Sassofortino Holiday Rentals, Roccastrada: Private House Rentals

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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.

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

Rp2.844.054

Rp3.189.638 total

includes taxes & fees

12 Oct - 13 Oct

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

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

2. La Melosa Resort & Spa - Adults Only

Roccastrada

Gillian

Rp1.545.992

Rp1.761.770 total

includes taxes & fees

1 Oct - 2 Oct

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.

3. Mercure Petriolo Siena Terme Spa Hotel

Civitella Paganico

Mike

Rp1.529.474

Rp1.682.421 total

includes taxes & fees

8 Oct - 9 Oct

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

A cozy living room with a fireplace, elegant furniture, and a chandelier.

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

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

4. Borgo Santo Pietro

Chiusdino

Rachel

Rp20.443.484

Rp22.692.267 total

includes taxes & fees

29 Oct - 30 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 balcony with a view of mountains, featuring a table with chairs, a bottle of wine, and a cactus decoration.

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.

5. Tenuta il Sassone - Wine & Food

Gavorrano

Christine

Rp2.288.648

Rp2.660.719 total

includes taxes & fees

6 Oct - 7 Oct

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

A narrow hallway with a brick archway, a window, and framed pictures on the walls.

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

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

6. B&B da Nada Locanda Toscana

Roccastrada

jean

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

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

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.

7. Historic Farmhouse Casa del Chiodo

Roccastrada

Ian

Rp1.824.581

Rp2.047.927 total

includes taxes & fees

5 Oct - 6 Oct

A historic stone building with multiple windows and a courtyard.

A breakfast buffet with various food items and beverages, set in a room with stone walls and a large window.

A stone staircase leading to an arched doorway, surrounded by stone walls and potted plants.

A bedroom with a large bed, wooden beams, a TV, and framed pictures on the wall.

8. Agriturismo Tenuta di Montemassi La Fattoria

Roccastrada

Alice

Rp2.115.901

Rp2.368.379 total

includes taxes & fees

30 Sept - 1 Oct

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 table set for a meal, featuring a tray with plates, glasses, and a bottle.

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.

9. Conti di San Bonifacio Wine Resort

Gavorrano

Hannah

Rp10.987.739

Rp12.168.085 total

includes taxes & fees

15 Oct - 16 Oct

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

An open window with a view of a mountainous landscape and a flower box on the windowsill.

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.

10. VIN Hotel - La Meridiana

Montieri

Anastasia

Rp2.602.886

Rp2.863.175 total

includes taxes & fees

30 Sept - 1 Oct

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

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.

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.

11. Montebelli Agriturismo & Country Hotel

Gavorrano

Jean-Olivier

Rp1.490.748

Rp1.762.483 total

includes taxes & fees

30 Sept - 1 Oct

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

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

A building with a stone facade and multiple windows.

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

12. 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

Rp1.538.837

Rp1.754.051 total

includes taxes & fees

5 Oct - 6 Oct

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 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.

13. Country House il Ciliegio

Roccastrada

Maaike

Rp1.641.036

Rp1.846.027 total

includes taxes & fees

28 Oct - 29 Oct

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

A beach with blue umbrellas and a wooden deck.

A golf course with a pond, trees, and hills in the background.

A modern hotel room with a sofa, a bed, a small table with a vase, and a balcony with chairs.

14. Il Pelagone Hotel & Golf Resort Toscana

Gavorrano

Matthias

Rp2.933.171

Rp3.348.846 total

includes taxes & fees

12 Oct - 13 Oct

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

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.

15. Hotel Girifalco - Nature & Relax

Massa Marittima

Lucy

Rp946.132

Rp1.244.675 total

includes taxes & fees

12 Oct - 13 Oct

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

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

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.

16. Valdonica Winery - Chill in Nature Lodge

Roccastrada

Rp3.382.374

Rp3.761.499 total

includes taxes & fees

4 Oct - 5 Oct

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 historic building with a stone facade, surrounded by a well-maintained garden with yellow flowers and tall trees.

17. Antico Casale L'Impostino

Civitella Paganico

Maria

Rp2.377.618

Rp2.615.400 total

includes taxes & fees

19 Oct - 20 Oct

A stone house with a swimming pool, red shutters, and a covered patio.

A stone building with a red shuttered window, a colorful mosaic, and a staircase leading to a hilltop view.

A rustic stone building with a courtyard, a wooden cart, and a tree.

A stone building with a staircase leading to a terrace, flags, and a view of a parking area and hills.

18. NonnaNara

Grosseto

"Grosse maison perdue dans la campagne qui a été une superbe découverte. Nous avions un magnifique appartement qui donnait sur une belle piscine magnifiquement entretenue. Le personnel est très avenant avec un remerciement spécial pour Fatima qui nous a accueillis en français est s'est occupé de nous toute la soirée. Elle nous a concocté un excellent repas le soir avec des produits du terroir. Un grand merci pour elle qui était encore présente tôt au petit déjeuner. Excellente expérience à...

Marie

Rp2.341.658

Rp2.575.824 total

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

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

19. Tenuta Casteani

Gavorrano

Andrew

Rp2.207.896

Rp2.510.459 total

includes taxes & fees

30 Sept - 1 Oct

An outdoor dining area with a table set for two, overlooking a lush green landscape and a hill in the distance.

A couple sitting by a pool under a pergola with a view of a house and hills in the background.

A cozy kitchen with wooden cabinets, a dining area with a table and chairs, and a red sofa with a patterned cushion.

A cozy kitchen with wooden cabinets, a stove, and a dining area with a table and chairs.

20. Podere Cascatelle & Agriletizia

Massa Marittima

Ciarán

Rp995.188

Rp1.237.811 total

includes taxes & fees

30 Sept - 1 Oct

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Top Sassofortino Hotel Reviews

Podere Brizio

10/10 Excellent

"From the moment we arrived to the time we left was excellent, the staff, the room, Breakfast, and pool were all very good, we reserved a table with them in the evening of which was also a lovely experience, on the whole its a lovely and most relaxing place to be. we definitely will return."

Le Ragnaie

10/10 Excellent

"This was a top-notch stay from beginning to end. We stayed 3 nights in the panoramic suite. Every night we watched the sunset. The suite was incredible!! We even made dinner one night. The staff were so helpful - even when my husband thought he lost his backpack! Juliana helped us find it! The owner was gracious and told us we could walk through the vineyards. It was the last day of harvest when we did. Great breakfast with lots of variety. Best stay! Can’t wait to come back!!! Grazie mille!"

Grand Hotel Bastiani

10/10 Excellent

"Great location inside the city walls to explore Grosetto. Lots of great restaurants."

Hotel La Pineta

8/10 Good

"Excellent breakfast and dinner at same restaurant with beautiful patio. Nice lunch cafe in front also for aperitif. Close to street though. Very friendly staff. Rooms are a bit cold with no decor. Rooms close to stairs and elevator are noisy. We had room 112. Heard everything from the hallways which was annoying at night. Room had a very strong disinfectant odor. Overall highly recommend the hotel."

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."

Castiglion del Bosco, A Rosewood Hotel

10/10 Excellent

"Very warm and friendly service."

Hotel Girifalco - Nature & Relax

10/10 Excellent

"Charming hotel. Excellent breakfast. I would recommend it"

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."

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 Sassofortino

Agriturismo Bio Fattoria Casetta

VIA DEI PIANETTI 6 Gavorrano GR

Rp1.640.569

Rp1.886.198 total

5 Oct - 6 Oct

includes taxes & fees

Hotel Massa Vecchia

Massa Vecchia, 23 Massa Marittima GR

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8.6/10 Excellent! (11 reviews)

Guadalupe Tuscany Resort

Strada Provinciale Del Bozzone Grosseto GR

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9.8/10 Exceptional! (28 reviews)

Bio Tenuta di Paganico - I Roggeti

Via Della Stazione, 10 Civitella Paganico GR

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8/10 Very good! (1 review)

Podere Valmarina

Via Aurelia Nord 10 Grosseto GR

Get rates

9.2/10 Wonderful! (5 reviews)

Rinidia Bio

loc. Colombaie snc, San Rocco a Pilli Sovicille SI

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10/10 Exceptional! (5 reviews)

Frequently asked questions

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 traveller data. Other good options for your stay in the area are Grand Hotel Bastiani and Borgo Santo Pietro. See all available top hotels, or vacation rentals in Sassofortino.

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

Yes, the majority of hotel reservations are refundable provided that you cancel prior to the hotel's cancellation deadline, which often is within 24-48 hours of your arrival date. If your reservation is non-refundable, it might still be possible to cancel it and be given a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Sassofortino.

What's the best dog-friendly accommodation option in Sassofortino?

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

What are some accommodation options 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 with an on-site 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 it like to stay in Sassofortino?

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

What should I do while I'm visiting 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. Take a look at what more there is to see and do in Expedia's Sassofortino guide.

What's the seasonal weather like in Sassofortino?

The hottest months are usually August and July, with an average temperature of 23°C, while the coldest months are January and February, with an average of 9°C. Average annual precipitation for Sassofortino is 788 mm.

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Find hotels in Sassofortino from Rp1.205.067

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Sassofortino

Check prices for these dates

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Our top choices for Sassofortino hotels

1. Valdonica Winery & Vineyard Residence

2. La Melosa Resort & Spa - Adults Only

3. Mercure Petriolo Siena Terme Spa Hotel

4. Borgo Santo Pietro

5. Tenuta il Sassone - Wine & Food

6. B&B da Nada Locanda Toscana

7. Historic Farmhouse Casa del Chiodo

8. Agriturismo Tenuta di Montemassi La Fattoria

9. Conti di San Bonifacio Wine Resort

10. VIN Hotel - La Meridiana

11. Montebelli Agriturismo & Country Hotel

12. Agriturismo San Galgano

13. Country House il Ciliegio

14. Il Pelagone Hotel & Golf Resort Toscana

15. Hotel Girifalco - Nature & Relax

16. Valdonica Winery - Chill in Nature Lodge

17. Antico Casale L'Impostino

18. NonnaNara

19. Tenuta Casteani

20. Podere Cascatelle & Agriletizia

Top Sassofortino Hotel Reviews

Podere Brizio

Le Ragnaie

Grand Hotel Bastiani

Hotel La Pineta

Castello Di Vicarello

Castiglion del Bosco, A Rosewood Hotel

Hotel Girifalco - Nature & Relax

Montebelli Agriturismo & Country Hotel

Mercure Petriolo Siena Terme Spa Hotel

More cheap stays in Sassofortino

Agriturismo Bio Fattoria Casetta

Hotel Massa Vecchia

Guadalupe Tuscany Resort

Bio Tenuta di Paganico - I Roggeti

Podere Valmarina

Rinidia Bio

Frequently asked questions

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