Montemassi Holidays

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Top hotels in Montemassi

Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel

5 out of 5
Localita Castiglion del Bosco Montalcino SI
Fully refundableReserve now, pay when you stay
The price is Rp16.327.268 per night from 2 Dec to 3 Dec
Rp16.327.268
Rp18.161.566 total
2 Dec - 3 Dec
includes taxes & fees
10/10 Exceptional! (87 reviews)
"Unique property well maintained and quite Serene , great staff"

Reviewed on 30 Oct 2026

Castiglion del Bosco, A Rosewood Hotel
Grand Hotel Bastiani

Grand Hotel Bastiani

4 out of 5
Piazza Gioberti 64 Grosseto GR
Fully refundableReserve now, pay when you stay
The price is Rp1.483.161 per night from 7 Dec to 8 Dec
Rp1.483.161
Rp1.631.517 total
7 Dec - 8 Dec
includes taxes & fees
8.6/10 Excellent! (260 reviews)
"Great staff, nice breakfast, beautiful building and location."

Reviewed on 9 Oct 2026

Grand Hotel Bastiani
The Sense Experience Resort - Preferred Hotels & Resorts

The Sense Experience Resort - Preferred Hotels & Resorts

5 out of 5
Viale Italia 315 Follonica GR
Get rates
The Sense Experience Resort - Preferred Hotels & Resorts
See all 2,125 properties in Montemassi
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

Winery tour and wine tasting in Maremma - Grosseto

Winery tour and wine tasting in Maremma - Grosseto

Rp565.667
per adult
Winery tour and wine tasting in Maremma - Grosseto
Tuscany Horseback Riding Experience in Buonconvento

Tuscany Horseback Riding Experience in Buonconvento

Rp1.131.335
per adult
Tuscany Horseback Riding Experience in Buonconvento
Tuscany: Horseback Riding Experience in Buonconvento

Tuscany: Horseback Riding Experience in Buonconvento

Rp1.050.525
per adult
Tuscany: Horseback Riding Experience in Buonconvento
See all activities in Montemassi

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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.