Montemassi Holidays from £377

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Your Montemassi Holiday

When you organise a holiday package to Montemassi, you can relax and enjoy your break knowing that all your travel plans are in order. Uncover the many charms of this lively city while based in a neighbourhood like Valpiana, which is good for views. Make your trip to Montemassi even more enjoyable by going sightseeing. Podere Ristella Vineyards and Winery, Church of San Nicola and Sassoforte Castle are among the major attractions worth exploring. Whatever your travel plans or the size of your budget, putting together the ultimate tailored Montemassi holiday is a cinch with Expedia.

Top Montemassi Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
La Villa di STR

La Villa di STR

3 out of 5
Siena Historical Center
Save 100% on your flight
Price was £721, price is now £377 per person
£377
per person
20 Aug - 27 Aug
found 12 hours ago
Return flight included
London (LON) to Florence (FLR)
9.2/10 Wonderful! (435 reviews)
Air conditioning wasn’t that cold otherwise it was great!

Reviewed on 15 Jun 2026

Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was £768, price is now £387 per person
£387
per person
18 Aug - 22 Aug
found 6 hours ago
Return direct flight included
Birmingham (BHX) to Florence (FLR)
7.4/10 Good! (1,008 reviews)
It was not entirely clean, the staff don't do much. Breakfast is from the day before. Air conditioning excellent.

Reviewed on 3 Jul 2026

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was £1,093, price is now £568 per person
£568
per person
14 Sept - 18 Sept
found 16 hours ago
Return direct flight included
Birmingham (BHX) to Florence (FLR)
7.6/10 Good! (1,006 reviews)
Clean, conveniently located hotel with friendly, helpful staff.

Reviewed on 5 Jul 2026

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Price was £3,677, price is now £1,921 per person
£1,921
per person
10 Sept - 17 Sept
found 1 day ago
Return flight included
London (LGW) to Florence (FLR)
9.6/10 Exceptional! (147 reviews)
It’s a beautiful property, but be aware that it is secluded and that the restaurant menu is quite limited and after a couple of days, we were happy to go elsewhere. The waiting staff was attentive and nice, front desk not as much (maybe the la guard barrier?)

Reviewed on 19 Jun 2026

Hotel La Scaletta Al Ponte Vecchio

Hotel La Scaletta Al Ponte Vecchio

4 out of 5
Historic Centre of Florence
Price was £1,093, price is now £575 per person
£575
per person
7 Sept - 11 Sept
found 1 day ago
Return flight included
London (LON) to Florence (FLR)
8.8/10 Excellent! (1,002 reviews)
Room was great, super clean and roomy. Staff awesome and the rooftop bar with view of the city made the stay all the more memorable!

Reviewed on 4 Jul 2026

Montemassi Essential Information

Language
Italian
Currency
Euros
Local Welcome
Ciao
Local Goodbye
Ciao
Population
180
Max Temp Winter
13ºC
Max Temp Summer
27ºC
Top Sights
Podere Ristella Vineyards and Winery, Castello del Belagaio and Sassoforte Castle

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 £1,451 per night from 2 Aug to 3 Aug
£1,451
2 Aug - 3 Aug
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 £549 per night from 30 Jul to 31 Jul
£549
30 Jul - 31 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 £90 per night from 2 Aug to 3 Aug
£90
2 Aug - 3 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
See all 2,210 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.
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All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

What to do in Montemassi

La Maliosa Farm Experience & Wine Tasting

La Maliosa Summer Farm Experience & Wine Tasting

£39
per adult
100% of travellers recommend
La Maliosa Summer Farm Experience & Wine Tasting
Welcome to Casale del Bosco

Welcome to Casale del Bosco

£30
per adult
Welcome to Casale del Bosco
Porto Santo Stefano: Giglio & Giannutri Mini Cruise and Meal

Porto Santo Stefano: Giglio & Giannutri Mini Cruise and Meal

£95
per adult
Porto Santo Stefano: Giglio & Giannutri Mini Cruise and Meal
See all activities in Montemassi

Frequently asked questions

How much does a Montemassi travel package cost?
Go from looking to booking with our Montemassi travel packages, which start from a low £377. Choose the hotels and flights that fit your travel plans. Then, add on one or two experiences or tours for an unforgettable adventure.
If I'm not able to travel, can I cancel my Montemassi travel package?
Plans can change in the blink of an eye, so yes, you can. You may be able to cancel or amend your Montemassi travel package at no cost within 24 hours of booking. For bookings older than that, you can still make changes, but your hotel, car rental company or airline may charge additional fees. Want more information? Visit our Customer Service Portal. We're here to help make sure your trip goes off without a hitch.
How do I get a cheap travel package to Montemassi?
Booking a Montemassi travel package with Expedia is the easiest way to save. We have more than 550 partner airlines and 1,000,000 properties all over the world. With such an awesome range to pick from, you'll have no difficulty pulling together your perfect adventure.
Does Expedia offer Book Now, Pay Later Montemassi holidays?
Your bank balance shouldn't prevent you from taking a holiday, so Expedia has devised a solution to help. Now that we've formed a partnership with online lender Klarna, it's easier than ever to book your dream getaway without eating away at your savings. Klarna offers flexible payment options at checkout that take the worry out of budgeting for your escape. Consider one of these flexible payment options:

  • Pay monthly holidays: If paying bite-sized amounts each month is what works best for you, Klarna can help. Paying in easy monthly instalments will make your getaway dreams come true.
  • Pay in instalments holidays: Like the idea of paying down your holiday in multiple transactions? Then check out this Book Now, Pay Later option from Klarna.
  • Low deposit holidays: If paying a small percentage of your trip (rather than the total upfront) makes it easier to hit that "book now" button, choose a low deposit holiday payment plan with Klarna.

Where should I stay in Montemassi?
There's so much to see in Montemassi, so stay near its best attractions and spend more time sightseeing. Podere Ristella Vineyards and Winery is one spot to put on your itinerary.
What are the top hotels in Montemassi?
Get your escape off to an excellent start by booking a stay at Valdonica Winery And Vineyard Residence. It's one of most sought-after properties in Montemassi. Another top option is La Melosa Resort & Spa.
How far in advance should I book my Montemassi holiday?
While not all airlines release tickets early, you can normally compare international airfares on Expedia up to 12 months in advance. This is when you can score some fantastic deals. If you're booking late, there's a chance you could get lucky. Discounted prices occasionally become available just weeks prior to departure.
What does an Expedia Montemassi travel package include?
You can select from a combination of hotels, flights and rental cars. Once you've made your booking, you can add some experiences and activities. Want to pick your fare class? That's possible too. The choice is all yours when it comes to arranging your ideal Montemassi getaway.
What should I know before booking a Montemassi travel package?
We already have low prices. However, you'll enjoy even more bargains when you book your hotels, flights and car rentals together. With an Expedia travel package, you'll get transparent pricing and lots of choice.
Can I choose my airline with a Montemassi Expedia travel package?
Expedia has access to more than 550 airline partners globally, so you definitely can. Simply pick your preferred air carrier and craft your ideal Montemassi holiday.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.