Montemassi Holidays from £459
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- Rest easyPackages with flights are ATOL protected
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.
Aurum Uffizi
Historic Centre of Florence
£459
per person
26 Oct - 30 Oct
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Florence (FLR)
7.6/10 Good! (1,003 reviews)
Clean room, convenient location. has AC and lift. Breakfast was ok. Would stay again
Reviewed on 12 Aug 2026
Eden Rock Resort
£478
per person
9 Oct - 12 Oct
found 1 day ago
Return flight included
London (LON) to Florence (FLR)
9.8/10 Exceptional! (109 reviews)
This was a beautiful property about 10 mins away from Florence. You get the beauty of Tuscany without having to go too far. The hotel only has 12 rooms and everyone knows you by name. We traveled with 2 kids and the rooms were very spacious. Staff are wonderful, Onsite restaurant was great. Views were breathtaking. We didn't have a car, and the hotel was able to help us with cabs easily. Service was excellent and we would highly recommend this hotel!
Reviewed on 18 Jul 2026
Dimora Palanca Boutique & SPA
Historic Centre of Florence
£1,074
per person
11 Oct - 18 Oct
found 15 hours ago
Return flight included
Birmingham (BHX) to Florence (FLR)
9.2/10 Wonderful! (68 reviews)
Lovely hotel, very friendly staff and great location just outside hustle and bustle of Florence.
Reviewed on 21 Apr 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
Grand Hotel Bastiani
Piazza Gioberti 64 Grosseto GR
Fully refundableReserve now, pay when you stay
£70
21 Sept - 22 Sept
includes taxes & fees
8.6/10 Excellent! (247 reviews)
"Gorgeous, historic hotel, room was spacious with very high ceilings. Breakfast was delicious too. It was a little loud outside at night but obviously nothing the hotel can do about that and it wasn't really a problem for me. Great location, kind and helpful staff. I'd happily stay here again, for ..."
Reviewed on 19 Jun 2026
Castiglion del Bosco, A Rosewood Hotel
Localita Castiglion del Bosco Montalcino SI
10/10 Exceptional! (80 reviews)
"Best hotel ever."
Reviewed on 27 Jul 2026
Fattoria La Principina Hotel & Congress
Via Dei Girasoli, 1 (Via del Tarabuso) Grosseto GR
Fully refundableReserve now, pay when you stay
£74
20 Sept - 21 Sept
includes taxes & fees
8.4/10 Very good! (192 reviews)
"great facility but needs a general upgrade and remodeling"
Reviewed on 15 Aug 2026
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
£38
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 £459. 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.
