Montescudaio Vacations from $1,148
Book a Hotel + Flight or Car together to unlock savings
The Latest Montescudaio Vacation Packages
- Aurum Uffizi
Oct 15 - Oct 20Aurum Uffizi + Flight
Historic Centre of Florence4 nights4.0 star property7.6/10 - Good (1,003 reviews)"The room was clean and air conditioning worked well for the size of room. However, the room was a little small for a family of four. The location was one of the best aspects of the hotel: it was right in the historic centre and near all the attractions. Staff were also very helpful, promptly responding to our requests."Reviewed August 2, 2026Roundtrip • Boston (BOS) - Florence (FLR)BOS - FLR • 1 stop FLR - BOS • 1 stop$1,695$1,148found 1 day agoper traveler - Eurostars Florence Boutique
Oct 3 - Oct 9Eurostars Florence Boutique + Flight
Historic Centre of Florence5 nights4.0 star property8.6/10 - Excellent (497 reviews)Roundtrip • Boston (BOS) - Florence (FLR)BOS - FLR • 1 stop FLR - BOS • 1 stop$2,133$1,459found 1 day agoper traveler - Precise Tale Poggio Alla Sala
Sep 14 - Sep 19Precise Tale Poggio Alla Sala + Flight
Montepulciano4 nights5.0 star property9.6/10 - Exceptional (156 reviews)"The place it’s an Amazing. Very clean. Is more beautiful than the pictures."Reviewed August 2, 2026Roundtrip • Boston (BOS) - Florence (FLR)BOS - FLR • 1 stop FLR - BOS • 2 stops - Relais Uffizi, Tailor made Hotel
Oct 18 - Oct 24Relais Uffizi, Tailor made Hotel + Flight
Historic Centre of Florence5 nights4.0 star property9.2/10 - Wonderful (155 reviews)"While the bathrooms were clean I was very disappointed to see a stain on my bedsheets."Reviewed August 2, 2026Roundtrip • New York (NYC) - Florence (FLR)JFK - FLR • 1 stop FLR - EWR • 2 stops$2,071$1,476found 0 hours agoper traveler - 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 (1,004 reviews)"I’ve stayed at this property several times over recent years so I have seen changes - some good and some not great. The staff is very nice and helpful. That has always been my experience. The lobby changed to the first floor a couple years ago and is a much nicer welcome! The rooms are clean but found the bathroom to be very tiny in the section of the hotel we were in. No elevator to rooms means the poor employees have to lug heavy luggage up and down the long staircase for guests and I found..."Reviewed August 2, 2026Roundtrip • Boston (BOS) - Florence (FLR)BOS - FLR • 1 stop FLR - BOS • 1 stop$2,330$1,664found 1 day agoper traveler
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.