Title: Montemassi Vacation Packages 2026 from $937 | Expedia.com [Montemassi Travel Guide](https://expedia.com/Montemassi.dx6361379)[Hotels in Montemassi](https://expedia.com/Montemassi-Hotels.d6361379.Travel-Guide-Hotels)[Vacation Rentals in Montemassi](https://expedia.com/Montemassi-Vacation-Rentals.d6361379.Travel-Guide-VacationRentals)[Flights to Montemassi](https://expedia.com/Cheap-Flights-To-Montemassi.d6361379.Travel-Guide-Flights)[Car Rentals in Montemassi](https://expedia.com/Car-Rentals-In-Montemassi.d6361379.Car-Rental-Guide) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Montemassi Vacations from $937 ## 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](https://www.expedia.com/Podere-Ristella-Vineyards-And-Winery-Roccastrada.d553248621532497683.Vacation-Attraction), [Church of San Nicola](https://www.expedia.com/Church-Of-San-Nicola-Roccastrada.d553248621532497684.Vacation-Attraction) and [Sassoforte Castle](https://www.expedia.com/Sassoforte-Castle-Roccastrada.d685924565073498112.Vacation-Attraction) 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 Uffizi](https://images.trvl-media.com/lodging/3000000/2550000/2541700/2541615/862ad26c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Aurum Uffizi Historic Centre of Florence Save 100% on your flight $937 per person Apr 27 - May 2 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 ![Grotta Giusti Thermal Spa Resort Tuscany, Autograph Collection](https://images.trvl-media.com/lodging/1000000/910000/904300/904294/00eb5246_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Grotta Giusti Thermal Spa Resort Tuscany, Autograph Collection $3,793 per person Apr 21 - Apr 24 found 1 day ago Roundtrip flight included Boston (BOS) to Florence (FLR) 8.8/10 Excellent! (176 reviews) We spent our honeymoon here as we were married in San Miniato. The staff was wonderful especially Laura! There was a slight issue with our room, not only were they considerate, they upgraded our room and sent a gift to our room complimentary once hearing about our wedding. We will definitely make this a priority to our next visit! Reviewed on Nov 24, 2025 ![AC Hotel Firenze by Marriott](https://images.trvl-media.com/lodging/2000000/1600000/1593300/1593256/d315d5b0_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### AC Hotel Firenze by Marriott Santa Maria Novella $3,905 per person Apr 21 - Apr 24 found 1 day ago Roundtrip flight included Boston (BOS) to Florence (FLR) 8.6/10 Excellent! (780 reviews) Not much to do around, the hotel should have a more inviting lobby, maybe happy hour. The lobby felt very empty. Reviewed on Dec 28, 2025 ![The Moon Boutique Hotel & Spa](https://images.trvl-media.com/lodging/23000000/22260000/22255000/22254976/205f9600_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Moon Boutique Hotel & Spa Historic Centre of Florence Save 100% on your flight $1,283 per person Apr 14 - Apr 20 found 22 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 ![Sina Villa Medici, Autograph Collection](https://images.trvl-media.com/lodging/1000000/20000/18300/18229/72404b44_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sina Villa Medici, Autograph Collection Historic Centre of Florence $4,198 per person Apr 21 - Apr 24 found 1 day ago Roundtrip flight included Boston (BOS) to Florence (FLR) 8.6/10 Excellent! (308 reviews) Staff was very helpful despite the hot weather. Great stay, very serene environment for vacation. Reviewed on Sep 28, 2025 Don't see what you're looking for? See all available trips from Columbus to Montemassi [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-08/2026-03-15/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=GRS&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ### 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. [](https://expedia.com/I-Canaloni-Del-Torrente-Farma-Roccastrada.d553248634041940720.Vacation-Attraction) #### 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. [](https://expedia.com/Castello-Del-Belagaio-Roccastrada.d553248622636430376.Vacation-Attraction) ### What to do in Montemassi ![La Maliosa Farm Experience & Wine Tasting](https://mediaim.expedia.com/localexpert/44638298/2d7ee171-839d-48ec-b768-c660cead2473.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### La Maliosa Farm Experience & Wine Tasting $53 per adult **100%** of travellers recommend [](https://expedia.com/things-to-do/la-maliosa-farm-experience-wine-tasting.a44638298.activity-details) ![In the Footstep of the Etruscans: Hike & Wine Tasting](https://mediaim.expedia.com/localexpert/47811075/9b29f97e-8b7f-40d8-9519-dd33720676e7.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### In the Footstep of the Etruscans: Hike & Wine Tasting $260 per adult **100%** of travellers recommend [](https://expedia.com/things-to-do/in-the-footstep-of-the-etruscans-hike-wine-tasting.a47811075.activity-details) [See all activities in Montemassi](https://expedia.com/things-to-do/search?rid=6361379) ## Montemassi Hotel Deals ![Rosewood Castiglion del Bosco](https://images.trvl-media.com/lodging/3000000/2180000/2173600/2173539/9ace3d4a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Rosewood Castiglion del Bosco Localita Castiglion del Bosco Montalcino SI 9.8/10 Exceptional! (73 reviews) Wonderful stay Reviewed on Nov 25, 2025 [Get rates](https://expedia.com/Hotel-Search?startDate=2%2F22%2F2026&endDate=2%2F23%2F2026&selected=2173539&PinnedHotelID=2173539&HadPinnedHotel=true®ionId=6361379) [](https://expedia.com/Hotel-Search?startDate=2%2F22%2F2026&endDate=2%2F23%2F2026&selected=2173539&PinnedHotelID=2173539&HadPinnedHotel=true®ionId=6361379) ![Borgo Santo Pietro](https://images.trvl-media.com/lodging/5000000/4650000/4644800/4644735/32bc8809_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Borgo Santo Pietro 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 [Get rates](https://expedia.com/Hotel-Search?startDate=2%2F22%2F2026&endDate=2%2F23%2F2026&selected=4644735&PinnedHotelID=4644735&HadPinnedHotel=true®ionId=6361379) [](https://expedia.com/Hotel-Search?startDate=2%2F22%2F2026&endDate=2%2F23%2F2026&selected=4644735&PinnedHotelID=4644735&HadPinnedHotel=true®ionId=6361379) ![Grand Hotel Bastiani](https://images.trvl-media.com/lodging/2000000/1280000/1277600/1277581/e5c725af_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Grand Hotel Bastiani Piazza Gioberti 64 Grosseto GR Fully refundableReserve now, pay when you stay $91 nightly $100 total Feb 11 - Feb 12 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 [](https://expedia.com/Hotel-Search?startDate=2%2F11%2F2026&endDate=2%2F12%2F2026&selected=1277581&PinnedHotelID=1277581&HadPinnedHotel=true®ionId=6361379) [See all 2,036 properties in Montemassi](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F9%2F2026&endDate=2%2F10%2F2026®ionId=6361379) 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](https://www.expedia.com/Podere-Ristella-Vineyards-And-Winery-Roccastrada.d553248621532497683.Vacation-Attraction), [Castello del Belagaio](https://www.expedia.com/Castello-Del-Belagaio-Roccastrada.d553248622636430376.Vacation-Attraction) and [Sassoforte Castle](https://www.expedia.com/Sassoforte-Castle-Roccastrada.d685924565073498112.Vacation-Attraction) | ## More vacations you might like ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.com/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.com/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Kid Friendly Vacations [](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.click) 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![](https://forever.travel-assets.com/flex/flexmanager/images/2023/04/04/EPS-RBC-SummerBeachVacations-AdobeStock_206356322.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Cheap Vacations [](https://expedia.com/lp/theme-vacations/cheap-vacations?rfrr=editorial.Cheap_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/06/26/1175883311.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Solo Vacations [](https://expedia.com/lp/b/vacations/solo-vacations?rfrr=editorial.Solo_Vacations.click) ## Frequently asked questions ### How much does a Montemassi vacation package cost? ### What are the cheapest months to go to Montemassi? ### How many days is enough for Montemassi? ### How to find the best Montemassi package deals? ### Is it cheaper to book a Montemassi vacation as a package? ### When to book a vacation package to Montemassi? ### 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](https://www.expedia.com/why/trip-planning) 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](https://www.expedia.com/Things-To-Do-In-Montemassi.d6361379.Travel-Guide-Activities) 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? \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save even more - get up to 20% on select hotels when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. 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