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

Roccastrada Holiday Rentals

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

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 S$126
includes taxes & fees
8 Nov - 9 Nov
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 S$115
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, (31 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is S$106
includes taxes & fees
2 Nov - 3 Nov
Tuscasì Aparthotel
An aerial view of a historic stone building complex with a swimming pool, surrounded by lush greenery and vineyards.

4. Bosco della Spina

Bosco della Spina
Murlo
9.6 out of 10, Exceptional, (183 reviews)
"Lovely stay! I would highly recommend this hotel. The indoor pool was just so enjoyable after a day out sightseeing. "
United Kingdom
Lizl
The price is S$136
includes taxes & fees
1 Nov - 2 Nov
Bosco della Spina
A restaurant with tables and wicker chairs, large windows, and a view of buildings and greenery.

5. Palazzo Saloni

Palazzo Saloni
Montalcino
9.8 out of 10, Exceptional, (10 reviews)
"Excellent location to tour wine country montalcino."
United States
Michael
The price is S$337
includes taxes & fees
8 Nov - 9 Nov
Palazzo Saloni
A spacious hotel room with a large bed, a sitting area with chairs, and a view through an arched doorway to another room.

6. La Terrazza Sul Campo Rooming House

La Terrazza Sul Campo Rooming House
Siena City Centre
9.8 out of 10, Exceptional, (251 reviews)
"Great stay. Thanks for the hospitality and kindness."
United Kingdom
Agnieszka
The price is S$147
includes taxes & fees
2 Nov - 3 Nov
La Terrazza Sul Campo Rooming House
A wine cellar with stone walls, wine racks, and tables with glasses and candles.

7. Il Battistero Siena - Residenza d'Epoca

Il Battistero Siena - Residenza d'Epoca
Siena City Centre
9.6 out of 10, Exceptional, (222 reviews)
"The room was so unique and convenient for everything we wanted to do. Wish we could have spent more than one night!"
United States
Kellie
The price is S$192
includes taxes & fees
5 Nov - 6 Nov
Il Battistero Siena - Residenza d'Epoca
A wooden door with a metal handle, a brick archway, a staircase, and a flower pot on the wall.

8. Idolina Guest House

Idolina Guest House
Montalcino
9.6 out of 10, Exceptional, (118 reviews)
"Felt like home. The central kitchen / coffee area felt like home."
United States
Bradley
The price is S$131
includes taxes & fees
27 Oct - 28 Oct
Idolina Guest House
A dining table with a bottle of wine, two wine glasses, a candle, and a vase with flowers.

9. B&B Le Scalette di Piazza

B&B Le Scalette di Piazza
Montalcino
9.4 out of 10, Exceptional, (105 reviews)
The price is S$170
includes taxes & fees
14 Oct - 15 Oct
B&B Le Scalette di Piazza
A hotel room with a bed, a bedside table with a lamp, a potted plant, and a view of the outside through the window.

10. PALAZZO DEL PAPA

PALAZZO DEL PAPA
Siena City Centre
9.6 out of 10, Exceptional, (116 reviews)
"Hamza is so helpful!! Finding the property is a little tricky, but he helped every step of the way! He also provided excellent dining suggestions and a great cooking class!"
United States
Charles
The price is S$261
includes taxes & fees
3 Nov - 4 Nov
PALAZZO DEL PAPA
A table set with breakfast items on a balcony overlooking a historic town.

11. Residenza d'Epoca Palazzo Borghesi

Residenza d'Epoca Palazzo Borghesi
Siena City Centre
9.6 out of 10, Exceptional, (132 reviews)
"We had a great experience Property is perfectly located."
United States
Roman
The price is S$217
includes taxes & fees
4 Nov - 5 Nov
Residenza d'Epoca Palazzo Borghesi
A bakery display with pastries and a coffee station.

12. B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (214 reviews)
The price is S$121
includes taxes & fees
4 Nov - 5 Nov
B&B Il Corso
A large estate with multiple buildings, a swimming pool, and a well-maintained garden.

13. 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 S$430
includes taxes & fees
25 Oct - 26 Oct
Dimora Santa Margherita - Boutique Hotel
A poolside area with two glasses of water, candles, and a stone pathway.

14. Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.2 out of 10, Wonderful, (101 reviews)
"Great location and lovely pool. Rooms were large but the place is definitely dated. Breakfast was decent with a lot of options. Parking wasn’t all that great but nevertheless on the property itself"
Canada
Sunil
The price is S$246
includes taxes & fees
12 Oct - 13 Oct
Casanova - Panoramic Rooms and Suites
A couple seated at a table with drinks, overlooking a pool area with lounge chairs and umbrellas.

15. Fattoria Maremmana

Fattoria Maremmana
4.0 star property
Grosseto
8.0 out of 10, Very good, (11 reviews)
"Staff very friendly and helpful. Very quiet stay as we visited at the beginning of the slow season. "
United States
James
The price is S$309
includes taxes & fees
10 Oct - 11 Oct
Fattoria Maremmana
Outdoor pool

16. Residence Arianna

Residence Arianna
Sovicille
9.6 out of 10, Exceptional, (9 reviews)
"The place is excellent! The owner and her daughter extremely friendly and kind! They helped us with everything we needed. I will definitely stay here again. I highly recommend this place!"
United States
Violeta
The price is S$192
includes taxes & fees
9 Nov - 10 Nov
Residence Arianna
A bathroom with a window view of a historic building and a tiled roof.

17. Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (487 reviews)
"Great location right in the heart of everything and next to an escalator that takes you to the main plaza. Very comfortable bed, friendly staff. Convenient parking option very close by."
United States
Heather
The price is S$163
includes taxes & fees
2 Nov - 3 Nov
Siena Vip
A rectangular pool with a metal ladder, surrounded by wooden lounge chairs and a stone deck.

18. Corte Francigena - Apartments

Corte Francigena - Apartments
Montalcino
9.8 out of 10, Exceptional, (19 reviews)
"The unit is very clean, awesome breakfast, beautiful view"
Canada
Ivan
The price is S$163
includes taxes & fees
8 Nov - 9 Nov
Corte Francigena - Apartments
An outdoor swimming pool with a wooden pergola, lounge chairs, and a stone wall backdrop.

19. Guild Living Siena Senior Resort & Residence

Guild Living Siena Senior Resort & Residence
Scacciapensieri
8.8 out of 10, Excellent, (55 reviews)
"Amazing! Thank you!"
United Kingdom
Lucy
The price is S$186
includes taxes & fees
9 Nov - 10 Nov
Guild Living Siena Senior Resort & Residence
A stone courtyard with a bench, potted plants, and a building in the background.

20. Casa di Campagna in Toscana

Casa di Campagna in Toscana
Sovicille
9.6 out of 10, Exceptional, (27 reviews)
"A wonderful stay. "
United States
Sally
The price is S$147
includes taxes & fees
18 Oct - 19 Oct
Casa di Campagna in Toscana
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

Hotel Athena

Hotel Athena

10/10 Excellent
"Lovely hotel in Siena. Well located for exploring on foot with the main Palazzo and the Duomo no more than 15 minutes away. Really enjoyed the rooftop patio!"
Hillaine 3-night trip
Posted 3 hours ago
Hotel Athena

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.