Hotels in Roccastrada

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Check prices for these dates

Tonight
5 Nov - 6 Nov
Tomorrow
6 Nov - 7 Nov
This weekend
6 Nov - 8 Nov
Next weekend
13 Nov - 15 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 6 November 2026.
A spacious dining area with a large table and chairs, stone walls, and a view of the mountains.

1. 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 3.796.999 ₫
4.263.413 ₫ total
includes taxes & fees
8 Nov - 9 Nov
Valdonica Winery & Vineyard Residence
A stone building with multiple windows and a balcony, a table set for dining, and lush greenery in the foreground.

2. Historic Farmhouse Casa del Chiodo

Historic Farmhouse Casa del Chiodo
Roccastrada
10.0 out of 10, Exceptional, (6 reviews)
The price is 2.731.475 ₫
3.062.432 ₫ total
includes taxes & fees
9 Nov - 10 Nov
Historic Farmhouse Casa del Chiodo
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 1.869.228 ₫
2.113.959 ₫ total
includes taxes & fees
6 Nov - 7 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 4.572.113 ₫
5.087.133 ₫ total
includes taxes & fees
8 Nov - 9 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 2.258.019 ₫
2.541.630 ₫ total
includes taxes & fees
6 Nov - 7 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 2.841.385 ₫
3.125.524 ₫ total
includes taxes & fees
17 Nov - 18 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 2.165.359 ₫
2.381.895 ₫ total
includes taxes & fees
8 Nov - 9 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, (179 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 5.155.406 ₫
5.902.298 ₫ total
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 8.355.711 ₫
9.480.385 ₫ total
includes taxes & fees
19 Nov - 20 Nov
Capanna Suites
A villa with a swimming pool, surrounded by trees and hills.

10. 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 23.412.640 ₫
26.042.949 ₫ total
includes taxes & fees
2 Dec - 3 Dec
Castiglion del Bosco, A Rosewood Hotel
A stone wall with a view of rolling hills and mountains.

11. Castello Banfi - Il Borgo - Relais et Chateaux

Castello Banfi - Il Borgo - Relais et Chateaux
5.0 star property
Montalcino
10.0 out of 10, Exceptional, (139 reviews)
Escape to this Montalcino retreat where you can savour Italian cuisine at La Taverna or unwind by the seasonal pool. Near Castello Banfi and Poggio Antico, this peaceful haven offers massages, a fitness centre, and a poolside bar.
The price is 34.948.161 ₫
38.732.022 ₫ total
includes taxes & fees
7 Nov - 8 Nov
Castello Banfi - Il Borgo - Relais et Chateaux
A modern wooden cabin with a glass-bottomed pool, surrounded by lush greenery.

12. ADLER Thermae

ADLER Thermae
5.0 star property
San Quirico d'Orcia
9.6 out of 10, Exceptional, (84 reviews)
Nestled in San Quirico d'Orcia, this luxury hotel offers a winery, 2 outdoor pools, and an indoor pool. Rejuvenate at the spa with deep-tissue massages and aromatherapy, then dine at the on-site restaurant. Free breakfast, WiFi, and parking enhance your Tuscan retreat.
The price is 17.991.208 ₫
19.934.851 ₫ total
includes taxes & fees
2 Dec - 3 Dec
ADLER Thermae
A modern house with a stone facade, a swimming pool, and outdoor seating.

13. Castello Di Vicarello

Castello Di Vicarello
Cinigiano
9.6 out of 10, Exceptional, (27 reviews)
Experience rural luxury at this Cinigiano farm stay castle featuring 2 outdoor pools, a winery, and wellness treatments. After enjoying free breakfast, explore nearby attractions or unwind at the bar. Free WiFi and parking add convenience.
The price is 22.544.271 ₫
24.856.507 ₫ total
includes taxes & fees
8 Nov - 9 Nov
Castello Di Vicarello
A room with a view of a cityscape, featuring a pool, a table with candles, and two chairs.

14. Hotel Airone

Hotel Airone
4.0 star property
Grosseto
8.4 out of 10, Very good, (126 reviews)
This spa hotel offers panoramic views from a stunning rooftop terrace, just 14 minutes from Grosseto Station. Unwind with deep-tissue massages at the full-service spa, enjoy complimentary breakfast, or relax in the hot tub after exploring nearby Bastione Fortezza.
The price is 3.153.191 ₫
3.468.539 ₫ total
includes taxes & fees
6 Nov - 7 Nov
Hotel Airone
A balcony with a view of a green landscape and a sunset. There are two lounge chairs and a small table with a glass of wine.

15. Conti di San Bonifacio Wine Resort

Conti di San Bonifacio Wine Resort
Gavorrano
9.4 out of 10, Exceptional, (29 reviews)
Immerse yourself in Gavorrano's wine country at this golf property with winery and outdoor pool. Enjoy poolside drinks, cafe bites, and plush beds with dressing gowns. Free breakfast, WiFi and parking enhance your stay near Podere Ristella vineyards.
The price is 14.071.864 ₫
15.478.935 ₫ total
includes taxes & fees
11 Nov - 12 Nov
Conti di San Bonifacio Wine Resort
A spa area with a stone wall, wooden beams, a large window with a view, and a hot tub.

16. Mastrojanni Relais - Small Luxury Hotels of the World

Mastrojanni Relais - Small Luxury Hotels of the World
Montalcino
9.8 out of 10, Exceptional, (84 reviews)
Immerse yourself in wine country at this serene Montalcino relais with on-site winery. Enjoy complimentary breakfast before lounging by the seasonal outdoor pool. The restaurant, garden terrace, and free parking create a perfect Tuscan retreat near Abbazia di Sant'Antimo.
The price is 10.359.371 ₫
11.684.353 ₫ total
includes taxes & fees
7 Nov - 8 Nov
Mastrojanni Relais - Small Luxury Hotels of the World
A stone building with a pool overlooking a mountainous landscape.

17. Castello di Velona Resort Thermal SPA & Winery

Castello di Velona Resort Thermal SPA & Winery
5.0 star property
Montalcino
9.0 out of 10, Wonderful, (380 reviews)
Immerse yourself in Tuscan luxury at this thermal spa resort with indoor and outdoor pools near Abbazia di Sant'Antimo. Enjoy 3 restaurants, poolside drinks, and winery experiences while staying in this serene countryside retreat with free breakfast and parking.
The price is 12.997.168 ₫
14.585.930 ₫ total
includes taxes & fees
30 Nov - 1 Dec
Castello di Velona Resort Thermal SPA & Winery
A historic building complex with multiple structures, including a large central building with arches and smaller surrounding buildings.

18. Hotel Athena

Hotel Athena
4.0 star property
Siena Historical Center
9.2 out of 10, Wonderful, (1,006 reviews)
Steps from Santa Maria della Scala, this hotel offers local cuisine at Mangia restaurant, free WiFi and parking. Guests love the delicious breakfast and helpful staff. Florence Airport is just 66 minutes away.
The price is 2.364.913 ₫
2.688.117 ₫ total
includes taxes & fees
29 Nov - 30 Nov
Hotel Athena
A person relaxing in a hot tub with a view of a vineyard and mountains in the background.

19. Villa Le Prata - Residenza del Vescovo

Villa Le Prata - Residenza del Vescovo
Montalcino
10.0 out of 10, Exceptional, (95 reviews)
This Montalcino hotel features its own winery where you can sample local vintages after a refreshing dip in the seasonal outdoor pool. Unwind in the hot tub, enjoy free breakfast, and relax with complimentary WiFi and parking while exploring nearby Corte Pavone Winery.
The price is 9.665.663 ₫
10.921.274 ₫ total
includes taxes & fees
6 Nov - 7 Nov
Villa Le Prata - Residenza del Vescovo
A bedroom with a bed, a chair, a table, and a stone wall.

20. 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 4.769.242 ₫
5.477.403 ₫ total
includes taxes & fees
6 Nov - 7 Nov
Dimora delle Muse
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

A spacious dining area with a large table and chairs, stone walls, and a view of the mountains.
Valdonica Winery & Vineyard Residence

Valdonica Winery & Vineyard Residence

Valdonica Winery & Vineyard Residence
Roccastrada
9.2 out of 10, Wonderful, (46)
The price is 3.796.999 ₫
4.263.413 ₫ total
includes taxes & fees
8 Nov - 9 Nov
Valdonica Winery & Vineyard Residence
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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Pool
Pool
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Pet friendly
Pet friendly

When is the best time to visit Roccastrada?

Our prices for hotels in Roccastrada are cheapest in March

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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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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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 spacious dining area with a large table and chairs, stone walls, and a view of the mountains.
Valdonica Winery & Vineyard Residence

Valdonica Winery & Vineyard Residence

Valdonica Winery & Vineyard Residence
Roccastrada

10/10 Exceptional

A stunning property. This was our favourite stay over a 4 week holiday and is a place to truly relax. We weren’t sure at time of booking if it was too far off the beaten track but booked it for the promise of a view, and it certainly did not disappoint. The view from the pool and breakfast area is truly spectacular, and whilst the location is away from the main tourist sites, it’s very peaceful and still well within reach of Siena, San Gimignano etc for a daytrip by car. Real care has been taken...
United Kingdom
Anonymous traveller
Reviewed August 3, 2019
Valdonica Winery & Vineyard Residence

Frequently Asked Questions

How much does a hotel room cost in Roccastrada?

You can choose a great hotel in Roccastrada from 1,869,228 ₫ with properties to suit all budgets and needs. If you're looking for an affordable hotel in Roccastrada that meets all of your requirements, just sort hotels by "Price: low to high" after applying your filters when searching on Hotels.com.

How can I find deals and earn rewards at Roccastrada hotels?

Discover great deals on Roccastrada hotel stays with Hotels.com. You can also look at hotel prices mid-week or during the low season to find off-peak deals. If you're up for a spontaneous trip, don't forget to check out our last-minute deals on Roccastrada hotels.

Can I book Roccastrada hotels with free cancellation?

To book a refundable Roccastrada hotel on Hotels.com, just filter hotels by "Property cancellation options" and select "Fully refundable property". The majority of hotels offer free cancellation, so you can receive a refund if you need to cancel. Some hotels do require cancelling more than 24 hours before check-in, so double-check your booking beforehand.

What are the top-rated luxury hotels in Roccastrada?

One of the most popular luxury hotels in Roccastrada is Valdonica Winery & Vineyard Residence. Valdonica Winery & Vineyard Residence is a luxury farm stay with a high guest rating amongst our travellers, and it offers a full-service spa and a seasonal outdoor pool, plus champagne service in the guestrooms.

What are some top pet-friendly hotels in Roccastrada?

Consider one of our travellers' favourite pet-friendly hotels in Roccastrada:

You can also use the "Amenities" filter in your search on Hotels.com and check "Pet friendly" to discover more pet-friendly hotels in Roccastrada.

What are some of the best hotels in Roccastrada for couples?

Stay at a top-rated Roccastrada romantic hotel and make the most of your couple's holiday. Our travellers love La Melosa Resort & Spa - Adults Only, a hotel with a restaurant. Another romantic hotel with top reviews is Historic Farmhouse Casa del Chiodo . This farm stay offers couples/private dining as well as champagne service for a perfect stay. Discover more hotels in Roccastrada on Hotels.com for couples by using the "Traveller experience" filter in your search and selecting "Adults only" or "Romantic".

What are the top Roccastrada hotels with a pool?

Discover some of the best Roccastrada hotels with a pool for a little extra luxury on your trip. Tenuta Di Maro is a great country house with a seasonal outdoor pool and a guest rating of 10 out of 10. Tenuta Montemassi Podere Montauzzo is a popular farm stay that features an outdoor pool along with free parking. You can select "Pool" in the "Amenities" filter of your search on Hotels.com to find even more places to stay in Roccastrada with a pool.

What are some of the best Roccastrada hotels with free parking?

If you're exploring by car, finding a great Roccastrada hotel with free parking is a win. Our travellers' favourites include:

What are some popular hotels in central Roccastrada?

For hotels in central Roccastrada, check out B&B Podere Camaiano and Historic Farmhouse Casa del Chiodo . Travellers love B&B Podere Camaiano for its location, as well as the free buffet breakfast, free parking and terrace this bed & breakfast offers. Historic Farmhouse Casa del Chiodo is another popular central farm stay with a free local cuisine breakfast, couples/private dining and proposal/romance packages.