Montemassi Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Montemassi

Hotel La Pineta
Hotel La Pineta
3 out of 5
Via Delle Collacchie, 67, Follonica, GR
8.8/10 Excellent! (234 reviews)
"Booked this hotel as part of a trip and everything was well organised at the hotel when we arrived. Lifts to all floors and clean tidy and well equipped room. Extra charge of 10 euros per night which was not excessive however there was plenty of on street parking available. Breakfast was very good ..."

Reviewed on 28 May 2025

Get rates
Hotel La Pineta
The Sense Experience Resort
The Sense Experience Resort
5 out of 5
Viale Italia 315, Follonica, GR
Fully refundableReserve now, pay when you stay
9/10 Wonderful! (169 reviews)
"It was migical."

Reviewed on 21 Jun 2025

Get rates
The Sense Experience Resort
Rosewood Castiglion del Bosco
Rosewood Castiglion del Bosco
5 out of 5
Localita Castiglion del Bosco, Montalcino, SI
Fully refundableReserve now, pay when you stay
The price is 63.506.632 ₫ per night from 17 Jul to 18 Jul
63.506.632 ₫
70.158.379 ₫ total
17 Jul - 18 Jul
includes taxes & fees
10/10 Exceptional! (64 reviews)
"Peaceful, Relaxing Stay in Tuscany We had a great experience here. The setting is quiet and secluded—felt like a true escape from everyday life. The golf was excellent, the food was consistently good, and the service was friendly and professional. It is remote, which adds to the charm, but just a ..."

Reviewed on 21 Jun 2025

Rosewood Castiglion del Bosco
See all 2,105 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.

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.

Popular places to visit

Podere Ristella Vineyards and Winery

You can enjoy a tasting or tour at Podere Ristella Vineyards and Winery during your travels to Roccastrada. Wander the gardens or discover the area's countryside.

Podere Ristella Vineyards and Winery

Castello del Belagaio

You can find out about the history of Roccastrada with a visit to Castello del Belagaio. Discover the area's countryside and wineries.

Castello del Belagaio

Sassoforte Castle

You can find out about the history of Roccastrada with a visit to Sassoforte Castle. While you're in the area, wander around the natural setting.

Sassoforte Castle