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Go beyond your typical stay in Roccastrada

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Nov 6 - Nov 7
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Nov 7 - Nov 8
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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

Valdonica Winery & Vineyard Residence
Roccastrada
9.2 out of 10, Wonderful, (46 reviews)
"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...
United States
Audrey
The price is ₩200,239
₩224,837 total
includes taxes & fees
Nov 8 - Nov 9
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)
"Everything about this place is perfect, highly recommend."
United States
Ian
The price is ₩144,047
₩161,501 total
includes taxes & fees
Nov 9 - Nov 10
Historic Farmhouse Casa del Chiodo
A restaurant with outdoor seating, a bar area, and a view of the landscape.

3. B&B da Nada Locanda Toscana

B&B da Nada Locanda Toscana
Roccastrada
9.6 out of 10, Exceptional, (18 reviews)
"Ras"
France
jean
The price is ₩98,576
₩111,483 total
includes taxes & fees
Nov 7 - Nov 8
B&B da Nada Locanda Toscana
A group of people dining at a table with a view of a valley and mountains.

4. Valdonica Winery - Chill in Nature Lodge

Valdonica Winery - Chill in Nature Lodge
Roccastrada
The price is ₩241,115
₩268,276 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.

5. 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 ₩119,079
₩134,036 total
includes taxes & fees
Nov 8 - Nov 9
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.

6. Le Vie del Mare Camere

Le Vie del Mare Camere
Ribolla
The price is ₩150,015
₩165,016 total
includes taxes & fees
Nov 7 - Nov 8
Le Vie del Mare Camere
A pool with a modern water feature and a stone structure.

7. 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)
"We had a great time. I would recommend this hotel when in Tuscany. "
United States
Mike
The price is ₩114,323
₩125,755 total
includes taxes & fees
Nov 8 - Nov 9
Mercure Petriolo Siena Terme Spa Hotel
A stone wall with a view of rolling hills and mountains.

8. Castello Banfi - Il Borgo - Relais et Chateaux

Castello Banfi - Il Borgo - Relais et Chateaux
5.0 star property
Montalcino
10.0 out of 10, Exceptional, (139 reviews)
"This property is pristine. Absolutely beautiful with some of the best views in Tuscany. I would recommend this experience to anyone."
United States
Jeanine
The price is ₩1,843,029
₩2,042,574 total
includes taxes & fees
Nov 7 - Nov 8
Castello Banfi - Il Borgo - Relais et Chateaux
A stone building with a pool, lounge chairs, and a garden with flowers.

9. Podere Brizio

Podere Brizio
Montalcino
9.8 out of 10, Exceptional, (180 reviews)
"Lovely setting. Great views and incredibly helpful staff. Really enjoyed our two days. Can’t wait to come back 👍"
United States
Aseem
The price is ₩271,876
₩311,264 total
includes taxes & fees
Nov 16 - Nov 17
Podere Brizio
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.

10. Conti di San Bonifacio Wine Resort

Conti di San Bonifacio Wine Resort
Gavorrano
9.4 out of 10, Exceptional, (29 reviews)
"Unbelievable beautiful place. We absolutely loved our time there. "
United States
Hannah
The price is ₩742,095
₩816,298 total
includes taxes & fees
Nov 11 - Nov 12
Conti di San Bonifacio Wine Resort
A spa area with a stone wall, wooden beams, a large window with a view, and a hot tub.

11. Mastrojanni Relais - Small Luxury Hotels of the World

Mastrojanni Relais - Small Luxury Hotels of the World
Montalcino
9.8 out of 10, Exceptional, (84 reviews)
"Beautiful property and five star service. We loved everything about our stay!"
United States
Suelina
The price is ₩527,689
₩595,701 total
includes taxes & fees
Nov 7 - Nov 8
Mastrojanni Relais - Small Luxury Hotels of the World
A poolside area with lounge chairs, a table with drinks, and a view of hills.

12. Capanna Suites

Capanna Suites
Montalcino
9.8 out of 10, Exceptional, (169 reviews)
"This is our new favorite place to stay near Montalcino. It is beautiful beyond words, and the rooms are fantastic, spacious, comfortable, and just perfect. We will be back!"
United States
Silvana
The price is ₩348,610
₩398,714 total
includes taxes & fees
Nov 29 - Nov 30
Capanna Suites
A villa with a swimming pool, surrounded by trees and hills.

13. Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel
5.0 star property
Montalcino
10.0 out of 10, Exceptional, (87 reviews)
"Unique property well maintained and quite Serene , great staff"
United States
KEDARNATH
The price is ₩1,234,691
₩1,373,403 total
includes taxes & fees
Dec 2 - Dec 3
Castiglion del Bosco, A Rosewood Hotel
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

Villa Le Prata - Residenza del Vescovo
Montalcino
10.0 out of 10, Exceptional, (95 reviews)
"A lovely place to enjoy the wine and the region. Rooms are spacious and extremely clean. House has a magical feel to it. Staff were so kind and always on hand to help out. A wonderful visit!"
Canada
Karen
The price is ₩509,729
₩575,945 total
includes taxes & fees
Nov 11 - Nov 12
Villa Le Prata - Residenza del Vescovo
A stone building with a pool overlooking a mountainous landscape.

15. Castello di Velona Resort Thermal SPA & Winery

Castello di Velona Resort Thermal SPA & Winery
5.0 star property
Montalcino
9.0 out of 10, Wonderful, (380 reviews)
"Loved our stay at the hotel - super relaxing and great for our honeymoon. The staff were so kind and really helpful"
United States
Melanie
The price is ₩685,420
₩769,205 total
includes taxes & fees
Nov 30 - Dec 1
Castello di Velona Resort Thermal SPA & Winery
A restaurant with tables and wicker chairs, large windows, and a view of buildings and greenery.

16. Palazzo Saloni

Palazzo Saloni
Montalcino
10.0 out of 10, Exceptional, (14 reviews)
"Excellent location to tour wine country montalcino."
United States
Michael
The price is ₩346,755
₩396,498 total
includes taxes & fees
Dec 7 - Dec 8
Palazzo Saloni
A hot tub with a view of a historic building and mountains.

17. Casa Franci Montalcino

Casa Franci Montalcino
Montalcino
9.8 out of 10, Exceptional, (47 reviews)
"Fantastic accommodations, friendly and helpful staff"
United States
Jim
The price is ₩314,284
₩360,956 total
includes taxes & fees
Nov 7 - Nov 8
Casa Franci Montalcino
A terrace with wicker chairs and a table set for breakfast, overlooking a historic town with terracotta buildings and cypress trees.

18. Villa del Sole Siena

Villa del Sole Siena
Siena City Centre
9.8 out of 10, Exceptional, (689 reviews)
"Beautiful place. The views are amazing and the rooms are wonderful."
United States
Lynda
The price is ₩170,398
₩192,011 total
includes taxes & fees
Dec 3 - Dec 4
Villa del Sole Siena
A stone building with a stone staircase, surrounded by lush greenery and a stone pathway.

19. Le Ragnaie

Le Ragnaie
Montalcino
9.2 out of 10, Wonderful, (343 reviews)
"Amazing stay very welcoming and gorgeous views!"
United States
Trevor
The price is ₩124,717
₩152,432 total
includes taxes & fees
Nov 10 - Nov 11
Le Ragnaie
A hotel room with a large bed, a desk with a computer, a lamp, and a door leading to another room.

20. Maestrale Resort Hotel - Alberese, Grosseto

Maestrale Resort Hotel - Alberese, Grosseto
4.0 star property
Grosseto
9.0 out of 10, Wonderful, (18 reviews)
"Great team, easy stay. Thank you!"
United States
Eric
The price is ₩111,759
₩122,935 total
includes taxes & fees
Nov 7 - Nov 8
Maestrale Resort Hotel - Alberese, Grosseto
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

Compare top 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

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

Historic Farmhouse Casa del Chiodo

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

B&B da Nada Locanda Toscana

Roccastrada
View
A courtyard with stone steps leading to a small building, surrounded by lush greenery and stone buildings in the background.

Country House il Ciliegio

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

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 ₩200,239
₩224,837 total
includes taxes & fees
Nov 8 - Nov 9
The price is ₩144,047
₩161,501 total
includes taxes & fees
Nov 9 - Nov 10
The price is ₩98,576
₩111,483 total
includes taxes & fees
Nov 7 - Nov 8
The price is ₩119,079
₩134,036 total
includes taxes & fees
Nov 8 - Nov 9
The price is ₩114,323
₩125,755 total
includes taxes & fees
Nov 8 - Nov 9
  • 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

An outdoor dining area with stone buildings, tables with orange tablecloths, and string lights.
Historic Farmhouse Casa del Chiodo

Historic Farmhouse Casa del Chiodo

Historic Farmhouse Casa del Chiodo
Roccastrada

10/10 Excellent

The Casa Del Chiodo was the perfect Tuscan B&B experience for us. From the moment Marco greeted us to the amazing multiple course evening meal that owner/chef Paola prepared to the breakfast served by Irene, it was the epitome of Italian hospitality. While the evening meal was extra, it was definitely worth it as it showcased local farm grown and hunted/gathered foods (such as mushrooms, venison and roasted chestnuts). Our room was clean, true to historical construction with modern amenities....
United States
Nita Marie
Reviewed October 29, 2026
Historic Farmhouse Casa del Chiodo

Frequently Asked Questions

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

Yes! The majority of room reservations are refundable provided that you cancel before the accommodation's cancellation deadline, which is often 24 or 48 hours before your arrival date. If you have a reservation that's non-refundable, it might still be possible to cancel it and be given a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Roccastrada.

Where can I learn more about changing or cancelling my trip to Roccastrada?

For more information about changing or cancelling your trip to Roccastrada, head over to our customer service page.

What is the favorite LGBTQ-friendly hotel in Roccastrada?

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

What's the best pet-friendly hotel in Roccastrada?

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

What's the best hotel to stay with easy access to Castello del Belagaio?

Hotel Residence Sant'Uberto is one of the top choices for your stay based on our traveler data, and this 3-star hotel offers a restaurant and an outdoor pool. It's located 3.1 mi (5 km) from Castello del Belagaio. Other good options within 5 miles include Il Boscaiolo and La Pergola.

What about the best place to stay near I Canaloni del Torrente Farma?

One of the top choices for your stay is La Pergola, located 1.3 mi (2.1 km) from I Canaloni del Torrente Farma, and this vacation home offers an outdoor pool and free parking. Il Boscaiolo and Hotel Residence Sant'Uberto are two other good choices within 5 miles.

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 with an onsite 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's the best place to stay near Peretola Airport (FLR)?

Hotel Cosmopolitan is a popular 4-star hotel featuring free WiFi and a bar. It's located a short 0.7 mi (1.2 km) from Peretola Airport. Other good choices close to the airport are Best Western Plus CHC Florence and Hotel Mirage.

What is staying in Roccastrada like?

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

What should I see while I'm 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. Check out what more to see and do in Expedia's Roccastrada guide.

How should 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 like in Roccastrada?

The hottest months are usually August and July with an average temp of 74°F, while the coldest months are January and February with an average of 48°F. Average annual precipitation for Roccastrada is 31 inches.

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 traveler data. Two other choices for your trip to the area are Hotel Executive and NH Siena. See all available top hotels, or vacation rentals in Roccastrada.