Montemassi Vacations from ￥402,274
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.
Hotel L'Orologio Firenze
Historic Centre of Florence
￥506,825
per person
Dec 27 - Jan 2
found 13 hours ago
Roundtrip flight included
Osaka (KIX) to Florence (FLR)
9.6/10 Exceptional! (1,000 reviews)
It gave a old school elegant feel. The rooms was very spacious and the staff was friendly and informative.
Reviewed on Oct 23, 2026
Find the Best Montemassi Vacation Packages
Montemassi Hotel Deals
Castiglion del Bosco, A Rosewood Hotel
Localita Castiglion del Bosco Montalcino SI
Fully refundableReserve now, pay when you stay
￥195,677
￥217,001 total
Nov 3 - Nov 4
includes taxes & fees
10/10 Exceptional! (86 reviews)
"Fabulous service. Gorgeous location and pristine hotel. Great food choices and services."
Reviewed on Oct 23, 2026
Grand Hotel Bastiani
Piazza Gioberti 64 Grosseto GR
Fully refundableReserve now, pay when you stay
￥10,854
￥11,939 total
Nov 25 - Nov 26
includes taxes & fees
8.6/10 Excellent! (260 reviews)
"Great staff, nice breakfast, beautiful building and location."
Reviewed on Oct 9, 2026
The Sense Experience Resort - Preferred Hotels & Resorts
Viale Italia 315 Follonica GR
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
La Maliosa Summer Farm Experience & Wine Tasting
￥8,108
per adult
100% of travellers recommend
Winery Visit, Vineyard Walk & Wine Tasting near Grosseto
￥8,829
per adult
Frequently asked questions
How much does a Montemassi vacation package cost?
You'll find cheap prices from ￥402,274 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.
