Title: Montemassi Holidays 2026 from £153 | Expedia.co.uk [Montemassi Travel Guide](https://expedia.co.uk/Montemassi.dx6361379)[Hotels in Montemassi](https://expedia.co.uk/Montemassi-Hotels.d6361379.Travel-Guide-Hotels)[Holiday Rentals in Montemassi](https://expedia.co.uk/Montemassi-Holiday-Rentals.d6361379.Travel-Guide-HolidayRentals)[Montemassi Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Montemassi.d6361379.Car-Hire-Guide) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Montemassi Holidays from £153 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to £335 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 Packages with flights are ATOL protected #### Your Montemassi Holiday When you organise a holiday 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 neighbourhood 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.co.uk/Podere-Ristella-Vineyards-And-Winery-Roccastrada.d553248621532497683.Attraction), [Church of San Nicola](https://www.expedia.co.uk/Church-Of-San-Nicola-Roccastrada.d553248621532497684.Attraction) and [Sassoforte Castle](https://www.expedia.co.uk/Sassoforte-Castle-Roccastrada.d685924565073498112.Attraction) are among the major attractions worth exploring. Whatever your travel plans or the size of your budget, putting together the ultimate tailored Montemassi holiday is a cinch with Expedia. ## Top Montemassi Flight + Hotel Deals Price found within the past 48 hours. Click for updated prices. ![Hotel Del Borgo](https://images.trvl-media.com/lodging/3000000/2600000/2599000/2598944/409059c0_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Del Borgo Save 100% on your flight £153 per person 27 Apr - 1 May found 1 day ago Return flight included London (LON) to Pisa (PSA) 8.4/10 Very Good! (46 reviews) All together, is was a fantastic surprise, the room was very spacious, spotless and warm. The check-in and the check-out, were very quick, no big fuss. The breakfast was very good, other than the traditional continental breakfast, there was some hot food as well. And the owners, were friendly, pleasant and very professinal. All in all a trully pleasant stay. Grazzie mille. Reviewed on 5 Jan 2026 ![Hotel Miceli - Civico 50](https://images.trvl-media.com/lodging/32000000/31800000/31795300/31795212/36111d3b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Miceli - Civico 50 Historic Centre of Florence Save 100% on your flight £732 per person 1 May - 8 May found 1 day ago Return flight included London (LGW) to Florence (FLR) 9/10 Wonderful! (232 reviews) I loved everything on and around this property. Sitting at the heart of that shopping district, every place I wanted to visit, was just max 15 mins walking distance. Reviewed on 29 Dec 2025 ![Hotel Duomo Firenze](https://images.trvl-media.com/lodging/3000000/2550000/2541700/2541603/fdd7cf48_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Duomo Firenze Historic Centre of Florence Save 100% on your flight £997 per person 1 May - 8 May found 1 day ago Return flight included London (LGW) to Florence (FLR) 9.2/10 Wonderful! (1,002 reviews) All good experience! Reviewed on 6 Feb 2026 ![Palazzo Firenze by Baglioni Hotels & Resorts](https://images.trvl-media.com/lodging/2000000/1160000/1152300/1152276/479e9ac2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Palazzo Firenze by Baglioni Hotels & Resorts Historic Centre of Florence Save 100% on your flight £1,407 per person 21 Apr - 24 Apr found 5 hours ago Return direct flight included Birmingham (BHX) to Florence (FLR) 9.4/10 Exceptional! (233 reviews) Gorgeous boutique hotel, like museum Beautiful rooms!!! Thank you Giovanni for all ur help and knowledge organizing everything for us, and breakfast waiters were great!!! Reviewed on 21 Aug 2025 ![Relais Uffizi, Tailor made Hotel](https://images.trvl-media.com/lodging/3000000/2550000/2542800/2542717/3e59e5ae_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Relais Uffizi, Tailor made Hotel Historic Centre of Florence Save 100% on your flight £1,012 per person 1 May - 8 May found 1 day ago Return flight included London (LGW) to Florence (FLR) 9.4/10 Exceptional! (120 reviews) Phenomenal location! Reviewed on 18 Oct 2025 ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-uk-fr-de.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Holiday Sale Members save up to 40% on hotels and holiday homes. Plan this year’s big trip and save. [Book now](https://expedia.co.uk/cheap-deals?rfrr=PKG_SPRING_PROMO_6361379) ## Montemassi Essential Information | Language | Italian | | --------------- | -------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | | Currency | Euros | | Local Welcome | Ciao | | Local Goodbye | Ciao | | Population | 180 | | Max Temp Winter | 13ºC | | Max Temp Summer | 27ºC | | Top Sights | [Podere Ristella Vineyards and Winery](https://www.expedia.co.uk/Podere-Ristella-Vineyards-And-Winery-Roccastrada.d553248621532497683.Attraction), [Castello del Belagaio](https://www.expedia.co.uk/Castello-Del-Belagaio-Roccastrada.d553248622636430376.Attraction) and [Sassoforte Castle](https://www.expedia.co.uk/Sassoforte-Castle-Roccastrada.d685924565073498112.Attraction) | ## Top hotels in Montemassi ![Hotel Airone](https://images.trvl-media.com/lodging/23000000/22490000/22481500/22481472/c64e3088_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hotel Airone Via Senese, 35 Grosseto GR Fully refundableReserve now, pay when you stay £94 20 Feb - 21 Feb includes taxes & fees 8.4/10 Very Good! (110 reviews) Clean rooms, friendly staff Reviewed on 15 Oct 2025 [](https://expedia.co.uk/Hotel-Search?startDate=20%2F02%2F2026&endDate=21%2F02%2F2026&selected=22481472&PinnedHotelID=22481472&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 [Get rates](https://expedia.co.uk/Hotel-Search?startDate=05%2F03%2F2026&endDate=06%2F03%2F2026&selected=4644735&PinnedHotelID=4644735&HadPinnedHotel=true®ionId=6361379) [](https://expedia.co.uk/Hotel-Search?startDate=05%2F03%2F2026&endDate=06%2F03%2F2026&selected=4644735&PinnedHotelID=4644735&HadPinnedHotel=true®ionId=6361379) ![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 £1,078 21 Mar - 22 Mar includes taxes & fees [](https://expedia.co.uk/Hotel-Search?startDate=21%2F03%2F2026&endDate=22%2F03%2F2026&selected=2173539&PinnedHotelID=2173539&HadPinnedHotel=true®ionId=6361379) [See all 2,032 properties in Montemassi](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=20%2F02%2F2026&endDate=21%2F02%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. ![](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 Holidays [](https://expedia.co.uk/lp/theme-holidays/all-inclusive-holidays?rfrr=editorial.All_Inclusive%20Holidays.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 Holidays [](https://expedia.co.uk/lp/theme-holidays/beach-holidays?rfrr=editorial.Beach_Holidays.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) Family Friendly Holidays [](https://expedia.co.uk/lp/theme-holidays/kid-friendly-holidays?rfrr=editorial.Family_Friendly%20Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Holidays [](https://expedia.co.uk/lp/theme-holidays/golf-holidays?rfrr=editorial.Golf_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Holidays [](https://expedia.co.uk/lp/theme-holidays/luxury-holidays?rfrr=editorial.Luxury_Holidays.click) ![gay friendly holidays](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) LGBTQ+ Holidays [](https://expedia.co.uk/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ+_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Holidays [](https://expedia.co.uk/lp/theme-holidays/romantic-holidays?rfrr=editorial.Romantic_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Holidays [](https://expedia.co.uk/lp/theme-holidays/ski-holidays?rfrr=editorial.Ski_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/22/hero-image-pet-friendly_copy.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Pet Friendly Holidays [](https://expedia.co.uk/lp/theme-holidays/pet-friendly-holidays?rfrr=editorial.Pet_Friendly%20Holidays.click) ![Holiday in Month](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when [](https://expedia.co.uk/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ### Popular places to visit #### Podere Ristella Vineyards and Winery You can enjoy a tasting or tour at Podere Ristella Vineyards and Winery during your travels to Roccastrada. Wander the gardens or discover the area's countryside. [](https://expedia.co.uk/Podere-Ristella-Vineyards-And-Winery-Roccastrada.d553248621532497683.Attraction) ### What to do in Montemassi ![From Fiumicino Airport: 1-Way Bus Transfer to Paganico](https://mediaim.expedia.com/localexpert/48206464/247937e6-d734-4208-917c-ad2494f7279f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### From Fiumicino Airport: 1-Way Bus Transfer to Paganico £8 per adult [](https://expedia.co.uk/things-to-do/from-fiumicino-airport-1-way-bus-transfer-to-paganico.a48206464.activity-details) ![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 £39 per adult **100%** of travellers recommend [](https://expedia.co.uk/things-to-do/la-maliosa-farm-experience-wine-tasting.a44638298.activity-details) ![Welcome to Casale del Bosco](https://mediaim.expedia.com/localexpert/49075566/38f4ac08-b80d-4ccf-bb46-3f53fdc0db59.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Welcome to Casale del Bosco £30 per adult [](https://expedia.co.uk/things-to-do/welcome-to-casale-del-bosco.a49075566.activity-details) [See all activities in Montemassi](https://expedia.co.uk/things-to-do/search?rid=6361379) ## Explore a world of travel with Expedia \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels when you book in the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app