Montemassi Vacations from $1,214

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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 $1,939, price is now $1,214 per person
$1,214
per person
Sep 2 - Sep 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Florence (FLR)
7.4/10 Good! (1,039 reviews)
This was a great place to stay, especially if your planning, like we did, to take trips on the Train to other cities during the day!(for us, we went to Pisa one day & Venice another day) Staff was friendly, and breakfast was amazing with the rooftop views. Definitely would suggests this hotel, if your looking for easy access to the train system, and a nice walking distance to local attractions.

Reviewed on Jun 24, 2026

Donati Luxury Tower Suites

Donati Luxury Tower Suites

5 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $2,396, price is now $1,588 per person
$1,588
per person
Aug 26 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.8/10 Exceptional! (68 reviews)
Agradable estancia. Excelente servicio. La habitación la mantenían siempre limpia. Todo queda cerca del área. Muy recomendable

Reviewed on May 23, 2026

Hotel La Scaletta Al Ponte Vecchio

Hotel La Scaletta Al Ponte Vecchio

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $2,981, price is now $2,025 per person
$2,025
per person
Sep 2 - Sep 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Florence (FLR)
8.8/10 Excellent! (1,000 reviews)
We had a wonderful stay at this hotel in Florence. From the moment we arrived, the staff was kind, welcoming, and very helpful. The communication before and during our stay was excellent, which made everything feel smooth and easy. The location was perfect for enjoying Florence, and the hotel itself felt comfortable, clean, and well cared for. After long days walking through the city, it was a great place to come back to and relax. What stood out most was the hospitality. The staff made us feel taken care of without it ever feeling forced. You can tell they genuinely care about their guests having a great experience. We would absolutely stay here again and highly recommend it to anyone visiting Florence.

Reviewed on Jun 16, 2026

Relais Uffizi, Tailor made Hotel

Relais Uffizi, Tailor made Hotel

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $3,333, price is now $2,280 per person
$2,280
per person
Sep 2 - Sep 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Florence (FLR)
9.4/10 Exceptional! (145 reviews)
Great location for our purposes and centrally located. Breakfast was good and the room was quiet.

Reviewed on Jun 17, 2026

Residenza Florentia

Residenza Florentia

1 out of 5
Historic Centre of Florence
Price was $1,966, price is now $1,376 per person
$1,376
per person
Sep 6 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Florence (FLR)
8.4/10 Very Good! (53 reviews)
Staff was helpful, the property was not very well maintained.

Reviewed on Jun 1, 2026

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

Porto Santo Stefano: Giglio & Giannutri Mini Cruise and Meal

Porto Santo Stefano: Giglio & Giannutri Mini Cruise and Meal

$128
per adult
Porto Santo Stefano: Giglio & Giannutri Mini Cruise and Meal
La Maliosa Farm Experience & Wine Tasting

La Maliosa Summer Farm Experience & Wine Tasting

$52
per adult
100% of travellers recommend
La Maliosa Summer Farm Experience & Wine Tasting
In the Footstep of the Etruscans: Hike & Wine Tasting

In the Footstep of the Etruscans: Hike & Wine Tasting

$198
per adult
100% of travellers recommend
In the Footstep of the Etruscans: Hike & Wine Tasting
See all activities in Montemassi

Montemassi Hotel Deals

The Sense Experience Resort - Preferred Hotels & Resorts

The Sense Experience Resort - Preferred Hotels & Resorts

5 out of 5
Viale Italia 315 Follonica GR
$504 nightly
The price is $561 total per night from Jul 17 to Jul 18
$561 total
Jul 17 - Jul 18
Total with taxes and fees
9.2/10 Wonderful! (217 reviews)
"We had a most enjoyable relaxing three days by the beach following 14 travelling through Tuscany. The standards and service were exemplary, the staff are all levels were so professional and friendly. The breakfast could not be improved and with such a setting it was great. Very high standards for ..."

Reviewed on Jun 6, 2026

The Sense Experience Resort - Preferred Hotels & Resorts
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
$2,305 nightly
The price is $2,547 total per night from Jul 20 to Jul 21
$2,547 total
Jul 20 - Jul 21
Total with taxes and fees
Castiglion del Bosco, A Rosewood Hotel
Hotel La Pineta

Hotel La Pineta

3 out of 5
Via Delle Collacchie, 67 Follonica GR
$134 nightly
The price is $152 total per night from Jun 29 to Jun 30
$152 total
Jun 29 - Jun 30
Total with taxes and fees
9/10 Wonderful! (309 reviews)
"Recently remodeled. Very nice location."

Reviewed on Jun 19, 2026

Hotel La Pineta
See all 2,196 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 $1,214 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.