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 S$3,269 per night from 28 Jul to 29 Jul
S$3,269
28 Jul - 29 Jul
includes taxes & fees
Castiglion del Bosco, A Rosewood Hotel
The Sense Experience Resort - Preferred Hotels & Resorts

The Sense Experience Resort - Preferred Hotels & Resorts

5 out of 5
Viale Italia 315 Follonica GR
The price is S$945 per night from 27 Jul to 28 Jul
S$945
27 Jul - 28 Jul
includes taxes & fees
9.2/10 Wonderful! (217 reviews)
"We had a most enjoyable relaxing three days by the beach following 14 travelling through Tuscany. The standards and service were exemplary, the staff are all levels were so professional and friendly. The breakfast could not be improved and with such a setting it was great. Very high standards for ..."

Reviewed on 6 Jun, 2026

The Sense Experience Resort - Preferred Hotels & Resorts
Fattoria La Principina

Fattoria La Principina

4 out of 5
Via Dei Girasoli, 1 (Via del Tarabuso) Grosseto GR
Fully refundableReserve now, pay when you stay
The price is S$156 per night from 2 Aug to 3 Aug
S$156
2 Aug - 3 Aug
includes taxes & fees
8.4/10 Very good! (184 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

Fattoria La Principina
See all 2,205 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

Porto Santo Stefano: Giglio & Giannutri Mini Cruise and Meal

Porto Santo Stefano: Giglio & Giannutri Mini Cruise and Meal

S$163
per adult
Porto Santo Stefano: Giglio & Giannutri Mini Cruise and Meal
Welcome to Casale del Bosco

Welcome to Casale del Bosco

S$52
per adult
Welcome to Casale del Bosco
Wine, Stories and Traditions: Authentic Chianti Experience

Wine, Stories and Traditions: Authentic Chianti Experience

S$48
per adult
Wine, Stories and Traditions: Authentic Chianti Experience
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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.