Montemassi Vacations from $882

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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.
The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $1,317, price is now $882 per person
$882
per person
Apr 16 - Apr 20
found 7 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
9.6/10 Exceptional! (495 reviews)
The spa was wonderful though the jacuzzi could be hotter I think! The only complaint was that the bed wasn’t very comfortable (it was pretty hard) and the pillows were rather flat.

Reviewed on Jan 2, 2026

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $1,691, price is now $996 per person
$996
per person
Apr 16 - Apr 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,000 reviews)
This is not a typical hotel where there is a lobby or staff to greet you . Instead it is a set of apartments in a corner building . The person who let us in was awaiting for us at the door at check in. Breakfast was serve in a buffet style . Staff would ask if you would order something else if you like. Continental breakfast is available .Overall it was comfortable and easy to find . Shops and restaurants are all walking distance.

Reviewed on Jan 15, 2026

Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $1,626, price is now $970 per person
$970
per person
Apr 16 - Apr 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Florence (FLR)
7.6/10 Good! (1,002 reviews)
9 day stay. The property hit my must-haves! Central location, clean, affordable, and safe. 5/5 in all these areas! There is nothing they can do about dirty streets but the filth did not cross the threshold. T2 tram from the airport is 2 blocks away. The central market is 2 blocks in the other direction. Key card swipe after dark. 24 hour desk service. Breakfast on the 5th floor with views. Very courteous staff. The only complaint is breakfast tables are cleared very quickly while I went for a americano refill. Will definitely return here.

Reviewed on Jan 3, 2026

Portrait Firenze - Lungarno Collection

Portrait Firenze - Lungarno Collection

5 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $5,248, price is now $3,434 per person
$3,434
per person
Apr 20 - Apr 26
found 23 hours ago
Roundtrip non-stop flight included
New York (NYC) to Florence (FLR)
9.8/10 Exceptional! (299 reviews)
Great location and got fantastic service from the hotel. Room was very clean and comfortable. Definitely my first choice for staying in Firenze!

Reviewed on Nov 17, 2025

Cappuccina Country Resort

Cappuccina Country Resort

4 out of 5
Price was $1,743, price is now $1,170 per person
$1,170
per person
Apr 20 - Apr 26
found 22 hours ago
Roundtrip non-stop flight included
Ontario (ONT) to Florence (FLR)
8.6/10 Excellent! (91 reviews)
Great stay. Very good experience.

Reviewed on Oct 20, 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
In the Footstep of the Etruscans: Hike & Wine Tasting

In the Footstep of the Etruscans: Hike & Wine Tasting

$256
per adult
100% of travellers recommend
In the Footstep of the Etruscans: Hike & Wine Tasting
See all activities in Montemassi

Montemassi Hotel Deals

Rosewood Castiglion del Bosco

Rosewood Castiglion del Bosco

5 out of 5
Localita Castiglion del Bosco Montalcino SI
9.8/10 Exceptional! (73 reviews)
Wonderful stay

Reviewed on Nov 25, 2025

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Rosewood Castiglion del Bosco
Borgo Santo Pietro

Borgo Santo Pietro

5 out of 5
Loc. Palazzetto Chiusdino SI
9.6/10 Exceptional! (57 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

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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 $100 total per night from Jan 28 to Jan 29
$100 total
Jan 28 - Jan 29
Total with taxes and fees
8.4/10 Very Good! (219 reviews)
We had a wonderful stay at the Grand Hotel Bastiani in Grosseto. The hotel is beautifully maintained and perfectly located in the historic center, making it ideal for exploring the city on foot. From the moment we arrived, the staff was welcoming, professional, and always ready to help with recommendations ...

Reviewed on Jan 13, 2026

Grand Hotel Bastiani
See all 2,029 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 $882 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.