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Go beyond your typical stay in Roccastrada

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Check prices for these dates

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Nov 15 - Nov 16
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Nov 16 - Nov 17
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Nov 20 - Nov 22
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Our top choices for Roccastrada hotels

A corridor with stone walls and wooden benches.

1. 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 ₩139,253
₩156,125 total
includes taxes & fees
Nov 16 - Nov 17
Historic Farmhouse Casa del Chiodo
A swimming pool with white lounge chairs and a view of the landscape.

2. 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 ₩116,824
₩131,456 total
includes taxes & fees
Nov 18 - Nov 19
Country House il Ciliegio
An outdoor seating area with tables and chairs, surrounded by a wooden fence, and string lights overhead.

3. Valdonica Winery - Chill in Nature Lodge

Valdonica Winery - Chill in Nature Lodge
Roccastrada
The price is ₩233,092
₩259,348 total
includes taxes & fees
Nov 22 - Nov 23
Valdonica Winery - Chill in Nature Lodge
A bedroom with a bed, a nightstand, a wall-mounted lamp, a window with a view, and a ceiling light fixture.

4. Le Vie del Mare Camere

Le Vie del Mare Camere
Ribolla
The price is ₩145,022
₩159,524 total
includes taxes & fees
Nov 16 - Nov 17
Le Vie del Mare Camere
A pool area with lounge chairs and umbrellas, surrounded by trees and a building.

5. 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 ₩110,518
₩121,570 total
includes taxes & fees
Nov 16 - Nov 17
Mercure Petriolo Siena Terme Spa Hotel
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.

6. 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 ₩717,347
₩789,080 total
includes taxes & fees
Nov 23 - Nov 24
Conti di San Bonifacio Wine Resort
A stone building with a pool, lounge chairs, and a garden with flowers.

7. Podere Brizio

Podere Brizio
Montalcino
9.8 out of 10, Exceptional, (181 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 ₩262,825
₩300,902 total
includes taxes & fees
Nov 17 - Nov 18
Podere Brizio
A view through a window of a town with traditional architecture, cobblestone streets, and a rural landscape.

8. 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 ₩339,083
₩387,726 total
includes taxes & fees
Dec 15 - Dec 16
Palazzo Saloni
A modern wooden cabin with a glass-bottomed pool, surrounded by lush greenery.

9. ADLER Thermae

ADLER Thermae
5.0 star property
San Quirico d'Orcia
9.6 out of 10, Exceptional, (84 reviews)
"Good dining."
United Kingdom
Abdel
The price is ₩1,014,641
₩1,123,474 total
includes taxes & fees
Dec 10 - Dec 11
ADLER Thermae
A person relaxing in a hot tub with a view of a vineyard and mountains in the background.

10. Villa Le Prata - Residenza del Vescovo

Villa Le Prata - Residenza del Vescovo
Montalcino
10.0 out of 10, Exceptional, (96 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 ₩492,761
₩556,773 total
includes taxes & fees
Nov 23 - Nov 24
Villa Le Prata - Residenza del Vescovo
A terrace with wicker chairs and a table set for breakfast, overlooking a historic town with terracotta buildings and cypress trees.

11. 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 ₩153,885
₩173,695 total
includes taxes & fees
Nov 30 - Dec 1
Villa del Sole Siena
A stone house with a pool and outdoor seating.

12. Mastrojanni Relais - Small Luxury Hotels of the World

Mastrojanni Relais - Small Luxury Hotels of the World
Montalcino
9.8 out of 10, Exceptional, (85 reviews)
"Beautiful property and five star service. We loved everything about our stay!"
United States
Suelina
The price is ₩516,498
₩582,884 total
includes taxes & fees
Nov 16 - Nov 17
Mastrojanni Relais - Small Luxury Hotels of the World
A stone building with a pool overlooking a mountainous landscape.

13. 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, (384 reviews)
"Great breakfast and amazing property. Staff oa there to please at every moment."
United States
Sean
The price is ₩778,043
₩870,584 total
includes taxes & fees
Dec 9 - Dec 10
Castello di Velona Resort Thermal SPA & Winery
A villa with a swimming pool, surrounded by trees and hills.

14. Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel
5.0 star property
Montalcino
10.0 out of 10, Exceptional, (88 reviews)
"Unique property well maintained and quite Serene , great staff"
United States
KEDARNATH
The price is ₩1,193,589
₩1,327,684 total
includes taxes & fees
Dec 2 - Dec 3
Castiglion del Bosco, A Rosewood Hotel
A stone building with a staircase leading to a door, surrounded by stone walls and potted plants.

15. 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 ₩272,860
₩314,882 total
includes taxes & fees
Dec 13 - Dec 14
Casa Franci Montalcino
A four-poster bed with a bench, stone flooring, and a stone wall.

16. 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 ₩337,005
₩385,441 total
includes taxes & fees
Nov 29 - Nov 30
Capanna Suites
A table with breakfast items and a wicker chair, overlooking a scenic landscape.

17. Palazzo Ravizza

Palazzo Ravizza
4.0 star property
Siena Historical Center
9.4 out of 10, Exceptional, (904 reviews)
"Beautiful hotel with lovely rear courtyard overlooking Tuscany. Very nice breakfast and charming rooms with a view."
Canada
Dwight
The price is ₩142,266
₩160,914 total
includes taxes & fees
Dec 7 - Dec 8
Palazzo Ravizza
A cozy dining area with a table set for two, a vase of dried flowers, and candles on the table.

18. Sangallo Park Hotel

Sangallo Park Hotel
3.0 star property
Vico Alto
9.0 out of 10, Wonderful, (623 reviews)
"Excellent staff"
United Kingdom
Marcio Tadeu
The price is ₩139,989
₩158,409 total
includes taxes & fees
Nov 20 - Nov 21
Sangallo Park Hotel
An outdoor dining area with tables and chairs, surrounded by a brick wall and greenery.

19. Hotel Athena

Hotel Athena
4.0 star property
Siena Historical Center
9.2 out of 10, Wonderful, (1,000 reviews)
"Hotel Athena was a great property in Siena right inside the town walls. Very convenient as we had a rental car and did day trips throughout Tuscany. Breakfast buffet was included and great selection and quality of food. Would definitely stay here again and recommend to others."
United States
Dawn
The price is ₩126,068
₩142,936 total
includes taxes & fees
Nov 29 - Nov 30
Hotel Athena
A rectangular swimming pool with a stone border, surrounded by a brick deck and a metal fence.

20. 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 ₩125,387
₩152,662 total
includes taxes & fees
Nov 16 - Nov 17
Le Ragnaie
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 corridor with stone walls and wooden benches.

Historic Farmhouse Casa del Chiodo

Roccastrada
View
A swimming pool with white lounge chairs and a view of the landscape.

Country House il Ciliegio

Roccastrada
View
A pool area with lounge chairs and umbrellas, surrounded by trees and a building.

Mercure Petriolo Siena Terme Spa Hotel

5.0 star property
Civitella Paganico
View
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.

Conti di San Bonifacio Wine Resort

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

Podere Brizio

Montalcino
View
10.0
Exceptional
6 reviews
9.2
Wonderful
7 reviews
8.6
Excellent
267 reviews
9.4
Exceptional
29 reviews
9.8
Exceptional
181 reviews
The price is ₩139,253
₩156,125 total
includes taxes & fees
Nov 16 - Nov 17
The price is ₩116,824
₩131,456 total
includes taxes & fees
Nov 18 - Nov 19
The price is ₩110,518
₩121,570 total
includes taxes & fees
Nov 16 - Nov 17
The price is ₩717,347
₩789,080 total
includes taxes & fees
Nov 23 - Nov 24
The price is ₩262,825
₩300,902 total
includes taxes & fees
Nov 17 - Nov 18
  • Yes, Breakfast included
  • No Pool
  • No Spa
  • No Pet friendly
  • Yes, WiFi included
  • Yes, 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
  • Yes, Breakfast included
  • Yes, Pool
  • No Spa
  • Yes, Pet friendly
  • Yes, WiFi included
  • Yes, Parking
  • Yes, Breakfast included
  • Yes, Pool
  • Yes, Spa
  • No Pet friendly
  • Yes, 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

A corridor with stone walls and wooden benches.
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.