Castle of Montemassi, Tuscany, Italy

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Our top choices for Roccastrada hotels

B&B da Nada Locanda Toscana

B&B da Nada Locanda Toscana
Roccastrada
9.6 out of 10, Exceptional, (17 reviews)
"Ras"
France
jean
The price is CA $94
CA $106 total
includes taxes & fees
Jun 24 - Jun 25
B&B da Nada Locanda Toscana

Agriturismo Tenuta di Montemassi La Fattoria

Agriturismo Tenuta di Montemassi La Fattoria
3.0 star property
Roccastrada
9.6 out of 10, Exceptional, (9 reviews)
"Great place , welcoming owner and staff . Town is a little gem "
United States
Alice
The price is CA $134
CA $151 total
includes taxes & fees
Jun 29 - Jun 30
Agriturismo Tenuta di Montemassi La Fattoria

La Melosa Resort & Spa - Adults Only

La Melosa Resort & Spa - Adults Only
4.0 star property
Roccastrada
9.2 out of 10, Wonderful, (39 reviews)
"This resort was more than i expected, it was beautiful and food was great,tey there dinner "
United States
raul
The price is CA $138
CA $157 total
includes taxes & fees
Jun 18 - Jun 19
La Melosa Resort & Spa - Adults Only

Valdonica Winery - Chill in Nature Lodge

Valdonica Winery - Chill in Nature Lodge
Roccastrada
The price is CA $257
CA $286 total
includes taxes & fees
Jul 5 - Jul 6
Valdonica Winery - Chill in Nature Lodge

Valdonica Winery & Vineyard Residence

Valdonica Winery & Vineyard Residence
Roccastrada
9.6 out of 10, Exceptional, (34 reviews)
"Excellent location . Very nice wine and evening meal. Staff good ( especially Alice) . "
United Kingdom
Tim
The price is CA $207
CA $233 total
includes taxes & fees
Jun 21 - Jun 22
Valdonica Winery & Vineyard Residence

Country House il Ciliegio

Country House il Ciliegio
Roccastrada
9.2 out of 10, Wonderful, (7 reviews)
"It was a very pleasant stay, a warm welcome. A beautiful location surrounded by nature."
Netherlands
Maaike
The price is CA $135
CA $152 total
includes taxes & fees
Jun 17 - Jun 18
Country House il Ciliegio

Hotiday Grosseto Podere

Hotiday Grosseto Podere
Grosseto
The price is CA $96
CA $110 total
includes taxes & fees
Jun 18 - Jun 19
Hotiday Grosseto Podere

PALAZZO DEL CARDINALE

PALAZZO DEL CARDINALE
Montalcino
The price is CA $177
CA $211 total
includes taxes & fees
Jun 19 - Jun 20
PALAZZO DEL CARDINALE

Le Ragnaie

Le Ragnaie
Montalcino
9.2 out of 10, Wonderful, (327 reviews)
"I would not change a thing. It was amazing great hospitality nice clean. I would definitely go back. Highly recommended."
United States
Jeton
The price is CA $215
CA $253 total
includes taxes & fees
Jul 15 - Jul 16
Le Ragnaie

SI Montalcino Hotel

SI Montalcino Hotel
3.0 star property
Montalcino
9.2 out of 10, Wonderful, (391 reviews)
"The hotel was absolutely stunning! Our room was spacious, and the beds were incredibly comfortable. The staff were warm, welcoming, and very informative throughout our stay. Breakfast was delicious, and there was no better way to start the day than with an espresso while enjoying the beautiful view. We had a wonderful experience and would definitely stay here again."
Canada
Jacqueline
The price is CA $164
CA $194 total
includes taxes & fees
Jun 21 - Jun 22
SI Montalcino Hotel

Castello

Castello
3.0 star property
Sovicille
8.6 out of 10, Excellent, (74 reviews)
"Great little place to stay overnight. "
United States
Ivona
The price is CA $107
CA $124 total
includes taxes & fees
Jun 19 - Jun 20
Castello

Fattoria Pieve a Salti

Fattoria Pieve a Salti
Montalcino
9.0 out of 10, Wonderful, (41 reviews)
"Super stay !! "
Canada
Patryk
The price is CA $172
CA $196 total
includes taxes & fees
Jun 19 - Jun 20
Fattoria Pieve a Salti

Riva del Sole Resort & SPA

Riva del Sole Resort & SPA
4.0 star property
Castiglione della Pescaia
9.2 out of 10, Wonderful, (46 reviews)
"Lovely seat. Beautiful beach and swimming pool. Although pool not heated water was not too cold to easily get in and swim some laps. Only negative was restaurant, which has only passable food and was expensive. Breakfast was good and generous."
United States
Dan
The price is CA $693
CA $770 total
includes taxes & fees
Jul 11 - Jul 12
Riva del Sole Resort & SPA

Villa Montarioso

Villa Montarioso
Montarioso
8.8 out of 10, Excellent, (140 reviews)
"One of the best places during our stay in italy"
Canada
Michael
The price is CA $127
CA $147 total
includes taxes & fees
Jul 3 - Jul 4
Villa Montarioso

Podere Brizio

Podere Brizio
Montalcino
9.8 out of 10, Exceptional, (160 reviews)
"Stunning location & great reception from Vito. He looked after us & gave us some great recommendations for a wine tasting day out. The accommodation & views were beautiful. We also loved using the spa facilities & played tennis a couple of times overlooking the vineyard! Breakfast was great & dinner in the restaurant was amazing. A great stay & highly recommend! "
United Kingdom
karen
The price is CA $315
CA $360 total
includes taxes & fees
Jul 6 - Jul 7
Podere Brizio

Palazzo di Valli

Palazzo di Valli
3.0 star property
Siena
9.6 out of 10, Exceptional, (424 reviews)
"We had a blast, and the proprietors were fantastic. They had plenty of local knowledge and seemed to have a real passion for what they do. Plus the venue is wonderful, and they have the best patio with views of the Tuscan hills. Would recommend, and would stay again."
United States
John
The price is CA $177
CA $203 total
includes taxes & fees
Jul 15 - Jul 16
Palazzo di Valli

Mastrojanni Relais - Small Luxury Hotels of the World

Mastrojanni Relais - Small Luxury Hotels of the World
Montalcino
10.0 out of 10, Exceptional, (70 reviews)
"Wonderfully Beautiful Winery… Stunning views. Fabulous rooms and very welcoming staff."
United States
Laura
The price is CA $748
CA $839 total
includes taxes & fees
Jul 6 - Jul 7
Mastrojanni Relais - Small Luxury Hotels of the World

Capanna Suites

Capanna Suites
Montalcino
9.8 out of 10, Exceptional, (141 reviews)
"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
The price is CA $621
CA $699 total
includes taxes & fees
Jul 15 - Jul 16
Capanna Suites

Palace Hotel Due Ponti

Palace Hotel Due Ponti
3.0 star property
Due Ponti
8.4 out of 10, Very good, (60 reviews)
"A little far away from Siena, but buses came by regularly and taxi's only cost about 12 Euros to get you to and from Siena."
United States
Jack
The price is CA $118
CA $138 total
includes taxes & fees
Jul 5 - Jul 6
Palace Hotel Due Ponti

Relais la Costa - Dimora Storica

Relais la Costa - Dimora Storica
Monteriggioni
9.6 out of 10, Exceptional, (78 reviews)
"Whole place felt amazing, staff was super! Def recommend!"
United States
Roberto Javier Sanz
The price is CA $254
CA $288 total
includes taxes & fees
Jun 29 - Jun 30
Relais la Costa - Dimora Storica
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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Stay near popular Roccastrada attractions

Learn more about Roccastrada

Hike through the dramatic rock formations of I Canaloni del Torrente Farma, where natural pools invite summer swimming between towering canyon walls. Medieval history comes alive at Sassoforte Castle, while nearby Podere Ristella offers wine tastings showcasing Tuscan varietals grown on sun-drenched slopes.

Image of landscape near Roccastrada Tuscany Italy at sunset in autumn; Shutterstock ID 224935198; Purchase Order: -

Top Roccastrada Hotel Reviews

More cheap stays in Roccastrada

Frequently asked questions

What is the best area to stay in Roccastrada?
The best area to stay in Roccastrada is within the hilltop town itself for a classic Tuscan village experience, or in the surrounding countryside for a more secluded retreat.

Staying directly in Roccastrada town provides a genuine insight into local life. You'll find a selection of local shops, a few traditional eateries, and the historic Rocca Aldobrandesca, offering lovely views of the Maremma region. It's a small, walkable town, superb for those who appreciate a slower pace and want to experience an authentic Tuscan community.

For couples seeking a romantic and tranquil escape, the countryside immediately surrounding Roccastrada offers numerous agriturismi and renovated farmhouses. These properties often feature private pools, expansive gardens, and offer opportunities for wine tasting or cooking classes. You're typically a short drive from the main town, allowing for both seclusion and convenient access to local amenities.
What are the best hotels in Roccastrada that travellers recommend?
For an excellent hotel in Roccastrada that travellers highly recommend, consider La Melosa Resort & Spa - Adults Only.

This 4-star resort, with an outstanding 9.4 rating, offers a luxurious experience. Guests frequently highlight the beautiful, clean rooms. The resort features a refreshing outdoor pool with comfortable sun loungers and a convenient poolside bar. For relaxation, there is a Turkish bath or hammam, and the premium bedding ensures a comfortable stay.
What are the best family hotels in Roccastrada?
For family-friendly accommodation in Roccastrada, consider the Agriturismo Tenuta di Montemassi La Fattoria, Valdonica Winery & Vineyard Residence, and B&B Podere Camaiano.

The 3-star Agriturismo Tenuta di Montemassi La Fattoria, with an impressive 9.6 rating, is an excellent choice for families. It offers complimentary cots, highchairs, and sofa beds, and connecting rooms are available. Guests can also benefit from free rollaway extra beds and a complimentary buffet breakfast.

The Valdonica Winery & Vineyard Residence, rated 9.4, also caters well to families, providing free cots and sofa beds. Guests can enjoy complimentary breakfast, free self-parking, and free WiFi. Pets are also welcome to stay free of charge.

Another highly-rated option is the B&B Podere Camaiano, which boasts a superb 10.0 rating. This property offers complimentary cots, a free buffet breakfast, and free WiFi. Like Valdonica, it also provides free self-parking and allows pets to stay without charge.
What are the best spa hotels in Roccastrada?
For an excellent spa experience in Roccastrada, consider La Melosa Resort & Spa - Adults Only or Valdonica Winery & Vineyard Residence.

The 4-star La Melosa Resort & Spa - Adults Only, rated 9.4, offers a full-service spa with a wide array of treatments including facial treatments, body treatments, body scrubs, manicures, and pedicures. Guests can also enjoy couples' treatment rooms, massage services, a sauna, a hot tub, a steam room, and a Turkish bath or hammam. Guests frequently comment on the beautiful and clean rooms.

Valdonica Winery & Vineyard Residence, with an impressive 9.4 rating, also features a full-service spa that is available daily, offering relaxing massage services. This hotel provides free breakfast, free WiFi, free toiletries, and complimentary self-parking. Pets are also welcome to stay free of charge.
What hotels in Roccastrada offer free breakfast?
For hotels in Roccastrada that offer complimentary breakfast, consider the Valdonica Winery & Vineyard Residence, B&B da Nada Locanda Toscana, B&B Podere Camaiano, and Agriturismo Tenuta di Montemassi La Fattoria.

The Valdonica Winery & Vineyard Residence, with an exceptional rating of 9.4, provides free breakfast and also allows pets to stay free of charge. Guests can also benefit from free self-parking and complimentary WiFi.

Another excellent option is the B&B da Nada Locanda Toscana, which also boasts a 9.4 rating. This establishment offers free buffet breakfast and free WiFi, ensuring a comfortable start to your day.

The B&B Podere Camaiano stands out with a superb 10.0 rating. Here, guests can enjoy a free buffet breakfast, along with free WiFi, free self-parking, and the convenience of pets staying free.

Finally, the 3-star Agriturismo Tenuta di Montemassi La Fattoria, rated 9.6, provides a free buffet breakfast. Additional amenities include free WiFi, free toiletries, and complimentary parking nearby, making it a well-rounded choice.
What are the top pet-friendly hotels in Roccastrada?
For top pet-friendly hotels in Roccastrada, consider the B&B Podere Camaiano, Agriturismo Tenuta di Montemassi La Fattoria, and Valdonica Winery & Vineyard Residence.

B&B Podere Camaiano stands out with an exceptional 10.0 rating, offering free accommodation for pets, complimentary breakfast, free WiFi, and free self-parking.

The 3-star Agriturismo Tenuta di Montemassi La Fattoria, with a 9.6 rating, permits dogs and provides free buffet breakfast.

Another excellent choice is the Valdonica Winery & Vineyard Residence, rated 9.4. This residence welcomes both dogs and cats, allows pets to stay for free, and offers complimentary breakfast, free self-parking, and free WiFi.

The B&B da Nada Locanda Toscana, with a 9.4 rating, also welcomes both dogs and cats, and provides complimentary breakfast, including a buffet option, along with free WiFi.
What are the best budget hotels in Roccastrada?
For a budget-friendly hotel in Roccastrada, consider the Agriturismo Tenuta di Montemassi La Fattoria.

This 3-star agriturismo, with an impressive 9.6 rating, offers a wonderful stay with several complimentary features. Guests can enjoy free WiFi, a free breakfast buffet, and free toiletries. For those travelling with infants, a free crib is available. Additionally, both nearby and on-site self-parking are free, adding to the convenience for those arriving by car.
What are the most romantic hotels in Roccastrada for couples?
For a romantic getaway in Roccastrada, consider the delightful La Melosa Resort & Spa - Adults Only or the charming Valdonica Winery & Vineyard Residence.

The 4-star La Melosa Resort & Spa - Adults Only, with an exceptional rating of 9.4, is designed for couples seeking relaxation and pampering. It features a full-service spa with a hot tub, sauna, steam room, and even couples' treatment rooms for shared massages and body treatments. Guests can also enjoy the outdoor pool with sun loungers and a poolside bar, great for a tranquil afternoon together.

Another wonderful option is the Valdonica Winery & Vineyard Residence, which also boasts an impressive rating of 9.4. This residence offers complimentary breakfast and free WiFi, making for a comfortable stay. Many rooms include a balcony, providing a lovely spot for couples to enjoy the views.
When is the best time to go to Roccastrada?
The best time to go to Roccastrada is during the spring (April to June) and autumn (September to October) months. These periods offer the most pleasant weather for exploring the Maremma region.

During spring, the countryside around Roccastrada is lush and green, with wildflowers in bloom, making it a beautiful time for scenic drives and enjoying the natural beauty. Temperatures are comfortably mild, typically ranging from 15°C to 25°C, superb for outdoor activities like hiking or visiting local vineyards without the intense summer heat.

Autumn also provides excellent conditions, with comfortable temperatures similar to spring, usually between 18°C and 26°C. This season is particularly appealing for those interested in food and wine, as it coincides with the grape harvest and olive picking. You'll find many local festivals celebrating these traditions, offering a genuine taste of Tuscan life.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Roccastrada.
How can I save on a Roccastrada hotel booking with Expedia?
Members always get our best prices. Find our best Roccastrada hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings.
How much is the nightly rate at a Roccastrada hotel?
Prices for hotels in Roccastrada often vary, but you can find a great deal from CA $106 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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