Hotels in Roccastrada

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This weekend
Nov 13 - Nov 15
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Nov 20 - Nov 22

Where to stay in Roccastrada?

Properties are selected based on real traveler reviews and popularity among guests who’ve booked a night in Roccastrada on Hotels.com. These Roccastrada hotels consistently deliver on quality, location and traveler experience. Last updated on .

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, (47 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 CA $212
CA $236 total
includes taxes & fees
Nov 29 - Nov 30
Valdonica Winery & Vineyard Residence
An outdoor dining area with stone buildings, tables with orange tablecloths, and string lights.

2. Historic Farmhouse Casa del Chiodo

Historic Farmhouse Casa del Chiodo
Roccastrada
10.0 out of 10, Exceptional, (6 reviews)
The price is CA $150
CA $168 total
includes taxes & fees
Nov 12 - Nov 13
Historic Farmhouse Casa del Chiodo
A group of people dining at a table with a view of a valley and mountains.

3. 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 CA $229
CA $256 total
includes taxes & fees
Nov 16 - Nov 17
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.

4. 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 CA $125
CA $140 total
includes taxes & fees
Nov 13 - Nov 14
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.

5. Le Vie del Mare Camere

Le Vie del Mare Camere
Ribolla
The price is CA $156
CA $172 total
includes taxes & fees
Nov 12 - Nov 13
Le Vie del Mare Camere
A pool with a modern water feature and a stone structure.

6. 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 CA $119
CA $131 total
includes taxes & fees
Nov 12 - Nov 13
Mercure Petriolo Siena Terme Spa Hotel
A stone building with a stone staircase, surrounded by lush greenery and a stone pathway.

7. 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 CA $159
CA $191 total
includes taxes & fees
Dec 2 - Dec 3
Le Ragnaie
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, (181 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 CA $280
CA $320 total
includes taxes & fees
Nov 16 - Nov 17
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 CA $362
CA $414 total
includes taxes & fees
Nov 19 - Nov 20
Capanna Suites
A poolside area with lounge chairs, a table with wine glasses and a bottle, and a view of a mountainous landscape.

10. 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 CA $166
CA $219 total
includes taxes & fees
Nov 12 - Nov 13
SI Montalcino Hotel
A table set for dining with a scenic view of rolling hills and distant mountains.

11. 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 CA $102
CA $122 total
includes taxes & fees
Dec 3 - Dec 4
Castello di Leonina Relais
A bedroom with a bed, a chair, a table, and a stone wall.

12. Dimora delle Muse

Dimora delle Muse
Montalcino
10.0 out of 10, Exceptional, (76 reviews)
Wake up to complimentary breakfast at this cozy 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 CA $251
CA $289 total
includes taxes & fees
Nov 12 - Nov 13
Dimora delle Muse
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 cozy 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 CA $296
CA $341 total
includes taxes & fees
Nov 12 - Nov 13
Casa Franci Montalcino
A wooden door with a metal handle, a brick archway, a staircase, and a flower pot on the wall.

14. Idolina Guest House

Idolina Guest House
Montalcino
9.6 out of 10, Exceptional, (118 reviews)
The price is CA $132
CA $158 total
includes taxes & fees
Nov 30 - Dec 1
Idolina Guest House
A lobby with a marble floor, a chandelier, a reception desk, and large green plants.

15. Hotel Chiusarelli

Hotel Chiusarelli
3.0 star property
Siena City Centre
9.0 out of 10, Wonderful, (1,001 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 CA $114
CA $130 total
includes taxes & fees
Dec 9 - Dec 10
Hotel Chiusarelli
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, (67 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 cozy bar lounge.
The price is CA $138
CA $158 total
includes taxes & fees
Nov 15 - Nov 16
L'Orto delle Terme
A hot tub with a central platform and candles.

17. 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 CA $102
CA $119 total
includes taxes & fees
Nov 24 - Nov 25
Grand Hotel Impero - Wellness & Exclusive SPA
A historic building with a sign reading "Bastiani Grand Hotel."

18. 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 CA $117
CA $128 total
includes taxes & fees
Nov 25 - Nov 26
Grand Hotel Bastiani
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.

19. 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 bathrobes. Free breakfast, WiFi and parking enhance your stay near Podere Ristella vineyards.
The price is CA $771
CA $848 total
includes taxes & fees
Nov 27 - Nov 28
Conti di San Bonifacio Wine Resort
A bakery display with pastries and a coffee station.

20. B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (218 reviews)
Tucked beside Siena's iconic Piazza del Campo, this charming B&B combines comfort with convenience. Premium bedding ensures peaceful rest while Teatro dei Rozzi and Fonte Gaia lie just minutes away. Free WiFi and daily housekeeping enhance your Italian adventure.
The price is CA $104
CA $121 total
includes taxes & fees
Nov 15 - Nov 16
B&B Il Corso
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, (47)
The price is CA $212
CA $236 total
includes taxes & fees
Nov 29 - Nov 30
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.
View all properties

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.
Typical weather for Roccastrada
November
High 16°C / low 10°C. Sunny most days.
View properties in November
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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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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

Travelers might want a tour of Podere Ristella Vineyards and Winery, just one of the places to visit, and 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

L'Orto delle Terme

L'Orto delle Terme

10/10 Excellent
"This was a wonderful stay. Bagno Vignoni and the surrounding area are truly magical and i absolutely loved staying at Orto Le Terme - this is one of those instances where the room photos did not do it justice. I loved the room - it felt warm and inviting with supremely tasteful decor and a big comfortable bathroom with separate shower and freestanding bath. The breakfasts were next level. I think one of the best hotel breakfasts i've had. Lots of amazing local Tuscan produce. Cannot recommend enough."
Pat 4-night trip
Posted 7 hours ago
L'Orto delle Terme

Frequently asked questions

How much does a hotel room cost in Roccastrada?
You can choose a great hotel in Roccastrada from CA $117 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 travelers, 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 travelers' favorite 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 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. Plus, you can make the most of its free buffet breakfast and free parking. Tenuta Montemassi Podere Montauzzo is a popular farm stay that features an outdoor pool along with free parking. To find more stays in Roccastrada with a pool, use the "Amenities" filter on Hotels.com in your search and select "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 travelers' favorites 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. Travelers 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.
Can I book a refundable hotel in Roccastrada?
If you want the flexibility to change your plans to Roccastrada, most accommodations offer refundable* rates you can book. You can see these accommodations 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 vacation home instead of a traditional hotel?
If you want a good alternative to a hotel, review our selection of 77 vacation 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 temp of 74°F. January and February are the chilliest months when the average temp is 48°F. 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, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.

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