Montemassi Vacations from $1,378

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Your Montemassi Vacation

When you organize a vacation 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 neighborhood 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 vacation is a cinch with Expedia.

The Latest Montemassi vacation packages

Price found within the past 48 hours. Click for updated prices.
Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Price was $2,090, price is now $1,378 per person
$1,378
per person
Jun 3 - Jun 9
found 8 hours ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
7.6/10 Good! (1,006 reviews)
Great simple place.

Reviewed on Apr 9, 2026

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was $2,473, price is now $1,522 per person
$1,522
per person
Jun 3 - Jun 9
found 9 hours ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
7.6/10 Good! (1,000 reviews)
The room was clean and newly renovated. Having breakfast included was great for a quick bite so I could focus on exploring instead of searching and waiting in line. Would definitely recommend a stay here

Reviewed on Apr 9, 2026

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Save 100% on your flight
Price was $4,065, price is now $2,853 per person
$2,853
per person
May 22 - May 26
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Florence (FLR)
9.4/10 Exceptional! (124 reviews)
Most gorgeous setting, lovely staff and delicious food. We will definitely be back!

Reviewed on Apr 5, 2026

Portrait Firenze - Lungarno Collection

Portrait Firenze - Lungarno Collection

5 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $6,294, price is now $4,493 per person
$4,493
per person
Jun 3 - Jun 9
found 9 hours ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
9.8/10 Exceptional! (307 reviews)
The rooms are beautiful and immaculately kept. The staff is so personable and thoughtful. The location is unmatched highly recommend this hotel!

Reviewed on Apr 3, 2026

Dimora Palanca Boutique & SPA

Dimora Palanca Boutique & SPA

5 out of 5
Historic Centre of Florence
Price was $3,013, price is now $2,206 per person
$2,206
per person
May 25 - May 31
found 3 hours ago
Roundtrip non-stop flight included
New York (NYC) to Florence (FLR)
9.2/10 Wonderful! (62 reviews)
I particularly love the authenticity of the building being hundreds of hundreds of years old and yet well cut, beautiful staff beautiful spa only lacking in the dining aspect but everything else was perfect. Highly recommend but recommend going out for dinner.

Reviewed on Nov 5, 2025

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Discover the most popular places to visit in Montemassi

I Canaloni del Torrente Farma

Commune with nature and explore the great outdoors at I Canaloni del Torrente Farma during your travels in Roccastrada. Discover the area's countryside and spas.

I Canaloni del Torrente Farma

Castello del Belagaio

You can find out about the history of Roccastrada with a trip to Castello del Belagaio. Discover the area's countryside and wineries.

Castello del Belagaio

What to do in Montemassi

La Maliosa Farm Experience & Wine Tasting

La Maliosa Farm Experience & Wine Tasting

$52
per adult
100% of travellers recommend
La Maliosa Farm Experience & Wine Tasting
Porto Santo Stefano: Giglio & Giannutri Mini Cruise and Meal

Porto Santo Stefano: Giglio & Giannutri Mini Cruise and Meal

$127
per adult
Porto Santo Stefano: Giglio & Giannutri Mini Cruise and Meal
In the Footstep of the Etruscans: Hike & Wine Tasting

In the Footstep of the Etruscans: Hike & Wine Tasting

$197
per adult
100% of travellers recommend
In the Footstep of the Etruscans: Hike & Wine Tasting
See all activities in Montemassi

Montemassi Hotel Deals

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
$1,434 nightly
The price is $1,589 total per night from Apr 19 to Apr 20
$1,589 total
Apr 19 - Apr 20
Total with taxes and fees
10/10 Exceptional! (75 reviews)
If you don’t like th it s place, then there will never be a place on earth that you like.. it’s actually above a 5 star!! Over the top service.. food seasons breakfast fantastic…fell very lucky to have stayed here.. thank you

Reviewed on Apr 8, 2026

Castiglion del Bosco, A Rosewood Hotel
Borgo Santo Pietro

Borgo Santo Pietro

5 out of 5
Loc. Palazzetto Chiusdino SI
Get rates
Borgo Santo Pietro
Grand Hotel Bastiani

Grand Hotel Bastiani

4 out of 5
Piazza Gioberti 64 Grosseto GR
Fully refundableReserve now, pay when you stay
$91 nightly
The price is $105 total per night from Apr 15 to Apr 16
$105 total
Apr 15 - Apr 16
Total with taxes and fees
8.6/10 Excellent! (228 reviews)
This is Not a 4star hotel!!!!!! No Bathroom amenities but a liquid soap to do all!! And the one in the shower didn’t even work! No boxes of tissues! Just Horrible, no bell service, had no Water for 4 hours!, Breakfast was subpar, would not recommend anyone to stay here!!! Staff also was no Friendly ...

Reviewed on Mar 20, 2026

Grand Hotel Bastiani
See all 2,108 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.

Find the Best Montemassi Vacation Packages

Montemassi Essential Information

Language
Italian
Currency
Euros
Local Welcome
Ciao
Local Goodbye
Ciao
Population
180
Max Temp Winter
55ºF
Max Temp Summer
80ºF
Top Sights
Podere Ristella Vineyards and Winery, Castello del Belagaio and Sassoforte Castle

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Frequently asked questions

How much does a Montemassi vacation package cost?
You'll find cheap prices from $1,378 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 vacation to Montemassi costs.
What are the cheapest months to go to Montemassi?
October, November and December are great times to look for cheap Montemassi vacation packages. Opting to travel in less busy periods means you'll typically find lower prices on hotels and flights.
How many days is enough for Montemassi?
Typically, a handful of days is enough to explore the major sights during your Montemassi vacation. But if you want to have more time to kick back or go on day trips, consider extending your itinerary.
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 customize 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 traveling on a weekday, when prices are often lower.
Is it cheaper to book a Montemassi vacation as a package?
You can enjoy significant savings on your next Montemassi retreat by booking a personalized vacation 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 vacation 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 the right time to travel: Your schedule, favorite season and the type of weather you enjoy can all influence your decision on when to go to Montemassi.
  2. Budget wisely: On top of the cost of your stay, you'll need to consider other expenses. These include flights, food and transportation. Also, set aside some extra funds for unexpected costs that could crop up during your trip to Montemassi.
  3. Use Expedia's trip planning tool to discover Montemassi: Research every part of your trip to Montemassi with this handy planner. Invite your family and friends to collaborate on a group trip, search for hotels or things to do and make bookings.
  4. Determine how many days away: Start by making a list of all the attractions and activities you'd like to get to in Montemassi. Then, estimate how long you'll need for each, including any travel time.
  5. Bundle your airfare and accommodations: After you've nailed down your dates and duration, lock in the ideal Montemassi vacation package for you.
  6. Add on experiences and excursions: Have a look at our dedicated travel guide to find some fun things to do in Montemassi in Montemassi. Book tickets or make reservations as soon as you can to save time and skip the hassle of searching for activities when you arrive.

Does Expedia offer Book Now, Pay Later Montemassi vacation packages?
Set off on your dream trip to Montemassi with help from Expedia's Book Now, Pay Later vacations. There's no need to save like crazy or wait until payday — we've partnered with online lender Affirm to give you flexibility with your finances. Our vacation packages with payment plans mean you can spread the cost across 3, 6 or 12 months. With no late payment fees or hidden charges, it's a breeze to stick to your budget and snap up travel deals while they last.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.