Montescudaio Vacations from $1,047
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The Latest Montescudaio Vacation Packages
- Aurum Uffizi
Oct 16 - Oct 22Aurum Uffizi + Flight
Historic Centre of Florence5 nights4.0 star property7.6/10 - Good (1,001 reviews)"Great little hotel in heart of city"Reviewed July 30, 2026Roundtrip • New York (NYC) - Florence (FLR)JFK - FLR • 1 stop FLR - EWR • 1 stop$1,545$1,047found 1 day agoper traveler - Grand Hotel Cavour
Oct 16 - Oct 22Grand Hotel Cavour + Flight
Historic Centre of Florence5 nights4.0 star property9.2/10 - Wonderful (1,002 reviews)"Great location, helpful staff, don’t miss the rooftop bar at night for a great view of the Duomo"Reviewed July 29, 2026Roundtrip • New York (NYC) - Florence (FLR)JFK - FLR • 1 stop FLR - EWR • 1 stop - Eurostars Florence Boutique
Oct 2 - Oct 8Eurostars Florence Boutique + Flight
Historic Centre of Florence5 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 • New York (EWR) - Florence (FLR)EWR - FLR • 1 stop FLR - EWR • 1 stop$2,156$1,536found 1 day agoper traveler - The Moon Boutique Hotel & Spa
Oct 1 - Oct 6The Moon Boutique Hotel & Spa + Flight
Historic Centre of Florence4 nights4.0 star property9.6/10 - Exceptional (577 reviews)"The hotel was very well-maintained with helpful staff. The breakfast was fantastic. The only problem was, it was a far walk to the city centre. Despite the walk , I highly recommend this hotel"Reviewed July 20, 2026Roundtrip • Boston (BOS) - Florence (FLR)BOS - FLR • 1 stop FLR - BOS • 1 stop$1,977$1,429found 1 day agoper traveler - Precise Tale Poggio Alla Sala
Oct 11 - Oct 15Precise Tale Poggio Alla Sala + Flight
Montepulciano4 nights5.0 star property9.6/10 - Exceptional (155 reviews)"Magical location, pools, staff, property."Reviewed July 19, 2026Roundtrip • New York (JFK) - Florence (FLR)JFK - FCO • Nonstop FCO - JFK • 1 stop$2,376$1,752found 13 hours agoper traveler
Montescudaio Hotel Deals
Riparbella Country Suite
Riparbella Country Suite
Hotiday Toscana Riparbella
Hotiday Toscana Riparbella
Casa Cerboneschi
Casa Cerboneschi
B&B Podere San Filippo
B&B Podere San Filippo
Locanda dell'Aioncino
Locanda dell'Aioncino
Punti Di Vista B&B Food&Wine Experience
Punti Di Vista B&B Food&Wine ExperienceFrequently Asked Questions
How much does a Montescudaio vacation package cost?
You can snap up a vacation package to this destination from $1,047 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.