Montemassi Vacations from $734

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • 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.
Eurostars Florence Boutique

Eurostars Florence Boutique

4 out of 5
Historic Centre of Florence
Price was $1,098, price is now $734 per person
$734
per person
Mar 1 - Mar 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
8.6/10 Excellent! (476 reviews)
The room was clean and the staff very accommodating. The breakfast was quite sufficient and had a good variety. The location is great. It's a short walk from the square, shopping and from restaurants.

Reviewed on Dec 13, 2025

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $1,562, price is now $907 per person
$907
per person
Mar 14 - Mar 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,000 reviews)
Great Locations walkable to all the placese.

Reviewed on Dec 15, 2025

Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $1,447, price is now $864 per person
$864
per person
Mar 14 - Mar 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Florence (FLR)
7.6/10 Good! (1,002 reviews)
The room was okay. For the price can’t ask for better. Everything work fine, fully equipped, and breakfast included with very good choices of items and coffees. I will return to this place if I have another opportunity because the staff it’s very friendly, very close to the train station and with lots of restaurants and stores around.

Reviewed on Dec 15, 2025

Art Atelier

Art Atelier

4 out of 5
Historic Centre of Florence
Price was $1,422, price is now $953 per person
$953
per person
Mar 14 - Mar 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Florence (FLR)
9.2/10 Wonderful! (1,001 reviews)
We loved how close everything is! The staff were quick to accommodate our needs and the complimentary breakfast was a nice addition to jumpstart our day.

Reviewed on Dec 4, 2025

Bernini Palace

Bernini Palace

5 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $1,682, price is now $1,138 per person
$1,138
per person
Mar 14 - Mar 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Florence (FLR)
9.6/10 Exceptional! (1,007 reviews)
Lovely room, good location, friendly,welcoming staff , beautiful breakfast room. Overall a super place to stay.

Reviewed on Dec 20, 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

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

$261
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
Fully refundableReserve now, pay when you stay
$1,300 nightly
The price is $1,442 total per night from Jan 4 to Jan 5
$1,442 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
10/10 Exceptional! (69 reviews)
Wonderful stay

Reviewed on Nov 25, 2025

Rosewood Castiglion del Bosco
Hotel Airone

Hotel Airone

4 out of 5
Via Senese, 35 Grosseto GR
Fully refundableReserve now, pay when you stay
$121 nightly
The price is $133 total per night from Dec 23 to Dec 24
$133 total
Dec 23 - Dec 24
Total with taxes and fees
8.4/10 Very Good! (109 reviews)
Clean rooms, friendly staff

Reviewed on Oct 15, 2025

Hotel Airone
Grand Hotel Bastiani

Grand Hotel Bastiani

4 out of 5
Piazza Gioberti 64 Grosseto GR
Fully refundableReserve now, pay when you stay
$90 nightly
The price is $99 total per night from Dec 23 to Dec 24
$99 total
Dec 23 - Dec 24
Total with taxes and fees
8.4/10 Very Good! (216 reviews)
Great breakfast, bathtub and shower.

Reviewed on Nov 1, 2025

Grand Hotel Bastiani
See all 2,042 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 $734 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.