Sassofortino Holiday Rentals, Roccastrada: Private House Rentals

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Go beyond your typical stay in Sassofortino

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Pool

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Spa

Hot tub

Family friendly

Farm

Waterpark

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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 room with a large window overlooking a vineyard and mountains. There is a stone wall and a wooden shelf with wine bottles and glasses.

A swimming pool with a view of a valley and mountains.

A balcony with two wooden chairs overlooking a vineyard and distant 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

30 Sept - 1 Oct

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

A rectangular pool with lounge chairs and umbrellas, surrounded by a brick patio.

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.

2. Country House il Ciliegio

Roccastrada

Maaike

Rp1.636.982

Rp1.841.466 total

includes taxes & fees

28 Oct - 29 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 spa area with two hot tubs, a decorative bowl with candles, and a person in a robe.

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

3. La Melosa Resort & Spa - Adults Only

Roccastrada

Gillian

Rp1.545.992

Rp1.761.770 total

includes taxes & fees

1 Oct - 2 Oct

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

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.

A dining table set with wine glasses and a vase with flowers, a fireplace with a fire, and a stone wall.

4. Historic Farmhouse Casa del Chiodo

Roccastrada

Ian

Rp1.820.074

Rp2.042.868 total

includes taxes & fees

5 Oct - 6 Oct

A breakfast table with a variety of fruits, a vase of flowers, and a lamp in the background.

A reception desk with large letters "HP" and stars on a glass window.

A row of bicycles parked outside a building with a sign that reads "BAR".

A modern living room with a white sofa, a flat-screen TV, and potted plants.

5. Hotel La Pineta

Follonica

Rp1.284.758

Rp1.494.806 total

includes taxes & fees

4 Oct - 5 Oct

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

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

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.

6. Hotel Girifalco - Nature & Relax

Massa Marittima

Lucy

Rp946.132

Rp1.244.675 total

includes taxes & fees

12 Oct - 13 Oct

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

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

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

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

7. VIN Hotel - La Meridiana

Montieri

Anastasia

Rp2.602.886

Rp2.863.175 total

includes taxes & fees

29 Sept - 30 Sept

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

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

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.

8. Valdonica Winery - Chill in Nature Lodge

Roccastrada

Rp3.374.019

Rp3.752.207 total

includes taxes & fees

4 Oct - 5 Oct

A room with a view of a cityscape, featuring a pool, a table with candles, and two chairs.

A buffet with various pastries and a floral centerpiece.

A balcony with a view of a church and tower, a chair, and red heart-shaped balloons.

An outdoor dining area with tables and chairs under a canopy, surrounded by greenery and buildings.

9. Hotel Airone

Grosseto

Lisa

Rp1.713.011

Rp1.976.080 total

includes taxes & fees

3 Oct - 4 Oct

A table with a glass of white wine, a metal pitcher, and a wooden board with various cheeses and cured meats.

A poolside area with lounge chairs, a table with wine glasses and a bottle, and a view of a mountainous landscape.

A kitchen with a buffet setup, including a variety of food items and glassware.

A hotel room with a large bed, a bedside table, a lamp, a window with curtains, and a view of greenery outside.

10. SI Montalcino Hotel

Montalcino

Sam

Rp1.723.875

Rp2.365.301 total

includes taxes & fees

23 Oct - 24 Oct

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

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.

A bedroom with a large bed, a wooden headboard, a nightstand, and a window with a view of the outdoors.

11. Agriturismo Giù al Pozzo

Gavorrano

Micaiah

Rp1.531.698

Rp1.766.439 total

includes taxes & fees

4 Oct - 5 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.

12. Podere Cascatelle & Agriletizia

Massa Marittima

Ciarán

Rp992.731

Rp1.234.755 total

includes taxes & fees

30 Sept - 1 Oct

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

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.

A spacious living room with a fireplace, multiple seating options, and large windows with curtains.

13. Antico Casale L'Impostino

Civitella Paganico

Maria

Rp2.377.618

Rp2.615.400 total

includes taxes & fees

19 Oct - 20 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.

14. Tenuta il Sassone - Wine & Food

Gavorrano

Christine

Rp2.054.612

Rp2.402.825 total

includes taxes & fees

6 Oct - 7 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.

A covered patio with a table and chairs, a small garden, and a building in the background.

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

15. Montebelli Agriturismo & Country Hotel

Gavorrano

Jean-Olivier

Rp1.758.895

Rp2.057.143 total

includes taxes & fees

1 Oct - 2 Oct

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

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

16. Il Belvedere Country Houses

Massa Marittima

hendrik

Rp1.334.813

Rp1.468.295 total

includes taxes & fees

21 Oct - 22 Oct

A historic stone building with multiple windows and a courtyard.

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

An outdoor patio with stone arches, terracotta flooring, and tables set for dining.

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

17. Agriturismo Tenuta di Montemassi La Fattoria

Roccastrada

Alice

A modern lobby with a reception desk, a globe, seating area, and large windows.

A modern dining area with tables and chairs, a reception desk, and a buffet counter.

A modern lobby with a teal sofa, a large abstract wall art, two standing lamps, and a Christmas tree.

A modern hotel lobby with a curved reception desk, seating area, and a large plant.

18. Hotel Nuova Grosseto

Grosseto

Karen

Rp1.625.302

Rp1.787.832 total

includes taxes & fees

16 Oct - 17 Oct

A person in a hot tub with water flowing over them.

A hotel named GRANDVCA with a fountain in the center, surrounded by a paved area with potted plants.

A room with a sofa, a coffee machine, and a decorative plant.

A spa area with a pool, marble columns, and a towel rack.

19. Granduca

Grosseto

Georges

Rp1.830.678

Rp2.105.576 total

includes taxes & fees

29 Sept - 30 Sept

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

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

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

A hotel room with a bed, towels, a painting, and a vase with flowers.

20. 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

Rp2.335.874

Rp2.569.461 total

includes taxes & fees

23 Oct - 24 Oct

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Top Sassofortino Hotel Reviews

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."

Podere Brizio

10/10 Excellent

"Lovely setting. Great views and incredibly helpful staff. Really enjoyed our two days. Can’t wait to come back 👍"

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

Get rates

8.6/10 Excellent! (11 reviews)

Guadalupe Tuscany Resort

Strada Provinciale Del Bozzone Grosseto GR

Get rates

9.8/10 Exceptional! (28 reviews)

Bio Tenuta di Paganico - I Roggeti

Via Della Stazione, 10 Civitella Paganico GR

Get rates

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

Get rates

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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Book Hotels in Sassofortino on Expedia.it

Find hotels in Sassofortino from Rp1.234.755

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Sassofortino

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Sassofortino hotels

1. Valdonica Winery & Vineyard Residence

2. Country House il Ciliegio

3. La Melosa Resort & Spa - Adults Only

4. Historic Farmhouse Casa del Chiodo

5. Hotel La Pineta

6. Hotel Girifalco - Nature & Relax

7. VIN Hotel - La Meridiana

8. Valdonica Winery - Chill in Nature Lodge

9. Hotel Airone

10. SI Montalcino Hotel

11. Agriturismo Giù al Pozzo

12. Podere Cascatelle & Agriletizia

13. Antico Casale L'Impostino

14. Tenuta il Sassone - Wine & Food

15. Montebelli Agriturismo & Country Hotel

16. Il Belvedere Country Houses

17. Agriturismo Tenuta di Montemassi La Fattoria

18. Hotel Nuova Grosseto

19. Granduca

20. NonnaNara

Top Sassofortino Hotel Reviews

Le Ragnaie

Grand Hotel Bastiani

Hotel La Pineta

Castello Di Vicarello

Castiglion del Bosco, A Rosewood Hotel

Podere Brizio

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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