Montemassi Vacations from $1,239
Book a Hotel + Flight or Car together to unlock savings
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.
Palazzo Leopoldo Dimora Storica & Spa
$1,716
per person
Oct 23 - Oct 30
found 9 hours ago
Roundtrip flight included
New York (NYC) to Florence (FLR)
9.2/10 Wonderful! (294 reviews)
Wonderful old building with character and charm. Set right in the middle of Radda. Be aware you can drive into the restricted zone if you’re staying at the hotel, for 20 mins. I advise calling the hotel before you arrive.
Reviewed on Aug 6, 2026
Albergo Le Terme
$2,004
per person
Oct 23 - Oct 30
found 9 hours ago
Roundtrip flight included
New York (NYC) to Florence (FLR)
9.2/10 Wonderful! (78 reviews)
Upon checking we were greeted by a lovely lady that gave great instructions on parking and use of the spa. Our room was very clean and the bed was comfortable. The thermal spa was very nice as we arrived after 10 pm after a long drive from Sorrento. We were able to relax and enjoy the water until midnight. The next morning the breakfast as absolutely superb. We walked around the town until checkout but are going back to the hotel after our stay in north Italy this week. Also it was nice that they had a dedicated parking lot. Our auto was very safe. Checkout was simple as we were in our way to cinque terre. Very Much a 5 star stay.
Reviewed on Jul 28, 2026
Relais Uffizi, Tailor made Hotel
Historic Centre of Florence
$2,759
per person
Sep 21 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Florence (FLR)
9.2/10 Wonderful! (154 reviews)
While the bathrooms were clean I was very disappointed to see a stain on my bedsheets.
Reviewed on Aug 2, 2026
What to do in Montemassi
La Maliosa Summer Farm Experience & Wine Tasting
$51
per adult
100% of travellers recommend
Porto Santo Stefano: Giglio & Giannutri Mini Cruise and Meal
$125
per adult
Montemassi Hotel Deals
Grand Hotel Bastiani
Piazza Gioberti 64 Grosseto GR
Fully refundableReserve now, pay when you stay
$89 nightly
$103 total
Sep 11 - Sep 12
Total with taxes and fees
8.6/10 Excellent! (244 reviews)
"Gorgeous, historic hotel, room was spacious with very high ceilings. Breakfast was delicious too. It was a little loud outside at night but obviously nothing the hotel can do about that and it wasn't really a problem for me. Great location, kind and helpful staff. I'd happily stay here again, for ..."
Reviewed on Jun 19, 2026
Castiglion del Bosco, A Rosewood Hotel
Localita Castiglion del Bosco Montalcino SI
$2,888 nightly
$3,188 total
Sep 2 - Sep 3
Total with taxes and fees
10/10 Exceptional! (80 reviews)
"Best hotel ever."
Reviewed on Jul 27, 2026
Fattoria La Principina Hotel & Congress
Via Dei Girasoli, 1 (Via del Tarabuso) Grosseto GR
$82 nightly
$95 total
Sep 11 - Sep 12
Total with taxes and fees
8.4/10 Very Good! (188 reviews)
Fattoria la Principina
"Good location, close to the town and beaches. Cleaning wise was good but lacking customer service. If you are not italian they won’t even try to welcome you or offer information if you need it. Breakfast is very limited and repetitive , not much choice. Same pastries, cakes, fruits every day. I would ..."
Reviewed on Aug 19, 2025
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 $1,239 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?
- 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.
- 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.
- 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.
- 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.
- Bundle your airfare and accommodations: After you've nailed down your dates and duration, lock in the ideal Montemassi vacation package for you.
- 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.