Hotels in Roccastrada

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Where to stay in Roccastrada?

A swimming pool with lounge chairs and umbrellas, surrounded by brick flooring and a hedge.

A bedroom with a stone wall, a bed with white linens, a wooden chair, a desk with a computer, and a window with curtains.

A large stone house with a swimming pool, surrounded by lush greenery and hills.

A rustic interior with exposed wooden beams, a central island with seating, and a stone wall.

1. La Melosa Resort & Spa - Adults Only

Roccastrada

$88

$101 total

includes taxes & fees

Oct 8 - Oct 9

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

A balcony with two wooden chairs overlooking a vineyard and distant mountains.

A swimming pool with a view of a valley and mountains.

A rustic stone house with a balcony, surrounded by tall grasses and trees, during sunset.

2. Valdonica Winery & Vineyard Residence

Roccastrada

$149

$167 total

includes taxes & fees

Sep 27 - Sep 28

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

A view through a window of a mountainous landscape with autumn foliage and a house in the distance.

A gazebo with a stone wall and a lamp post in a park setting.

A stone building with a wooden door, green shutters, and two potted plants.

3. Historic Farmhouse Casa del Chiodo

Roccastrada

$104

$117 total

includes taxes & fees

Sep 22 - Sep 23

A historic stone building with multiple windows and a courtyard.

A breakfast buffet with various food items and beverages, set in a room with stone walls and a large window.

A stone staircase leading to an arched doorway, surrounded by stone walls and potted plants.

A bedroom with a large bed, wooden beams, a TV, and framed pictures on the wall.

4. Agriturismo Tenuta di Montemassi La Fattoria

Roccastrada

$104

$116 total

includes taxes & fees

Sep 13 - Sep 14

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

A garden with a wooden chair and a table, surrounded by a stone wall and a wooden fence.

A panoramic view of a vineyard with rolling hills, a clear sky, and distant mountains.

A long table set for a formal outdoor event, surrounded by a vineyard.

5. Valdonica Winery - Chill in Nature Lodge

Roccastrada

$192

$214 total

includes taxes & fees

Sep 20 - Sep 21

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

A rectangular pool with lounge chairs and umbrellas, surrounded by a brick patio.

A hotel with a swimming pool, surrounded by greenery and adjacent to a road.

A cozy kitchen with a brick ceiling, wooden furniture, and a dining area with a table set for breakfast.

6. Country House il Ciliegio

Roccastrada

$96

$108 total

includes taxes & fees

Oct 9 - Oct 10

A swimming pool with a view of a hilltop castle.

An outdoor patio with a pergola, tables, chairs, and a view of rolling hills.

A wine cellar with wooden barrels, a wine rack, and a table set for dining.

A courtyard with a stone column, potted plants, and a view of a hilltop castle.

7. Agriturismo Podere Ristella - Wine&Food

Roccastrada

$80

$113 total

includes taxes & fees

Sep 14 - Sep 15

A modern living room with a sofa, a coffee table, a TV on a wooden cabinet, and a large potted plant.

A modern bathroom with a glass shower enclosure, a sink, a toilet, and a window providing natural light.

A bedroom with a bed, a nightstand, a wall-mounted lamp, a window with a view, and a ceiling light fixture.

A fruit basket with apples, pears, bananas, and cherries.

8. Le Vie del Mare Camere

Ribolla

$127

$140 total

includes taxes & fees

Oct 2 - Oct 3

A wooden interior with a glass-enclosed shower, large windows, and a wooden floor.

A pathway leading to a building with a stone-tiled entrance and a wooden door.

A living room with a wooden ceiling, a sofa, a dining table with chairs, a television, and a cabinet.

A small, modern house with a sliding glass door, surrounded by lush greenery and a well-maintained garden.

9. Agriturismo Benvenuti

Roccastrada

$77

$99 total

includes taxes & fees

Oct 1 - Oct 2

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

A stone building with a wooden deck and white lounge chairs.

A dining area with white tables and chairs, a large mirror, and a wine bottle on one table.

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

10. Podere Brizio

Montalcino

$227

$259 total

includes taxes & fees

Oct 11 - Oct 12

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

A buffet table with various desserts and a long dining area with tables and chairs.

A large, multi-story building with a swimming pool, surrounded by lush greenery.

An indoor swimming pool with clear glass walls, a tiled floor, and a stone wall with a mosaic pattern.

11. Mercure Petriolo Siena Terme Spa Hotel

Civitella Paganico

$92

$101 total

includes taxes & fees

Sep 15 - Sep 16

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

A kitchen with a buffet setup, including a variety of food items and glassware.

A hotel room with a large bed, a bedside table, a lamp, a window with curtains, and a view of greenery outside.

A hotel room with a bed, a sofa, a table with a vase of flowers, a TV, and a window with a view.

12. SI Montalcino Hotel

Montalcino

$108

$145 total

includes taxes & fees

Sep 29 - Sep 30

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

A room with a large window, a door, and a view of a landscape.

A four-poster bed with a bench, stone flooring, and a stone wall.

An open door leading to a patio with a view of the countryside, a table with plants, and a television on a wooden cabinet.

13. Capanna Suites

Montalcino

$467

$525 total

includes taxes & fees

Oct 9 - Oct 10

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

An outdoor patio with stone walls, green cushioned seating, a table with chairs, and a decorative umbrella.

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

A spacious living area with leather armchairs, a wooden cabinet with glass doors, and a red carpet.

14. Le Ragnaie

Montalcino

$142

$168 total

includes taxes & fees

Sep 20 - Sep 21

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

A piano with sheet music, an easel with a drawing, and a wine bottle in a stone-walled room.

An underground wine cellar with brick walls, wooden tables, and chairs.

An outdoor patio with stone walls, a pergola, and a table set for dining.

15. Dimora delle Muse

Montalcino

$221

$252 total

includes taxes & fees

Sep 18 - Sep 19

A serene infinity pool with lounge chairs and umbrellas, surrounded by natural scenery and a clear view of distant mountains.

A bathroom with a bathtub, a chandelier, and a view of the outdoors.

A rustic dining area with brick walls, hanging plants, and candle-lit tables.

A rustic interior with a chandelier, wooden furniture, and large windows offering a view of the outdoors.

16. Borgo Santo Pietro

Chiusdino

$1,375

$1,525 total

includes taxes & fees

Sep 11 - Sep 12

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

A stone house with a covered patio, a stone pathway, and well-maintained landscaping.

A landscaped garden with neatly trimmed bushes, a stone pathway, and umbrellas.

A picnic setup with a basket, blanket, pillows, and food items on a grassy area with a hilly landscape in the background.

17. Mastrojanni Relais - Small Luxury Hotels of the World

Montalcino

$484

$544 total

includes taxes & fees

Oct 5 - Oct 6

An aerial view of a historic town with stone buildings, a prominent church, and a castle-like structure with a sign reading "Castello di Monteverde."

A room with a wooden bench, potted plants, framed artwork, and a view of the outside.

An outdoor patio with terracotta-tiled flooring, metal tables and chairs, potted plants, and a view of the sea.

A stone building with a brick archway and a tall cypress tree in front.

18. Hotel Vecchia Oliviera

Montalcino

$170

$197 total

includes taxes & fees

Oct 11 - Oct 12

A swimming pool with a waterfall feature, large windows, and a lounge chair.

A living room with a grey sofa, a coffee table, and a potted plant with red flowers. There are shelves with various bottles and jars, and a wall-mounted display with three decorative plates.

A covered patio with a table and chairs, a small garden, and a building in the background.

A narrow corridor with a wooden ceiling and a tiled floor, leading to a door at the end.

19. Montebelli Agriturismo & Country Hotel

Gavorrano

$100

$117 total

includes taxes & fees

Sep 13 - Sep 14

A pool with a stone wall, a view of the countryside, and a building with a tiled roof.

A hotel with a classic facade, multiple windows with shutters, and a sign indicating it is the "Hotel dei Capitani."

A spacious lobby with a tiled floor, a wooden reception desk, a staircase, and a large floral painting on the wall.

A terrace with outdoor seating, a view of the landscape, and a building with large windows.

20. Hotel Dei Capitani

Montalcino

$160

$185 total

includes taxes & fees

Sep 29 - Sep 30

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Check out pet-friendly hotels in Roccastrada

Valdonica Winery & Vineyard Residence

Roccastrada

$149

$167 total

includes taxes & fees

Sep 27 - Sep 28

Agriturismo Tenuta di Montemassi La Fattoria

Roccastrada

$104

$116 total

includes taxes & fees

Sep 13 - Sep 14

Country House il Ciliegio

Roccastrada

$96

$108 total

includes taxes & fees

Oct 9 - Oct 10

Agriturismo Podere Ristella - Wine&Food

Roccastrada

$80

$113 total

includes taxes & fees

Sep 14 - Sep 15

Valdonica Winery - Chill in Nature Lodge

Roccastrada

$192

$214 total

includes taxes & fees

Sep 20 - Sep 21

Le Vie del Mare Camere

Ribolla

$127

$140 total

includes taxes & fees

Oct 2 - Oct 3

Agriturismo Benvenuti

Roccastrada

$77

$99 total

includes taxes & fees

Oct 1 - Oct 2

View all properties

Go beyond your typical stay in Roccastrada

Pet friendly

Apartment

Pool

Apart hotel

Spa

Hot tub

Farm

Family friendly

Our prices for hotels in Roccastrada are cheapest in January

Top landmarks in Roccastrada

I Canaloni del Torrente Farma

8.0/10 (1 review)

Listen to the relaxing sound of the water and take some great vacation pics at I Canaloni del Torrente Farma located 5.5 mi (8.8 km) from central Roccastrada.

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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.

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Castello del Belagaio

9.0/10 (2 reviews)

Castello del Belagaio is just one of the landmarks located 5.4 mi (8.6 km) from central Roccastrada, so you might want to stop by for a few pics during your trip.

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Sassoforte Castle

9.0/10 (2 reviews)

If seeing the sights is on your list of things to do, head to Sassoforte Castle— just one of the landmarks located 3.7 mi (5.9 km) from central Roccastrada.

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Church of San Nicola

8.0/10 (1 review)

Church of San Nicola is in the heart of Roccastrada, so why not stop by during your stay.

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Castello di Torniella

Castello di Torniella is in the heart of Torniella, so why not stop by during your stay.

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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

A rural landscape with rolling hills, vineyards, and scattered buildings.

Check out reviews of Roccastrada hotels guests love

Hotel Athena

8/10 Good

"Overall okay hotel. It’s meant more to come in during the morning while explore and out all day. Rooms are small and you can hear everything that’s going on in the hallway and in othe rooms (e.g., crying baby at 3am). Reception staff (Simone) was helpful and bartender (Lucas) was super nice. View in the terrace is good and peaceful but can’t be use if too close to dinner time."

NH Siena

10/10 Excellent

"Superior room not great, Very small with leaking shower and other issues. Upgraded to suite on 5th floor which was excellent. Very spacious, huge bathroom with bath and walk in shower. Great views and comfortable bed."

Castello di Velona Resort Thermal SPA & Winery

8/10 Good

"Staying here was a wonderful and truly unique experience. The only reason I’m giving it 4 stars instead of 5 was because of the challenges we had with the air conditioning in our room. That said, the staff really did make an effort to find a workaround for us. While it wasn’t a perfect solution, it definitely helped, and we appreciated how responsive and accommodating they were. The hotel itself is an old castle, and that alone makes staying here such a special experience. The property is beautiful, incredibly charming, and very well maintained. You simply can’t replicate the character, history, and ambiance that come with staying in a property like this. The setting and surroundings are beautiful. It was definitely one of those experiences that felt uniquely Italian and added something special to our trip. My only recommendation would be to visit when the temperatures aren’t quite as hot. Given the age and historic nature of the property, I can appreciate that modernizing certain things like the air conditioning may not be as straightforward as it would be in a newer hotel. During cooler weather, I imagine our experience would have been close to perfect. Overall, we really enjoyed our stay and are glad we had the opportunity to experience such a beautiful and unique property. I would absolutely recommend it, just perhaps not during the hottest part of the summer!"

Villa Scacciapensieri Boutique Hotel

10/10 Excellent

"The staff were very friendly and helpful. The bar service is the best."

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent

"All the staff in the hotel were very helpful and we would like to stay there again."

Hotel Chiusarelli

10/10 Excellent

"Great location. Wonderful staff, very helpful and polite."

The Sense Experience Resort - Preferred Hotels & Resorts

10/10 Excellent

"Great property, classy, staff crew are professionals. Egor is great. Staff remembers from year to year. Management is awesome and helpful all the time The manager Sylvia is a friendly and helpful. All over staff, front desk, waiters, cleaners, managements, and bellboys are the best of the best. Only missing thing in this hotel is a Gym , but they do some classes, but gym is needed to make it as a cherry on the top. Breakfast is great , dinners are lovely. We keep going there every year."

Il Chiostro del Carmine

8/10 Good

"Friendly staff"

L'Orto delle Terme

10/10 Excellent

"Great hotel in a beautiful area - rooms could use some upgrade but great thermal spa"

Frequently asked questions

What accommodations do travelers recommend in Roccastrada?

Guests like Mercure Petriolo Siena Terme Spa Hotel.

Where can I find free parking at my hotel in Roccastrada?

Park your car for free at these properties: Agriturismo Tenuta di Montemassi La Fattoria, Panorama Room 2 Pers With Breakfast In Tuscany and Lavanda Room With Bath.

Can I book a refundable hotel in Roccastrada?

If you want the flexibility to change your plans to Roccastrada, most accommodations offer refundable* rates you can book. You can see these accommodations by searching our site and using the "fully refundable" filter to narrow the results down.

Where can I stay in Roccastrada if I want a vacation home instead of a traditional hotel?

If you want a good alternative to a hotel, review our selection of 80 vacation homes. You can also book one of 45 apartments or 26 villas.

What will the weather in Roccastrada be like during my visit?

The warmest months in Roccastrada are usually August and July with an average temp of 74°F. January and February are the chilliest months when the average temp is 48°F. The rainiest months are November and October.

Why should I book my Roccastrada hotel with Hotels.com?

There are plenty of reasons to book your Roccastrada travel with us: our free cancellations on selected hotels gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.

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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. La Melosa Resort & Spa - Adults Only

2. Valdonica Winery & Vineyard Residence

3. Historic Farmhouse Casa del Chiodo

4. Agriturismo Tenuta di Montemassi La Fattoria

5. Valdonica Winery - Chill in Nature Lodge

6. Country House il Ciliegio

7. Agriturismo Podere Ristella - Wine&Food

8. Le Vie del Mare Camere

9. Agriturismo Benvenuti

10. Podere Brizio

11. Mercure Petriolo Siena Terme Spa Hotel

12. SI Montalcino Hotel

13. Capanna Suites

14. Le Ragnaie

15. Dimora delle Muse

16. Borgo Santo Pietro

17. Mastrojanni Relais - Small Luxury Hotels of the World

18. Hotel Vecchia Oliviera

19. Montebelli Agriturismo & Country Hotel

20. Hotel Dei Capitani