Hotels in Sassofortino

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Dates

November 2026

December 2026

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Where to stay in Sassofortino?

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

1. Hotel Girifalco - Nature & Relax

Massa Marittima

$70 total

includes taxes & fees

Oct 30 - Oct 31

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

2. La Melosa Resort & Spa - Adults Only

Roccastrada

$108 total

includes taxes & fees

Oct 29 - Oct 30

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

3. Valdonica Winery & Vineyard Residence

Roccastrada

$165 total

includes taxes & fees

Nov 8 - Nov 9

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.

4. Tenuta il Sassone - Wine & Food

Gavorrano

$124 total

includes taxes & fees

Oct 31 - Nov 1

5. B&B da Nada Locanda Toscana

Roccastrada

$91 total

includes taxes & fees

Nov 3 - Nov 4

A stone building with multiple windows and a balcony, a table set for dining, and lush greenery in the foreground.

6. Historic Farmhouse Casa del Chiodo

Roccastrada

$118 total

includes taxes & fees

Nov 2 - Nov 3

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

7. Antico Casale L'Impostino

Civitella Paganico

$143 total

includes taxes & fees

Nov 2 - Nov 3

A pool with lounge chairs and a sunset view.

8. Mercure Petriolo Siena Terme Spa Hotel

Civitella Paganico

$92 total

includes taxes & fees

Oct 28 - Oct 29

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.

9. Valdonica Winery - Chill in Nature Lodge

Roccastrada

$197 total

includes taxes & fees

Nov 9 - Nov 10

A building with a stone facade and multiple windows.

10. Agriturismo San Galgano

Chiusdino

$99 total

includes taxes & fees

Oct 29 - Oct 30

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

11. Le Vie del Mare Camere

Ribolla

$134 total

includes taxes & fees

Oct 28 - Oct 29

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

12. Agriturismo Giù al Pozzo

Gavorrano

$82 total

includes taxes & fees

Nov 3 - Nov 4

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

13. Tenuta Casteani

Gavorrano

$126 total

includes taxes & fees

Oct 29 - Oct 30

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

14. Casale San Galgano

Chiusdino

$97 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.

15. Il Belvedere Country Houses

Massa Marittima

$80 total

includes taxes & fees

Oct 28 - Oct 29

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

16. Country House il Ciliegio

Roccastrada

$98 total

includes taxes & fees

Nov 2 - Nov 3

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

17. Montebelli Agriturismo & Country Hotel

Gavorrano

$88 total

includes taxes & fees

Nov 1 - Nov 2

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.

18. Conti di San Bonifacio Wine Resort

Gavorrano

$598 total

includes taxes & fees

Nov 9 - Nov 10

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

19. Relais Le Macine di Stigliano

Sovicille

$180 total

includes taxes & fees

Nov 11 - Nov 12

A swimming pool with a view of a hilltop castle.

20. Agriturismo Podere Ristella - Wine&Food

Roccastrada

$133 total

includes taxes & fees

Oct 28 - Oct 29

View all properties

Go beyond your typical stay in Sassofortino

Check out reviews of Sassofortino hotels guests love

Historic Farmhouse Casa del Chiodo

Roccastrada

10/10 Exceptional

Ian

La Melosa Resort & Spa - Adults Only

Roccastrada

10/10 Exceptional

raul

Valdonica Winery & Vineyard Residence

Roccastrada

10/10 Exceptional

Josh

Tenuta il Sassone - Wine & Food

Gavorrano

10/10 Exceptional

Kathy

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

Antico Casale L'Impostino

Civitella Paganico

10/10 Exceptional

Mason

Relais Le Macine di Stigliano

Sovicille

10/10 Exceptional

Tim

Agriturismo Giù al Pozzo

Gavorrano

10/10 Exceptional

Micaiah

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

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.

Conti di San Bonifacio Wine Resort

Gavorrano

10/10 Exceptional

Paul

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

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

Mercure Petriolo Siena Terme Spa Hotel

Civitella Paganico

10/10 Exceptional

Anonymous traveler

Tenuta Casteani

Gavorrano

10/10 Exceptional

Hermes Affonso

A villa with a swimming pool, surrounded by trees and hills.

Castiglion del Bosco, A Rosewood Hotel

Montalcino

10/10 Exceptional

mauricio

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

Dimora delle Muse

Montalcino

10/10 Exceptional

Anonymous traveler

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.