Monsigliolo Vacations from $956

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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
Save 100% on your flight
Price was $1,533, price is now $956 per person
$956
per person
Apr 25 - Apr 28
found 22 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.6/10 Good! (1,002 reviews)
It was near the train and next to awesome places. The view if you get a balcony is so cute and peaceful

Reviewed on Feb 28, 2026

Eurostars Florence Boutique

Eurostars Florence Boutique

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $1,925, price is now $1,166 per person
$1,166
per person
May 13 - May 18
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
8.6/10 Excellent! (483 reviews)
The room was clean and the staff very accommodating. The breakfast was quite sufficient and had a good variety. The location is great. It's a short walk from the square, shopping and from restaurants.

Reviewed on Dec 13, 2025

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was $2,208, price is now $1,403 per person
$1,403
per person
Apr 22 - Apr 26
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.6/10 Good! (1,000 reviews)
Smaller room then expected and shower did flood the floor so not the best of showers. Bed very comfortable Nice friendly & helpful staff and perfect location to explore the city.

Reviewed on Feb 22, 2026

Relais Uffizi, Tailor made Hotel

Relais Uffizi, Tailor made Hotel

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $3,281, price is now $2,122 per person
$2,122
per person
May 13 - May 19
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Florence (FLR)
9.4/10 Exceptional! (120 reviews)
The room was stunning, it was large, the bed was comfy and the design was unique. Staff were very friendly and helpful.

Reviewed on Feb 26, 2026

Hotel La Scaletta Al Ponte Vecchio

Hotel La Scaletta Al Ponte Vecchio

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $2,220, price is now $1,509 per person
$1,509
per person
May 13 - May 18
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
8.8/10 Excellent! (965 reviews)
The staff at breakfast prepare plain scrambled eggs for our 7 month old son and were very sweet! This our second time staying here and we absolutely love the hotel. Location, views, comfort. 10/10!

Reviewed on Feb 28, 2026

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Discover the most popular places to visit in Monsigliolo

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

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

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

$105
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

$24
per adult
Oil museum and oil mill in Tuscany: tour and tasting
See all activities in Monsigliolo

Monsigliolo Hotel Deals

Relais Villa Grazianella - UNA Esperienze

Relais Villa Grazianella - UNA Esperienze

Via Grazianella 5 Montepulciano SI
$195 nightly
The price is $219 total per night from Mar 4 to Mar 5
$219 total
Mar 4 - Mar 5
Total with taxes and fees
9.8/10 Exceptional! (279 reviews)
Everything was perfect. Warm welcome, comfortable and spacious rooms, great breakfast. The staff was very kind and friendly. I also recommend the wine tasting experience. Highly recommended!

Reviewed on Dec 5, 2025

Relais Villa Grazianella - UNA Esperienze
Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Via Poggio alla Sala 10 Montepulciano SI
$339 nightly
The price is $380 total per night from Mar 20 to Mar 21
$380 total
Mar 20 - Mar 21
Total with taxes and fees
9.4/10 Exceptional! (123 reviews)
Perfect escape
Fantastic hotel in an incredible setting. Staff were extremely helpful, attentive and understanding. The perfect location for a relaxing break and a centre for exploring Tuscany

Reviewed on Oct 27, 2025

Precise Tale Poggio Alla Sala
Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World

5 out of 5
Localita Piazzano, C.P. 6 Cortona AR
$689 nightly
The price is $768 total per night from Apr 1 to Apr 2
$768 total
Apr 1 - Apr 2
Total with taxes and fees
9.8/10 Exceptional! (228 reviews)
Room was wonderful, bathroom spacious and well appointed. Staff amazing and so friendly

Reviewed on Nov 6, 2025

Villa di Piazzano - Small Luxury Hotel of the World
See all 5,101 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 $956 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.