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Go beyond your typical stay in Sassofortino

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Nov 5 - Nov 6
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Nov 6 - Nov 7
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Nov 6 - Nov 8
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Nov 13 - Nov 15

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Our top choices for Sassofortino hotels

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

1. Valdonica Winery & Vineyard Residence

Valdonica Winery & Vineyard Residence
Roccastrada
9.2 out of 10, Wonderful, (46 reviews)
"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...
United States
Audrey
The price is ₩197,953
₩222,269 total
includes taxes & fees
Nov 8 - Nov 9
Valdonica Winery & Vineyard Residence
A pool with a modern water feature and a stone structure.

2. Mercure Petriolo Siena Terme Spa Hotel

Mercure Petriolo Siena Terme Spa Hotel
5.0 star property
Civitella Paganico
8.6 out of 10, Excellent, (267 reviews)
"We had a great time. I would recommend this hotel when in Tuscany. "
United States
Mike
The price is ₩112,940
₩124,234 total
includes taxes & fees
Nov 8 - Nov 9
Mercure Petriolo Siena Terme Spa Hotel
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.

3. Conti di San Bonifacio Wine Resort

Conti di San Bonifacio Wine Resort
Gavorrano
9.4 out of 10, Exceptional, (29 reviews)
"Unbelievable beautiful place. We absolutely loved our time there. "
United States
Hannah
The price is ₩733,119
₩806,425 total
includes taxes & fees
Nov 14 - Nov 15
Conti di San Bonifacio Wine Resort
An outdoor dining area with stone buildings, tables with orange tablecloths, and string lights.

4. Historic Farmhouse Casa del Chiodo

Historic Farmhouse Casa del Chiodo
Roccastrada
10.0 out of 10, Exceptional, (6 reviews)
"Everything about this place is perfect, highly recommend."
United States
Ian
The price is ₩142,305
₩159,548 total
includes taxes & fees
Nov 18 - Nov 19
Historic Farmhouse Casa del Chiodo
A restaurant with outdoor seating, a bar area, and a view of the landscape.

5. B&B da Nada Locanda Toscana

B&B da Nada Locanda Toscana
Roccastrada
9.6 out of 10, Exceptional, (18 reviews)
"Ras"
France
jean
The price is ₩97,383
₩110,134 total
includes taxes & fees
Nov 11 - Nov 12
B&B da Nada Locanda Toscana
A rectangular swimming pool with a clear blue water, surrounded by a well-maintained lawn and several lounge chairs.

6. Antico Casale L'Impostino

Antico Casale L'Impostino
Civitella Paganico
9.4 out of 10, Exceptional, (53 reviews)
"Very nice stay"
United States
Maria
The price is ₩175,691
₩193,262 total
includes taxes & fees
Nov 11 - Nov 12
Antico Casale L'Impostino
A window with a view of a landscape, a woven basket, and a clay pot with plants.

7. Country House il Ciliegio

Country House il Ciliegio
Roccastrada
9.2 out of 10, Wonderful, (7 reviews)
"It was a very pleasant stay, a warm welcome. A beautiful location surrounded by nature."
Netherlands
Maaike
The price is ₩117,639
₩132,412 total
includes taxes & fees
Nov 9 - Nov 10
Country House il Ciliegio
A long table set for a meal outdoors with white tablecloths, woven placemats, and potted plants.

8. Agriturismo San Galgano

Agriturismo San Galgano
Chiusdino
9.0 out of 10, Wonderful, (45 reviews)
"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."
United Kingdom
Irene
The price is ₩135,775
₩153,871 total
includes taxes & fees
Nov 13 - Nov 14
Agriturismo San Galgano
A swimming pool with a waterfall feature, large windows, and a lounge chair.

9. Montebelli Agriturismo & Country Hotel

Montebelli Agriturismo & Country Hotel
4.0 star property
Gavorrano
8.6 out of 10, Excellent, (136 reviews)
"Toscane immersion spa hotel"
Canada
Jean-Olivier
The price is ₩150,474
₩165,522 total
includes taxes & fees
Nov 7 - Nov 8
Montebelli Agriturismo & Country Hotel
A large, multi-story residential building with multiple balconies, surrounded by well-maintained lawns and trees.

10. Il Pelagone Hotel & Golf Resort Toscana

Il Pelagone Hotel & Golf Resort Toscana
4.0 star property
Gavorrano
8.6 out of 10, Excellent, (25 reviews)
"We had a great time here. Everyone was helpful, golf course was great and rooms worked out well. The breakfast was probably the best of our trek throughout Italy. Loved it here."
United States
Jordan
The price is ₩174,184
₩191,602 total
includes taxes & fees
Dec 1 - Dec 2
Il Pelagone Hotel & Golf Resort Toscana
A group of people dining at a table with a view of a valley and mountains.

11. Valdonica Winery - Chill in Nature Lodge

Valdonica Winery - Chill in Nature Lodge
Roccastrada
The price is ₩238,199
₩265,031 total
includes taxes & fees
Nov 9 - Nov 10
Valdonica Winery - Chill in Nature Lodge
A covered patio area with stone walls, wooden beams, and outdoor furniture.

12. Casale San Galgano

Casale San Galgano
Chiusdino
10.0 out of 10, Exceptional, (24 reviews)
"Staff was great! Made the stay feel like home"
United States
Adam
The price is ₩166,001
₩187,122 total
includes taxes & fees
Dec 5 - Dec 6
Casale San Galgano
A modern living room with a sofa, a coffee table, a TV on a wooden cabinet, and a large potted plant.

13. Le Vie del Mare Camere

Le Vie del Mare Camere
Ribolla
The price is ₩148,200
₩163,020 total
includes taxes & fees
Nov 13 - Nov 14
Le Vie del Mare Camere
An outdoor patio with wooden tables and chairs, large windows offering a view of a mountainous landscape.

14. Agriturismo Giù al Pozzo

Agriturismo Giù al Pozzo
Gavorrano
9.6 out of 10, Exceptional, (5 reviews)
"This stay was beautiful! There was pretty countryside and the hotel grounds were very pretty as well."
United States
Micaiah
The price is ₩101,055
₩111,161 total
includes taxes & fees
Nov 15 - Nov 16
Agriturismo Giù al Pozzo
A stone wall with a view of rolling hills and mountains.

15. Castello Banfi - Il Borgo - Relais et Chateaux

Castello Banfi - Il Borgo - Relais et Chateaux
5.0 star property
Montalcino
10.0 out of 10, Exceptional, (139 reviews)
"This property is pristine. Absolutely beautiful with some of the best views in Tuscany. I would recommend this experience to anyone."
United States
Jeanine
The price is ₩1,820,737
₩2,017,870 total
includes taxes & fees
Nov 7 - Nov 8
Castello Banfi - Il Borgo - Relais et Chateaux
A room with a view of a cityscape, featuring a pool, a table with candles, and two chairs.

16. Hotel Airone

Hotel Airone
4.0 star property
Grosseto
8.4 out of 10, Very good, (126 reviews)
"I stay at this hotel at least one a year, Staff is always friendly and welcoming. Rooms are clean and quiet. The only thing I miss is having a hot pot to make tea."
United States
Lisa
The price is ₩164,276
₩180,705 total
includes taxes & fees
Nov 6 - Nov 7
Hotel Airone
A bedroom with a bed, a bedside table, a TV mounted on the wall, and a sliding glass door leading to a balcony with a view of greenery and hills.

17. Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (34 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is ₩83,546
₩111,478 total
includes taxes & fees
Nov 20 - Nov 21
Tuscasì Aparthotel
An outdoor patio with wicker furniture, potted plants, and a brick building in the background.

18. Locanda nel Cassero

Locanda nel Cassero
Civitella Paganico
9.4 out of 10, Exceptional, (6 reviews)
"Locanda confortevole e accogliente gentilezza e grande disponibilità "
Italy
Edoardo
The price is ₩117,128
₩128,841 total
includes taxes & fees
Dec 1 - Dec 2
Locanda nel Cassero
A stone building with multiple windows and a balcony, surrounded by lush greenery and trees.

19. Relais Le Macine di Stigliano

Relais Le Macine di Stigliano
4.0 star property
Sovicille
10.0 out of 10, Exceptional, (28 reviews)
"Charming boutique hotel with stunning views! Staff and housekeeping were excellent. We enjoyed our lovely stay very much."
United States
Rene
The price is ₩213,888
₩242,806 total
includes taxes & fees
Nov 8 - Nov 9
Relais Le Macine di Stigliano
A villa with a swimming pool, surrounded by trees and hills.

20. Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel
5.0 star property
Montalcino
10.0 out of 10, Exceptional, (87 reviews)
"Unique property well maintained and quite Serene , great staff"
United States
KEDARNATH
The price is ₩1,219,756
₩1,356,790 total
includes taxes & fees
Dec 2 - Dec 3
Castiglion del Bosco, A Rosewood Hotel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Sassofortino Hotel Reviews

An outdoor dining area with stone buildings, tables with orange tablecloths, and string lights.
Historic Farmhouse Casa del Chiodo

Historic Farmhouse Casa del Chiodo

Historic Farmhouse Casa del Chiodo
Roccastrada

10/10 Excellent

The Casa Del Chiodo was the perfect Tuscan B&B experience for us. From the moment Marco greeted us to the amazing multiple course evening meal that owner/chef Paola prepared to the breakfast served by Irene, it was the epitome of Italian hospitality. While the evening meal was extra, it was definitely worth it as it showcased local farm grown and hunted/gathered foods (such as mushrooms, venison and roasted chestnuts). Our room was clean, true to historical construction with modern amenities....
United States
Nita Marie
Reviewed October 29, 2026
Historic Farmhouse Casa del Chiodo

Frequently Asked Questions

If I need to cancel my hotel reservation in Sassofortino, will I receive a refund?

Yes! Most hotel room reservations are fully refundable as long as you cancel before the accommodation's cancellation deadline, which often is within 24-48 hours of the scheduled arrival. If you have a reservation that's non-refundable, it may still be possible to cancel it and get a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Sassofortino.

Where can I learn more about changing or cancelling my trip to Sassofortino?

To find more details about changing or cancelling your trip to Sassofortino, go to https://www.expedia.com/service/.

What's the best pet-friendly accommodation in Sassofortino?

Valdonica Winery - Chill in Nature Lodge is a top B&B for people traveling with their pets, and offers a winery and a restaurant for its human guests. Other good options for you and your pet include Valdonica Winery & Vineyard Residence and Agriturismo Campo al Crognolo. See more pet-friendly hotel accommodations in Sassofortino.

What are some accommodations with pools in Sassofortino?

Valdonica Winery & Vineyard Residence: Features a full-service spa, a seasonal outdoor pool, and daily. Rosewood Castiglion del Bosco and Borgo Santo Pietro are two additional hotels that offer an onsite pool. View all hotels with pools in Sassofortino.

What is the best spa hotel in Sassofortino?

Valdonica Winery & Vineyard Residence is a top spa hotel featuring a bar and a restaurant. Enjoy a massage at the on-site spa. See all spa hotels in Sassofortino.

What's the best place to stay near Peretola Airport (FLR)?

Hotel Cosmopolitan is a popular 4-star hotel featuring free WiFi and a bar. It's located a short 0.7 mi (1.2 km) from Peretola Airport. Other good choices close to the airport are Best Western Plus CHC Florence and Hotel Mirage.

How is it to stay in Sassofortino?

Travelers to Sassofortino will find plenty to explore and enjoy. In Sassofortino, there are 4 hotels and other accommodations to choose from. Find out more about Sassofortino.

What is there to see in Sassofortino?

Places to visit in the wider area include Podere Ristella Vineyards and Winery, I Canaloni del Torrente Farma, and Abbazia di San Galgano. You'll also find Rocca di Frassinello Winery and Terme Petriolo in the area. Check out what more to see and do in Expedia's Sassofortino guide.

What's the weather like in Sassofortino?

The hottest months are usually August and July with an average temp of 74°F, while the coldest months are January and February with an average of 48°F. Average annual precipitation for Sassofortino is 31 inches.

What's the best place for a stay in Sassofortino?

Castiglion del Bosco, A Rosewood Hotel, located 16.2 mi (26 km) from the heart of Sassofortino, is a top choice for your stay based on our traveler data. Two other options for your trip to the area are Grand Hotel Bastiani and Borgo Santo Pietro. See all available top hotels, or vacation rentals in Sassofortino.