Montescudaio Vacations from $1,148
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The Latest Montescudaio Vacation Packages
- Aurum Uffizi
Oct 15 - Oct 20Aurum Uffizi + Flight
Historic Centre of Florence4 nights4.0 star property7.6/10 - Good (1,002 reviews)Roundtrip • Boston (BOS) - Florence (FLR)BOS - FLR • 1 stop FLR - BOS • 1 stop$1,695$1,148found 0 hours agoper traveler - Precise Tale Poggio Alla Sala
Sep 13 - Sep 19Precise Tale Poggio Alla Sala + Flight
Montepulciano5 nights5.0 star property9.6/10 - Exceptional (155 reviews)"Magical location, pools, staff, property."Reviewed July 19, 2026Roundtrip • Boston (BOS) - Florence (FLR)BOS - FCO • 1 stop FCO - BOS • 2 stops - Hotel La Scaletta Al Ponte Vecchio
Oct 3 - Oct 9Hotel La Scaletta Al Ponte Vecchio + Flight
Historic Centre of Florence5 nights4.0 star property9.0/10 - Wonderful (1,003 reviews)"Very convenient to explore everything around Florence"Reviewed July 31, 2026Roundtrip • Boston (BOS) - Florence (FLR)BOS - FLR • 1 stop FLR - BOS • 1 stop$2,330$1,664found 4 hours agoper traveler - Hotel Palazzo del Capitano Wellness & Relais - Luxury Borgo Capitano Collection
Sep 13 - Sep 19Hotel Palazzo del Capitano Wellness & Relais - Luxury Borgo Capitano Collection + Flight
San Quirico d'Orcia5 nights4.0 star property9.2/10 - Wonderful (233 reviews)"THE AMAZING LOCATION THE VIEWS OF THE MOUNTAINS AND VALLEYS AND AMAZING POOL (WE DID NOT GET TO USE IT BECAUSE DUE TO THE TEMPERATURE BEING IN THE 60'S) THE RESTAURANT WHICH IS THE NEXT TO THE HOTEL WAS GREAT !!!"Reviewed October 29, 2025Roundtrip • Boston (BOS) - Florence (FLR)BOS - FCO • 1 stop FCO - BOS • 2 stops - Villa Cora
Sep 21 - Sep 26Villa Cora + Flight
Oltrarno4 nights5.0 star property9.8/10 - Exceptional (480 reviews)"Villa Cora was an interesting and pleasant stay with a nice pool, lovely staff, and a beautiful setting. We enjoyed our stay but likely will not return. Strengths: - Well-kept stately villa and grounds - Attractive, beautifully-designed room and indoor common areas - Helpful, kind, and capable staff pre-arrival and during our stay - A lovely pool environment, perfect for staying cool and relaxing in summer - Excellent fresh lunch at the poolside restaurant Le Bistrot - A general sense of peace..."Reviewed July 14, 2026Roundtrip • Boston (BOS) - Florence (FLR)BOS - FLR • 1 stop FLR - BOS • 1 stop
Montescudaio Hotel Deals
Riparbella Country Suite
Riparbella Country Suite
Hotiday Toscana Riparbella
Hotiday Toscana Riparbella
B&B Podere San Filippo
B&B Podere San Filippo
Relais Sant'Elena
Relais Sant'Elena
Punti Di Vista B&B Food&Wine Experience
Punti Di Vista B&B Food&Wine Experience
Locanda dell'Aioncino
Locanda dell'AioncinoFrequently Asked Questions
How much does a Montescudaio vacation package cost?
You can snap up a vacation package to this destination from $1,148 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.