Roccastrada Holiday Rentals, Tuscany: Private House Rentals

An ancient stone tower with a view of rolling hills and fields in the background.

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Our top choices for Roccastrada hotels

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

A spa area with two hot tubs, a decorative bowl with candles, and a person in a robe.

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.

1. La Melosa Resort & Spa - Adults Only

Roccastrada

Gillian

Rp1.537.776

Rp1.752.408 total

includes taxes & fees

25 Oct - 26 Oct

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

A swimming pool with a view of a valley and 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 balcony with two wooden chairs overlooking a vineyard and distant mountains.

2. 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

Rp2.828.941

Rp3.172.689 total

includes taxes & fees

30 Sept - 1 Oct

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

3. Historic Farmhouse Casa del Chiodo

Roccastrada

Ian

Rp1.810.401

Rp2.032.010 total

includes taxes & fees

28 Sept - 29 Sept

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

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.

A window with a view of buildings and a plant on the windowsill.

4. Country House il Ciliegio

Roccastrada

Maaike

Rp1.628.283

Rp1.831.680 total

includes taxes & fees

25 Oct - 26 Oct

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

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

5. Valdonica Winery - Chill in Nature Lodge

Roccastrada

Rp3.356.088

Rp3.732.265 total

includes taxes & fees

4 Oct - 5 Oct

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

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

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

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

6. Le Vie del Mare Camere

Ribolla

Rp2.218.122

Rp2.439.934 total

includes taxes & fees

1 Oct - 2 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.

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.

7. Agriturismo Tenuta di Montemassi La Fattoria

Roccastrada

Alice

Rp1.807.289

Rp2.028.587 total

includes taxes & fees

27 Sept - 28 Sept

A wooden interior with a glass-enclosed shower, large windows, and a wooden floor.

A small, modern house with a sliding glass door, surrounded by lush greenery and a well-maintained garden.

A living room with a wooden ceiling, a sofa, a dining table with chairs, a television, and a cabinet.

A pathway leading to a building with a stone-tiled entrance and a wooden door.

8. Agriturismo Benvenuti

Roccastrada

"La stanza era molto grande e tranquilla. C'è anche un giardino abbastanza ampio a disposizione esclusiva di ogni camera/appartamento. Estrema cortesia. Ovviamente si è in aperta campagna, non in vicinanza del mare o dentro un borgo, ma in auto si raggiungo facilmente molte località interessanti del luogo. Su alcuni particolari, potrebbe essere tenuto un po' meglio, ma nel complesso ha un ottimo rapporto qualità/prezzo per la zona."

Ivano

Rp1.261.334

Rp1.630.883 total

includes taxes & fees

23 Oct - 24 Oct

A swimming pool with a view of a hilltop castle.

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

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

A kitchen with wooden cabinets, a tiled backsplash, and a dining table with a fruit bowl.

9. Agriturismo Podere Ristella - Wine&Food

Roccastrada

"Non lasciarsi ingannare dalle foto, la struttura è fatiscente. L'alloggio non è adatto a bambini in quanto ha delle scale ripide" dove sono caduti senza passamano, e tutto nell'incuria, doccia bagni finestre cucina caldaia, sicuramente c'è molto verde ma non si può girare a piedi, è silenzioso, si paga tutto pure la carbonella per i barbecue, sembra più architettato per finire di costruire la struttura coi soldi dei malcapitati, infatti nessuno chiede se serve qualcosa ma si apprestano solo la...

eugenio

Rp1.478.748

Rp2.072.884 total

includes taxes & fees

6 Oct - 7 Oct

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

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

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

A balcony with a table, chairs, and a view of a street with buildings.

10. Hotel La Pineta

Follonica

christian vase

Rp1.277.931

Rp1.486.862 total

includes taxes & fees

28 Sept - 29 Sept

A courtyard with outdoor seating, a covered area, and a building with brick walls and green shutters.

A bedroom with a bed, a sofa, a desk, and a TV. There are windows with curtains and a view of greenery outside.

A restaurant with a high ceiling, brick walls, and a bar area with a variety of bottles. There are tables and chairs for dining, and a television is visible on the right side.

A living room with a white sofa, a coffee table, and a painting of a historical scene. There is a lamp, a small table with a plant, and a sign indicating room numbers.

11. Hotel Borgo Antico

Monteroni d'Arbia

Charles

Rp1.880.992

Rp2.170.453 total

includes taxes & fees

27 Sept - 28 Sept

A table with breakfast items and a wicker chair, overlooking a scenic landscape.

A bar area with a counter, bottles, and glasses.

A dining area with checkered flooring, tables set with white tablecloths, and wicker chairs.

A courtyard with wicker furniture, a building with multiple windows and arches, and well-maintained greenery.

12. Palazzo Ravizza

Siena Historical Center

Sherri

Rp3.361.446

Rp3.799.014 total

includes taxes & fees

25 Oct - 26 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.

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

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

13. Hotel Airone

Grosseto

Lisa

Rp1.703.907

Rp1.965.579 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 hotel room with a bed, a sofa, a table with a vase of flowers, a TV, and a window with a view.

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.

14. SI Montalcino Hotel

Montalcino

Sam

Rp2.126.925

Rp2.806.163 total

includes taxes & fees

4 Oct - 5 Oct

A room with a bed, a chair, a view through an open window, and a white dresser with bottles and glasses.

A courtyard with a stone wall, a small pond, and a waterfall. There are trees and plants around, and a building in the background.

A stone building with the name "Albergoggiardino" above the entrance. Inside, there is a chandelier, a clock, and a blue chair.

A hotel room with a bed, a nightstand with bottles, a chair, and a wardrobe.

15. Albergo Giardino

Montalcino

Norma

Rp2.153.773

Rp2.531.427 total

includes taxes & fees

15 Oct - 16 Oct

A lobby with a marble floor, a chandelier, a reception desk, and large green plants.

A modern hotel room with a large bed, a desk, and a chair. There is a painting on the wall and a lamp on the side table.

A hotel with a sign reading "HOTEL RISTORANTE CHIUSARELLI," surrounded by greenery and a brick wall.

A balcony with two chairs and a table, overlooking a building with a tiled roof and shutters.

16. Hotel Chiusarelli

Siena City Centre

sharon

Rp3.135.798

Rp3.550.821 total

includes taxes & fees

16 Oct - 17 Oct

A couple standing in a spacious room with a large window overlooking a vineyard.

A coastal town with a prominent hotel named "HOTEL CAPPRODO" and a marina with boats.

A coastal town with a marina, historic buildings, and a prominent church on a hill.

A dining area with blue patterned chairs, a wooden table, and a mural of a beach scene.

17. Hotel L'Approdo

Castiglione della Pescaia

Ernesto

Rp1.643.053

Rp1.904.725 total

includes taxes & fees

4 Oct - 5 Oct

A hot tub with a central platform and candles.

A modern interior with a large arched window, a reflective surface, and potted plants.

A spacious lobby with a central coffee table, seating area, and decorative wall art.

A table with a glass of white wine, a glass of iced tea, and a variety of appetizers on a balcony overlooking a scenic view during sunset.

18. Grand Hotel Impero - Wellness & Exclusive SPA

Castel del Piano

Lynn

Rp1.443.896

Rp1.669.423 total

includes taxes & fees

21 Oct - 22 Oct

A table set for breakfast with a scenic view of hills and a cloudy sky.

An open wooden door leading to a courtyard with potted plants and a view of buildings in the background.

An arched entrance with a brick pathway leading to a building, surrounded by lush greenery and purple flowering vines.

A two-story building with a central entrance, green shutters, and a brick staircase leading up to the door.

19. Palazzo di Valli

Siena

Payton

Rp2.688.633

Rp3.058.919 total

includes taxes & fees

21 Oct - 22 Oct

An outdoor patio with tables and chairs, surrounded by potted plants and a red building.

A swimming pool with a clear view of the water, a metal structure on the right, and a landscaped area with chairs and plants in the background.

A courtyard with brick buildings, a stone wall, and a view of the surrounding town.

A brick building with three windows, a round blue window, and a sign on the wall.

20. Borgo Grondaie

Siena

Simon

Rp2.152.412

Rp2.469.076 total

includes taxes & fees

19 Oct - 20 Oct

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Stay near popular Roccastrada attractions

I Canaloni del Torrente Farma

8.0/10 (1 review)

Commune with nature and explore the great outdoors at I Canaloni del Torrente Farma during your travels in Roccastrada. Discover the area's countryside and spas.

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Podere Ristella Vineyards and Winery

You can enjoy a tasting or tour at Podere Ristella Vineyards and Winery during your travels to Roccastrada. Wander the gardens or discover the area's countryside.

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Castello del Belagaio

9.0/10 (2 reviews)

You can find out about the history of Roccastrada with a visit to Castello del Belagaio. Discover the area's countryside and wineries.

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Sassoforte Castle

9.0/10 (2 reviews)

You can find out about the history of Roccastrada with a visit to Sassoforte Castle. While you're in the area, wander around the natural setting.

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Church of San Nicola

8.0/10 (1 review)

After visiting Church of San Nicola, make a plan to see the other sights and activities in Roccastrada. Visit the spas in this relaxing area or simply enjoy its wineries.

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Castello di Torniella

After visiting Castello di Torniella, make a plan to see the other sights and activities in Torniella.

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Learn more about Roccastrada

Hike through the dramatic rock formations of I Canaloni del Torrente Farma, where natural pools invite summer swimming between towering canyon walls. Medieval history comes alive at Sassoforte Castle, while nearby Podere Ristella offers wine tastings showcasing Tuscan varietals grown on sun-drenched slopes.

See all hotels in Roccastrada

Top Roccastrada Hotel Reviews

Hotel Athena

10/10 Excellent

"We had a wonderful stay at Hotel Athena in Siena. The hotel is very nice, with comfortable, well-appointed rooms and an excellent central location that makes exploring Siena very convenient. The breakfast was exceptional, with a great selection and excellent quality. The staff was consistently friendly, welcoming, and helpful. Overall, a very enjoyable stay, and we would definitely recommend Hotel Athena to anyone visiting Siena."

Corte Francigena - Apartments

10/10 Excellent

"The unit is very clean, awesome breakfast, beautiful view"

Hotel Chiusarelli

10/10 Excellent

"Got a lot of great help from the staff !"

Grand Hotel Bastiani

10/10 Excellent

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

NH Siena

10/10 Excellent

"El hotel está fuera de las murallas de la ciudad, fuera de la zona restringida para autos, pero cerca de las atracciones de la parte histórica de la ciudad."

Villa Scacciapensieri Boutique Hotel

10/10 Excellent

"The villa is amazing and the perfect little world in itself. Its closeness to Siena makes it easier to visit the city. The patio is the perfect place to view Siena at sunset. The staff was very courteous and ready to help. This hotel is a gem."

Grand Hotel Continental Siena – Starhotels Collezione

8/10 Good

"Our stay was just ok. Very noisy streets. And the bread at the breakfast buffet was extremely stale for both mornings. We could not eat it. If you are allergic to dust be warned that their curtains and bed headers are very dusty."

Castiglion del Bosco, A Rosewood Hotel

10/10 Excellent

"Very warm and friendly service."

Hotel Italia

8/10 Good

"Clean, well maintained property that you’ll feel safe spending the night."

More cheap stays in Roccastrada

Cannon d'Oro

Via Montanini 28 Siena SI

Rp1.037.281

Rp1.242.432 total

25 Oct - 26 Oct

includes taxes & fees

7.8/10 Good! (258 reviews)

Piccolo Hotel Etruria

Via delle Donzelle, 3 Siena SI

Rp1.748.164

Rp2.024.403 total

27 Sept - 28 Sept

includes taxes & fees

7.8/10 Good! (440 reviews)

Mediterraneo RTA

Via XXIV Maggio 68H, Marina di Grosseto Grosseto GR

Rp1.962.075

Rp2.225.221 total

25 Sept - 26 Sept

includes taxes & fees

Albergo Centrale

Via Cecco Angiolieri 26 Siena SI

Rp2.608.031

Rp2.970.257 total

12 Oct - 13 Oct

includes taxes & fees

8.8/10 Excellent! (108 reviews)

Torre del Fuggisole

Via di Fieravecchia 7 Siena SI

Rp2.847.959

Rp3.234.178 total

30 Sept - 1 Oct

includes taxes & fees

10/10 Exceptional! (49 reviews)

Porta Pispini Residence

Via Baldassarre Peruzzi 33 Siena SI

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Frequently asked questions

Where is the best place to stay in Roccastrada?

Hotel Athena, located 22.5 mi (36.1 km) from the heart of Roccastrada, is a top choice for your stay, based on our traveller data. Other good choices for your stay in the area are Hotel Executive and NH Siena. See all available top hotels, or vacation rentals in Roccastrada.

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

Yes! The majority of hotel bookings are fully refundable if you cancel before the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of the scheduled arrival. If you booked a non-refundable reservation, it might still be possible to cancel it and receive a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Roccastrada.

What is the favourite LGBTQ-friendly accommodation in Roccastrada?

La Melosa Resort & Spa - Adults Only is a top LGBTQ-friendly hotel that features a full-service spa and free Wi-Fi. See all available hotels listed as LGBTQ-friendly in Roccastrada.

What's the best dog-friendly place to stay in Roccastrada?

B&B da Nada Locanda Toscana is a top B&B for people travelling with their pets, and offers a restaurant and a bar/lounge for its human guests. Valdonica Winery & Vineyard Residence is another good option for you and your pet. See more pet-friendly hotel accommodations in Roccastrada.

What are some hotels with pools in Roccastrada?

The Sense Experience Resort - Preferred Hotels & Resorts: Features a children's pool, a seasonal outdoor pool and a private beach. Also, another option that offers an on-site pool is Castello di Velona Resort Thermal SPA & Winery. View all hotels with pools in Roccastrada.

What is the best spa hotel in Roccastrada?

Valdonica Winery & Vineyard Residence is a highly recommended luxury spa hotel featuring a bar and a restaurant. Enjoy a massage at the on-site spa. Another popular spa hotel in Roccastrada is La Melosa Resort & Spa - Adults Only. See all spa hotels in Roccastrada.

What is staying in Roccastrada like?

Visitors will definitely enjoy all that Roccastrada has to offer. This city also attracts tourists with its rich culture. In Roccastrada, there are 195 hotels and other accommodation options to choose from. Find out more about Roccastrada.

What is there to see in Roccastrada?

Landmarks like Castello del Belagaio and Sassoforte Castle might be worth a visit. The picturesque setting of I Canaloni del Torrente Farma and Val di Merse exemplify the area's natural beauty. Additionally, you might want to add Podere Ristella Vineyards and Winery to your itinerary. Take a look at what more there is to see and do in Expedia's Roccastrada guide.

How can I get around Roccastrada?

To see more of the surrounding area, ride one of the trains from Roccastrada Station or Sticciano Station. If you want to venture out around the area, you may want a rental car in Roccastrada for your journey.

What's the seasonal weather in Roccastrada?

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 Roccastrada is 788 mm.

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Book Hotels in Roccastrada on Expedia.it

Find hotels in Roccastrada from Rp1.242.432

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Roccastrada

Check prices for these dates

Filter by

Star rating

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Our top choices for Roccastrada hotels

1. La Melosa Resort & Spa - Adults Only

2. Valdonica Winery & Vineyard Residence

3. Historic Farmhouse Casa del Chiodo

4. Country House il Ciliegio

5. Valdonica Winery - Chill in Nature Lodge

6. Le Vie del Mare Camere

7. Agriturismo Tenuta di Montemassi La Fattoria

8. Agriturismo Benvenuti

9. Agriturismo Podere Ristella - Wine&Food

10. Hotel La Pineta

11. Hotel Borgo Antico

12. Palazzo Ravizza

13. Hotel Airone

14. SI Montalcino Hotel

15. Albergo Giardino

16. Hotel Chiusarelli

17. Hotel L'Approdo

18. Grand Hotel Impero - Wellness & Exclusive SPA

19. Palazzo di Valli

20. Borgo Grondaie

Stay near popular Roccastrada attractions

I Canaloni del Torrente Farma

Podere Ristella Vineyards and Winery

Castello del Belagaio

Sassoforte Castle

Church of San Nicola

Castello di Torniella

Learn more about Roccastrada

Top Roccastrada Hotel Reviews

Hotel Athena

Corte Francigena - Apartments

Hotel Chiusarelli

Grand Hotel Bastiani

NH Siena

Villa Scacciapensieri Boutique Hotel

Grand Hotel Continental Siena – Starhotels Collezione

Castiglion del Bosco, A Rosewood Hotel

Hotel Italia

More cheap stays in Roccastrada

Cannon d'Oro

Piccolo Hotel Etruria

Mediterraneo RTA

Albergo Centrale

Torre del Fuggisole

Porta Pispini Residence

Frequently asked questions

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