Montemassi Holidays from £239

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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.
Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
5 Oct - 7 Oct
found 12 hours ago
Return flight included
London (LGW) to Florence (FLR)
7.6/10 Good! (1,012 reviews)
Walking distance to all attractions and train station. Room little small but ok , loved the balcony for breakfast that was awesome. Very friendly staff.

Reviewed on 2 Aug 2025

The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
20 Oct - 25 Oct
found 1 day ago
Return direct flight included
Birmingham (BHX) to Florence (FLR)
9.6/10 Exceptional! (462 reviews)
Hands down the best place we have stayed. They accommodated to go breakfasts for our tours, arranged taxis, made cappuccino when we were heading out the door. Wonderful experience

Reviewed on 6 Jun 2025

Hotel Palazzo Ognissanti

Hotel Palazzo Ognissanti

4 out of 5
Historic Centre of Florence
per person
9 Oct - 16 Oct
found 1 day ago
Return flight included
London (LON) to Florence (FLR)
7.8/10 Good! (479 reviews)
We loved the location close to the Arno River and the city center. Had a delicious pizza around the corner and there is also a small grocery store for last minute necessities and water! The staff was very kind, and the breakfast was delicious. They offer free luggage storage which was convenient. Within walking distance from the main train station. We loved our stay and will be back!

Reviewed on 27 Jun 2025

Tenuta di Artimino Member of Meliá Collection

Tenuta di Artimino Member of Meliá Collection

4 out of 5
Save 100% on your flight
per person
6 Sept - 13 Sept
found 1 day ago
Return flight included
London (LHR) to Florence (FLR)
9.4/10 Exceptional! (117 reviews)
Property is beautiful everywhere you turn, straight out of a movie! Hotel is located at the top of a mountain and you get to over see the vineyards and cities., absolutely beautiful views. The only downside is the hotel only has 2 restaurants that offer diner and they alternate on which night they are opened, you also need reservations in advance and even then tables with a view are not guaranteed.

Reviewed on 25 Jul 2025

Hotel Bencista

Hotel Bencista

3 out of 5
Save 100% on your flight
per person
7 Sept - 14 Sept
found 1 day ago
Return direct flight included
London (LON) to Florence (FLR)
7.2/10 Good! (12 reviews)

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

The Sense Experience Resort

The Sense Experience Resort

5 out of 5
Viale Italia 315, Follonica, GR
The price is £278 per night from 1 Sept to 2 Sept
£278
1 Sept - 2 Sept
includes taxes & fees
9/10 Wonderful! (184 reviews)
"Absolutely stunning beach resort with impeccable service!!!"

Reviewed on 25 Jul 2025

The Sense Experience Resort
Fattoria La Principina

Fattoria La Principina

4 out of 5
Via Dei Girasoli, 1 (Via del Tarabuso), Principina Terra, Grosseto, GR
The price is £118 per night from 28 Aug to 29 Aug
£118
28 Aug - 29 Aug
includes taxes & fees
8.4/10 Very Good! (174 reviews)
"One night’s stay at Fattoria for me, my husband and our 17 year old. The hotel is geared up for a family who love their activities - a full timetable of events, football, tennis, a mini farm and 3 pools. The main pool area was lovely, with a well-stocked pool bar. One thing worth noting, as is sometime ..."

Reviewed on 16 Aug 2024

Fattoria La Principina
Hotel La Pineta

Hotel La Pineta

3 out of 5
Via Delle Collacchie, 67, Follonica, GR
The price is £142 per night from 7 Aug to 8 Aug
£142
7 Aug - 8 Aug
includes taxes & fees
8.8/10 Excellent! (241 reviews)
Perfect hotel by the beach!
"This cute hotel is a 1-minute walk to the beach! It is a little outside of central Follonica, but totally walkable. We are a family of three and we walked to town every night for dinner and gelato. We also walked to and from the train-station with heavy backpacks. They do have bikes to rent at the ..."

Reviewed on 1 Aug 2025

Hotel La Pineta
See all 2,137 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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Family Friendly Holidays

Popular places to visit

Podere Ristella Vineyards and Winery

You can enjoy a tasting or tour at Podere Ristella Vineyards and Winery during your travels to Roccastrada. Wander the gardens or discover the area's countryside.

Podere Ristella Vineyards and Winery

What to do in Montemassi

Welcome to Casale del Bosco

Welcome to Casale del Bosco

£31
per adult
Welcome to Casale del Bosco
Rocca di Frassinello Winery: Tour & Wine Tasting in Tuscany

Rocca di Frassinello Winery: Tour & Wine Tasting in Tuscany

£31
per adult
Rocca di Frassinello Winery: Tour & Wine Tasting in Tuscany
The Private Challenge of the Crus

The Private Challenge of the Crus

£66
per adult
The Private Challenge of the Crus
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 £239. 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.