Montemassi Holidays from £223
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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.
Hotel Duomo Firenze
Historic Centre of Florence
£561
per person
23 Dec - 26 Dec
found 1 day ago
Return flight included
London (LHR) to Florence (FLR)
9.2/10 Wonderful! (1,000 reviews)
This was a great choice for our hotel in Florence. It’s hard to imagine a better location. The hotel staff was very helpful in every way possible, from restaurant recommendations to setting up reservations, to providing a tour of the breakfast area when we arrived. The breakfast buffet was well thought out - smaller sizes on most offerings that will allow you to try many items without getting too full. They also offer free 24 hour gelato - be careful as it’s quite tasty. You should seriously consider this hotel for your stay in Florence.
Reviewed on 21 Oct 2026
Hotel Alessandra
Historic Centre of Florence
£281
per person
4 Dec - 8 Dec
found 1 day ago
Return flight included
London (LGW) to Florence (FLR)
9.2/10 Wonderful! (990 reviews)
The front desk personnel were very helpful and friendly and soothed my fears for getting a very early morning taxi. Shout out to Monti! Unique layout of rooms (stairs to bathroom!) and charming street for access to all Florence has to offer. Caution that there are about 30 steps to get to tiny elevator to take you to reception and rooms.
Reviewed on 20 Oct 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
Localita Castiglion del Bosco Montalcino SI
Fully refundableReserve now, pay when you stay
£1,050
4 Nov - 5 Nov
includes taxes & fees
Grand Hotel Bastiani
Piazza Gioberti 64 Grosseto GR
Fully refundableReserve now, pay when you stay
£65
26 Oct - 27 Oct
includes taxes & fees
8.6/10 Excellent! (260 reviews)
"Great staff, nice breakfast, beautiful building and location."
Reviewed on 9 Oct 2026
The Sense Experience Resort - Preferred Hotels & Resorts
Viale Italia 315 Follonica GR
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
La Maliosa Summer Farm Experience & Wine Tasting
£39
per adult
100% of travellers recommend
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 £223. 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.
* 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.
