now, pay when you stay
$76 nightly
The price is $91 total per night from Oct 26 to Oct 27
$91 total
Oct 26 - Oct 27
Total with taxes and fees
8.6/10 Excellent! (598 reviews)
"The perfect location. Gorgeous property. Excellent breakfast."

Reviewed on Oct 4, 2025

Hotel Relais II Chiostro di Pienza
See all 5,329 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.

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 $617 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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