Montescudaio Vacations from $1,139
Book a Hotel + Flight or Car together to unlock savings
The Latest Montescudaio Vacation Packages
- Alfieri9
Oct 12 - Oct 17Alfieri9 + Flight
Historic Centre of Florence4 nights3.0 star property9.6/10 - Exceptional (170 reviews)"More quiet residential area of Firenze in walking distance of center but away from the crowds. No elevator and two flight of stairs."Reviewed July 5, 2026Roundtrip • Boston (BOS) - Florence (FLR)BOS - FLR • 1 stop FLR - BOS • 1 stop$1,545$1,139found 8 hours agoper traveler - Precise Tale Poggio Alla Sala
Sep 29 - Oct 4Precise 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 • New York (NYC) - Florence (FLR)EWR - FLR • 1 stop FLR - EWR • 2 stops - Hotel La Scaletta Al Ponte Vecchio
Sep 26 - Oct 2Hotel La Scaletta Al Ponte Vecchio + Flight
Historic Centre of Florence5 nights4.0 star property9.0/10 - Wonderful (1,008 reviews)Roundtrip • New York (JFK) - Florence (FLR)JFK - FLR • 1 stop FLR - JFK • 1 stop - Villa Cora
Sep 13 - Sep 18Villa Cora + Flight
Oltrarno4 nights5.0 star property9.8/10 - Exceptional (481 reviews)Roundtrip • New York (NYC) - Florence (FLR)JFK - FLR • 1 stop FLR - EWR • 1 stop - Aurum Uffizi
Sep 9 - Sep 15Aurum Uffizi + Flight
Historic Centre of Florence5 nights4.0 star property7.6/10 - Good (1,004 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 • New York (NYC) - Florence (FLR)JFK - FLR • 1 stop FLR - EWR • 1 stop$1,643$1,189found 18 hours agoper traveler
Montescudaio Hotel Deals
"Super, family of 4. Everything easily available for our stay even things we didn’t know we needed, like an air compressor to blow up pool toys"
Riparbella Country Suite
Riparbella Country Suite"."
"The property is quite tired. Rooms need serious update. Bathroom tile has mold in showers. Bed mattress was not pleasant. Few electrical outlets. TV slightly larger than a computer monitor. WIFI does not work in the rooms. Linen needs replacement. Bathroom supplies inadequate . Parking poor. It appears that it may at some time been used for a children’s camp. Those points not withstanding , the property location and views are very nice. Pool is good. Price reflects quality . Online...
Casa Cerboneschi
Casa Cerboneschi"Wonderful place and wonderful hosts. Great homemade breakfast! Marianne "
B&B Podere San Filippo
B&B Podere San Filippo"B&B in centro a Bibbona molto carino, camere in ottime condizioni e molto pulite, ci sono pure acqua e snack a disposizione dei clienti compresi nel costo della camera. La colazione servita nel dehor è molto variegata e di ottima qualità considerando i i prodotti utilizzati. Molto consigliato"
Hotiday Toscana Riparbella
Hotiday Toscana Riparbella"I couldn’t even get to the venue, they didn’t answer their phones for a whole two days when I was trying to explore how best to get there. Very poor service, called, sent emails, no response. Never again!"
Relais Sant'Elena
Relais Sant'Elena"Relais Sant’Elena is the perfect retreat after the go-go-go of city travel - a peaceful, sanctuary to slow down and enjoy the beautiful scenery. The food was unbelievable: farm-to-fork in the truest sense, simple cooking done perfectly at both breakfast and dinner. We wish we could have stayed longer and hope to be back! Highly recommend, especially for a convenient place to stay before flying out of the Pisa airport."
Punti Di Vista B&B Food&Wine Experience
Punti Di Vista B&B Food&Wine Experience"Trotz Reservation war kein Personal da. Die zufällig präsente Person startete mit telefonieren, um das Zimmer bereit zu stellen. Warmes Wasser gab es nie während der zwei Tagen. Das inkl. Frühstück war am ersten Morgen spärlich und am zweiten inexistent. Das Zimmer wäre sehr hübsch, aber die Organisation total überfordert."
Frequently Asked Questions
How much does a Montescudaio vacation package cost?
You can snap up a vacation package to this destination from $1,139 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.