Top 10 Hotels in Montemassi (from $57) 2026 - Competitive Prices

Go beyond your typical stay in Montemassi

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Our top choices for Montemassi hotels

A swimming pool with lounge chairs and umbrellas, surrounded by brick flooring and a hedge.

A large stone house with a swimming pool, surrounded by lush greenery and hills.

A spa area with two hot tubs, a decorative bowl with candles, and a person in a robe.

A bedroom with a stone wall, a bed with white linens, a wooden chair, a desk with a computer, and a window with curtains.

1. La Melosa Resort & Spa - Adults Only

Roccastrada

Gillian

$81 nightly

$93 total

Oct 25 - Oct 26

Total with taxes and fees

A swimming pool with clear blue water, a person standing on the edge, and another person swimming. There are lounge chairs and an umbrella in the background.

A room with a desk, chair, and a large window with curtains.

A stone staircase leading up to a structure, surrounded by lush greenery and trees.

A hotel room with a fireplace, a desk with a chair, a bed with a blue and white bedspread, and a view of the outdoors through large windows.

2. Tenuta il Sassone - Wine & Food

Gavorrano

Christine

$118 nightly

$137 total

Oct 6 - Oct 7

Total with taxes and fees

A spacious dining area with a large table and chairs, stone walls, and a view of the mountains.

A balcony with two wooden chairs overlooking a vineyard and distant mountains.

A rustic stone house with a balcony, surrounded by tall grasses and trees, during sunset.

A room with a large window overlooking a vineyard and mountains. There is a stone wall and a wooden shelf with wine bottles and glasses.

3. Valdonica Winery & Vineyard Residence

Roccastrada

"After debating between many Tuscan vineyards/B&Bs to stay at, I am so glad we picked this one. The venue was beautiful, the room was nice and clean (with AC), and they had a gorgeous remote pool overlooking the vineyard. The people working were all incredibly kind and accommodating and went above and beyond to make our stay memorable, in addition to the owner. We enjoyed a wine tour/tasting and a cooking class, and had dinner at their restaurant that was one of our best meals in Italy. Our only...

Audrey

$158 nightly

$176 total

Oct 27 - Oct 28

Total with taxes and fees

A restaurant with outdoor seating, a bar area, and a view of the landscape.

A stone building with a wooden door and a circular window.

A narrow hallway with a brick archway, a window, and framed pictures on the walls.

4. B&B da Nada Locanda Toscana

Roccastrada

jean

$77 nightly

$86 total

Oct 5 - Oct 6

Total with taxes and fees

A balcony with a view of a green landscape and a sunset. There are two lounge chairs and a small table with a glass of wine.

A bedroom with a large bed, a view of the countryside, and a stone wall.

A cozy living room with a fireplace, wooden beams, stone walls, and a leather sofa.

A poolside area with a wooden deck, lounge chairs, and a stone building with arched windows.

5. Conti di San Bonifacio Wine Resort

Gavorrano

Hannah

$606 nightly

$671 total

Oct 16 - Oct 17

Total with taxes and fees

A modern living room with a sofa, a coffee table, a TV on a wooden cabinet, and a large potted plant.

A modern bathroom with a glass shower enclosure, a sink, a toilet, and a window providing natural light.

A fruit basket with apples, pears, bananas, and cherries.

A modern bedroom with a bed, bedside tables, a ceiling light, a window, and a wall-mounted artwork.

6. Le Vie del Mare Camere

Ribolla

$107 nightly

$117 total

Oct 5 - Oct 6

Total with taxes and fees

A swimming pool with water flowing from a tap, surrounded by lounge chairs and umbrellas.

A rustic room with a stone wall, a glass table with books, and a view of an outdoor patio with chairs and umbrellas.

A rustic interior with exposed wooden beams, a stone fireplace, a cozy seating area, and a large window with curtains.

An outdoor dining setup with a stone building in the background, a table with plates, cutlery, and a bottle of red drink.

7. Tenuta Casteani

Gavorrano

Andrew

$101 nightly

$115 total

Oct 16 - Oct 17

Total with taxes and fees

An outdoor dining area with stone buildings, tables with orange tablecloths, and string lights.

A gazebo with a stone wall and a lamp post in a park setting.

A stone building with a wooden door, green shutters, and two potted plants.

A view through a window of a mountainous landscape with autumn foliage and a house in the distance.

8. Historic Farmhouse Casa del Chiodo

Roccastrada

Ian

$93 nightly

$105 total

Oct 6 - Oct 7

Total with taxes and fees

A stone house with a swimming pool, red shutters, and a covered patio.

A stone building with a staircase leading to a terrace, flags, and a view of a parking area and hills.

A stone building with a red shuttered window, a colorful mosaic, and a staircase leading to a hilltop view.

A rustic stone building with a courtyard, a wooden cart, and a tree.

9. NonnaNara

Grosseto

"Grosse maison perdue dans la campagne qui a été une superbe découverte. Nous avions un magnifique appartement qui donnait sur une belle piscine magnifiquement entretenue. Le personnel est très avenant avec un remerciement spécial pour Fatima qui nous a accueillis en français est s'est occupé de nous toute la soirée. Elle nous a concocté un excellent repas le soir avec des produits du terroir. Un grand merci pour elle qui était encore présente tôt au petit déjeuner. Excellente expérience à...

Marie

$130 nightly

$143 total

Oct 23 - Oct 24

Total with taxes and fees

An outdoor patio with wooden tables and chairs, large windows offering a view of a mountainous landscape.

A marina with numerous boats docked, a central building, and a clear view of the sea.

A coastal beach with clear turquoise waters, a sandy shoreline, and a forested area with parked cars.

A bedroom with a large bed, a wooden headboard, a nightstand, and a window with a view of the outdoors.

10. Agriturismo Giù al Pozzo

Gavorrano

Micaiah

$81 nightly

$89 total

Nov 2 - Nov 3

Total with taxes and fees

A swimming pool with a waterfall feature, large windows, and a lounge chair.

A covered patio with a table and chairs, a small garden, and a building in the background.

A living room with a grey sofa, a coffee table, and a potted plant with red flowers. There are shelves with various bottles and jars, and a wall-mounted display with three decorative plates.

A narrow corridor with a wooden ceiling and a tiled floor, leading to a door at the end.

11. Montebelli Agriturismo & Country Hotel

Gavorrano

Jean-Olivier

$67 nightly

$74 total

Nov 1 - Nov 2

Total with taxes and fees

A group of people dining at a table with a view of a valley and mountains.

A long table set for a formal outdoor event, surrounded by a vineyard.

A panoramic view of a vineyard with rolling hills, a clear sky, and distant mountains.

A garden with a wooden chair and a table, surrounded by a stone wall and a wooden fence.

12. Valdonica Winery - Chill in Nature Lodge

Roccastrada

$170 nightly

$189 total

Nov 2 - Nov 3

Total with taxes and fees

A courtyard with stone steps leading to a small building, surrounded by lush greenery and stone buildings in the background.

A window with a view of buildings and a plant on the windowsill.

A rectangular pool with lounge chairs and umbrellas, surrounded by a brick patio.

A hotel with a swimming pool, surrounded by greenery and adjacent to a road.

13. Country House il Ciliegio

Roccastrada

Maaike

$78 nightly

$88 total

Nov 1 - Nov 2

Total with taxes and fees

A clear pool with visible mineral deposits, a pebble beach, and a mountainous landscape in the background.

A rustic interior with exposed brick walls, a stone fireplace, and wooden beams. There are leather sofas, a round table, and potted plants.

An interior with a brick archway, stone walls, and modern seating.

A table set outdoors with a view of rolling hills and a tall tree in the background.

14. VIN Hotel - La Meridiana

Montieri

Jinhee

$144 nightly

$158 total

Oct 4 - Oct 5

Total with taxes and fees

An outdoor dining area with a table set for two, overlooking a lush green landscape and a hill in the distance.

A couple sitting by a pool under a pergola with a view of a house and hills in the background.

A cozy kitchen with wooden cabinets, a dining area with a table and chairs, and a red sofa with a patterned cushion.

A cozy kitchen with wooden cabinets, a stove, and a dining area with a table and chairs.

15. Podere Cascatelle & Agriletizia

Massa Marittima

Ciarán

$134 nightly

$156 total

Oct 3 - Oct 4

Total with taxes and fees

A dining table with plates of food, a vase with flowers, and a view of a green landscape through large windows.

A bedroom with a four-poster bed, a balcony with a view, and a bedside table with a lamp.

A swimming pool with a curved edge, surrounded by lush greenery and a clear sky.

A bedroom with a canopy bed, a desk, and a view of greenery outside.

16. Hotel Girifalco - Nature & Relax

Massa Marittima

Lucy

$52 nightly

$57 total

Nov 2 - Nov 3

Total with taxes and fees

A swimming pool with a view of a hilltop castle.

A wine cellar with wooden barrels, a wine rack, and a table set for dining.

A kitchen with wooden cabinets, a tiled backsplash, and a dining table with a fruit bowl.

A courtyard with a stone column, potted plants, and a view of a hilltop castle.

17. Agriturismo Podere Ristella - Wine&Food

Roccastrada

"Non lasciarsi ingannare dalle foto, la struttura è fatiscente. L'alloggio non è adatto a bambini in quanto ha delle scale ripide" dove sono caduti senza passamano, e tutto nell'incuria, doccia bagni finestre cucina caldaia, sicuramente c'è molto verde ma non si può girare a piedi, è silenzioso, si paga tutto pure la carbonella per i barbecue, sembra più architettato per finire di costruire la struttura coi soldi dei malcapitati, infatti nessuno chiede se serve qualcosa ma si apprestano solo la...

eugenio

$92 nightly

$104 total

Oct 9 - Oct 10

Total with taxes and fees

A long table set for a meal outdoors with white tablecloths, woven placemats, and potted plants.

A building with a stone facade and multiple windows.

An outdoor patio with wooden tables and chairs, stone walls, and potted plants.

A swimming pool with lounge chairs and umbrellas, surrounded by trees and buildings.

18. Agriturismo San Galgano

Chiusdino

"I loved every moment at the Agriturismo San Galgano. Beautifully restored for modern times, interior decoration appointed with excellent taste. Lovely pond and pool on the property. It is very convenient to have the restaurant on the property. The location is magical right next to the famous Abbey of San Galgano. Looking forward to returning in the near future. Have wonderful memories of my stay."

Irene

$73 nightly

$83 total

Oct 29 - Oct 30

Total with taxes and fees

A large, multi-story residential building with multiple balconies, surrounded by well-maintained lawns and trees.

A beach with blue umbrellas and a wooden deck.

A pool area with lounge chairs and umbrellas, surrounded by buildings and trees.

An outdoor dining area with tables set for two, surrounded by palm trees and flowering plants.

19. Il Pelagone Hotel & Golf Resort Toscana

Gavorrano

Matthias

$146 nightly

$167 total

Oct 4 - Oct 5

Total with taxes and fees

A waiter pouring wine into a glass at an outdoor restaurant.

The exterior of Hotel Ducca del Mare with a well-lit entrance, a visible sign, and potted plants around the entrance.

A room with a large window offering a view of green fields and distant hills.

A cozy dining area with wooden furniture, a buffet table with food items, and a window with curtains.

20. Hotel Duca Del Mare

Massa Marittima

rosey

$83 nightly

$99 total

Oct 21 - Oct 22

Total with taxes and fees

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Top Montemassi Hotel Reviews

Hotel La Pineta

10/10 Excellent

"The beach is just steps away! Restaurants, pubs, etc were all within walking distance, as was the promenade. Beautiful walk among the trees right across the street. Perfect spot in the “quiet” part of Follonica."

Hotel Nuova Grosseto

8/10 Good

"The hotel was located in an excellent position form the train station especially if you were only staying overnight. Staff were very helpful and friendly and breakfast was lovely. Just wish milk is left in the room as not everyone drinks black coffee. Amenities were clean and comfortable."

Castiglion del Bosco, A Rosewood Hotel

10/10 Excellent

"Castiglion del Bosco is truly exquisite, the perfect way to experience Tuscany in luxury while still feeling completely surrounded by nature. The property is impeccable, from the beautiful gardens and grounds to the elegant rooms. Everything feels authentically Italian, refined and incredibly well maintained. The service is exceptional and very personalized. The staff genuinely goes out of their way to make you feel welcome. General Manager Nicola Migheli even greeted us personally upon arrival, which was a lovely touch. We also saw him regularly walking the property with his team, and it was clear how hands-on he is with every detail. One thing to know is that getting in and out requires about 40 minutes on a bumpy dirt road. It wasn’t terrible, but worth mentioning if you plan to explore frequently. That said, this is a hotel you don’t need to leave. It’s a beautiful place to slow down, relax and enjoy Tuscany in a truly special setting. We absolutely loved our stay!"

Grand Hotel Bastiani

10/10 Excellent

"Great location inside the city walls to explore Grosetto. Lots of great restaurants."

Hotel L'Approdo

10/10 Excellent

"Clean rooms excellent location"

Hotel Girifalco - Nature & Relax

10/10 Excellent

"Charming hotel. Excellent breakfast. I would recommend it"

Montebelli Agriturismo & Country Hotel

8/10 Good

"If you are driving here you may be surprised by the rough and sometimes narrow track to the hotel - especially if you meet oncoming cars. We liked the dining experience (lunch and dinner were very good and breakfast was ok). The spa was ok too - probably better on a cooler day. We loved the wine and overall had a very pleasant stay here. Very glad to have air con in the room."

Fattoria La Principina Hotel & Congress

8/10 Good

"great facility but needs a general upgrade and remodeling"

Mercure Petriolo Siena Terme Spa Hotel

10/10 Excellent

"Las habitaciones son super lindas y espaciosas. El desayuno es completo y variado. Estuve con mi familia muy a gusto. Fue una estancia placentera. Lo recomiendo."

More cheap stays in Montemassi

Hotel Massa Vecchia

Massa Vecchia, 23 Massa Marittima GR

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8.6/10 Excellent! (11 reviews)

Guadalupe Tuscany Resort

Strada Provinciale Del Bozzone Grosseto GR

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9.8/10 Exceptional! (28 reviews)

Baia Etrusca

Località Torre Mozza, 20 Piombino LI

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8/10 Very Good! (24 reviews)

Bio Tenuta di Paganico - I Roggeti

Via Della Stazione, 10 Civitella Paganico GR

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8/10 Very Good! (1 review)

Hotel C'era Una Volta

Via Balzini 11 Castiglione della Pescaia GR

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9.6/10 Exceptional! (49 reviews)

Podere Valmarina

Via Aurelia Nord 10 Grosseto GR

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9.2/10 Wonderful! (5 reviews)

Hotels in Montemassi with star-rating

Frequently asked questions

What is the best area to stay in Montemassi?

The best area to stay in Montemassi is directly within the village walls of Montemassi itself, or in the immediate countryside surrounding it.Montemassi is a small, historic hilltop village dominated by its medieval castle ruins. The village consists of a few narrow, winding streets that lead up to the castle, offering elevated views of the surrounding Tuscan landscape. There are a handful of traditional eateries and local shops within the village.For couples seeking a romantic and tranquil escape, staying within Montemassi offers an intimate experience. You'll enjoy quiet evenings with stunning views and the charm of historic architecture, superb for unwinding and savoring local cuisine.Travelers looking for a more expansive retreat with easy access to the village will find the countryside just outside Montemassi ideal.

When is the best time to go to Montemassi?

The best times to visit Montemassi are during the spring (April to June) and autumn (September to October) months.These shoulder seasons offer pleasant weather conditions, ideal for exploring the Tuscan countryside. You'll find comfortable temperatures for outdoor activities like vineyard tours or walks through olive groves. Additionally, these periods avoid the peak summer crowds, allowing for a more serene experience at Montemassi's historic sites and local trattorias.Couples often find these times superb for a romantic getaway. The spring brings blooming wildflowers and lush green landscapes, while autumn offers the beauty of changing leaves and the excitement of the grape harvest season.

Can I cancel my hotel reservation on Expedia?

You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Montemassi.

How much is the nightly rate at a Montemassi hotel?

Prices for hotels in Montemassi often vary, but you can find a great deal from $57 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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Go beyond your typical stay in Montemassi

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Our top choices for Montemassi hotels

1. La Melosa Resort & Spa - Adults Only

2. Tenuta il Sassone - Wine & Food

3. Valdonica Winery & Vineyard Residence

4. B&B da Nada Locanda Toscana

5. Conti di San Bonifacio Wine Resort

6. Le Vie del Mare Camere

7. Tenuta Casteani

8. Historic Farmhouse Casa del Chiodo

9. NonnaNara

10. Agriturismo Giù al Pozzo

11. Montebelli Agriturismo & Country Hotel

12. Valdonica Winery - Chill in Nature Lodge

13. Country House il Ciliegio

14. VIN Hotel - La Meridiana

15. Podere Cascatelle & Agriletizia

16. Hotel Girifalco - Nature & Relax

17. Agriturismo Podere Ristella - Wine&Food

18. Agriturismo San Galgano

19. Il Pelagone Hotel & Golf Resort Toscana

20. Hotel Duca Del Mare

Top Montemassi Hotel Reviews

Hotel La Pineta

Hotel Nuova Grosseto

Castiglion del Bosco, A Rosewood Hotel

Grand Hotel Bastiani

Hotel L'Approdo

Hotel Girifalco - Nature & Relax

Montebelli Agriturismo & Country Hotel

Fattoria La Principina Hotel & Congress

Mercure Petriolo Siena Terme Spa Hotel

More cheap stays in Montemassi

Hotel Massa Vecchia

Guadalupe Tuscany Resort

Baia Etrusca

Bio Tenuta di Paganico - I Roggeti

Hotel C'era Una Volta

Podere Valmarina

Hotels in Montemassi with star-rating

Frequently asked questions

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