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

Hotels in Roccastrada

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Dates

November 2026

December 2026

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Where to stay in Roccastrada?

Properties are selected based on real traveler reviews and popularity among guests who’ve booked a night in Roccastrada on Hotels.com. These Roccastrada hotels consistently deliver on quality, location and traveler experience. Last updated on November 5, 2026.

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

1. Valdonica Winery & Vineyard Residence

Roccastrada

NT$5,441 total

includes taxes & fees

Nov 8 - Nov 9

2. B&B da Nada Locanda Toscana

Roccastrada

NT$2,689 total

includes taxes & fees

Nov 6 - Nov 7

A stone building with multiple windows and a balcony, a table set for dining, and lush greenery in the foreground.

3. Historic Farmhouse Casa del Chiodo

Roccastrada

NT$3,895 total

includes taxes & fees

Nov 9 - Nov 10

A bedroom with a wooden headboard, a large bed, a framed picture on the wall, and a sliding glass door leading to an outdoor area.

4. Valdonica Winery - Chill in Nature Lodge

Roccastrada

NT$5,895 total

includes taxes & fees

Nov 10 - Nov 11

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

NT$3,233 total

includes taxes & fees

Nov 6 - Nov 7

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

NT$3,980 total

includes taxes & fees

Nov 6 - Nov 7

A pool with lounge chairs and a sunset view.

7. Mercure Petriolo Siena Terme Spa Hotel

Civitella Paganico

NT$3,033 total

includes taxes & fees

Nov 9 - Nov 10

A stone building with a tiled roof, a paved pathway, and a well-maintained garden.

8. Podere Brizio

Montalcino

NT$7,435 total

includes taxes & fees

Nov 16 - Nov 17

A modern hotel lobby with a high ceiling and a glass roof, featuring wooden paneling, comfortable seating, and a large wall mural.

9. Four Points by Sheraton Siena

Scacciapensieri

NT$4,704 total

includes taxes & fees

Nov 20 - Nov 21

A room with a view of a cityscape, featuring a pool, a table with candles, and two chairs.

10. Hotel Airone

Grosseto

NT$4,412 total

includes taxes & fees

Nov 6 - Nov 7

A historic building complex with multiple structures, including a large central building with arches and smaller surrounding buildings.

11. Hotel Athena

Siena Historical Center

NT$3,419 total

includes taxes & fees

Nov 29 - Nov 30

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

12. Dimora delle Muse

Montalcino

NT$6,900 total

includes taxes & fees

Nov 8 - Nov 9

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

13. Villa Le Prata - Residenza del Vescovo

Montalcino

NT$13,891 total

includes taxes & fees

Nov 6 - Nov 7

A table with a glass of white wine, a metal pitcher, and a wooden board with various cheeses and cured meats.

14. SI Montalcino Hotel

Montalcino

NT$4,230 total

includes taxes & fees

Nov 12 - Nov 13

A lobby with a chandelier, columns, sofas, and a reception desk.

15. NH Siena

Siena Historical Center

NT$3,860 total

includes taxes & fees

Nov 24 - Nov 25

A hotel courtyard with a paved walkway, benches, and potted plants.

16. Fattoria La Principina Hotel & Congress

Grosseto

NT$3,005 total

includes taxes & fees

Nov 6 - Nov 7

A stone building with a stone staircase, surrounded by lush greenery and a stone pathway.

17. Le Ragnaie

Montalcino

NT$3,773 total

includes taxes & fees

Nov 10 - Nov 11

A swimming pool with a water feature, a building with multiple balconies, and flags.

18. Hotel Terme Marine Leopoldo II

Grosseto

NT$3,235 total

includes taxes & fees

Nov 12 - Nov 13

A stone wall with a view of rolling hills and mountains.

19. Castello Banfi - Il Borgo - Relais et Chateaux

Montalcino

NT$48,774 total

includes taxes & fees

Nov 7 - Nov 8

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

Grosseto

NT$2,965 total

includes taxes & fees

Nov 6 - Nov 7

View all properties

Check out pet-friendly hotels in Roccastrada

Valdonica Winery & Vineyard Residence

Roccastrada

NT$5,441 total

includes taxes & fees

Nov 8 - Nov 9

View all properties

Go beyond your typical stay in Roccastrada

Our prices for hotels in Roccastrada are cheapest in November

Top landmarks in Roccastrada

Podere Ristella Vineyards and Winery

Travelers might want a tour of Podere Ristella Vineyards and Winery, just one of the places to visit, and located 6 mi (9.6 km) from central Roccastrada.

See properties

Learn more about Roccastrada

Roccastrada is well-known for its attractions such as I Canaloni del Torrente Farma and Podere Ristella Vineyards and Winery.

See all hotels in Roccastrada

Check out reviews of Roccastrada hotels guests love

Historic Farmhouse Casa del Chiodo

Roccastrada

10/10 Exceptional

Ian

Castello Banfi - Il Borgo - Relais et Chateaux

Montalcino

10/10 Exceptional

Castello Banfi - Il Borgo is either a great place to anchor your restoration or to invigorate your exploration. There's plenty to do on property: a wine tour through the high-tech wine production facility; wine tasting overlooking the Tuscan landscape (you have a substantial selection to choose from); lounging by the pool overlooking the many acres of grape vines, olive and plum trees, and the hills beyond; a visit to their glass museum; an intimate cooking class with one of the top Chefs in...

Greg

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

Castiglion del Bosco, A Rosewood Hotel

Montalcino

10/10 Exceptional

mauricio

Villa Le Prata - Residenza del Vescovo

Montalcino

10/10 Exceptional

John

A courtyard with outdoor seating, a building with multiple windows, and a stone wall.

Palazzo Saloni

Montalcino

10/10 Exceptional

Ashley

Dimora delle Muse

Montalcino

10/10 Exceptional

Anonymous traveler

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

Hotel Certosa Di Maggiano

Siena

10/10 Exceptional

Anonymous traveler

A stone building with multiple windows and a balcony, surrounded by lush greenery and trees.

Relais Le Macine di Stigliano

Sovicille

10/10 Exceptional

Tim

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

Mastrojanni Relais - Small Luxury Hotels of the World

Montalcino

10/10 Exceptional

Frank

A room with two striped armchairs, a small table with chess pieces, and a mirror reflecting a dining area.

La Dimora Dei Monaci

Siena City Centre

10/10 Exceptional

we stayed for 4 nights and used Seina as our base for our first visit to Tuscany. The owners were very helpful. They provided maps and information on all the local sights, plus some history of the town. One night we asked them to make dinner reservations and they had to call over 10 places due to a busy night. But they found us a great restaurant for dinner. Another day they provide a detailed schedule for buses to visit one of the towns we were interested in. The B&B is very close to the...

Alan

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

Torre del Fuggisole

Siena City Centre

10/10 Exceptional

Kristen M

A bathroom with a freestanding bathtub, a large window, and a mirror.

Casa Franci Montalcino

Montalcino

10/10 Exceptional

Sandra

Podere Brizio

Montalcino

10/10 Exceptional

Wonderful, beautiful property! The rooms are immaculate and nicely decorated. Breakfast is bountiful with wonderful homemade tarts, breads, frittatas. Do not miss dining in the restaurant for dinner. We had several dinners among the best of our 3 week trip to Italy. The staff is very professional, friendly and passionate about their job. Thank you Vito and Caterina for going above and beyond expectations and making our stay one I will never forget. We are already planning our return.

Sharon

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

Capanna Suites

Montalcino

10/10 Exceptional

This hotel set the bar EXTREMELY high for our 2 week vacation. The staff is truly invested in making sure your stay is superb. This is a relatively new-build hotel for Tuscany, but it’s built to look traditional with modern twists. Our room was very spacious and had a modern shower and changing closet. The bed and pillows were very comfortable. The pool is beautiful and the spa house is great. Currently you have to book the spa access a day ahead due to covid precautions; you get 1 hour to...

Anonymous traveler

A brick building with two arched windows, one with a metal grill and the other with a decorative glass design.

Hotel Palazzetto Rosso

Siena City Centre

10/10 Exceptional

Cristian

A pool area with lounge chairs and umbrellas, surrounded by stone flooring and trees.

Agriturismo Sweet Cottage

Grosseto

10/10 Exceptional

This place is AMAZING! I cannot stress what a wonderful (ENGLISH SPEAKING) staff they have! I wish I had planned 2 nights here instead of just one. Wife and I on 9 city tour from north to south (Naples, Anzio, Grosseto, Genoa, Pisa, Milan, Florence, Montepulciano, Rome). Some were 2 night stays (never been there) and others were 1 night only (been there at some time in past). DON’T FORGET TO RESERVE lunch and/or dinner on property. Breakfast was included, but you pay for lunch/supper and...

Michael

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 Exceptional

Stained here at the end of an eight day trip around Italy. This hotel was head and shoulders above the others I visited, it is a boutique hotel of seven rooms. Our room was a suite. It was bigger than many apartments, with a large living room with daybed, a beautiful master bathroom with jetted tub and separate shower with jets overhead as well as side jets, ample closet storage, fridge, and safe. The rooms here have antique furniture and hand painted ceilings. I loved the breakfast on the...

Susie

B&B da Nada Locanda Toscana

Roccastrada

10/10 Exceptional

We stayed here for three nights and had an incredible experience. The room was clean, offered a beautiful view, and had reliable Wi-Fi. The location is perfect for exploring, only an hour's drive to Montalcino and incredibly close to several fantastic wineries. The restaurant itself is absolutely fantastic: The panoramic views are amazing, the food is to die for (home cooking style), and the wine selection is excellent. Laura, her husband, and their son, Leonardo, are wonderful, welcoming...

Alexandre

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 Exceptional

Linna

Frequently Asked Questions

How much does a hotel room cost in Roccastrada?

You can choose a great hotel in Roccastrada from NT$2,377 with properties to suit all budgets and needs. If you're looking for an affordable hotel in Roccastrada that meets all of your requirements, just sort hotels by "Price: low to high" after applying your filters when searching on Hotels.com.

How can I find deals and earn rewards at Roccastrada hotels?

Discover great deals on Roccastrada hotel stays with Hotels.com. You can also look at hotel prices mid-week or during the low season to find off-peak deals. If you're up for a spontaneous trip, don't forget to check out our last-minute deals on Roccastrada hotels.

Can I book Roccastrada hotels with free cancellation?

To book a refundable Roccastrada hotel on Hotels.com, just filter hotels by "Property cancellation options" and select "Fully refundable property". The majority of hotels offer free cancellation, so you can receive a refund if you need to cancel. Some hotels do require cancelling more than 24 hours before check-in, so double-check your booking beforehand.

What are the top-rated luxury hotels in Roccastrada?

One of the most popular luxury hotels in Roccastrada is Valdonica Winery & Vineyard Residence. Valdonica Winery & Vineyard Residence is a luxury farm stay with a high guest rating amongst our travelers, and it offers a full-service spa and a seasonal outdoor pool, plus champagne service in the guestrooms.

What are some top pet-friendly hotels in Roccastrada?

Consider one of our travelers' favorite pet-friendly hotels in Roccastrada:

Valdonica Winery & Vineyard Residence: A farm stay with a guest rating of 9.2 out of 10
B&B Podere Camaiano: A bed & breakfast with a guest rating of 10
Tenuta Montemassi Podere Montauzzo: A farm stay with a guest rating of 10

You can also use the "Amenities" filter in your search on Hotels.com and check "Pet friendly" to discover more pet-friendly hotels in Roccastrada.

What are some of the best hotels in Roccastrada for couples?

Stay at a top-rated Roccastrada romantic hotel and make the most of your couple's vacation. Our travelers love La Melosa Resort & Spa - Adults Only, a hotel with a restaurant and an outdoor pool. Another romantic hotel with top reviews is Historic Farmhouse Casa del Chiodo . This farm stay offers couples/private dining as well as in-room champagne service for a perfect stay. Discover more hotels in Roccastrada on Hotels.com for couples by using the "Traveler experience" filter in your search and selecting "Adults only" or "Romantic".

What are the top Roccastrada hotels with a pool?

Discover some of the best Roccastrada hotels with a pool for a little extra luxury on your trip. Tenuta Di Maro is a great country house with a seasonal outdoor pool and a guest rating of 10 out of 10. Plus, you can make the most of its free buffet breakfast and free parking. Tenuta Montemassi Podere Montauzzo is a popular farm stay that features an outdoor pool along with free parking. To find more stays in Roccastrada with a pool, use the "Amenities" filter on Hotels.com in your search and select "Pool".

What are some of the best Roccastrada hotels with free parking?

If you're exploring by car, finding a great Roccastrada hotel with free parking is a win. Our travelers' favorites include:

B&B Podere Camaiano: A bed & breakfast with an average guest rating of 10 out of 10
Historic Farmhouse Casa del Chiodo : A farm stay with an average guest rating of 10
Tenuta Di Maro : A country house with an average guest rating of 10

What are some popular hotels in central Roccastrada?

For hotels in central Roccastrada, check out B&B Podere Camaiano and Historic Farmhouse Casa del Chiodo . Travelers love B&B Podere Camaiano for its location, as well as the free buffet breakfast, free parking and terrace this bed & breakfast offers. Historic Farmhouse Casa del Chiodo is another popular central farm stay with a free local cuisine breakfast, couples/private dining and proposal/romance packages.

Hotels in Roccastrada

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

Where to stay in Roccastrada?

1. Valdonica Winery & Vineyard Residence

2. B&B da Nada Locanda Toscana

3. Historic Farmhouse Casa del Chiodo

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. Podere Brizio

9. Four Points by Sheraton Siena

10. Hotel Airone

11. Hotel Athena

12. Dimora delle Muse

13. Villa Le Prata - Residenza del Vescovo

14. SI Montalcino Hotel

15. NH Siena

16. Fattoria La Principina Hotel & Congress

17. Le Ragnaie

18. Hotel Terme Marine Leopoldo II

19. Castello Banfi - Il Borgo - Relais et Chateaux

20. Maestrale Resort Hotel - Alberese, Grosseto

Check out pet-friendly hotels in Roccastrada

Valdonica Winery & Vineyard Residence

Go beyond your typical stay in Roccastrada

When is the best time to visit Roccastrada?

Price trends for hotels in Roccastrada

November

Top landmarks in Roccastrada

Podere Ristella Vineyards and Winery

Learn more about Roccastrada

Check out reviews of Roccastrada hotels guests love

Historic Farmhouse Casa del Chiodo

10/10 Exceptional

Frequently Asked Questions

How much does a hotel room cost in Roccastrada?

How can I find deals and earn rewards at Roccastrada hotels?

Can I book Roccastrada hotels with free cancellation?

What are the top-rated luxury hotels in Roccastrada?

What are some top pet-friendly hotels in Roccastrada?

What are some of the best hotels in Roccastrada for couples?

What are the top Roccastrada hotels with a pool?

What are some of the best Roccastrada hotels with free parking?

What are some popular hotels in central Roccastrada?

Keep exploring