Montescudaio Vacations from $1,251
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The Latest Montescudaio Vacation Packages
- Aurum Uffizi
Oct 5 - Oct 10Aurum Uffizi + Flight
Historic Centre of Florence4 nights4.0 star property7.6/10 - Good (1,001 reviews)"Clean room, close to all major attractions, friendly staff ready to help always, good breakfast."Reviewed July 13, 2026Roundtrip • Chicago (ORD) - Florence (FLR)ORD - FLR • 1 stop FLR - ORD • 1 stop$1,845$1,251found 4 hours agoper traveler - L'Andana
Sep 1 - Sep 7L'Andana + Flight
Castiglione della Pescaia5 nights5.0 star property9.4/10 - Exceptional (91 reviews)"Breathtaking views of the Tuscan countryside, as well as incredibly attentive staff."Reviewed June 9, 2026Roundtrip • Chicago (ORD) - Florence (FLR)ORD - FCO • 2 stops FCO - ORD • 1 stop$2,887$2,047found 1 day agoper traveler - Grand Hotel Cavour
Aug 30 - Sep 4Grand Hotel Cavour + Flight
Historic Centre of Florence4 nights4.0 star property9.2/10 - Wonderful (1,004 reviews)"Location is excellent for all the main sites. DO NOT ATTEMPT TO DRIVE YOURSELF TO THE HOTEL - roads and directions are a nightmare. Room was extremely noisy and lacked closet space. Lobby is grand and comfortable."Reviewed July 15, 2026Roundtrip • Boston (BOS) - Florence (FLR)BOS - FLR • 1 stop FLR - BOS • 1 stop$2,267$1,611found 9 hours agoper traveler - Residenza Florentia
Sep 27 - Oct 3Residenza Florentia + Flight
Historic Centre of Florence5 nights1.0 star property8.4/10 - Very Good (53 reviews)"Staff was helpful, the property was not very well maintained."Reviewed June 1, 2026Roundtrip • New York (EWR) - Florence (FLR)EWR - FLR • 1 stop FLR - EWR • 1 stop$1,776$1,275found 1 day agoper traveler - Borgo Scopeto Wine & Country Relais
Sep 1 - Sep 7Borgo Scopeto Wine & Country Relais + Flight
Castelnuovo Berardenga5 nights5.0 star property9.4/10 - Exceptional (215 reviews)"Borgo refers to something like little village and that’s what this property is. A cluster of beautiful stone buildings and gravel drives surrounded by acres of olive and lavender. Beautifully appointed common and areas in rooms. Excellent restaurant with elevated cuisine. Beautiful pool. Distance skyline view of Sienna, Really no negatives. Would definitely come back."Reviewed July 15, 2026Roundtrip • Chicago (ORD) - Florence (FLR)ORD - FCO • 2 stops FCO - ORD • 1 stop$2,940$2,110found 1 day agoper traveler
Montescudaio Hotel Deals
Hotiday Toscana Riparbella
Hotiday Toscana Riparbella
Riparbella Country Suite
Riparbella Country Suite
Frequently Asked Questions
How much does a Montescudaio vacation package cost?
You can snap up a vacation package to this destination from $1,251 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.