Montemassi Holidays
- Plan, book, travel with confidence
- Better togetherSave up to €900 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 Flight + Hotel Deals in Montemassi
Price found within the past 48 hours. Click for updated prices.
Aurum Uffizi
Historic Centre of Florence
€370
per person
28 Nov - 2 Dec
found 1 day ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
7.6/10 Good! (1,003 reviews)
The staff was excellent, especially Joshua. The room was cleaned daily. Breakfast was ok.
Reviewed on 20 Oct 2026
Eurostars Florence Boutique
Historic Centre of Florence
€502
per person
28 Nov - 2 Dec
found 1 day ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
8.6/10 Excellent! (503 reviews)
The bed was comfortable but low to the floor. The shower was very slippery and could have used a shower mat. The breakfast was great. The staff were very nice and helpful.
Reviewed on 10 Oct 2026
Top hotels in Montemassi
Castiglion del Bosco, A Rosewood Hotel
Localita Castiglion del Bosco Montalcino SI
Fully refundableReserve now, pay when you stay
€1,227
3 Nov - 4 Nov
includes taxes & fees
Grand Hotel Bastiani
Piazza Gioberti 64 Grosseto GR
Fully refundableReserve now, pay when you stay
€78
26 Oct - 27 Oct
includes taxes & fees
8.6/10 Excellent! (260 reviews)
"Great staff, nice breakfast, beautiful building and location."
Reviewed on 9 Oct 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
Tuscany Horseback Riding Experience in Buonconvento
€56
per adult
Frequently asked questions
How much does a Montemassi holiday package cost?
You'll find cheap prices from €370 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.
