Roccastrada Holiday Houses

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

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Our top choices for Roccastrada holiday homes

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

1. 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

includes taxes & fees

23 Oct - 24 Oct

A stone building with a tree in front, outdoor seating with tables and chairs, and a paved walkway.

2. Farmhouse "Casa Girasole" with Private Pool, Terraces & Wi-Fi

Roccastrada

includes taxes & fees

25 Oct - 26 Oct

A house with a patio, a table with chairs, and a large umbrella.

3. Casetta di campagna indipendente

Roccastrada

A patio with a wooden table, a blue lounge chair, a striped chair, and a large umbrella.

4. Detached house with a garden, just a few minutes from the Abbey of San Galgano

Toscana

Julie M.

includes taxes & fees

22 Oct - 23 Oct

An outdoor patio with a wooden floor, a covered seating area, and a view of a green landscape.

5. Farmhouse 'Le Gerlette - La Stalla' with Shared Pool, Wi-Fi and Air Conditioning

Braccagni

includes taxes & fees

26 Oct - 27 Oct

6. Villa Pianosa, Botri dei Lumachi

Toscana

includes taxes & fees

22 Oct - 23 Oct

7. Villa Giglio, Botri dei Lumachi

Toscana

includes taxes & fees

22 Oct - 23 Oct

A stone building with two windows, one with green shutters, and a rose bush in the foreground.

8. Exclusive Stone Tower.

Casciano

Ryan C.

includes taxes & fees

22 Oct - 23 Oct

A stone building with a wooden door and two windows with shutters.

9. The Casetta di Brunello, quiet and breathtaking views

Montalcino

MICHAEL H.

includes taxes & fees

3 Nov - 4 Nov

A historic stone building with multiple windows and a tower, situated by a beach with clear blue water.

10. Villino il Corbezzolo, Tuscany, sea, beach, heated swimming pool,spa, gym kneipp

Gavorrano Toscana

"Last year we have spent our holiday at this beautiful place with our big family. Nice large garden with plenty of flowers, trees, butterflies, small gecos. Quiet place, beautiful views. Nice place for grilling. Supermarket 5 min by car, the beach Follonica cca 15 min by car. We have booked all the villas except the smallest one, so nobody disturbed us. For us one of the best vacations. If possible will come again for sure!!"

N4Z5dL0p4M4YOjGgLujvG8U2R6jayhLXs+CXI2mhH5hzPz8z6DyPwetl2fEUoYi6GF8RFb+a1xxfKcZRUToFwkdqmIjIeNJLTf2m N.

includes taxes & fees

22 Oct - 23 Oct

A terrace with a table set for breakfast, overlooking a mountainous landscape.

11. Il Borghetto - The House on Elba, Rooftop Terrace with Panoramic Views

Castelnuovo dell'Abate

"Il Borghetto is a renovated house in the little village of Castelnuovo dell'Abate, one of the medieval hilltop villages in the UNESCO world heritage-listed Val D'Orcia. It is charming and the beds are very comfortable, but be prepared to take luggage up a steep street to the front door and then steep stairs to both bedrooms. Each bedroom is on a different floor so there is considerable privacy. The piece de la resistance is the rooftop terrace, with 180 degree panoramic views over the valley and...

Judith F.

includes taxes & fees

31 Oct - 1 Nov

A cozy room with a wooden ceiling, a dining table set with plates, cups, and a vase, and a sofa with a book on it.

12. Casa di Via del Corallo Gerfalco – Historic Village Apartment with Nature Reserve Access

Località Gerfalco Montieri

includes taxes & fees

31 Oct - 1 Nov

A gated entrance with a number plaque, a pathway leading to a building, and a parked vehicle.

13. Tuscan House: Spacious, Traditional Tuscan Apartment with Plenty of Outdoor Space and Breakfast Included

Monteroni d'Arbia

includes taxes & fees

22 Oct - 23 Oct

A balcony with a tiled roof, a table with chairs, and a guitar leaning against the wall.

14. Holiday Home 'La Nobiltà Del Tempo' with Balcony and Wi-Fi

Poggiobrucoli

includes taxes & fees

2 Nov - 3 Nov

A two-story building with a stone facade and a tiled roof.

15. A Nest with a View - A Romantic Retreat Within the City Walls

Radicondoli

includes taxes & fees

16 Nov - 17 Nov

A stone building with a sign reading "Borgo di Mezzo".

16. The Gelda house, relax with a view

Castelnuovo dell'Abate

Lisa K.

includes taxes & fees

26 Oct - 27 Oct

A pathway leading to a building with stone walls and a tree.

17. A typical Tuscan country house

Montalcino

includes taxes & fees

13 Nov - 14 Nov

A narrow stone alley with potted plants and benches.

18. The House of Alice, charm and relaxation

Montalcino (SI)

Robert S.

includes taxes & fees

1 Nov - 2 Nov

A stone building with a flat roof, multiple windows, and a small porch area.

19. Podere Cagnesi: Relaxation in nature

Podere Cagnesi

includes taxes & fees

22 Oct - 23 Oct

An outdoor patio with tables and chairs, surrounded by greenery and a view of distant hills.

20. Podere Belsogno-camera Lavanda

Montalcino

Johannes S.

includes taxes & fees

1 Nov - 2 Nov

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Top Roccastrada Hotel Reviews

Il Chiostro del Carmine

8/10 Good

"Air conditioning was not working well. The bathroom was beautiful but the shower was cycling between very hot to very cold"

Hotel Italia

10/10 Excellent

"We stayed at this basic but nice 3-star hotel just one night while visiting Siena. We had a room for 3 for my wife and I and our adult daughter. The hotel was easy walking distance from the train/bus station. It's kind of weird because you enter an indoor shopping area across the street from the station and then go up about 6 banks of escalators to get up the hillside. Then the hotel is just a block away. One of the AC units didn't work but friendly staff helped start the other one. All staff were very friendly and spoke English. Easy walk a few blocks into the old city. Wonderful breakfast!!! We were able to leave our bags for most of the day while we explored the city prior to leaving on the bus again. I would definitely stay again."

Villa Ermellina Siena, a Tribute Portfolio Hotel

8/10 Good

"We were in one of the other wings so it wasn't in the main building. It was a rainy week and we had a wedding and there were no rooms in the main building to accommodate us. There is no overhead so you will get wet and there are a million stairs to get to that wing (you will need help if you have a ton of luggage as well). The hotel is far from city center too, you need to plan your cabs out accordingly."

Valdonica Winery & Vineyard Residence

10/10 Excellent

"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 regret is that we could not stay longer. Seriously cannot overstate how relaxing and beautiful this place is, will be recommending to friends and family and hopefully returning soon ourselves!"

Find out more about Roccastrada

Roccastrada Holiday Homes information

Number of reviews	53
Accommodation	898 Holiday Homes
Lowest Price	NZ$159
Highest Price	NZ$11,777

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Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Roccastrada holiday homes

1. Agriturismo Benvenuti

2. Farmhouse "Casa Girasole" with Private Pool, Terraces & Wi-Fi

3. Casetta di campagna indipendente

4. Detached house with a garden, just a few minutes from the Abbey of San Galgano

5. Farmhouse 'Le Gerlette - La Stalla' with Shared Pool, Wi-Fi and Air Conditioning

6. Villa Pianosa, Botri dei Lumachi

7. Villa Giglio, Botri dei Lumachi

8. Exclusive Stone Tower.

9. The Casetta di Brunello, quiet and breathtaking views

10. Villino il Corbezzolo, Tuscany, sea, beach, heated swimming pool,spa, gym kneipp

11. Il Borghetto - The House on Elba, Rooftop Terrace with Panoramic Views

12. Casa di Via del Corallo Gerfalco – Historic Village Apartment with Nature Reserve Access

13. Tuscan House: Spacious, Traditional Tuscan Apartment with Plenty of Outdoor Space and Breakfast Included

14. Holiday Home 'La Nobiltà Del Tempo' with Balcony and Wi-Fi

15. A Nest with a View - A Romantic Retreat Within the City Walls

16. The Gelda house, relax with a view

17. A typical Tuscan country house

18. The House of Alice, charm and relaxation

19. Podere Cagnesi: Relaxation in nature

20. Podere Belsogno-camera Lavanda

Find holiday rentals that suit your style

Top Roccastrada Hotel Reviews

Il Chiostro del Carmine

Hotel Italia

Villa Ermellina Siena, a Tribute Portfolio Hotel

Castello di Velona Resort Thermal SPA & Winery

L'Orto delle Terme

Hotel Chiusarelli

Grand Hotel Bastiani

Four Points by Sheraton Siena

Valdonica Winery & Vineyard Residence

Find out more about Roccastrada

Roccastrada Holiday Homes information

Explore a world of travel with Expedia

Holiday Homes in Roccastrada

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Roccastrada holiday homes

1. Agriturismo Benvenuti

2. Farmhouse "Casa Girasole" with Private Pool, Terraces & Wi-Fi

3. Casetta di campagna indipendente

4. Detached house with a garden, just a few minutes from the Abbey of San Galgano

5. Farmhouse 'Le Gerlette - La Stalla' with Shared Pool, Wi-Fi and Air Conditioning

6. Villa Pianosa, Botri dei Lumachi

7. Villa Giglio, Botri dei Lumachi

8. Exclusive Stone Tower.

9. The Casetta di Brunello, quiet and breathtaking views

10. Villino il Corbezzolo, Tuscany, sea, beach, heated swimming pool,spa, gym kneipp

11. Il Borghetto - The House on Elba, Rooftop Terrace with Panoramic Views

12. Casa di Via del Corallo Gerfalco – Historic Village Apartment with Nature Reserve Access

13. Tuscan House: Spacious, Traditional Tuscan Apartment with Plenty of Outdoor Space and Breakfast Included

14. Holiday Home 'La Nobiltà Del Tempo' with Balcony and Wi-Fi

15. A Nest with a View - A Romantic Retreat Within the City Walls

16. The Gelda house, relax with a view

17. A typical Tuscan country house

18. The House of Alice, charm and relaxation

19. Podere Cagnesi: Relaxation in nature

20. Podere Belsogno-camera Lavanda

Find holiday rentals that suit your style

Top Roccastrada Hotel Reviews

Il Chiostro del Carmine

Find out more about Roccastrada

Roccastrada Holiday Homes information

Explore a world of travel with Expedia