Hotels in Sassofortino

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Where to stay in Sassofortino?

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

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.

A rustic interior with exposed wooden beams, a central island with seating, and a stone wall.

1. La Melosa Resort & Spa - Adults Only

Roccastrada

$85

$97 total

includes taxes & fees

Oct 27 - Oct 28

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.

2. Valdonica Winery & Vineyard Residence

Roccastrada

$148

$166 total

includes taxes & fees

Nov 5 - Nov 6

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 canopy bed, a desk, and a view of greenery outside.

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

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

3. Hotel Girifalco - Nature & Relax

Massa Marittima

$58

$75 total

includes taxes & fees

Oct 27 - Oct 28

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.

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

4. B&B da Nada Locanda Toscana

Roccastrada

$81

$91 total

includes taxes & fees

Nov 8 - Nov 9

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

A room with a wooden ceiling, a bed with a headboard, a chair, a table, and a window with curtains.

A corridor with stone walls and wooden benches.

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

5. Historic Farmhouse Casa del Chiodo

Roccastrada

$106

$119 total

includes taxes & fees

Nov 2 - Nov 3

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

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.

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

6. Valdonica Winery - Chill in Nature Lodge

Roccastrada

$177

$197 total

includes taxes & fees

Nov 8 - Nov 9

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

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

7. Antico Casale L'Impostino

Civitella Paganico

$131

$144 total

includes taxes & fees

Nov 1 - Nov 2

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

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.

8. Tenuta il Sassone - Wine & Food

Gavorrano

$115

$134 total

includes taxes & fees

Oct 27 - Oct 28

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

A building with a stone facade and multiple windows.

9. Agriturismo San Galgano

Chiusdino

$87

$99 total

includes taxes & fees

Oct 27 - Oct 28

A pool with a modern water feature and a stone structure.

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

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

A wicker dining table set with breakfast items, a vase of flowers, and a scenic view.

10. Mercure Petriolo Siena Terme Spa Hotel

Civitella Paganico

$84

$95 total

includes taxes & fees

Oct 27 - Oct 28

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

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

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.

11. Tenuta Casteani

Gavorrano

$116

$133 total

includes taxes & fees

Oct 30 - Oct 31

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

$75

$82 total

includes taxes & fees

Nov 3 - Nov 4

A covered patio area with stone walls, wooden beams, and outdoor furniture.

A long banquet table with chairs, a chandelier, and draped fabric on a stone wall.

A pathway leading to a stone building with multiple windows and a covered area on the left.

A room with a blue sofa, a dining table with chairs, a potted plant, and a view through a glass door to the outside.

13. Casale San Galgano

Chiusdino

$85

$97 total

includes taxes & fees

Oct 29 - Oct 30

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

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

14. Country House il Ciliegio

Roccastrada

$87

$98 total

includes taxes & fees

Nov 2 - Nov 3

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

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

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

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

15. Le Vie del Mare Camere

Ribolla

$122

$135 total

includes taxes & fees

Oct 27 - Oct 28

A swimming pool with a view of a hilltop castle.

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

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

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

16. Agriturismo Podere Ristella - Wine&Food

Roccastrada

$99

$134 total

includes taxes & fees

Oct 29 - Oct 30

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

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

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

A courtyard with a gravel ground, potted plants, and a stone building with a tiled roof.

17. Il Belvedere Country Houses

Massa Marittima

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

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

18. Conti di San Bonifacio Wine Resort

Gavorrano

$545

$600 total

includes taxes & fees

Nov 9 - Nov 10

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 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.

19. Montebelli Agriturismo & Country Hotel

Gavorrano

$80

$88 total

includes taxes & fees

Nov 1 - Nov 2

An outdoor patio with wicker furniture, potted plants, and a brick building in the background.

A rustic interior with stone walls, a wooden barrel, and a chalkboard menu.

A narrow street with stone buildings, a wrought iron staircase, and a wooden door.

A historic building with a sign reading "LOANDA" and a stone staircase leading to the entrance.

20. Locanda nel Cassero

Civitella Paganico

$94

$103 total

includes taxes & fees

Oct 27 - Oct 28

View all properties

Go beyond your typical stay in Sassofortino

Check out reviews of Sassofortino hotels guests love

La Melosa Resort & Spa - Adults Only

Roccastrada

10/10 Exceptional

raul

Historic Farmhouse Casa del Chiodo

Roccastrada

10/10 Exceptional

Ian

Valdonica Winery & Vineyard Residence

Roccastrada

10/10 Exceptional

Josh

B&B da Nada Locanda Toscana

Roccastrada

10/10 Exceptional

We stayed here for three nights and had an incredible experience. The room was clean, offered a beautiful view, and had reliable Wi-Fi. The location is perfect for exploring, only an hour's drive to Montalcino and incredibly close to several fantastic wineries. The restaurant itself is absolutely fantastic: The panoramic views are amazing, the food is to die for (home cooking style), and the wine selection is excellent. Laura, her husband, and their son, Leonardo, are wonderful, welcoming...

Alexandre

Tenuta il Sassone - Wine & Food

Gavorrano

10/10 Exceptional

Kathy

Casale San Galgano

Chiusdino

10/10 Exceptional

Jose Manuel

Hotel Girifalco - Nature & Relax

Massa Marittima

10/10 Exceptional

Juan

Antico Casale L'Impostino

Civitella Paganico

10/10 Exceptional

Mason

A stone building with multiple windows and a balcony, surrounded by lush greenery and trees.

A wooden pathway leading to a table set for a meal, surrounded by lush greenery and flowering plants.

A window with white curtains, a view of buildings, and greenery.

A stone building with a balcony, surrounded by lush greenery and a view of distant hills.

Relais Le Macine di Stigliano

Sovicille

10/10 Exceptional

Tim

Agriturismo Giù al Pozzo

Gavorrano

10/10 Exceptional

Micaiah

Conti di San Bonifacio Wine Resort

Gavorrano

10/10 Exceptional

Paul

A serene infinity pool with lounge chairs and umbrellas, surrounded by natural scenery and a clear view of distant mountains.

A rustic interior with a chandelier, wooden furniture, and large windows offering a view of the outdoors.

A bathroom with a bathtub, a chandelier, and a view of the outdoors.

A rustic dining area with brick walls, hanging plants, and candle-lit tables.

Borgo Santo Pietro

Chiusdino

10/10 Exceptional

My husband and I have been fortunate to stay in many of the best hotels, both large and small, in the world. Borgo Santo Pietro has now seized the "top spot", surpassing our former favorite on the Amalfi coast. No detail has been missed. The rooms are exquisite, the service impeccable, the grounds beautiful and the food is world class. We enjoyed our five course tasting menu so much one evening that we requested the alternative tasting menu the following evening. While incredibly inventive, the...

A.K.Y.

A stone building with a tiled roof, a paved pathway, and a well-maintained garden.

A room with a wooden ceiling, a dining table with chairs, a bed, and a window with curtains.

A dining area with white tables and chairs, a large mirror, and a wine bottle on one table.

A stone building with a wooden deck and white lounge chairs.

Podere Brizio

Montalcino

10/10 Exceptional

Wonderful, beautiful property! The rooms are immaculate and nicely decorated. Breakfast is bountiful with wonderful homemade tarts, breads, frittatas. Do not miss dining in the restaurant for dinner. We had several dinners among the best of our 3 week trip to Italy. The staff is very professional, friendly and passionate about their job. Thank you Vito and Caterina for going above and beyond expectations and making our stay one I will never forget. We are already planning our return.

Sharon

Tenuta Casteani

Gavorrano

10/10 Exceptional

Hermes Affonso

Mercure Petriolo Siena Terme Spa Hotel

Civitella Paganico

10/10 Exceptional

Anonymous traveler

An infinity pool with lounge chairs and umbrellas, surrounded by a forested hillside.

A stone-walled room with a large arched doorway, a sofa, a table with a vase, and a view of the landscape.

An open archway leading to a kitchen with a wooden ceiling, a hanging lantern, and a tiled backsplash.

A rural landscape with a stone house, a swimming pool, and rolling hills in the background.

Castiglion del Bosco, A Rosewood Hotel

Montalcino

10/10 Exceptional

mauricio

A bedroom with a bed, a chair, a table, and a stone wall.

An underground wine cellar with brick walls, wooden tables, and chairs.

An outdoor patio with stone walls, a pergola, and a table set for dining.

An underground wine cellar with wooden tables, wine bottles, and a piano.

Dimora delle Muse

Montalcino

10/10 Exceptional

Anonymous traveler

Montebelli Agriturismo & Country Hotel

Gavorrano

10/10 Exceptional

G&J

Frequently Asked Questions

What accommodations do travelers like in Sassofortino?

Guests like Borgo Santo Pietro and Antico Casale L'Impostino.

Where can I find free parking with my stay in Sassofortino?

Park your car for free at these properties: Lavanda Room With Bath and Panorama Room 2 Pers With Breakfast In Tuscany.

Can I book refundable hotels in Sassofortino?

If you need the flexibility to change your plans to Sassofortino, most accommodations offer refundable* bookable rates. You can see these properties by searching our site and using the "fully refundable" filter to narrow the results down.

Where can I stay in Sassofortino if I want a vacation rental instead of a traditional hotel?

If you want to find a good alternative to a hotel, review our selection of 10 vacation homes.

What will the weather in Sassofortino be like during my trip?

August and July are typically the warmest months in Sassofortino when the average temp is 74°F. January and February are the coldest months when the average temperature is 48°F. November and October are the months with the most rain.

Why should I book my Sassofortino hotel through Hotels.com?

There are lots of reasons to book your Sassofortino trip with us: our free cancellations on selected hotels* gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™** on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.