Montemassi Hotel & Accommodation Deals 2026 from AU$98 - Compare prices by date

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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

AU$123

includes taxes & fees

26 Oct - 27 Oct

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

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

A balcony with a view of mountains, featuring a table with chairs, a bottle of wine, and a cactus decoration.

2. Tenuta il Sassone - Wine & Food

Gavorrano

Christine

AU$177

includes taxes & fees

31 Oct - 1 Nov

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

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.

A swimming pool with a view of a valley and mountains.

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

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

AU$236

includes taxes & fees

8 Nov - 9 Nov

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

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

A wooden interior with a reception desk, potted plants, and a tray with toiletries.

4. Conti di San Bonifacio Wine Resort

Gavorrano

Hannah

AU$856

includes taxes & fees

18 Nov - 19 Nov

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.

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

5. B&B da Nada Locanda Toscana

Roccastrada

jean

AU$124

includes taxes & fees

10 Nov - 11 Nov

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

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

A bedroom with a bed, a nightstand, a wall-mounted lamp, a window with a view, and a ceiling light fixture.

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

6. Le Vie del Mare Camere

Ribolla

AU$179

includes taxes & fees

12 Nov - 13 Nov

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

A cozy kitchen with a brick ceiling, wooden furniture, and a dining area with a table set for breakfast.

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

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

7. Country House il Ciliegio

Roccastrada

Maaike

AU$137

includes taxes & fees

23 Oct - 24 Oct

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

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

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

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

8. Tenuta Casteani

Gavorrano

Andrew

AU$177

includes taxes & fees

31 Oct - 1 Nov

A bedroom with a wooden headboard, a large bed, a framed picture on the wall, and a sliding glass door leading to an outdoor area.

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

A bedroom with a bed, a desk with a bottle and glasses, a red cabinet, and a view of the outdoors.

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

9. Valdonica Winery - Chill in Nature Lodge

Roccastrada

AU$270

includes taxes & fees

22 Nov - 23 Nov

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.

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

10. Hotel Girifalco - Nature & Relax

Massa Marittima

Harpreet

AU$107

includes taxes & fees

23 Oct - 24 Oct

A stone building with multiple windows and a central entrance.

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

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

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

11. Historic Farmhouse Casa del Chiodo

Roccastrada

Ian

AU$180

includes taxes & fees

3 Nov - 4 Nov

Two champagne glasses on a table with a towel and a view of a mountain and a body of water.

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.

12. VIN Hotel - La Meridiana

Montieri

Tatyana

AU$206

includes taxes & fees

24 Oct - 25 Oct

A bedroom with a bed, a hanging light fixture, and a view of a patio with a table and chairs.

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

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

A dining area with a long table set for breakfast, featuring various food items and a clock on the wall.

13. Agriturismo Giù al Pozzo

Gavorrano

Micaiah

AU$124

includes taxes & fees

28 Oct - 29 Oct

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

An aerial view of a property with a swimming pool, manicured lawns, and a variety of trees.

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

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.

14. Montebelli Agriturismo & Country Hotel

Gavorrano

Jean-Olivier

AU$127

includes taxes & fees

1 Nov - 2 Nov

A rectangular swimming pool with a clear blue water, surrounded by a well-maintained lawn and several lounge chairs.

A spacious living room with a fireplace, multiple seating options, and large windows with curtains.

A covered outdoor seating area with stone pillars, a table, and chairs.

A rustic stone building with a tiled roof, a covered patio with outdoor seating, and well-maintained gardens.

15. Antico Casale L'Impostino

Civitella Paganico

Maria

AU$205

includes taxes & fees

11 Nov - 12 Nov

A glass-enclosed structure with a wooden deck, surrounded by various plants and a garden.

A pathway leading to a building with a stone-tiled entrance and a wooden door.

A wooden interior with a glass-enclosed shower, large windows, and a wooden floor.

A small, modern house with a sliding glass door, surrounded by lush greenery and a well-maintained garden.

16. Agriturismo Benvenuti

Roccastrada

"La stanza era molto grande e tranquilla. C'è anche un giardino abbastanza ampio a disposizione esclusiva di ogni camera/appartamento. Estrema cortesia. Ovviamente si è in aperta campagna, non in vicinanza del mare o dentro un borgo, ma in auto si raggiungo facilmente molte località interessanti del luogo. Su alcuni particolari, potrebbe essere tenuto un po' meglio, ma nel complesso ha un ottimo rapporto qualità/prezzo per la zona."

Ivano

AU$129

includes taxes & fees

23 Oct - 24 Oct

A pool with lounge chairs and a sunset view.

A large, multi-story building with a swimming pool, surrounded by lush greenery.

A buffet table with various desserts and a long dining area with tables and chairs.

An indoor swimming pool with clear glass walls, a tiled floor, and a stone wall with a mosaic pattern.

17. Mercure Petriolo Siena Terme Spa Hotel

Civitella Paganico

Mike

AU$135

includes taxes & fees

28 Oct - 29 Oct

A swimming pool with a view of a hilltop castle.

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

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

An outdoor patio with a pergola, tables, chairs, and a view of rolling hills.

18. 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

AU$168

includes taxes & fees

25 Oct - 26 Oct

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.

A large estate with multiple buildings, expansive fields, and a winding road connecting them.

19. 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

AU$134

includes taxes & fees

28 Oct - 29 Oct

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

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

A covered outdoor dining area with tables set for a meal, surrounded by glass walls and wooden beams.

A beach with blue umbrellas and a wooden deck.

20. Il Pelagone Hotel & Golf Resort Toscana

Gavorrano

Matthias

AU$240

includes taxes & fees

1 Nov - 2 Nov

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Top Montemassi Hotel Reviews

Recent Reviews in Montemassi

Grand Hotel Bastiani

10/10 Excellent

"Great staff, nice breakfast, beautiful building and location."

Riva del Sole Resort & SPA

10/10 Excellent

"Helpful staff. Very clean rooms. Great location. Beach was lovely. Would stay again."

Camping Maremma Sans Souci

10/10 Excellent

"Impressively clean and well ran campsite. Access to the beach, has its own market, restaurant, coffee bar etc. Enjoyed our two nights stay!"

Castello Di Vicarello

10/10 Excellent

"AMAZING hotel, I cannot stress enough how insanely perfect our whole experience and stay was. Truly something magical and something you have to experience for yourself to understand."

Hotel L'Approdo

10/10 Excellent

"Clean rooms excellent location"

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."

PuntAla Camp & Resort

10/10 Excellent

"Lovely camping, very safe and clean! Calm if you choose to be, or active if you choose to be…. Activities organized for young and old… nice beach, sun beds for rent, or your own towel…. Easy to rent water equipment, reasonable prices in restaurants, good choice of cuisine, delicious and satisfying portion size…Camp stuff extremely friendly, helpful, welcoming, speak well English for Non-Italian speakers! Would recommend for young couples, families, elderly couples, singles… nice atmosphere! The bungalow Limo was very well equipped and enough room for 5. Overall to be highly recommended!"

More cheap accommodation in Montemassi

Hotel Massa Vecchia

Massa Vecchia, 23 Massa Marittima GR

Get rates

8.6/10 Excellent! (11 reviews)

Guadalupe Tuscany Resort

Strada Provinciale Del Bozzone Grosseto GR

Get rates

9.8/10 Exceptional! (29 reviews)

Baia Etrusca

Località Torre Mozza, 20 Piombino LI

Get rates

8/10 Very good! (24 reviews)

Bio Tenuta di Paganico - I Roggeti

Via Della Stazione, 10 Civitella Paganico GR

Get rates

8/10 Very good! (1 review)

Hotel C'era Una Volta

Via Balzini 11 Castiglione della Pescaia GR

Get rates

9.6/10 Exceptional! (49 reviews)

Podere Valmarina

Via Aurelia Nord 10 Grosseto GR

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9.2/10 Wonderful! (5 reviews)

Frequently asked questions

What is the best area to stay in Montemassi?

The best area to stay in Montemassi is directly within the historic hilltop village itself.This ancient village is perched atop a hill, offering stunning panoramic views of the Tuscan countryside, including vineyards and olive groves. The main area consists of narrow, cobbled streets winding around the Montemassi Castle ruins, with a few local eateries and small shops scattered throughout. It's a truly authentic Tuscan experience, far removed from bustling tourist centres.Couples seeking a tranquil and romantic escape will find Montemassi perfect. The quiet evenings, breathtaking sunsets from the castle walls, and the opportunity to enjoy local wine and cuisine create an unforgettable setting. It's an ideal base for leisurely strolls and unwinding in a picturesque environment.For those who appreciate a relaxed pace and a genuine connection with local life, Montemassi offers an unparalleled experience.

When is the best time to go to Montemassi?

The best time to visit Montemassi is during the spring (April to June) and autumn (September to October) months.These periods offer pleasant weather, ideal for exploring the Tuscan countryside. You'll find comfortable temperatures for outdoor activities like hiking or cycling through the olive groves and vineyards without the intense heat of summer. The landscapes are particularly beautiful, with blooming wildflowers in spring and the rich colours of the harvest season in autumn.For couples seeking a romantic and relaxed getaway, spring is particularly lovely. The gentle warmth and fewer crowds allow for peaceful strolls through Montemassi's historic streets and leisurely meals at local trattorias, savouring the fresh, seasonal produce.Travellers interested in wine tasting and culinary experiences will find autumn to be an excellent choice. This is harvest season, so many local wineries and farms offer tours and tastings of new wines and olive oils.

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 cancelled 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 can I save on a hotel booking in Montemassi with Expedia?

One Key™—Expedia's free travel rewards program—gives you instant access to discounts with Member Prices on Montemassi hotels. Plus, you'll earn OneKeyCash™* on eligible bookings to use on future trips. Booking an Expedia hotel and flight package is another great way to save, where bundling can result in significant savings. *Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

How much is the nightly rate for a hotel in Montemassi?

Prices for hotels in Montemassi often vary, but you can find a great deal from AU$98 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 our cheapest rates.

Search Montemassi hotels

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Montemassi

Check prices for these dates

Filter by

Property class

Guest rating

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. Conti di San Bonifacio Wine Resort

5. B&B da Nada Locanda Toscana

6. Le Vie del Mare Camere

7. Country House il Ciliegio

8. Tenuta Casteani

9. Valdonica Winery - Chill in Nature Lodge

10. Hotel Girifalco - Nature & Relax

11. Historic Farmhouse Casa del Chiodo

12. VIN Hotel - La Meridiana

13. Agriturismo Giù al Pozzo

14. Montebelli Agriturismo & Country Hotel

15. Antico Casale L'Impostino

16. Agriturismo Benvenuti

17. Mercure Petriolo Siena Terme Spa Hotel

18. Agriturismo Podere Ristella - Wine&Food

19. Agriturismo San Galgano

20. Il Pelagone Hotel & Golf Resort Toscana

Top Montemassi Hotel Reviews

Recent Reviews in Montemassi

Grand Hotel Bastiani

Riva del Sole Resort & SPA

Camping Maremma Sans Souci

Castello Di Vicarello

Hotel L'Approdo

Montebelli Agriturismo & Country Hotel

Fattoria La Principina Hotel & Congress

Mercure Petriolo Siena Terme Spa Hotel

PuntAla Camp & Resort

More cheap accommodation in Montemassi

Hotel Massa Vecchia

Guadalupe Tuscany Resort

Baia Etrusca

Bio Tenuta di Paganico - I Roggeti

Hotel C'era Una Volta

Podere Valmarina

Frequently asked questions

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