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

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Roccastrada holiday rentals

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

1. Country House il Ciliegio

Country House il Ciliegio
Roccastrada
9.2 out of 10, Wonderful, (7 reviews)
"It was a very pleasant stay, a warm welcome. A beautiful location surrounded by nature."
Netherlands
Maaike
The price is 2.207.357 ₫
2.486.275 ₫ total
includes taxes & fees
23 Oct - 24 Oct
Country House il Ciliegio
A wooden interior with a glass-enclosed shower, large windows, and a wooden floor.

2. Agriturismo Benvenuti

Agriturismo Benvenuti
Roccastrada
6.0 out of 10, (3 reviews)
"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."
Italy
Ivano
The price is 1.808.920 ₫
2.338.902 ₫ total
includes taxes & fees
23 Oct - 24 Oct
Agriturismo Benvenuti
A bedroom with a bed, a bedside table, a TV mounted on the wall, and a sliding glass door leading to a balcony with a view of greenery and hills.

3. Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (32 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is 1.613.960 ₫
2.153.536 ₫ total
includes taxes & fees
4 Nov - 5 Nov
Tuscasì Aparthotel
A bakery display with pastries and a coffee station.

4. B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (215 reviews)
"We enjoyed our stay very much. Staff was very friendly and offered great advise on places to eat. The rooms had great charm to them. We were delighted with our selection of where to stay."
United States
Enrique
The price is 1.911.902 ₫
2.219.456 ₫ total
includes taxes & fees
2 Nov - 3 Nov
B&B Il Corso
A restaurant with tables and wicker chairs, large windows, and a view of buildings and greenery.

5. Palazzo Saloni

Palazzo Saloni
Montalcino
10.0 out of 10, Exceptional, (11 reviews)
"Excellent location to tour wine country montalcino."
United States
Michael
The price is 6.694.086 ₫
7.654.373 ₫ total
includes taxes & fees
17 Nov - 18 Nov
Palazzo Saloni
A large estate with multiple buildings, a swimming pool, and a well-maintained garden.

6. Dimora Santa Margherita - Boutique Hotel

Dimora Santa Margherita - Boutique Hotel
Cinigiano
8.2 out of 10, Very good, (12 reviews)
"We had a great time at this place. The room was spectacular and the views were some of the best on this entire trip. We would definitely come back. The only thing that we didn’t love was the menu at the restaurant is quite limited and there were not many things on the menu that appealed to us, as we were looking for more traditional Tuscan food. Breakfast was great and very traditional. The staff was fantastic and very helpful. Loved it."
Canada
Nicole
The price is 8.876.769 ₫
9.822.512 ₫ total
includes taxes & fees
22 Oct - 23 Oct
Dimora Santa Margherita - Boutique Hotel
An aerial view of a historic stone building complex with a swimming pool, surrounded by lush greenery and vineyards.

7. Bosco della Spina

Bosco della Spina
Murlo
9.6 out of 10, Exceptional, (185 reviews)
"Very peaceful and scenic. Wish we had stayed longer."
United States
Amir
The price is 2.300.818 ₫
2.763.626 ₫ total
includes taxes & fees
26 Oct - 27 Oct
Bosco della Spina
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Roccastrada Hotel Reviews

Castello di Velona Resort Thermal SPA & Winery

Castello di Velona Resort Thermal SPA & Winery

10/10 Excellent
"La vue est panoramique et le château est grandiose"
Annie 4-night trip
Posted 2 days ago
Castello di Velona Resort Thermal SPA & Winery

Frequently asked questions

Can I find holiday rentals in Roccastrada?

Yes, there are holiday rentals close to the most popular sights in Roccastrada, or you can select a more secluded option if you're looking for a relaxing stay.

How many holiday rentals are there in Roccastrada?

Choose from 77 Expedia holiday rentals in Roccastrada for a memorable holiday.

What’s there to see and do in Roccastrada?

I Canaloni del Torrente Farma and Val di Merse are a couple of lovely local spots to get outside and enjoy nature. Podere Ristella Vineyards and Winery and Castello del Belagaio are other places to visit while you're in town.

What’s a holiday rental in Roccastrada like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Roccastrada. Holiday rentals provide amenities such as WiFi and washers and dryers so your stay will be comfortable. If you're concerned about cleanliness, a holiday rental can provide a sense of seclusion away from shared hotel lifts and busy concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for small groups.