Montescudaio Vacations from $1,178
Book a Hotel + Flight or Car together to unlock savings
The Latest Montescudaio Vacation Packages
- Aurum Uffizi
Oct 14 - Oct 20Aurum Uffizi + Flight
Historic Centre of Florence5 nights4.0 star property7.6/10 - Good (1,000 reviews)"La chambre est bien équipée"Reviewed July 18, 2026Roundtrip • Boston (BOS) - Florence (FLR)BOS - FLR • 1 stop FLR - BOS • 1 stop - Precise Tale Poggio Alla Sala
Sep 5 - Sep 11Precise Tale Poggio Alla Sala + Flight
Montepulciano5 nights5.0 star property9.6/10 - Exceptional (154 reviews)"Magical location, pools, staff, property."Reviewed July 19, 2026Roundtrip • New York (NYC) - Florence (FLR)JFK - FLR • 1 stop FLR - JFK • 1 stop - Tombolo Talasso & Beach Resort
Aug 25 - Aug 31Tombolo Talasso & Beach Resort + Flight
Castagneto Carducci6 nights5.0 star property8.8/10 - Excellent (146 reviews)"Where as we enjoyed our time here we did have a bit of an issue with our room temperature. We asked for it to be lowered as it was 81 degrees. We found out, after a very uncomfortable night and requesting 2 more times, that the AC was not working. As an aside: we could not open a window as our room was on the 1st floor and only had doors to a common area. We were moved to a new room. Other than that- the staff was lovely the pools and Spa are great. Location is wonderful with close..."Reviewed May 21, 2026Roundtrip • New York (NYC) - Florence (FLR)JFK - FLR • 1 stop FLR - JFK • 1 stop - Relais Uffizi, Tailor made Hotel
Sep 30 - Oct 4Relais Uffizi, Tailor made Hotel + Flight
Historic Centre of Florence3 nights4.0 star property9.4/10 - Exceptional (152 reviews)"Firstly this hotel is on a side street and not easy to find. We arrived with two young children on an intense heat wave day to check in for a confirmed, family room booked through Expedia. At check-in we were told the air conditioning in our room was broken. They made no attempt to inform us in advance of the issue or rebook us into a different room. The front desk declined to move us to another room and offered only a refund — which doesn’t help when an equivalent room for the same dates now..."Reviewed July 2, 2026Roundtrip • New York (NYC) - Florence (FLR)JFK - FLR • 1 stop FLR - EWR • 1 stop$2,049$1,411found 1 day agoper traveler - Eurostars Florence Boutique
Sep 28 - Oct 3Eurostars Florence Boutique + Flight
Historic Centre of Florence4 nights4.0 star property8.6/10 - Excellent (494 reviews)"Very good location. Clean hotel. Our ac was broken but they handled us a new room inmediately. The hotel is confortable and size of the rooms are decent. Bigger than average in the area."Reviewed June 26, 2026Roundtrip • Los Angeles (LAX) - Florence (FLR)LAX - FLR • 1 stop FLR - LAX • 1 stop$2,528$1,837found 19 hours agoper traveler
Montescudaio Hotel Deals
Riparbella Country Suite
Riparbella Country Suite
Hotiday Toscana Riparbella
Hotiday Toscana Riparbella
Casa Cerboneschi
Casa Cerboneschi
Punti Di Vista B&B Food&Wine Experience
Punti Di Vista B&B Food&Wine Experience
Vintage Hotel Tornese - Business & Events
Vintage Hotel Tornese - Business & Events
Relais Sant'Elena
Relais Sant'ElenaFrequently Asked Questions
How much does a Montescudaio vacation package cost?
You can snap up a vacation package to this destination from $1,178 on Expedia. However, how much your vacation to Montescudaio costs will depend on factors like the length of stay, hotel choice and season.
What are the cheapest months to go to Montescudaio?
If you'd like to book a cheap Montescudaio vacation package, consider planning a trip in November, December and January. You'll generally find better prices on flights and hotels during these months — perfect for travelers wishing to save money.
How many days is enough for Montescudaio?
Typically, a handful of days is enough to tick off the major sights during your Montescudaio vacation. But if you'd like to have time to chill out or go on day trips, think about extending your trip.
How to find the best Montescudaio package deals?
Use Expedia's filter tool to find some of the best Montescudaio 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 adventure for midweek, or browse for Montescudaio package deals in the off-season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to book your vacation package as early as possible.
Is it cheaper to book a Montescudaio vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll generally get a better deal than booking each component individually. And you'll still enjoy the freedom to create a personalized Montescudaio vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation package to Montescudaio?
Secure incredible discounts by booking your flights early with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for a spur-of-the-moment Montescudaio trip.
Does Expedia offer Book Now, Pay Later Montescudaio vacation packages?
If you're like us, you love jet-setting around the world but don't love the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the cost of your Montescudaio vacation over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up great vacation packages with payment plans as soon as you spot them.