Title: Visit Roccastrada: Best of Roccastrada Tourism | Expedia Travel Guide - Expedia.ca

[Hotels in Roccastrada](https://expedia.ca/Roccastrada-Hotels.d601758.Travel-Guide-Hotels)[Vacation Rentals in Roccastrada](https://expedia.ca/Roccastrada-Vacation-Rentals.d601758.Travel-Guide-VacationRentals)[Roccastrada Car Rentals](https://expedia.ca/Car-Rentals-In-Roccastrada.d601758.Car-Rental-Guide)[Roccastrada Vacation Packages](https://expedia.ca/Roccastrada.d601758.Destination-Travel-Guides)

# Roccastrada

## Travel Guide

![Castle of Montemassi, Tuscany, Italy](https://images.trvl-media.com/place/601758/b177ea3b-d73b-423c-ada5-9c658c881e58.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)

![Restored old stone house in Montemassi in the province of Grosseto. Tuscany. Italy](https://images.trvl-media.com/place/601758/7123c6a0-ae1c-405b-b84a-0322e2172403.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)

![Montemassi a fortified village in the province of Grosseto. Tuscany. Italy](https://images.trvl-media.com/place/601758/cbd46b19-911c-4035-8de4-1eccc9e0b9ee.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)

![Image of landscape near Roccastrada Tuscany Italy at sunset in autumn; Shutterstock ID 224935198; Purchase Order: -](https://images.trvl-media.com/place/601758/c011ef90-987c-4f91-a667-267f1110507c.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)

![Image of landscape near Roccastrada Tuscany Italy at sunset in autumn, Shutterstock ID 224935198, Purchase Order: -](https://images.trvl-media.com/place/601758/9946376e-022d-4f94-a65d-cf4cf576cd78.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)

## Visit Roccastrada

Things to do

- Roccastrada Hotel Deals
- Vacation Rentals in Roccastrada

![Hotel Chiusarelli](https://images.trvl-media.com/lodging/2000000/1120000/1110900/1110843/f43eb5fd_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hotel Chiusarelli

Viale Curtatone 15 Siena SI

CA $156

CA $180 total

Mar 29 - Mar 30

includes taxes & fees

Book a stay at this business-friendly hotel in Siena. Enjoy free breakfast, free WiFi, and room service. Our guests praise the breakfast and the helpful staff ...

8.8/10 Excellent! (1,001 reviews)

The hotel was just outside of the town, so the location was good. It was a beautiful property. The breakfast was good. Just be prepared to walk stairs. No lifts. But overall, good.

Reviewed on Mar 22, 2026

[](https://expedia.ca/Hotel-Search?startDate=29%2F03%2F2026&endDate=30%2F03%2F2026&selected=1110843&PinnedHotelID=1110843&HadPinnedHotel=true&regionId=601758)

![ Palazzo Ravizza](https://images.trvl-media.com/lodging/2000000/1770000/1760200/1760168/5eddd92b_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

 Palazzo Ravizza

Pian dei Mantellini 34 Siena SI

CA $162

CA $186 total

Mar 25 - Mar 26

includes taxes & fees

Stay at this hotel in Siena. Enjoy free WiFi, room service, and parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular ...

9.4/10 Exceptional! (763 reviews)

This is a gem and well worth the stay!!! So so amazing

Reviewed on Mar 20, 2026

[](https://expedia.ca/Hotel-Search?startDate=25%2F03%2F2026&endDate=26%2F03%2F2026&selected=1760168&PinnedHotelID=1760168&HadPinnedHotel=true&regionId=601758)

![Hotel Executive](https://images.trvl-media.com/lodging/1000000/10000/3600/3559/cbe470ec_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hotel Executive

Via Nazareno Orlandi 32 Siena SI

CA $174

CA $199 total

Apr 15 - Apr 16

includes taxes & fees

Book a stay at this family-friendly hotel in Siena. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...

8.4/10 Very Good! (528 reviews)

The staff were super great .Took care of all our needs .Suggested the best winery tour .And the food was terrific .

Reviewed on Nov 2, 2025

[](https://expedia.ca/Hotel-Search?startDate=15%2F04%2F2026&endDate=16%2F04%2F2026&selected=3559&PinnedHotelID=3559&HadPinnedHotel=true&regionId=601758)

[See all 4,973 properties in Roccastrada](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=25%2F03%2F2026&endDate=26%2F03%2F2026&regionId=601758)

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.

![Tenuta Di Litiano With Pool, Roccastrada, Italy](https://images.trvl-media.com/lodging/60000000/59640000/59631100/59631084/6435f1b2_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Tenuta Di Litiano With Pool, Roccastrada, Italy

 Roccastrada 

Stay at this villa in Roccastrada. Enjoy free WiFi, private pools, and a garden.

[](https://expedia.ca/Roccastrada-Hotels-Tenuta-Di-Litiano-With-Pool.h59631084.Hotel-Information)

![Casanova - Panoramic Rooms and Suites](https://images.trvl-media.com/lodging/52000000/51830000/51829000/51828901/9867dcf1_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Casanova - Panoramic Rooms and Suites

Strada Provinciale 146 di Chianciano San Quirico d'Orcia SI

Stay at this residence in San Quirico d'Orcia. Enjoy free breakfast, free WiFi, and an outdoor pool. Popular attractions Horti Leonini and Chapel of our Lady ...

[](https://expedia.ca/San-Quirico-DOrcia-Hotels-Resort-Casanova-Panoramic-Rooms-And-Suites.h51828901.Hotel-Information)

![Il Battistero Siena - Residenza d'Epoca](https://images.trvl-media.com/lodging/11000000/10540000/10536200/10536156/bc901666_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Il Battistero Siena - Residenza d'Epoca

Piazza San Giovanni, 13 Siena SI

Stay at this residence in Siena. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular attractions ...

9.6/10 Exceptional! (200 reviews)

Excellent service! Great communication. A beautiful set up for our family with two rooms. Very accommodating and we loved the slippers. Elevator was great for luggage. A must stay in a beautiful and centrally located area.

Reviewed on Dec 31, 2025

[](https://expedia.ca/Siena-Hotels-Il-Battistero-Siena-Residenza-DEpoca.h10536156.Hotel-Information)

[See all properties in Roccastrada](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&regionId=601758&sort=VACATION_RENTAL)

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.

## Check Roccastrada hotel availability

[Tonight

](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=601758&startDate=2026-03-24&endDate=2026-03-25)[Mar 24 - Mar 25](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=601758&startDate=2026-03-24&endDate=2026-03-25)

[Tomorrow night

](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=601758&startDate=2026-03-25&endDate=2026-03-26)[Mar 25 - Mar 26](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=601758&startDate=2026-03-25&endDate=2026-03-26)

[This weekend

](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=601758&startDate=27%2F03%2F2026&endDate=29%2F03%2F2026)[Mar 27 - Mar 29](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=601758&startDate=27%2F03%2F2026&endDate=29%2F03%2F2026)

[Next weekend

](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=601758&startDate=03%2F04%2F2026&endDate=05%2F04%2F2026)[Apr 3 - Apr 5](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true&regionId=601758&startDate=03%2F04%2F2026&endDate=05%2F04%2F2026)

### Popular places to visit

#### I Canaloni del Torrente Farma

Commune with nature and explore the great outdoors at I Canaloni del Torrente Farma during your travels in Roccastrada. Discover the area's countryside and spas. 

[](https://expedia.ca/I-Canaloni-Del-Torrente-Farma-Roccastrada.d553248634041940720.Vacation-Attraction)

#### Podere Ristella Vineyards and Winery

You can enjoy a tasting or tour at Podere Ristella Vineyards and Winery during your travels to Roccastrada. Wander the gardens or discover the area's countryside. 

[](https://expedia.ca/Podere-Ristella-Vineyards-And-Winery-Roccastrada.d553248621532497683.Vacation-Attraction)

#### Castello del Belagaio

You can find out about the history of Roccastrada with a trip to Castello del Belagaio. Discover the area's countryside and wineries. 

[](https://expedia.ca/Castello-Del-Belagaio-Roccastrada.d553248622636430376.Vacation-Attraction)

#### Sassoforte Castle

You can find out about the history of Roccastrada with a visit to Sassoforte Castle. While you're in the area, wander around the natural setting. 

[](https://expedia.ca/Sassoforte-Castle-Roccastrada.d685924565073498112.Vacation-Attraction)

#### Castello di Torniella

After visiting Castello di Torniella, make a plan to see the other sights and activities in Torniella. 

[](https://expedia.ca/Castello-Di-Torniella-Roccastrada.d982579348374679552.Vacation-Attraction)

#### Church of San Nicola

After visiting Church of San Nicola, make a plan to see the other sights and activities in Roccastrada. Visit the spas in this relaxing area, or simply enjoy its wineries. 

[](https://expedia.ca/Church-Of-San-Nicola-Roccastrada.d553248621532497684.Vacation-Attraction)

### Things to do

![La Maliosa Farm Experience & Wine Tasting](https://mediaim.expedia.com/localexpert/44638298/2d7ee171-839d-48ec-b768-c660cead2473.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### La Maliosa Farm Experience & Wine Tasting

CA $73

per adult

**100%** of travellers recommend

[](https://expedia.ca/things-to-do/la-maliosa-farm-experience-wine-tasting.a44638298.activity-details)

![Welcome to Casale del Bosco](https://mediaim.expedia.com/localexpert/49075566/38f4ac08-b80d-4ccf-bb46-3f53fdc0db59.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Welcome to Casale del Bosco

CA $56

per adult

[](https://expedia.ca/things-to-do/welcome-to-casale-del-bosco.a49075566.activity-details)

![The Private Challenge of the Crus](https://mediaim.expedia.com/localexpert/49151397/8bceb296-2c45-41d1-bf0a-6bcb4ee118bb.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### The Private Challenge of the Crus

CA $121

per adult

[](https://expedia.ca/things-to-do/the-private-challenge-of-the-crus.a49151397.activity-details)

[See all activities in Roccastrada](https://expedia.ca/Things-To-Do-In-Roccastrada.d601758.Travel-Guide-Activities)

## Cities near Roccastrada

![Porto Ercole village and boats in harbor in a sea bay. Aerial view. Monte Argentario, Maremma Grosseto Tuscany, Italy, Shutterstock ID 583938877, SF SSA Case with Manager Approval: Case 07151371, Job:](https://images.trvl-media.com/place/7512/691e9998-8560-43fd-8d57-b4774baf1617.jpg?impolicy=fcrop&w=512&h=288&q=medium)

### Grosseto

![Massa Marittima showing heritage architecture as well as a large group of people](https://images.trvl-media.com/place/6034961/a3912cc3-d920-46fa-9771-1589748c79a2.jpg?impolicy=fcrop&w=512&h=288&q=medium)

### Massa Marittima

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- [Visit Ville di Corsano ](https://www.expedia.ca/Ville-Di-Corsano.dx6361513)

- [Car rental La Pesta ](https://www.expedia.ca/Car-Rentals-In-La-Pesta.d6361376.Car-Rental-Guide)
- [Luxury Car Rentals in Brunello di Montalcino Wine Area ](https://www.expedia.ca/Luxury-Car-Rentals-In-Brunello-Di-Montalcino-Wine-Area.d6342620-tLuxury.Car-Rental-Guide-Class)

- [Brunello di Montalcino Wine Area Vacation Rentals ](https://www.expedia.ca/Brunello-Di-Montalcino-Wine-Area-Vacation-Rentals.d6342620.Travel-Guide-VacationRentals)

- [Things to do in Campagnatico ](https://www.expedia.ca/Things-To-Do-In-Campagnatico.d6046357.Travel-Guide-Activities)
- [Things to do in Civitella Paganico ](https://www.expedia.ca/Things-To-Do-In-Civitella-Paganico.d6059330.Travel-Guide-Activities)
- [Things to do in Paganico ](https://www.expedia.ca/Things-To-Do-In-Paganico.d6047023.Travel-Guide-Activities)

- Cities near Roccastrada
- Places of interest

[Grosseto](https://expedia.ca/Grosseto.dx7512)[Massa Marittima](https://expedia.ca/Massa-Marittima.dx6034961)[Roccatederighi](https://expedia.ca/Roccatederighi.dx6049327)[Tatti](https://expedia.ca/Tatti.dx6361459)[Sticciano](https://expedia.ca/Sticciano.dx3000026145)

- [Fortezza Medicea ](https://expedia.ca/Fortezza-Medicea-Siena-Historical-Center.d6287282.Vacation-Attraction)
- [Tenuta Greppo Franco Biondi Santi ](https://expedia.ca/Tenuta-Greppo-Franco-Biondi-Santi-Montalcino.d6103260.Vacation-Attraction)
- [Fortress of Montalcino ](https://expedia.ca/Fortress-Of-Montalcino-Montalcino.d553248621533000896.Vacation-Attraction)

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