Montemassi Holidays

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Top Flight + Hotel Deals in Montemassi

Price found within the past 48 hours. Click for updated prices.
Hotel San Luca

Hotel San Luca

4 out of 5
Cortona Old Town
Price was €655, price is now €500 per person
€500
per person
7 Sept - 13 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Florence (FLR)
8.6/10 Excellent! (434 reviews)
Wonderful place to stay in Cortona Great breakfast

Reviewed on 23 Jul 2026

Villa Neroli

Villa Neroli

4 out of 5
Coverciano
Save 100% on your flight
Price was €1,253, price is now €849 per person
€849
per person
7 Sept - 13 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Florence (FLR)
9.6/10 Exceptional! (636 reviews)
We loved this place! We are a family of 4 and got a joined room. It was lovely. Would stay here again.

Reviewed on 14 Jul 2026

The Social Hub Florence Lavagnini

The Social Hub Florence Lavagnini

4 out of 5
San Lorenzo
Save 100% on your flight
Price was €1,253, price is now €858 per person
€858
per person
7 Sept - 13 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Florence (FLR)
9/10 Wonderful! (1,461 reviews)
The room is spacious, though this is a block that houses students as well, so it could be a bit noisy. Pool has a stunning view, highly recommend. Located just outside the centre for some quiet, but easy enough to walk to everywhere.

Reviewed on 23 Jul 2026

Hotel Borgo di Cortefreda Relais

Hotel Borgo di Cortefreda Relais

4 out of 5
Save 100% on your flight
Price was €1,145, price is now €820 per person
€820
per person
7 Sept - 13 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Florence (FLR)
9.4/10 Exceptional! (499 reviews)
The resort is absolutely gorgeous and tranquil. We loved the pool, the delicious breakfast included with our stay in the spacious king suite with its own huge patio! Wish we were able to stay longer!

Reviewed on 23 Jul 2026

The Social Hub Florence Belfiore

The Social Hub Florence Belfiore

4 out of 5
Santa Maria Novella
Price was €1,047, price is now €954 per person
€954
per person
7 Sept - 13 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Florence (FLR)
9.4/10 Exceptional! (627 reviews)
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Reviewed on 23 Jul 2026

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 €1,717 per night from 2 Aug to 3 Aug
€1,717
2 Aug - 3 Aug
includes taxes & fees
Castiglion del Bosco, A Rosewood Hotel
Fattoria La Principina Hotel & Congress

Fattoria La Principina Hotel & Congress

4 out of 5
Via Dei Girasoli, 1 (Via del Tarabuso) Grosseto GR
The price is €135 per night from 23 Aug to 24 Aug
€135
23 Aug - 24 Aug
includes taxes & fees
8.4/10 Very good! (185 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 Hotel & Congress
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 €667 per night from 23 Aug to 24 Aug
€667
23 Aug - 24 Aug
includes taxes & fees
9.2/10 Wonderful! (224 reviews)
"Beautiful property."

Reviewed on 15 Jul 2026

The Sense Experience Resort - Preferred Hotels & Resorts
See all 2,174 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

€110
per adult
Porto Santo Stefano: Giglio & Giannutri Mini Cruise and Meal
Picture 2 for Activity Organic farm picnic in Maremma Tuscany

Maliosa Natural Picnic

€45
per adult
Maliosa Natural Picnic
Welcome to Casale del Bosco

Welcome to Casale del Bosco

€35
per adult
Welcome to Casale del Bosco
See all activities in Montemassi

Frequently asked questions

How much does a Montemassi holiday package cost?
You'll find cheap prices from €500 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.