Montemassi Vacations from ￥190,955
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥109,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Montemassi Vacation Packages
Price found within the past 48 hours. Click for updated prices.
The Moon Boutique Hotel & Spa
Historic Centre of Florence
￥194,144
per person
Nov 13 - Nov 17
found 6 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Florence (FLR)
9.6/10 Exceptional! (592 reviews)
The Moon Hotel exceeded my expectations and is highly recommended.
The restaurant services and breakfast offerings were excellent
Management and particularly Ivan was absolutely outstanding.
Reviewed on Sep 9, 2026
Hotel Santa Maria Novella
Historic Centre of Florence
￥210,249
per person
Nov 13 - Nov 17
found 6 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Florence (FLR)
9.6/10 Exceptional! (1,007 reviews)
We just left this hotel and on our way to Amalfi I just had to leave this review. This hotel is a 10/10. The hotel is beautifully decorated, the staff is amazing, the rooms are a good size. You are right in the center and in walking distance to everything.
The train station is only steps away.
It can’t get better than that.
Loved it!
Reviewed on Sep 8, 2026
Dimora Palanca Boutique & SPA
Historic Centre of Florence
￥223,402
per person
Nov 13 - Nov 17
found 6 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Florence (FLR)
9.2/10 Wonderful! (69 reviews)
The accommodation very much complimented our wonderful experience and love for Florence. Our room, the connected amenities and the wonderful attentive service made our trip very memorable.
Reviewed on Sep 7, 2026
Find the Best Montemassi Vacation Packages
Montemassi Hotel Deals
Fattoria La Principina Hotel & Congress
Via Dei Girasoli, 1 (Via del Tarabuso) Grosseto GR
Fully refundableReserve now, pay when you stay
￥12,332
￥14,368 total
Oct 11 - Oct 12
includes taxes & fees
8.4/10 Very Good! (194 reviews)
"great facility but needs a general upgrade and remodeling"
Reviewed on Aug 15, 2026
Castiglion del Bosco, A Rosewood Hotel
Localita Castiglion del Bosco Montalcino SI
￥364,959
￥403,239 total
Oct 8 - Oct 9
includes taxes & fees
10/10 Exceptional! (80 reviews)
"Best hotel ever."
Reviewed on Jul 27, 2026
The Sense Experience Resort - Preferred Hotels & Resorts
Viale Italia 315 Follonica GR
￥31,849
￥36,105 total
Oct 4 - Oct 5
includes taxes & fees
9.2/10 Wonderful! (231 reviews)
"Great property, classy, staff crew are professionals. Egor is great. Staff remembers from year to year. Management is awesome and helpful all the time The manager Sylvia is a friendly and helpful. All over staff, front desk, waiters, cleaners, managements, and bellboys are the best of the best. Only ..."
Reviewed on Sep 7, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
What to do in Montemassi
Porto Santo Stefano: Giglio & Giannutri Mini Cruise and Meal
￥20,401
per adult
La Maliosa Summer Farm Experience & Wine Tasting
￥8,346
per adult
100% of travellers recommend
Frequently asked questions
How much does a Montemassi vacation package cost?
You'll find cheap prices from ￥190,955 on Expedia for your Montemassi getaway. However, a range of factors like the season, length of stay and your choice of hotel will influence how much your vacation to Montemassi costs.
What are the cheapest months to go to Montemassi?
Plan your trip for the shoulder or low season and you're likely to get cheap Montemassi vacation packages. Bear in mind that school vacation periods and local festivals and events can have an impact on prices, so do some research before you go.
How many days is enough for Montemassi?
Generally, a handful of days is enough to visit the major sights during your Montemassi vacation. But if you prefer to have more time to chill out or take day tours, consider extending your trip.
How to find the best Montemassi package deals?
Finding a cheap Montemassi package deal is easy with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your budget, apply a couple of filters and see what's available. You can customize your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most affordable Montemassi package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are often lower.
Is it cheaper to book a Montemassi vacation as a package?
You can enjoy significant savings on your next Montemassi retreat by booking a personalized vacation package. Click on the "Package" heading, then select your travel dates and destination to see the best hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Montemassi?
Enjoy incredible bargains by booking your flights ahead of time with Expedia. If spontaneity is more your style, snap up one of our last-minute deals for a spur-of-the-moment Montemassi adventure.
How to plan a trip to Montemassi?
- Choose when to travel: Check your diary and get your bags packed. Your preferred season and the type of activities available will also help you decide when to vacation in Montemassi.
- Budget wisely: As well as the cost of your stay, you'll need to factor in other expenses. These include food, transportation and flights. Also, set aside some extra funds for unexpected expenses that may come up during your trip to Montemassi.
- Determine how many days away: Start by compiling a list of the activities and attractions you want to get to in Montemassi. Then, estimate how long you'll need for each, including any travel time.
- Bundle your bookings: With your travel dates in place, you can combine your car rental, flights, hotels and more into a customized Montemassi vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
