Roccastrada Holiday Rentals, Tuscany: Private House Rentals

Q: What are some hotels with pools in Roccastrada?

The Sense Experience Resort - Preferred Hotels & Resorts : Features a children's pool, a seasonal outdoor pool and a private beach. Also, another option that offers an on-site pool is Castello di Velona Resort Thermal SPA & Winery . View all hotels with pools in Roccastrada .

Q: Where is the best place to stay in Roccastrada?

Hotel Athena , located 22.5 mi (36.1 km) from the heart of Roccastrada, is a top choice for your stay, based on our traveller data. Other good choices for your stay in the area are Hotel Executive and NH Siena . See all available top hotels , or vacation rentals in Roccastrada .

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Our top choices for Roccastrada hotels

A spacious dining area with a large table and chairs, stone walls, and a view of the mountains.

1. Valdonica Winery & Vineyard Residence

Roccastrada

"After debating between many Tuscan vineyards/B&Bs to stay at, I am so glad we picked this one. The venue was beautiful, the room was nice and clean (with AC), and they had a gorgeous remote pool overlooking the vineyard. The people working were all incredibly kind and accommodating and went above and beyond to make our stay memorable, in addition to the owner. We enjoyed a wine tour/tasting and a cooking class, and had dinner at their restaurant that was one of our best meals in Italy. Our only...

Audrey

Rp3.004.418 total

includes taxes & fees

15 Nov - 16 Nov

An outdoor dining area with stone buildings, tables with orange tablecloths, and string lights.

2. Historic Farmhouse Casa del Chiodo

Roccastrada

Ian

Rp2.135.647 total

includes taxes & fees

10 Nov - 11 Nov

A restaurant with outdoor seating, a bar area, and a view of the landscape.

3. B&B da Nada Locanda Toscana

Roccastrada

jean

Rp1.484.209 total

includes taxes & fees

11 Nov - 12 Nov

A group of people dining at a table with a view of a valley and mountains.

4. Valdonica Winery - Chill in Nature Lodge

Roccastrada

Rp3.547.613 total

includes taxes & fees

10 Nov - 11 Nov

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

Roccastrada

Maaike

Rp1.785.337 total

includes taxes & fees

13 Nov - 14 Nov

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

Ribolla

Rp2.182.139 total

includes taxes & fees

10 Nov - 11 Nov

A pool with a modern water feature and a stone structure.

7. Mercure Petriolo Siena Terme Spa Hotel

Civitella Paganico

Mike

Rp1.662.962 total

includes taxes & fees

10 Nov - 11 Nov

A villa with a swimming pool, surrounded by trees and hills.

8. Castiglion del Bosco, A Rosewood Hotel

Montalcino

KEDARNATH

Rp18.161.566 total

includes taxes & fees

2 Dec - 3 Dec

A poolside area with lounge chairs, a table with drinks, and a view of hills.

9. Capanna Suites

Montalcino

Silvana

Rp5.272.498 total

includes taxes & fees

29 Nov - 30 Nov

A stone building with a pool, lounge chairs, and a garden with flowers.

10. Podere Brizio

Montalcino

Aseem

Rp4.116.084 total

includes taxes & fees

16 Nov - 17 Nov

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.

11. Conti di San Bonifacio Wine Resort

Gavorrano

Hannah

Rp10.793.937 total

includes taxes & fees

11 Nov - 12 Nov

A spa area with a stone wall, wooden beams, a large window with a view, and a hot tub.

12. Mastrojanni Relais - Small Luxury Hotels of the World

Montalcino

Suelina

Rp8.247.689 total

includes taxes & fees

10 Nov - 11 Nov

A stone building with a pool overlooking a mountainous landscape.

13. Castello di Velona Resort Thermal SPA & Winery

Montalcino

Melanie

Rp8.510.184 total

includes taxes & fees

9 Dec - 10 Dec

A person relaxing in a hot tub with a view of a vineyard and mountains in the background.

14. Villa Le Prata - Residenza del Vescovo

Montalcino

Karen

Rp7.616.166 total

includes taxes & fees

11 Nov - 12 Nov

A table with breakfast items and a wicker chair, overlooking a scenic landscape.

15. Palazzo Ravizza

Siena Historical Center

Roy

Rp2.201.156 total

includes taxes & fees

7 Dec - 8 Dec

A restaurant with tables and wicker chairs, large windows, and a view of buildings and greenery.

16. Palazzo Saloni

Montalcino

Michael

Rp5.303.742 total

includes taxes & fees

9 Dec - 10 Dec

A hot tub with a view of a historic building and mountains.

17. Casa Franci Montalcino

Montalcino

Jim

Rp4.664.297 total

includes taxes & fees

10 Nov - 11 Nov

A stone building with a pool, white lounge chairs, and umbrellas.

18. Le Ragnaie

Montalcino

Trevor

Rp2.230.918 total

includes taxes & fees

16 Nov - 17 Nov

A couple in a hot spring with a large rock formation in the background.

19. ADLER Thermae

San Quirico d'Orcia

Abdel

Rp13.140.226 total

includes taxes & fees

10 Dec - 11 Dec

A modern house with a stone facade, a swimming pool, and outdoor seating.

20. Castello Di Vicarello

Cinigiano

hala

Rp17.334.562 total

includes taxes & fees

10 Nov - 11 Nov

View all properties

Compare top hotels in Roccastrada

Valdonica Winery & Vineyard Residence Roccastrada View	Historic Farmhouse Casa del Chiodo Roccastrada View	B&B da Nada Locanda Toscana Roccastrada View	Country House il Ciliegio Roccastrada View	Mercure Petriolo Siena Terme Spa Hotel 5.0 star property Civitella Paganico View
9.2 Wonderful 46 reviews	10.0 Exceptional 6 reviews	9.6 Exceptional 18 reviews	9.2 Wonderful 7 reviews	8.6 Excellent 267 reviews
The price is Rp2.694.640 Rp3.004.418 total includes taxes & fees 15 Nov - 16 Nov	The price is Rp1.904.848 Rp2.135.647 total includes taxes & fees 10 Nov - 11 Nov	The price is Rp1.312.632 Rp1.484.209 total includes taxes & fees 11 Nov - 12 Nov	The price is Rp1.586.384 Rp1.785.337 total includes taxes & fees 13 Nov - 14 Nov	The price is Rp1.511.784 Rp1.662.962 total includes taxes & fees 10 Nov - 11 Nov
Yes, Breakfast included Yes, Pool Yes, Spa Yes, Pet-friendly Yes, WiFi included Yes, Parking	Yes, Breakfast included No Pool No Spa No Pet-friendly Yes, WiFi included Yes, Parking	Yes, Breakfast included No Pool No Spa Yes, Pet-friendly Yes, WiFi included No Parking	No Breakfast included Yes, Pool No Spa Yes, Pet-friendly Yes, WiFi included Yes, Parking	No Breakfast included Yes, Pool Yes, Spa Yes, Pet-friendly No WiFi included Yes, Parking

Stay near popular Roccastrada attractions

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.

See properties

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.

See all hotels in Roccastrada

An ancient stone tower with a view of rolling hills and fields in the background.

Top Roccastrada Hotel Reviews

Valdonica Winery & Vineyard Residence

Roccastrada

10/10 Excellent

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...

Anonymous traveller

Castiglion del Bosco, A Rosewood Hotel

Montalcino

10/10 Excellent

Abigail

A bedroom with a bed, a chair, a table, and a stone wall.

Dimora delle Muse

Montalcino

10/10 Excellent

What a wonderful find. The hotel is just 4 rooms, beautifully and carefully designed with a lot of attention to detail. Rooms are large, fantastic powerful shower and amazing mattress! Best sleep I'd had in months! Sara and Michele bought the historic building after years of experience in 5 start hotels, so you get 5 start care and attention in a beautifully designed boutique hotel. You can tell they love what they do and are passionate about making your stay as comfortable as possible....

Anonymous traveller

Podere Brizio

Montalcino

10/10 Excellent

Julie

Villa Le Prata - Residenza del Vescovo

Montalcino

10/10 Excellent

Nadia

A motorcycle parked in front of a brick building with arched doorways and a street lamp.

Torre del Fuggisole

Siena City Centre

10/10 Excellent

An absolute little gem in Siena! ⭐⭐⭐⭐⭐ Sara and Carolina were fantastic from start to finish. They couldn’t do enough for us. They let us know exactly where to park, which was really helpful as Siena has traffic restrictions for visitors, helped us book a winery tour and gave us some great recommendations for sightseeing and restaurants. The communication was brilliant and they made everything so easy for us. The hotel itself is lovely, in a perfect location, beautifully restored and...

Jane

Capanna Suites

Montalcino

10/10 Excellent

Mike

A hotel room with a large bed, a vanity with a mirror, and a green archway.

Hotel Certosa Di Maggiano

Siena

10/10 Excellent

Lizzy

Mercure Petriolo Siena Terme Spa Hotel

Civitella Paganico

10/10 Excellent

Steve

A terrace with wicker chairs and a table set for breakfast, overlooking a historic town with terracotta buildings and cypress trees.

Villa del Sole Siena

Siena City Centre

10/10 Excellent

Seasoned travel

A table set for two with a wine glass, a bowl of nuts, and a glass of water.

Relais degli Angeli

Siena City Centre

10/10 Excellent

Olivia

Castello Di Vicarello

Cinigiano

10/10 Excellent

The residence is absolutely gorgeous in the middle of nowhere in Tuscany. The road is a bit bumpy to come but it’s worth it. The suites are very confortable and all the amenities are clean and very well decorated. I have to give a special wow to the breakfast in the morning, Simoh the chef, and his staff are simply amazing. Kind and very caring, they are top notch and the products they serve are simply delicious. The general atmosphere of the castle is great too. The place where you take dinner...

Vithaya

Frequently Asked Questions

If I need to cancel my hotel reservation in Roccastrada, will I receive a refund?

Yes! The majority of hotel bookings are fully refundable if you cancel before the hotel’s cancellation deadline, which in most cases is within 24 or 48 hours of the scheduled arrival. If you booked a non-refundable reservation, it might still be possible to cancel it and receive a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Roccastrada.

What is the favourite LGBTQ-friendly accommodation in Roccastrada?

La Melosa Resort & Spa - Adults Only is a top LGBTQ-friendly hotel that features a full-service spa and free Wi-Fi. See all available hotels listed as LGBTQ-friendly in Roccastrada.

What's the best dog-friendly place to stay in Roccastrada?

Valdonica Winery & Vineyard Residence is a top dog-friendly option for your stay. See more pet-friendly hotel accommodations in Roccastrada.

What are some hotels with pools in Roccastrada?

The Sense Experience Resort - Preferred Hotels & Resorts: Features a children's pool, a seasonal outdoor pool and a private beach. Also, another option that offers an on-site pool is Castello di Velona Resort Thermal SPA & Winery. View all hotels with pools in Roccastrada.

What is the best spa hotel in Roccastrada?

Valdonica Winery & Vineyard Residence is a highly recommended luxury spa hotel featuring a bar and a restaurant. Enjoy a massage at the on-site spa. Another popular spa hotel in Roccastrada is La Melosa Resort & Spa - Adults Only. See all spa hotels in Roccastrada.

What is staying in Roccastrada like?

Visitors will definitely enjoy all that Roccastrada has to offer. This city also attracts tourists with its rich culture. In Roccastrada, there are 192 hotels and other accommodation options to choose from. Find out more about Roccastrada.

What is there to see in Roccastrada?

Landmarks like Castello del Belagaio and Sassoforte Castle might be worth a visit. The picturesque setting of I Canaloni del Torrente Farma and Val di Merse exemplify the area's natural beauty. Additionally, you might want to add Podere Ristella Vineyards and Winery to your itinerary. Take a look at what more there is to see and do in Expedia's Roccastrada guide.

How can I get around Roccastrada?

To see more of the surrounding area, ride one of the trains from Roccastrada Station or Sticciano Station. If you want to venture out around the area, you may want a rental car in Roccastrada for your journey.

What's the seasonal weather in Roccastrada?

The hottest months are usually August and July, with an average temperature of 23°C, while the coldest months are January and February, with an average of 9°C. Average annual precipitation for Roccastrada is 788 mm.

Where is the best place to stay in Roccastrada?

Hotel Athena, located 22.5 mi (36.1 km) from the heart of Roccastrada, is a top choice for your stay, based on our traveller data. Other good choices for your stay in the area are Hotel Executive and NH Siena. See all available top hotels, or vacation rentals in Roccastrada.

Find hotels in Roccastrada from Rp1.186.935

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Roccastrada

Check prices for these dates

Filter by

Property class

Guest rating

Our top choices for Roccastrada hotels

1. Valdonica Winery & Vineyard Residence

2. Historic Farmhouse Casa del Chiodo

3. B&B da Nada Locanda Toscana

4. Valdonica Winery - Chill in Nature Lodge

5. Country House il Ciliegio

6. Le Vie del Mare Camere

7. Mercure Petriolo Siena Terme Spa Hotel

8. Castiglion del Bosco, A Rosewood Hotel

9. Capanna Suites

10. Podere Brizio

11. Conti di San Bonifacio Wine Resort

12. Mastrojanni Relais - Small Luxury Hotels of the World

13. Castello di Velona Resort Thermal SPA & Winery

14. Villa Le Prata - Residenza del Vescovo

15. Palazzo Ravizza

16. Palazzo Saloni

17. Casa Franci Montalcino

18. Le Ragnaie

19. ADLER Thermae

20. Castello Di Vicarello

Compare top hotels in Roccastrada

Valdonica Winery & Vineyard Residence

Historic Farmhouse Casa del Chiodo

B&B da Nada Locanda Toscana

Country House il Ciliegio

Mercure Petriolo Siena Terme Spa Hotel

Stay near popular Roccastrada attractions

Podere Ristella Vineyards and Winery

Learn more about Roccastrada

Top Roccastrada Hotel Reviews

Valdonica Winery & Vineyard Residence

10/10 Excellent

Frequently Asked Questions

If I need to cancel my hotel reservation in Roccastrada, will I receive a refund?

What is the favourite LGBTQ-friendly accommodation in Roccastrada?

What's the best dog-friendly place to stay in Roccastrada?

What are some hotels with pools in Roccastrada?

What is the best spa hotel in Roccastrada?

What is staying in Roccastrada like?

What is there to see in Roccastrada?

How can I get around Roccastrada?

What's the seasonal weather in Roccastrada?

Where is the best place to stay in Roccastrada?