Montemassi Vacations from $856

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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.
Giovanni Rooms Manarola

Giovanni Rooms Manarola

1 out of 5
Save 100% on your flight
per person
Oct 22 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Pisa (PSA)
8/10 Very Good! (86 reviews)
This property is in the centre of Manarola. A lovely, well-looked-after place. If you want to experience waking up in this amazing part of the world, we recommend this location.

Reviewed on Apr 26, 2025

Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Sep 25 - Sep 30
found 1 hour ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.6/10 Good! (1,000 reviews)
Very small rooms and bathrooms. Breakfast and breakfast staff were awesome and on the top floor. Hotel room small and nothing special. Great location and quiet…but good luck getting out of a car with luggage.

Reviewed on Aug 4, 2025

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Sep 24 - Sep 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,001 reviews)
I initially felt concerned about the hotel's location, but quickly realized it's in an old, historical part of town, where narrow alleys are the norm. We never felt unsafe, nor did we experience noise during our stay. This is a no-frills hotel, and an excellent deal for this being Florence. The breakfast was good. It is within walking distance to eateries, shopping, and museums. It met the needs of our family, including our son who gets around in a wheelchair. We will definitely continue to stay here when we return to Florence.

Reviewed on Aug 4, 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
Oct 7 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
9.4/10 Exceptional! (228 reviews)
I VERY MUCH ENJOYED THE STAY

Reviewed on Jul 18, 2025

LHP River Club

LHP River Club

5 out of 5
Santa Croce
Save 100% on your flight
per person
Oct 22 - Oct 28
found 14 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
10/10 Exceptional! (1 review)
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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

Rocca di Frassinello Winery: Tour & Wine Tasting in Tuscany

Rocca di Frassinello Winery: Tour & Wine Tasting in Tuscany

$41
per adult
Rocca di Frassinello Winery: Tour & Wine Tasting in Tuscany
See all activities in Montemassi

Montemassi Hotel Deals

The Sense Experience Resort

The Sense Experience Resort

5 out of 5
Viale Italia 315, Follonica, GR
$346 nightly
The price is $388 total per night from Sep 1 to Sep 2
$388 total
Sep 1 - Sep 2
Total includes taxes and fees
9/10 Wonderful! (185 reviews)
"Great rooms and great beach"

Reviewed on Aug 3, 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
$138 nightly
The price is $157 total per night from Aug 28 to Aug 29
$157 total
Aug 28 - Aug 29
Total includes taxes and 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 Aug 16, 2024

Fattoria La Principina
Hotel La Pineta

Hotel La Pineta

3 out of 5
Via Delle Collacchie, 67, Follonica, GR
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 Aug 1, 2025

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Hotel La Pineta
See all 2,131 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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Frequently asked questions

How much does a Montemassi vacation package cost?
You'll find cheap prices from $856 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.