Montemassi Vacations from $760

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to $1,045 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

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
Save 100% on your flight
per person
Sep 4 - Sep 9
found 19 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,000 reviews)
If one is not there for a fancy hotel room, but for sightseeing, this is a great, clean, bare bones room. It is close to the train station. We were on the 5th floor and had a great view! Breakfast was also on the 5th floor. Close proximity to all the museums and Duomo, 20 minute walk or less to everything. We walked everywhere!

Reviewed on Jun 21, 2025

Residenza Hotel Cimabue

Residenza Hotel Cimabue

3 out of 5
Historic Centre of Florence
per person
Aug 18 - Aug 25
found 20 hours ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
7.6/10 Good! (361 reviews)
Great place and staff

Reviewed on Jun 6, 2025

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Sep 9 - Sep 14
found 18 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,002 reviews)
Great place to stay, so close to all attractions. Fantastic staff and service. A happy traveller.

Reviewed on Jun 25, 2025

Grand Hotel Cavour

Grand Hotel Cavour

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Sep 4 - Sep 9
found 19 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.2/10 Wonderful! (1,003 reviews)
Fantastic people and best view in Florence at night. Breakfast the best in Florence. Would go back in a heart beat

Reviewed on Jun 25, 2025

Palazzo Firenze by Baglioni Hotels & Resorts

Palazzo Firenze by Baglioni Hotels & Resorts

5 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Sep 4 - Sep 9
found 19 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.4/10 Exceptional! (225 reviews)
It was a beautiful property. For the price the quality of the breakfast could have been better, and we asked for a bag to be mailed and they wouldn’t do it because it was a Sunday. We had hoped to not have to bring it on the train again. Overall, however, the staff was great and the property is beautiful and conveniently located.

Reviewed on May 25, 2025

Don't see what you're looking for?
See all available trips from Columbus to Montemassi
View all trips

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

Rocca di Frassinello Winery: Tour & Wine Tasting in Tuscany

Rocca di Frassinello Winery: Tour & Wine Tasting in Tuscany

$40
per adult
Rocca di Frassinello Winery: Tour & Wine Tasting in Tuscany
See all activities in Montemassi

Montemassi Hotel Deals

Hotel La Pineta
Hotel La Pineta
3 out of 5
Via Delle Collacchie, 67, Follonica, GR
8.8/10 Excellent! (234 reviews)
"Booked this hotel as part of a trip and everything was well organised at the hotel when we arrived. Lifts to all floors and clean tidy and well equipped room. Extra charge of 10 euros per night which was not excessive however there was plenty of on street parking available. Breakfast was very good ..."

Reviewed on May 28, 2025

Get rates
Hotel La Pineta
The Sense Experience Resort
The Sense Experience Resort
5 out of 5
Viale Italia 315, Follonica, GR
Fully refundableReserve now, pay when you stay
9/10 Wonderful! (171 reviews)
"It was migical."

Reviewed on Jun 21, 2025

Get rates
The Sense Experience Resort
Rosewood Castiglion del Bosco
Rosewood Castiglion del Bosco
5 out of 5
Localita Castiglion del Bosco, Montalcino, SI
$2,888 nightly
The price is $3,188 total per night from Jul 17 to Jul 18
$3,188 total
Jul 17 - Jul 18
Total includes taxes and fees
10/10 Exceptional! (64 reviews)
"Peaceful, Relaxing Stay in Tuscany We had a great experience here. The setting is quiet and secluded—felt like a true escape from everyday life. The golf was excellent, the food was consistently good, and the service was friendly and professional. It is remote, which adds to the charm, but just a ..."

Reviewed on Jun 21, 2025

Rosewood Castiglion del Bosco
See all 2,112 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

More vacations you might like

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Montemassi vacation package cost?
You'll find cheap prices from $760 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.