Book The Best Hotels in Montemassi for 2026 from CA $94 - Fully Refundable Options

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Our top choices for Montemassi hotels

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 swimming pool with a view of a valley and mountains.

1. 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

CA $210

CA $236 total

includes taxes & fees

Nov 8 - Nov 9

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

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.

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

2. La Melosa Resort & Spa - Adults Only

Roccastrada

Gillian

CA $107

CA $122 total

includes taxes & fees

Oct 15 - Oct 16

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.

3. Tenuta il Sassone - Wine & Food

Gavorrano

Christine

CA $142

CA $167 total

includes taxes & fees

Oct 29 - Oct 30

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

A dining table with a scenic view, wine bottles on shelves, and a potted plant.

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

4. B&B da Nada Locanda Toscana

Roccastrada

jean

CA $108

CA $122 total

includes taxes & fees

Nov 8 - Nov 9

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

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

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

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

5. Le Vie del Mare Camere

Ribolla

CA $155

CA $171 total

includes taxes & fees

Oct 17 - Oct 18

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

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

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

6. Conti di San Bonifacio Wine Resort

Gavorrano

Hannah

CA $776

CA $853 total

includes taxes & fees

Nov 8 - Nov 9

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 stone building with a red door, surrounded by gravel and potted plants.

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

7. Tenuta Casteani

Gavorrano

Andrew

CA $155

CA $177 total

includes taxes & fees

Oct 16 - Oct 17

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

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

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

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

8. Valdonica Winery - Chill in Nature Lodge

Roccastrada

CA $242

CA $269 total

includes taxes & fees

Oct 21 - Oct 22

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 dining area with wooden beams, stone walls, and a fireplace. Tables are set with wine glasses and cutlery.

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

9. Historic Farmhouse Casa del Chiodo

Roccastrada

Ian

CA $136

CA $152 total

includes taxes & fees

Oct 19 - Oct 20

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.

10. Country House il Ciliegio

Roccastrada

Maaike

CA $126

CA $142 total

includes taxes & fees

Nov 5 - Nov 6

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

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

11. Montebelli Agriturismo & Country Hotel

Gavorrano

Jean-Olivier

CA $113

CA $125 total

includes taxes & fees

Nov 13 - Nov 14

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

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.

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

12. Agriturismo Giù al Pozzo

Gavorrano

Micaiah

CA $97

CA $113 total

includes taxes & fees

Oct 27 - Oct 28

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

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

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

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

13. VIN Hotel - La Meridiana

Montieri

Tatyana

CA $181

CA $199 total

includes taxes & fees

Oct 22 - Oct 23

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

A covered courtyard with stone columns, a brick floor, and a grassy area.

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

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

14. Hotel Girifalco - Nature & Relax

Massa Marittima

Harpreet

CA $71

CA $94 total

includes taxes & fees

Oct 28 - Oct 29

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.

15. 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

CA $113

CA $159 total

includes taxes & fees

Oct 25 - Oct 26

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

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

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

A swimming pool with lounge chairs and umbrellas, surrounded by a building with a balcony and a view of trees.

16. Hotel Duca Del Mare

Massa Marittima

rosey

CA $119

CA $142 total

includes taxes & fees

Oct 21 - Oct 22

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

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

A living room with a wooden ceiling, a sofa, a dining table with chairs, a television, and a cabinet.

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

17. 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

CA $99

CA $128 total

includes taxes & fees

Oct 23 - Oct 24

An outdoor seating area with a wooden bench, potted plants, and a table with a purple chair.

A swimming pool with a clear blue water, surrounded by white lounge chairs and a wooden deck.

A room with a bed, a chair, a green door, a window with a view of trees, and a painting on the wall.

A kitchen with white cabinets, a checkered backsplash, a dining table with a quilted tablecloth, and a green upholstered chair.

18. Il Belvedere Country Houses

Massa Marittima

hendrik

CA $104

CA $115 total

includes taxes & fees

Oct 14 - Oct 15

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

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

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

A building with a stone facade and multiple windows.

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

CA $116

CA $133 total

includes taxes & fees

Oct 28 - Oct 29

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

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

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

A beach with blue umbrellas and a wooden deck.

20. Il Pelagone Hotel & Golf Resort Toscana

Gavorrano

Matthias

CA $217

CA $239 total

includes taxes & fees

Nov 1 - Nov 2

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Top Montemassi Hotel Reviews

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!"

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."

Castello Banfi - Il Borgo - Relais et Chateaux

10/10 Excellent

"Beautiful property, spacious room, so well maintained. Pool was lovely but a little too quiet, some music would have been a nice touch. A little awkward to get drink/snack at pool and carry it outside while juggling entrance key. White wine appeared to complimentary pool side, why not red? Would love to have experienced e-bikes but unfortunately rained during our available time slot. Enjoyed lunch at the on-site casual restaurant, food and wine parings were excellent, never left us with an empty wine glass. Enjoyed the onsite museum even though not all the information was in English. Would love to return one day."

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."

More cheap stays 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

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9.8/10 Exceptional! (29 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

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

Get rates

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 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 CA $94 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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Find hotels in Montemassi from CA $94

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Montemassi

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Montemassi hotels

1. Valdonica Winery & Vineyard Residence

2. La Melosa Resort & Spa - Adults Only

3. Tenuta il Sassone - Wine & Food

4. B&B da Nada Locanda Toscana

5. Le Vie del Mare Camere

6. Conti di San Bonifacio Wine Resort

7. Tenuta Casteani

8. Valdonica Winery - Chill in Nature Lodge

9. Historic Farmhouse Casa del Chiodo

10. Country House il Ciliegio

11. Montebelli Agriturismo & Country Hotel

12. Agriturismo Giù al Pozzo

13. VIN Hotel - La Meridiana

14. Hotel Girifalco - Nature & Relax

15. Agriturismo Podere Ristella - Wine&Food

16. Hotel Duca Del Mare

17. Agriturismo Benvenuti

18. Il Belvedere Country Houses

19. Agriturismo San Galgano

20. Il Pelagone Hotel & Golf Resort Toscana

Top Montemassi Hotel Reviews

Grand Hotel Bastiani

Riva del Sole Resort & SPA

Camping Maremma Sans Souci

Hotel Nuova Grosseto

Castello Banfi - Il Borgo - Relais et Chateaux

Hotel L'Approdo

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

Frequently asked questions

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