Title: The Best 5 Star Hotels in Montemassi from $92 | 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)[Things to do in Montemassi](https://expedia.com/Things-To-Do-In-Montemassi.d6361379.Travel-Guide-Activities)[Car Rentals in Montemassi](https://expedia.com/Car-Rentals-In-Montemassi.d6361379.Car-Rental-Guide)[Montemassi Vacation Packages](https://expedia.com/Montemassi.d6361379.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Upfront pricing Our total price for your stay includes taxes and fees - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save 10% or more on over 100,000 hotels worldwide with Member Prices [Learn about One Key](https://www.expedia.com/welcome-one-key) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Montemassi 5 Star Hotels Tonight [Mar 20 - Mar 21](https://www.expedia.com/Hotel-Search?regionId=6361379&startDate=2026-03-20&endDate=2026-03-21&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 21 - Mar 22](https://www.expedia.com/Hotel-Search?regionId=6361379&startDate=2026-03-21&endDate=2026-03-22&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Mar 20 - Mar 22](https://www.expedia.com/Hotel-Search?regionId=6361379&startDate=2026-03-20&endDate=2026-03-22&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Mar 27 - Mar 29](https://www.expedia.com/Hotel-Search?regionId=6361379&startDate=2026-03-27&endDate=2026-03-29&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Montemassi 5-star hotels ![Villa (Agresto) | Living area | LCD TV, pay movies](https://images.trvl-media.com/lodging/3000000/2180000/2173600/2173539/fd17fc16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 outdoor pools, open 8:30 AM to 6:30 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/3000000/2180000/2173600/2173539/92f35956.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Building design](https://images.trvl-media.com/lodging/3000000/2180000/2173600/2173539/576c77ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast, lunch, dinner served; Italian cuisine](https://images.trvl-media.com/lodging/3000000/2180000/2173600/2173539/7c5ee645.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Castiglion del Bosco, A Rosewood Hotel [](https://www.expedia.com/Montalcino-Hotels-Rosewood-Castiglion-Del-Bosco.h2173539.Hotel-Information) Montalcino 10/10 Exceptional (73 reviews) "Wonderful stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Talib $1,137 nightly $1,262 total Mar 21 - Mar 22 Total with taxes and fees [](https://www.expedia.com/Montalcino-Hotels-Rosewood-Castiglion-Del-Bosco.h2173539.Hotel-Information) ![Outdoor pool, free cabanas, pool umbrellas](https://images.trvl-media.com/lodging/5000000/4650000/4644800/4644735/b4af0af2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, Garden Area (Casa dell'Unicorno) | Premium bedding, down comforters, minibar, in-room safe](https://images.trvl-media.com/lodging/5000000/4650000/4644800/4644735/f9e297ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, Poolside (Casa Gerda) | Bathroom | Designer toiletries, hair dryer, bathrobes, slippers](https://images.trvl-media.com/lodging/5000000/4650000/4644800/4644735/4e565ea7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, lunch, dinner served; Modern European cuisine](https://images.trvl-media.com/lodging/5000000/4650000/4644800/4644735/dd7837ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Borgo Santo Pietro [](https://www.expedia.com/Chiusdino-Hotels-Relais-Borgo-Santo-Pietro.h4644735.Hotel-Information) Chiusdino 9.6/10 Exceptional (57 reviews) "Always wonderful stay here " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrew [](https://www.expedia.com/Chiusdino-Hotels-Relais-Borgo-Santo-Pietro.h4644735.Hotel-Information) ![Private beach, sun loungers, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/32000000/31890000/31888200/31888190/44e9cb7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/32000000/31890000/31888200/31888190/e1d40514.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/32000000/31890000/31888200/31888190/96961bf2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/32000000/31890000/31888200/31888190/bf377f27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Sense Experience Resort - Preferred Hotels & Resorts [](https://www.expedia.com/Follonica-Hotels-The-Sense-Experience-Resort.h31888190.Hotel-Information) Follonica 9.2/10 Wonderful (211 reviews) "Lovely hotel that " ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Nicola [](https://www.expedia.com/Follonica-Hotels-The-Sense-Experience-Resort.h31888190.Hotel-Information) ![Check-in/check-out kiosk](https://images.trvl-media.com/lodging/2000000/1150000/1145100/1145020/5c89a2c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/2000000/1150000/1145100/1145020/31e3bee2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1150000/1145100/1145020/1bfc3095.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor spa tub](https://images.trvl-media.com/lodging/2000000/1150000/1145100/1145020/4a39c203.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### L'Andana [](https://www.expedia.com/Castiglione-Della-Pescaia-Hotels-LAndana.h1145020.Hotel-Information) Castiglione della Pescaia 9.4/10 Exceptional (86 reviews) "This is such a beautiful place in every way and we always love it here. Everything is very special and it is wonderful to spend time in this tranquil setting. " ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Pauline [](https://www.expedia.com/Castiglione-Della-Pescaia-Hotels-LAndana.h1145020.Hotel-Information) ![Indoor pool, seasonal outdoor pool](https://images.trvl-media.com/lodging/2000000/1860000/1860000/1859917/edcbe88c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast area](https://images.trvl-media.com/lodging/2000000/1860000/1860000/1859917/1668ce93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Couples treatment rooms, sauna, hot tub, steam room, hot springs](https://images.trvl-media.com/lodging/2000000/1860000/1860000/1859917/aa58ef8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Buffet](https://images.trvl-media.com/lodging/2000000/1860000/1860000/1859917/06ba300f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mercure Petriolo Siena Terme Spa Hotel [](https://www.expedia.com/Civitella-Paganico-Hotels-Mercure-Petriolo-Siena-Terme-Spa-Hotel.h1859917.Hotel-Information) Civitella Paganico 8.6/10 Excellent (240 reviews) "We had a great time. I would recommend this hotel when in Tuscany. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mike $86 nightly $95 total Mar 23 - Mar 24 Total with taxes and fees [](https://www.expedia.com/Civitella-Paganico-Hotels-Mercure-Petriolo-Siena-Terme-Spa-Hotel.h1859917.Hotel-Information) ![Junior Suite | View from room](https://images.trvl-media.com/lodging/5000000/4780000/4774100/4774015/cda9c123.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/5000000/4780000/4774100/4774015/09b92259.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, lunch, dinner served; Italian cuisine](https://images.trvl-media.com/lodging/5000000/4780000/4774100/4774015/9b5cebd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/5000000/4780000/4774100/4774015/91a951f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Castello Banfi - Il Borgo - Relais et Chateaux [](https://www.expedia.com/Montalcino-Hotels-Castello-Banfi-Il-Borgo.h4774015.Hotel-Information) Montalcino 10/10 Exceptional (126 reviews) "The setting, scenery and hotel were 5 star plus!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Diana $894 nightly $995 total Apr 16 - Apr 17 Total with taxes and fees [](https://www.expedia.com/Montalcino-Hotels-Castello-Banfi-Il-Borgo.h4774015.Hotel-Information) ![Sauna, hot tub, steam room, Turkish bath, body treatments, aromatherapy](https://images.trvl-media.com/lodging/2000000/1670000/1661500/1661497/4ea4b817.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sauna, hot tub, steam room, Turkish bath, body treatments, aromatherapy](https://images.trvl-media.com/lodging/2000000/1670000/1661500/1661497/21d7ddba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1670000/1661500/1661497/83bf9dad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/2000000/1670000/1661500/1661497/31ae7257.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Castel Porrona Relais & Spa [](https://www.expedia.com/Cinigiano-Hotels-Castel-Porrona-Relais-Spa.h1661497.Hotel-Information) Cinigiano 9.6/10 Exceptional (7 reviews) "Stayed here for one night in August. Fantastic and helpful staff offered welcome drinks and showed around the beautiful property. Was offered a complimentary upgrade. Pool area is really nice and quiet with spa facilities right next to it. Restaurant perfect for a romantic dinner. Will definitely plan for a longer visit in the future." ![Finland](https://a.travel-assets.com/egds/marks/flags/fi.svg) Joona [](https://www.expedia.com/Cinigiano-Hotels-Castel-Porrona-Relais-Spa.h1661497.Hotel-Information) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Montemassi-Hotels.s50-0-d6361379.Travel-Guide-Filter-Hotels)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Montemassi-Hotels.s50-0-d6361379.Travel-Guide-Filter-Hotels) ## Explore similar 4-star hotels Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Montemassi. ![Grand Hotel Bastiani](https://images.trvl-media.com/lodging/2000000/1280000/1277600/1277581/e5c725af_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Grand Hotel Bastiani Piazza Gioberti 64 Grosseto GR $89 nightly $104 total Mar 22 - Mar 23 Total with taxes and fees 8.6/10 Excellent! (227 reviews) [](https://expedia.com/Grosseto-Hotels-Grand-Hotel-Bastiani.h1277581.Hotel-Information) ![Hotel Airone](https://images.trvl-media.com/lodging/23000000/22490000/22481500/22481472/597bc4bc_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hotel Airone Via Senese, 35 Grosseto GR $116 nightly $133 total Mar 22 - Mar 23 Total with taxes and fees 8.4/10 Very Good! (112 reviews) [](https://expedia.com/Grosseto-Hotels-Hotel-Airone.h22481472.Hotel-Information) ![Granduca](https://images.trvl-media.com/lodging/3000000/2700000/2692600/2692524/85b0450b_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Granduca Via Senese 170 Grosseto GR $79 nightly $92 total Mar 29 - Mar 30 Total with taxes and fees 8/10 Very Good! (103 reviews) [](https://expedia.com/Grosseto-Hotels-Granduca.h2692524.Hotel-Information) Still don't see what you're looking for? [See all properties in Montemassi.](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F21%2F2026&endDate=3%2F22%2F2026®ionId=6361379&star=50) You can also use these popular filters to refine your search. [Pool](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F21%2F2026&endDate=3%2F22%2F2026®ionId=6361379&star=50&star=50&amenities=POOL)[Spa](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F21%2F2026&endDate=3%2F22%2F2026®ionId=6361379&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F21%2F2026&endDate=3%2F22%2F2026®ionId=6361379&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F21%2F2026&endDate=3%2F22%2F2026®ionId=6361379&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=3%2F21%2F2026&endDate=3%2F22%2F2026®ionId=6361379&star=50&star=50&amenities=WATER_PARK) 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. ## Top Montemassi Hotel Reviews ![Mercure Petriolo Siena Terme Spa Hotel](https://images.trvl-media.com/lodging/2000000/1860000/1860000/1859917/edcbe88c_y.jpg) ### Mercure Petriolo Siena Terme Spa Hotel 6/10 Okay "This hotel has all the luxuries one would expect from a chain like Mercure. The building is huge, at times feeling like a set for the film ‘Shining’. It is not for me, simply because it has no soul, no character or style. The fittings are cheap, the vibe a bit large group holidays. Spa is accessible with a 30 euro fee." [](https://expedia.com/Civitella-Paganico-Hotels-Mercure-Petriolo-Siena-Terme-Spa-Hotel.h1859917.Hotel-Information) ![The Sense Experience Resort - Preferred Hotels & Resorts](https://images.trvl-media.com/lodging/32000000/31890000/31888200/31888190/44e9cb7b_y.jpg) ### The Sense Experience Resort - Preferred Hotels & Resorts 10/10 Excellent "Though the property we booked at Expedia was not what we expected as the description was unclear and Four adults could not stay in the bungalow suite the property gave us another room at no expense Their goal is to make you happy with your stay" [](https://expedia.com/Follonica-Hotels-The-Sense-Experience-Resort.h31888190.Hotel-Information) ![L'Andana](https://images.trvl-media.com/lodging/2000000/1150000/1145100/1145020/5c89a2c0_y.jpg) ### L'Andana 10/10 Excellent "This is such a beautiful place in every way and we always love it here. Everything is very special and it is wonderful to spend time in this tranquil setting. " [](https://expedia.com/Castiglione-Della-Pescaia-Hotels-LAndana.h1145020.Hotel-Information) ## Find out more about Montemassi You enjoy the finer things in life, both at home and on vacation. Add even more enjoyment on your next trip to Montemassi by treating yourself to the best of the best when it comes to accommodation. It's an ideal pairing. There's no reason to delay a getaway to Montemassi any longer. You'll join the multitudes of vacationers who have made Montemassi so fashionable in the last year. You can also expect excellent customer service from these hotels, so get ready to kick back and indulge. You deserve an outstanding getaway. Reserve one of our 5-star hotels in Montemassi and indulge in the finer things in life for a while. ### Get a Great Deal on 5-Star Hotels in Montemassi You'll have a fantastic time at one of these 5-star hotels. Michelin-starred restaurants, concierges, and in-room spa sessions are all at the ready. You're sure to find exactly the accommodation you need. You'll also enjoy a high standard of care and meticulous guest relations, so get ready for a wonderful adventure. What kind of amenities will make your stay a wonderful one? 24-hour room service, so you can order that chocolate soufflé© in the wee hours of the morning? A body scrub that will leave you feeling like a million bucks? Butler services? Whatever it is your heart desires, you're bound to find it here. Can't wait to get outside? We've got you covered. From doing a bit of shopping to embracing the great outdoors, you'll never be bored on this retreat. Whatever you plan to do, the 5-star hotels in Montemassi are the perfect place to relax after an exciting day. Ready to learn more? Then check out our listings and pick the perfect accommodation for your needs. ### Make Your Escape The results are in, and Montemassi 5-star hotels are the place to be when you book your next vacation. If you've been dreaming about a vacation set here, then go ahead and book it. Your great getaway is just a mouse-click away -- Expedia can help you land a great deal on accommodation. Decide on one of our Montemassi 5-star hotels today and dive into in the lap of luxury when you're ready. ## Frequently asked questions ### How much does it cost to stay in a 5-star hotel in Montemassi? > - Search for the lowest price per night from $92 ### What makes a hotel 5 stars in Montemassi? ### Are there any 5-star all-inclusive resorts in Montemassi? ## Explore a world of travel with Expedia - More ways to book - [Book 5 Star Hotels in Montemassi on Expedia.it ](https://www.expedia.it/5Stelle-Montemassi-Hotel.s50-0-d6361379.Guida-Viaggi-Filtro-Hotel)