Montemassi Vacations from $698

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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 $959, price is now $698 per person
$698
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,007 reviews)
We were able to check-in early. It is walkable from Santa Maria Novella train station and so are the points of interest. When we arrived, the electric metal blinds was not working. Letitia gave us a sheet to temporarily give us privacy. When we came back from our tour the next day, it was already fixed. Great place to stay. Worth the money we paid for. Santa Maria Novella Basilica is close by. Worth visiting. Well recommended.

Reviewed on Oct 19, 2025

Collegio alla Querce, Auberge Collection

Collegio alla Querce, Auberge Collection

5 out of 5
Le Cure
Save 100% on your flight
Price was $2,755, price is now $1,817 per person
$1,817
per person
Dec 9 - Dec 12
found 1 hour ago
Roundtrip non-stop flight included
Miami (MIA) to Florence (FLR)
10/10 Exceptional! (3 reviews)
Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was $1,031, price is now $716 per person
$716
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,015 reviews)
Very central. You can walk to

Reviewed on Oct 20, 2025

Villa Cora

Villa Cora

5 out of 5
Oltrarno
Price was $1,535, price is now $1,101 per person
$1,101
per person
Jan 8 - Jan 11
found 22 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.8/10 Exceptional! (465 reviews)
The hotel is very beautiful, and the surrounding environment is also excellent.

Reviewed on Sep 26, 2025

The St. Regis Florence

The St. Regis Florence

5 out of 5
Historic Centre of Florence
Price was $1,567, price is now $1,125 per person
$1,125
per person
Jan 8 - Jan 11
found 22 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.6/10 Exceptional! (261 reviews)
Nice property in a great location.

Reviewed on Jun 29, 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
Wine Tasting in Toscana with Priority Access

Wine Tasting in Toscana with Priority Access

$17
per adult
Wine Tasting in Toscana with Priority Access
Welcome to Casale del Bosco

Welcome to Casale del Bosco

$41
per adult
Welcome to Casale del Bosco
See all activities in Montemassi

Montemassi Hotel Deals

Hotel La Pineta

Hotel La Pineta

3 out of 5
Via Delle Collacchie, 67, Follonica, GR
$71 nightly
The price is $79 total per night from Oct 22 to Oct 23
$79 total
Oct 22 - Oct 23
Total with taxes and fees
8.8/10 Excellent! (254 reviews)
"Nicely renovated room. Staff was very friendly and helpful."

Reviewed on Sep 25, 2025

Hotel La Pineta
Rosewood Castiglion del Bosco

Rosewood Castiglion del Bosco

5 out of 5
Localita Castiglion del Bosco, Montalcino, SI
$1,264 nightly
The price is $1,402 total per night from Nov 21 to Nov 22
$1,402 total
Nov 21 - Nov 22
Total with taxes and fees
10/10 Exceptional! (67 reviews)
"Beautiful property and great service. Was a little disappointed they charge double the price for wine they make in their back yard then I pay here in Montreal."

Reviewed on Aug 3, 2025

Rosewood Castiglion del Bosco
Borgo Santo Pietro

Borgo Santo Pietro

5 out of 5
Loc. Palazzetto, Chiusdino, SI
$1,538 nightly
The price is $1,704 total per night from Oct 24 to Oct 25
$1,704 total
Oct 24 - Oct 25
Total with taxes and fees
9.6/10 Exceptional! (56 reviews)
"This pristine and beautiful property took our breath away upon arrival. Five star service and amenities abound. Our suite was stunning and well appointed. We felt as if we stepped back in time and were reminded of what outstanding service and accommodations should be like ~ a much needed respite ..."

Reviewed on Sep 17, 2025

Borgo Santo Pietro
See all 2,103 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 $698 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.