Montemassi Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to Rp16.000.000 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
Top hotels in Montemassi
Grand Hotel Bastiani
Piazza Gioberti 64 Grosseto GR
Rp1.698.053
Rp1.960.953 total
24 Aug - 25 Aug
includes taxes & fees
8.6/10 Excellent! (243 reviews)
"Gorgeous, historic hotel, room was spacious with very high ceilings. Breakfast was delicious too. It was a little loud outside at night but obviously nothing the hotel can do about that and it wasn't really a problem for me. Great location, kind and helpful staff. I'd happily stay here again, for ..."
Reviewed on 19 Jun 2026
Fattoria La Principina Hotel & Congress
Via Dei Girasoli, 1 (Via del Tarabuso) Grosseto GR
Rp1.537.478
Rp1.784.321 total
6 Sept - 7 Sept
includes taxes & fees
8.4/10 Very good! (188 reviews)
Fattoria la Principina
"Good location, close to the town and beaches. Cleaning wise was good but lacking customer service. If you are not italian they won’t even try to welcome you or offer information if you need it. Breakfast is very limited and repetitive , not much choice. Same pastries, cakes, fruits every day. I would ..."
Reviewed on 19 Aug 2025
Castiglion del Bosco, A Rosewood Hotel
Localita Castiglion del Bosco Montalcino SI
Rp53.030.232
Rp58.540.216 total
2 Sept - 3 Sept
includes taxes & fees
10/10 Exceptional! (80 reviews)
"Best hotel ever."
Reviewed on 27 Jul 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
Rp2.268.436
per adult
Tuscany: Horseback Riding Experience in Buonconvento
Rp1.072.352
per adult
Tuscany Horseback Riding Experience in Buonconvento
Rp1.031.107
per adult
Frequently asked questions
How much does a Montemassi holiday package cost?
You'll find cheap prices 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 holiday 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 holiday packages. Bear in mind that school holiday 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 holiday. 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 customise 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 travelling on a weekday, when prices are often lower.
Is it cheaper to book a Montemassi holiday as a package?
You can enjoy significant savings on your next Montemassi retreat by booking a personalised holiday 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 holiday 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 holiday 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 customised Montemassi holiday package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
