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 bedroom with a stone wall, a bed with white linens, a wooden chair, a desk with a computer, and a window with curtains.

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

1. La Melosa Resort & Spa - Adults Only

Roccastrada

Gillian

฿4,393

฿4,947 total

includes taxes & fees

26 Aug - 27 Aug

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 balcony with two wooden chairs overlooking a vineyard and distant mountains.

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

2. Valdonica Winery & Vineyard Residence

Roccastrada

Tim

฿4,878

฿5,480 total

includes taxes & fees

30 Aug - 31 Aug

A historic stone building with multiple windows and a courtyard.

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

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

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

3. Agriturismo Tenuta di Montemassi La Fattoria

Roccastrada

Alice

฿3,399

฿3,815 total

includes taxes & fees

3 Sept - 4 Sept

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

A modern bathroom with a glass shower enclosure, a sink, a toilet, and a window providing natural light.

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

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

4. Le Vie del Mare Camere

Ribolla

฿4,481

฿4,929 total

includes taxes & fees

6 Sept - 7 Sept

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

A hotel with a swimming pool, surrounded by greenery and adjacent to a road.

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.

5. Country House il Ciliegio

Roccastrada

Maaike

฿3,496

฿3,922 total

includes taxes & fees

31 Aug - 1 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 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.

6. Valdonica Winery - Chill in Nature Lodge

Roccastrada

฿6,314

฿7,021 total

includes taxes & fees

6 Sept - 7 Sept

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.

A courtyard with a stone column, potted plants, and a view of a hilltop castle.

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

7. 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

฿2,926

฿4,057 total

includes taxes & fees

14 Sept - 15 Sept

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

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

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

A rustic interior with a chandelier, wooden furniture, and large windows offering a view of the outdoors.

8. Borgo Santo Pietro

Chiusdino

Rachel

฿34,518

฿38,351 total

includes taxes & fees

31 Aug - 1 Sept

A stone wall with a view of rolling hills and mountains.

A courtyard with stone buildings, potted plants, and outdoor seating.

An outdoor dining area with tables and chairs, a flower arrangement, and a view of the countryside.

A large stone castle with multiple towers, surrounded by vineyards and cypress trees.

9. Castello Banfi - Il Borgo - Relais et Chateaux

Montalcino

Jason

฿51,343

฿56,859 total

includes taxes & fees

29 Aug - 30 Aug

A stone building with arched windows and outdoor seating.

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 chair, a desk, and a television. There are two windows with curtains, a chandelier, and a view of the countryside.

10. Conti di San Bonifacio Wine Resort

Gavorrano

Hannah

฿21,867

฿24,206 total

includes taxes & fees

27 Aug - 28 Aug

A pool with a modern water feature and a stone structure.

A buffet table with various desserts and a long dining area with tables and chairs.

A large, multi-story building with a swimming pool, surrounded by lush greenery.

A wicker dining table set with breakfast items, a vase of flowers, and a scenic view.

11. Mercure Petriolo Siena Terme Spa Hotel

Civitella Paganico

Mike

฿3,014

฿3,315 total

includes taxes & fees

26 Aug - 27 Aug

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

A dining area with white tables and chairs, a large mirror, and a wine bottle on one table.

A stone building with a pool, lounge chairs, and a garden with flowers.

A room with a wooden ceiling, a dining table with chairs, a bed, and a window with curtains.

12. Podere Brizio

Montalcino

Orlando Santini

฿7,431

฿8,479 total

includes taxes & fees

30 Aug - 31 Aug

A modern house with a stone facade, a swimming pool, and outdoor seating.

A covered outdoor dining area with stone flooring and metal chairs, overlooking a lush landscape.

A cozy living room with a large wooden table, comfortable seating, and a view of the countryside.

A stone tower with a glass extension, surrounded by greenery and a gravel path.

13. Castello Di Vicarello

Cinigiano

John

฿43,401

฿47,818 total

includes taxes & fees

26 Aug - 27 Aug

A poolside area with lounge chairs, a table with drinks, and a view of hills.

A villa with a swimming pool, stone buildings, and a view of the surrounding countryside.

A four-poster bed with a bench, stone flooring, and a stone wall.

An open door leading to a patio with a view of the countryside, a table with plants, and a television on a wooden cabinet.

14. Capanna Suites

Montalcino

Michael

฿12,606

฿14,249 total

includes taxes & fees

26 Aug - 27 Aug

A person relaxing in a hot tub with a view of a vineyard and mountains in the background.

A dining area with a wooden table set for a meal, a fireplace, and a painting on the wall.

A picnic setup with blankets and cushions on a gravel surface, surrounded by cypress trees and a sunset in the background.

A stone building with a garden and a gazebo.

15. Villa Le Prata - Residenza del Vescovo

Montalcino

Jeffery

฿16,314

฿18,327 total

includes taxes & fees

26 Aug - 27 Aug

A stone building with a pool overlooking a mountainous landscape.

A stone pathway leading to a gate with tall cypress trees on either side, illuminated by soft lighting.

A terrace with stone walls, potted plants, and outdoor furniture overlooking a valley with a river and distant hills during sunset.

A dining area with a table and chairs, a vase with flowers, and a view of the countryside through an arched window.

16. Castello di Velona Resort Thermal SPA & Winery

Montalcino

Rachael

฿25,216

฿28,120 total

includes taxes & fees

28 Aug - 29 Aug

A stone building with a courtyard, surrounded by lush greenery and a hillside.

A wooden pathway leading to a table set for a meal, surrounded by lush greenery and flowering plants.

A stone building with a balcony, surrounded by lush greenery and a view of distant hills.

17. Relais Le Macine di Stigliano

Sovicille

Trevor

฿8,524

฿9,567 total

includes taxes & fees

28 Aug - 29 Aug

An aerial view of a historic town with stone buildings, a prominent church, and a castle-like structure with a sign reading "Castello di Monteverde."

An aerial view of a two-story stone building with a swimming pool in the foreground.

A room with a wooden bench, potted plants, framed artwork, and a view of the outside.

A stone building with a brick archway and a tall cypress tree in front.

18. Hotel Vecchia Oliviera

Montalcino

Roy

฿5,026

฿5,681 total

includes taxes & fees

28 Aug - 29 Aug

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

A modern interior with a large window, a visible staircase, and a seating area.

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

A buffet with various pastries and a floral centerpiece.

19. Hotel Airone

Grosseto

Lisa

฿4,995

฿5,666 total

includes taxes & fees

30 Aug - 31 Aug

A spacious lounge area with a high ceiling, ornate chandelier, and a variety of seating options including sofas and armchairs.

A pool area with lounge chairs and umbrellas, surrounded by lush greenery and hills in the background.

An indoor water feature with a brick archway and a view to the outside.

A table with a bottle of wine, glasses, and a variety of food items including bread and cured meats.

20. L'Andana

Castiglione della Pescaia

Shelby

฿17,282

฿19,392 total

includes taxes & fees

1 Sept - 2 Sept

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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.

See properties

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

A rural landscape with rolling hills, vineyards, and scattered buildings.

Top Roccastrada Hotel Reviews

Hotel Italia

10/10 Excellent

"Staff were most courteous, both at front desk (local map offered on checkin) and in breakfast room. Breakfast buffet offered plenty of choices. Room and bathroom clean and tidy. City attractions dispersed throughout city, but walking made them accessible."

Hotel Minerva

10/10 Excellent

"Had a very nice stay here during the Palio. Easy walk to IL Campo. Located in the Lupa Contrada. Nice neighborhood. Easy walk (10-15 minutes) to the train station. Will stay here again when I return to Siena."

L'Orto delle Terme

8/10 Good

"Nice hotel and good location"

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent

"Everything was absolutely perfect, this is our newest favorite hotel in sienna and we will definitely come back"

Hotel Athena

10/10 Excellent

"We had a superior room, which was very comfortable. We had dinner in the restaurant several times, and the food and drink was excellent. One evening we just enjoyed the cocktail bar, and the staff were fun! Breakfast buffet has everything one could want, and was always fresh. Free parking! You will have an uphill walk to the town centre, but no matter where you go in Siena it’s either up or down. Highly recommended."

The Sense Experience Resort - Preferred Hotels & Resorts

8/10 Good

"Best sand beach in Italy :), Superior rooms have no views and are relatively Dark… Breakfast was very good. No comment to Staff"

Fattoria La Principina Hotel & Congress

8/10 Good

"great facility but needs a general upgrade and remodeling"

Castello di Velona Resort Thermal SPA & Winery

10/10 Excellent

"This property was amazing from the moment we booked. Chiara was extremely helpful with looking into horseback riding and other tours for us. I made a mistake in booking and she caught it and corrected it before we even arrived. She was great. Additionally, the room was beautiful and really clean. The food was delicious and every waitstaff that we encountered was polite and attentive--it could not have been a better experience."

Mastrojanni Relais - Small Luxury Hotels of the World

10/10 Excellent

"Perfect, pristine, could not be any better!"

More cheap stays in Roccastrada

Mediterraneo RTA

Via XXIV Maggio 68H, Marina di Grosseto Grosseto GR

฿2,396

฿2,762 total

21 Sept - 22 Sept

includes taxes & fees

Cannon d'Oro

Via Montanini 28 Siena SI

฿2,535

฿2,980 total

28 Aug - 29 Aug

includes taxes & fees

7.8/10 Good! (258 reviews)

Piccolo Hotel Etruria

Via delle Donzelle, 3 Siena SI

฿3,205

฿3,716 total

27 Aug - 28 Aug

includes taxes & fees

Torre del Fuggisole

Via di Fieravecchia 7 Siena SI

฿3,734

฿4,298 total

30 Aug - 31 Aug

includes taxes & fees

10/10 Exceptional! (48 reviews)

Porta Pispini Residence

Via Baldassarre Peruzzi 33 Siena SI

Get rates

9.4/10 Exceptional! (23 reviews)

Hotel Massa Vecchia

Massa Vecchia, 23 Massa Marittima GR

Get rates

8.6/10 Excellent! (11 reviews)

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 Grand Hotel Continental Siena – Starhotels Collezione and Castello di Velona Resort Thermal SPA & Winery. 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 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?

Castello di Velona Resort Thermal SPA & Winery: Provides 2 outdoor swimming pools, an indoor pool and 3 restaurants. Castello di Leonina Relais and Mastrojanni Relais - Small Luxury Hotels of the World are two additional hotels that offer an on-site pool. 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 197 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 ฿2,762

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Roccastrada

Check prices for these dates

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Our top choices for Roccastrada hotels

1. La Melosa Resort & Spa - Adults Only

2. Valdonica Winery & Vineyard Residence

3. Agriturismo Tenuta di Montemassi La Fattoria

4. Le Vie del Mare Camere

5. Country House il Ciliegio

6. Valdonica Winery - Chill in Nature Lodge

7. Agriturismo Podere Ristella - Wine&Food

8. Borgo Santo Pietro

9. Castello Banfi - Il Borgo - Relais et Chateaux

10. Conti di San Bonifacio Wine Resort

11. Mercure Petriolo Siena Terme Spa Hotel

12. Podere Brizio

13. Castello Di Vicarello

14. Capanna Suites

15. Villa Le Prata - Residenza del Vescovo

16. Castello di Velona Resort Thermal SPA & Winery

17. Relais Le Macine di Stigliano

18. Hotel Vecchia Oliviera

19. Hotel Airone

20. L'Andana

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 Italia

Hotel Minerva

L'Orto delle Terme

Grand Hotel Continental Siena – Starhotels Collezione

Hotel Athena

The Sense Experience Resort - Preferred Hotels & Resorts

Fattoria La Principina Hotel & Congress

Castello di Velona Resort Thermal SPA & Winery

Mastrojanni Relais - Small Luxury Hotels of the World

More cheap stays in Roccastrada

Mediterraneo RTA

Cannon d'Oro

Piccolo Hotel Etruria

Torre del Fuggisole

Porta Pispini Residence

Hotel Massa Vecchia

Frequently asked questions

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