Roccastrada Hotels

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Check prices for these dates

Tonight
8 Nov - 9 Nov
Tomorrow
9 Nov - 10 Nov
Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov

Where to stay in Roccastrada?

Properties are selected based on real traveller reviews and popularity among guests who’ve booked a night in Roccastrada on Hotels.com. These Roccastrada hotels consistently deliver on quality, location and traveller experience. Last updated on 8 November 2026.
A stone building with multiple windows and a balcony, a table set for dining, and lush greenery in the foreground.

1. Historic Farmhouse Casa del Chiodo

Historic Farmhouse Casa del Chiodo
Roccastrada
10.0 out of 10, Exceptional, (6 reviews)
The price is S$151
includes taxes & fees
9 Nov - 10 Nov
Historic Farmhouse Casa del Chiodo
A spacious dining area with a large table and chairs, stone walls, and a view of the mountains.

2. Valdonica Winery & Vineyard Residence

Valdonica Winery & Vineyard Residence
Roccastrada
9.2 out of 10, Wonderful, (46 reviews)
Immerse yourself in wine country charm at this Roccastrada vineyard residence. Enjoy massages at the spa, sip local vintages at the winery bar, and cool off in the seasonal pool. Free breakfast, WiFi, and parking enhance your stay near Sassoforte Castle.
The price is S$214
includes taxes & fees
9 Nov - 10 Nov
Valdonica Winery & Vineyard Residence
Point of interest

3. B&B da Nada Locanda Toscana

B&B da Nada Locanda Toscana
Roccastrada
9.6 out of 10, Exceptional, (18 reviews)
Experience Tuscan countryside charm at this cosy B&B featuring the convenient Locanda Da Nada restaurant serving three daily meals. Enjoy complimentary breakfast and WiFi while exploring nearby Sassoforte Castle and local vineyards.
The price is S$105
includes taxes & fees
11 Nov - 12 Nov
B&B da Nada Locanda Toscana
A bedroom with a wooden headboard, a large bed, a framed picture on the wall, and a sliding glass door leading to an outdoor area.

4. Valdonica Winery - Chill in Nature Lodge

Valdonica Winery - Chill in Nature Lodge
Roccastrada
Immerse yourself in Italian countryside at this Roccastrada winery lodge. Enjoy Italian cuisine at the on-site restaurant, indulge in massages, or sip local vintages by the seasonal pool. Nearby attractions include Sassoforte Castle and charming vineyard estates.
The price is S$219
includes taxes & fees
10 Nov - 11 Nov
Valdonica Winery - Chill in Nature Lodge
A courtyard with stone steps leading to a small building, surrounded by lush greenery and stone buildings in the background.

5. Country House il Ciliegio

Country House il Ciliegio
Roccastrada
9.2 out of 10, Wonderful, (7 reviews)
Escape to this tranquil apartment in Roccastrada featuring a seasonal outdoor pool with dedicated children's area. The rooftop terrace offers sweeping views while conveniences like washing machines make extended stays comfortable. Sassoforte Castle is nearby.
The price is S$127
includes taxes & fees
13 Nov - 14 Nov
Country House il Ciliegio
A modern living room with a sofa, a coffee table, a TV on a wooden cabinet, and a large potted plant.

6. Le Vie del Mare Camere

Le Vie del Mare Camere
Ribolla
The price is S$155
includes taxes & fees
9 Nov - 10 Nov
Le Vie del Mare Camere
A pool with lounge chairs and a sunset view.

7. Mercure Petriolo Siena Terme Spa Hotel

Mercure Petriolo Siena Terme Spa Hotel
5.0 star property
Civitella Paganico
8.6 out of 10, Excellent, (267 reviews)
The price is S$118
includes taxes & fees
9 Nov - 10 Nov
Mercure Petriolo Siena Terme Spa Hotel
A stone building with a pool, lounge chairs, and a garden with flowers.

8. Podere Brizio

Podere Brizio
Montalcino
9.8 out of 10, Exceptional, (180 reviews)
Immerse yourself in authentic Tuscany at this Montalcino farm stay. Savour free breakfast before exploring nearby wineries, then return for tennis matches or spa treatments featuring aromatherapy and hydrotherapy. The outdoor pool offers perfect vineyard relaxation.
The price is S$289
includes taxes & fees
16 Nov - 17 Nov
Podere Brizio
A poolside area with lounge chairs, a table with drinks, and a view of hills.

9. Capanna Suites

Capanna Suites
Montalcino
9.8 out of 10, Exceptional, (169 reviews)
Immerse yourself in Montalcino's vineyard views at this charming farm stay. Enjoy the winery, seasonal outdoor pool, and Italian dining at Il Passaggio by Capanna restaurant. Free breakfast, WiFi, and parking complement easy access to Cantina di Montalcino and Caparzo Winery.
The price is S$374
includes taxes & fees
29 Nov - 30 Nov
Capanna Suites
A stone building with a stone staircase, surrounded by lush greenery and a stone pathway.

10. Le Ragnaie

Le Ragnaie
Montalcino
9.2 out of 10, Wonderful, (343 reviews)
Wine lovers will adore this Montalcino farm stay with complimentary breakfast and WiFi. After exploring nearby Poggio Antico, unwind by the seasonal outdoor pool or stroll through the garden. Free parking makes day trips to Tuscan attractions effortless.
The price is S$162
includes taxes & fees
16 Nov - 17 Nov
Le Ragnaie
A historic building with a sign reading "Bastiani Grand Hotel."

11. Grand Hotel Bastiani

Grand Hotel Bastiani
4.0 star property
Grosseto
8.6 out of 10, Excellent, (260 reviews)
This luxury hotel offers buffet breakfast and excellent access to nearby attractions like Colonna Romana and Piazza Dante. Explore local trails with hiking and mountain biking options, then return to this well-maintained property praised by travellers.
The price is S$112
includes taxes & fees
7 Dec - 8 Dec
Grand Hotel Bastiani
A poolside area with lounge chairs, a table with wine glasses and a bottle, and a view of a mountainous landscape.

12. SI Montalcino Hotel

SI Montalcino Hotel
3.0 star property
Montalcino
9.2 out of 10, Wonderful, (419 reviews)
Escape to this charming Montalcino retreat near the historic fortress with free perks including breakfast, WiFi, and parking. Cool off in the seasonal pool or unwind at the bar after exploring nearby Tenuta Greppo Franco Biondi Santi.
The price is S$197
includes taxes & fees
12 Nov - 13 Nov
SI Montalcino Hotel
A hot tub with a view of a historic building and mountains.

13. Casa Franci Montalcino

Casa Franci Montalcino
Montalcino
9.8 out of 10, Exceptional, (47 reviews)
Immerse yourself in Tuscan charm at this cosy B&B near the historic Fortress of Montalcino. Enjoy complimentary full breakfast each morning, free WiFi, and dining options at 2 on-site restaurants, all while exploring the cultural treasures of this wine region.
The price is S$331
includes taxes & fees
9 Nov - 10 Nov
Casa Franci Montalcino
A balcony with a table set for a meal, overlooking a scenic view of a town and mountains.

14. Grand Hotel Impero - Wellness & Exclusive SPA

Grand Hotel Impero - Wellness & Exclusive SPA
4.0 star property
Castel del Piano
9.2 out of 10, Wonderful, (100 reviews)
Immerse yourself in wellness at this Castel del Piano sanctuary with indulgent spa treatments and Ayurvedic therapies. The hotel's La Corte restaurant serves delicious local cuisine, while Mount Amiata Fauna Park awaits nearby exploration.
The price is S$107
includes taxes & fees
24 Nov - 25 Nov
Grand Hotel Impero - Wellness & Exclusive SPA
A courtyard with brick buildings, a column, and potted plants.

15. Castello di Leonina Relais

Castello di Leonina Relais
4.0 star property
Asciano
9.2 out of 10, Wonderful, (168 reviews)
This restored castle relais offers an enchanting escape with an outdoor pool and hot tub. Enjoy Italian cuisine at Il Balcone di Leonina restaurant, then unwind with deep-tissue massages. Just 9 minutes from Asciano Arbia Station and near Siena Circuit.
The price is S$107
includes taxes & fees
3 Dec - 4 Dec
Castello di Leonina Relais
A stone building with a pathway leading to a door, surrounded by trees and illuminated by warm lights.

16. L'Orto delle Terme

L'Orto delle Terme
San Quirico d'Orcia
9.6 out of 10, Exceptional, (64 reviews)
Unwind at this charming B&B with on-site hot springs and massage services in the heart of Tuscany. Enjoy complimentary breakfast at the café, then explore nearby Piazza delle Sorgenti or sip drinks at the cosy bar lounge.
The price is S$163
includes taxes & fees
9 Nov - 10 Nov
L'Orto delle Terme
A villa with a swimming pool, surrounded by trees and hills.

17. Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel
5.0 star property
Montalcino
10.0 out of 10, Exceptional, (87 reviews)
The price is S$1,288
includes taxes & fees
4 Dec - 5 Dec
Castiglion del Bosco, A Rosewood Hotel
A table set for two with a wine glass, a bowl of nuts, and a glass of water.

18. Relais degli Angeli

Relais degli Angeli
Siena City Centre
9.8 out of 10, Exceptional, (347 reviews)
Wake up to medieval splendour at this centrally located inn with free WiFi. Explore nearby Palazzo Salimbeni on foot or venture further using hiking trails. After sightseeing, unwind on the rooftop terrace while the helpful staff ensures a memorable Tuscan stay.
The price is S$162
includes taxes & fees
1 Dec - 2 Dec
Relais degli Angeli
A bedroom with a bed, a chair, a table, and a stone wall.

19. Dimora delle Muse

Dimora delle Muse
Montalcino
10.0 out of 10, Exceptional, (76 reviews)
Wake up to complimentary breakfast at this cosy Montalcino retreat. Nearby attractions include Poggio Antico and the historic Abbazia di Sant'Antimo. With free WiFi and parking, this B&B offers a perfect base for exploring Tuscan wine country.
The price is S$292
includes taxes & fees
10 Nov - 11 Nov
Dimora delle Muse
A lobby with a marble floor, a chandelier, a reception desk, and large green plants.

20. Hotel Chiusarelli

Hotel Chiusarelli
3.0 star property
Siena City Centre
9.0 out of 10, Wonderful, (1,002 reviews)
Wake up to a celebrated breakfast at this Tuscan treasure, just a 10-minute walk from Piazza del Campo and near Stadio Artemio Franchi. The garden, terrace, and attentive staff create a refreshing retreat after exploring Siena's medieval marvels.
The price is S$113
includes taxes & fees
9 Dec - 10 Dec
Hotel Chiusarelli
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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Check out pet-friendly hotels in Roccastrada

Point of interest
B&B da Nada Locanda Toscana

B&B da Nada Locanda Toscana

B&B da Nada Locanda Toscana
Roccastrada
9.6 out of 10, Exceptional, (18)
The price is S$105
includes taxes & fees
11 Nov - 12 Nov
B&B da Nada Locanda 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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Go beyond your typical stay in Roccastrada

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When is the best time to visit Roccastrada?

Our prices for hotels in Roccastrada are cheapest in January

Price trends for hotels in Roccastrada

Pricing is based on two traveller single night rates
View properties in November
Currently viewing crowd sizes and weather for November.

November

High 16°C / low 10°C. Sunny most days.
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November, no crowd data, average high temperature 16 degrees Celsius, average low temperature 10 degrees Celsius. Sunny most days.
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December, no crowd data, average high temperature 13 degrees Celsius, average low temperature 7 degrees Celsius. Sunny most days.
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11°
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January, no crowd data, average high temperature 11 degrees Celsius, average low temperature 5 degrees Celsius. Sunny most days.
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12°
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February, no crowd data, average high temperature 12 degrees Celsius, average low temperature 5 degrees Celsius. Sunny most days.
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15°
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March, no crowd data, average high temperature 15 degrees Celsius, average low temperature 7 degrees Celsius. Sunny most days.
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18°
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April, no crowd data, average high temperature 18 degrees Celsius, average low temperature 10 degrees Celsius. Sunny most days.
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21°
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May, no crowd data, average high temperature 21 degrees Celsius, average low temperature 13 degrees Celsius. Sunny most days.
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26°
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June, no crowd data, average high temperature 26 degrees Celsius, average low temperature 17 degrees Celsius. Sunny most days.
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July, no crowd data, average high temperature 30 degrees Celsius, average low temperature 20 degrees Celsius. Sunny most days.
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August, no crowd data, average high temperature 30 degrees Celsius, average low temperature 21 degrees Celsius. Sunny most days.
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26°
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September, no crowd data, average high temperature 26 degrees Celsius, average low temperature 18 degrees Celsius. Sunny most days.
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October, no crowd data, average high temperature 21 degrees Celsius, average low temperature 14 degrees Celsius. Sunny most days.
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Monthly weather averages (˚C)

Top landmarks in Roccastrada

Podere Ristella Vineyards and Winery

Travellers might want a tour of Podere Ristella Vineyards and Winery, just one of the places to visit, located 6 mi (9.6 km) from central Roccastrada.
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Learn more about Roccastrada

Roccastrada is well known for its attractions such as I Canaloni del Torrente Farma and Podere Ristella Vineyards and Winery.

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

Check out reviews of Roccastrada hotels guests love

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

Capanna Suites

Capanna Suites
Montalcino

10/10 Exceptional

We thoroughly enjoyed our stay at Capanna Suites - the property and room was very well thought out and beautiful, the sunset view was amazing and the staff were extremely helpful (thanks in particular to Giulia). We felt well recharged after our stay, especially after the spa session.
Singapore
Jonathan
Reviewed June 8, 2026
Capanna Suites

Frequently Asked Questions

Can I book a refundable accommodation option in Roccastrada?

If you want the flexibility to change your plans to Roccastrada, most hotels offer refundable* rates that you can book. You can see this accommodation by searching our site and using the "fully refundable" filter to narrow the results down.

Where can I stay in Roccastrada if I want a holiday rental instead of a hotel?

If you're looking for a good alternative to a hotel, review our selection of 77 holiday homes. You can also book one of 46 apartments or 26 villas.

What will the weather in Roccastrada be like during my visit?

The warmest months in Roccastrada are usually August and July, with an average temperature of 23°C. January and February are the chilliest months, when the average temperature is 9°C. The rainiest months are November and October.

Why should I book my Roccastrada hotel with Hotels.com?

There are plenty of reasons to book your Roccastrada travel with us: our free cancellations on selected hotels* gives you the flexibility you're looking for, our Price Guarantee ensures that you always get the lowest price, and you can earn rewards on every booking.

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