Hotels in Roccastrada

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

Tonight
Oct 27 - Oct 28
Tomorrow
Oct 28 - Oct 29
This weekend
Oct 30 - Nov 1
Next weekend
Nov 6 - Nov 8

Where to stay in Roccastrada?

A swimming pool with lounge chairs and umbrellas, surrounded by brick flooring and a hedge.

1. La Melosa Resort & Spa - Adults Only

La Melosa Resort & Spa - Adults Only
4.0 star property
Roccastrada
9.2 out of 10, Wonderful, (46 reviews)
Set among the rolling hills of Roccastrada, this adults-only haven features an outdoor pool and poolside bar for sun-drenched relaxation. Pamper yourself at the spa with facials or manicures before savoring local cuisine at Il Canto del Gusto restaurant.
The price is $96
$109 total
includes taxes & fees
Oct 29 - Oct 30
La Melosa Resort & Spa - Adults Only
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 $147
$165 total
includes taxes & fees
Nov 8 - Nov 9
Valdonica Winery & Vineyard Residence
A stone building with multiple windows and a balcony, a table set for dining, and lush greenery in the foreground.

3. Historic Farmhouse Casa del Chiodo

Historic Farmhouse Casa del Chiodo
Roccastrada
10.0 out of 10, Exceptional, (5 reviews)
The price is $106
$118 total
includes taxes & fees
Nov 10 - Nov 11
Historic Farmhouse Casa del Chiodo
Point of interest

4. 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 cozy 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 $81
$91 total
includes taxes & fees
Nov 3 - Nov 4
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.

5. 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 $177
$197 total
includes taxes & fees
Nov 8 - Nov 9
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.

6. 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 $87
$98 total
includes taxes & fees
Nov 2 - Nov 3
Country House il Ciliegio
A swimming pool with a view of a hilltop castle.

7. Agriturismo Podere Ristella - Wine&Food

Agriturismo Podere Ristella - Wine&Food
Roccastrada
2.0 out of 10, (1 review)
Immerse yourself in rustic charm at this Roccastrada farmstay with an inviting seasonal outdoor pool and onsite winery. Nearby hiking trails and mountain biking routes beckon outdoor enthusiasts, while free WiFi and parking enhance your Tuscan countryside experience.
The price is $99
$133 total
includes taxes & fees
Oct 28 - Oct 29
Agriturismo Podere Ristella - Wine&Food
A modern living room with a sofa, a coffee table, a TV on a wooden cabinet, and a large potted plant.

8. Le Vie del Mare Camere

Le Vie del Mare Camere
Ribolla
The price is $122
$134 total
includes taxes & fees
Oct 30 - Oct 31
Le Vie del Mare Camere
A glass-enclosed structure with a wooden deck, surrounded by various plants and a garden.

9. Agriturismo Benvenuti

Agriturismo Benvenuti
Roccastrada
6.0 out of 10, Good, (3 reviews)
This Roccastrada farmhouse vacation home offers outdoor private hot tubs and a spa featuring massages and facials. Enjoy the restaurant, sauna, and fully equipped kitchens. Nearby attractions include Piscina Il Giunco and Tenuta Dodici Winery.
Agriturismo Benvenuti
A pool with lounge chairs and a sunset view.

10. 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 $84
$92 total
includes taxes & fees
Oct 28 - Oct 29
Mercure Petriolo Siena Terme Spa Hotel
A stone building with a tiled roof, a paved pathway, and a well-maintained garden.

11. Podere Brizio

Podere Brizio
Montalcino
9.8 out of 10, Exceptional, (177 reviews)
Immerse yourself in authentic Tuscany at this Montalcino farm stay. Savor 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 $200
$229 total
includes taxes & fees
Nov 16 - Nov 17
Podere Brizio
A stone building with a stone staircase, surrounded by lush greenery and a stone pathway.

12. Le Ragnaie

Le Ragnaie
Montalcino
9.2 out of 10, Wonderful, (342 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 $92
$113 total
includes taxes & fees
Nov 10 - Nov 11
Le Ragnaie
A table with a glass of white wine, a metal pitcher, and a wooden board with various cheeses and cured meats.

13. SI Montalcino Hotel

SI Montalcino Hotel
3.0 star property
Montalcino
9.2 out of 10, Wonderful, (418 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 $94
$130 total
includes taxes & fees
Nov 9 - Nov 10
SI Montalcino Hotel
A stone building with multiple windows and a balcony, surrounded by lush greenery and trees.

14. Relais Le Macine di Stigliano

Relais Le Macine di Stigliano
4.0 star property
Sovicille
10.0 out of 10, Exceptional, (27 reviews)
This Tuscan retreat offers a seasonal outdoor pool, hot tub, and sauna, plus a restaurant and bar for post-exploration refreshment. Near Val di Merse, with complimentary breakfast, WiFi, and parking to enhance your countryside getaway.
The price is $159
$180 total
includes taxes & fees
Nov 15 - Nov 16
Relais Le Macine di Stigliano
A stone building with a pathway leading to a door, surrounded by trees and illuminated by warm lights.

15. L'Orto delle Terme

L'Orto delle Terme
San Quirico d'Orcia
9.6 out of 10, Exceptional, (61 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 $123
$139 total
includes taxes & fees
Nov 24 - Nov 25
L'Orto delle Terme
A pool with a stone wall, a view of the countryside, and a building with a tiled roof.

16. Hotel Dei Capitani

Hotel Dei Capitani
3.0 star property
Montalcino
8.8 out of 10, Excellent, (479 reviews)
Soak in the beauty of Tuscany at this charming hotel near Piazza del Popolo. The outdoor pool offers refreshing relaxation, while free perks include daily continental breakfast, WiFi, and parking. Explore nearby museums with helpful staff to guide your wine country adventures.
The price is $130
$152 total
includes taxes & fees
Oct 28 - Oct 29
Hotel Dei Capitani
A dining area with a table set for four, chairs, a television mounted on the wall, and a cabinet with glass doors.

17. L'Aia di Argia

L'Aia di Argia
Monteroni d'Arbia
9.2 out of 10, Wonderful, (17 reviews)
Just 4 minutes from Monteroni D'Arbia Ponte A Tressa Station, this country house offers rejuvenating massages, body scrubs, and manicures in tranquil surroundings. Enjoy free WiFi and parking while exploring nearby Porta Romana and Porta Tufi attractions.
The price is $73
$85 total
includes taxes & fees
Nov 22 - Nov 23
L'Aia di Argia
A pool with a wooden deck and lounge chairs, surrounded by trees and hills in the background.

18. Fattoria Pieve a Salti

Fattoria Pieve a Salti
Montalcino
9.0 out of 10, Wonderful, (51 reviews)
The price is $110
$125 total
includes taxes & fees
Oct 29 - Oct 30
Fattoria Pieve a Salti
A historic building with a sign reading "Bastiani Grand Hotel."

19. 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 travelers.
The price is $79
$87 total
includes taxes & fees
Nov 26 - Nov 27
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.

20. 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 $544
$598 total
includes taxes & fees
Nov 11 - Nov 12
Conti di San Bonifacio Wine Resort
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

Get last-minute hotel deals in Roccastrada and save more

Sign in to unlock great savings.
Showing deals for:Nov 6 - Nov 8
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 reviews)
$51 off
The price is $145
per night
$323 total
includes taxes & fees
Valdonica Winery & Vineyard Residence

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 $81
$91 total
includes taxes & fees
Nov 3 - Nov 4
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.
View all properties

Go beyond your typical stay in Roccastrada

pet friendly image
Pet friendly
Pet friendly
Pool image
Pool
Pool

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 traveler single night rates
View properties in October
Currently viewing crowd sizes and weather for October.

October

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

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 stone building with multiple windows and a balcony, a table set for dining, and lush greenery in the foreground.
Historic Farmhouse Casa del Chiodo

Historic Farmhouse Casa del Chiodo

Historic Farmhouse Casa del Chiodo
Roccastrada

10/10 Exceptional

Everything about this place is perfect, highly recommend.
United States
Ian
Reviewed December 6, 2025
Historic Farmhouse Casa del Chiodo

Frequently Asked Questions

What accommodations do travelers recommend in Roccastrada?

Guests like Borgo Santo Pietro.

Where can I find free parking at my hotel in Roccastrada?

Park your car for free at these properties: Agriturismo Tenuta di Montemassi La Fattoria, Panorama Room 2 Pers With Breakfast In Tuscany and Lavanda Room With Bath.

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.