Roccastrada Vacation Homes from ￥7,958

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Find vacation rentals that suit your style

Check prices for these dates

Next weekend

In two weeks

In one month

In two months

Our top choices for Roccastrada vacation homes

A stone building with a tree in front, outdoor seating with tables and chairs, and a paved walkway.

1. Farmhouse "Casa Girasole" with Private Pool, Terraces & Wi-Fi

Roccastrada

￥1,053,102 total

includes taxes & fees

Nov 13 - Nov 14

A patio with a wooden table, a blue lounge chair, a striped chair, and a large umbrella.

2. Detached house with a garden, just a few minutes from the Abbey of San Galgano

Toscana

Julie M.

￥20,160 total

includes taxes & fees

Nov 10 - Nov 11

3. Villa Pianosa, Botri dei Lumachi

Toscana

￥51,654 total

includes taxes & fees

Dec 4 - Dec 5

An infinity pool with a clear view of the sunset and distant mountains.

4. Villa Giglio, Botri dei Lumachi

Toscana

￥51,654 total

includes taxes & fees

Dec 4 - Dec 5

An outdoor patio with a wooden floor, a covered seating area, and a view of a green landscape.

5. Farmhouse 'Le Gerlette - La Stalla' with Shared Pool, Wi-Fi and Air Conditioning

Braccagni

￥20,063 total

includes taxes & fees

Nov 7 - Nov 8

A stone building with two windows, one with green shutters, and a rose bush in the foreground.

6. Exclusive Stone Tower.

Casciano

Ryan C.

￥22,477 total

includes taxes & fees

Nov 7 - Nov 8

A stone building with a sign reading "Borgo di Mezzo".

7. The Gelda house, relax with a view

Castelnuovo dell'Abate

Lisa K.

￥23,873 total

includes taxes & fees

Nov 8 - Nov 9

A stone building with a flat roof, multiple windows, and a small porch area.

8. Podere Cagnesi: Relaxation in the Heart of Nature

Podere Cagnesi

￥33,011 total

includes taxes & fees

Nov 7 - Nov 8

A narrow stone staircase leading to a door with a glass panel, flanked by brick walls and metal railings.

9. Holiday Home 'La Nobiltà Del Tempo' with Balcony and Wi-Fi

Poggiobrucoli

￥44,704 total

includes taxes & fees

Nov 8 - Nov 9

A stone building with a wooden door and two windows with shutters.

10. The Casetta di Brunello, quiet and breathtaking views

Montalcino

MICHAEL H.

￥34,305 total

includes taxes & fees

Nov 11 - Nov 12

An open doorway leading to an outdoor area with a bench, a television on a cabinet, and a framed picture on the wall.

11. Tuscan House: Spacious Traditional Apartment with a Large Outdoor Area and Breakfast Included

Monteroni d'Arbia

￥25,464 total

includes taxes & fees

Nov 23 - Nov 24

A balcony with a view of a stone building and surrounding landscape.

12. A Nest with a View - A Romantic Getaway Within the City Walls

Radicondoli

￥28,647 total

includes taxes & fees

Nov 10 - Nov 11

A pathway leading to a building with stone walls and a tree.

13. A typical Tuscan country house

Montalcino

￥27,551 total

includes taxes & fees

Nov 13 - Nov 14

A narrow stone alley with potted plants and benches.

14. Alice's House, charm and relaxation

Montalcino (SI)

Robert S.

￥32,891 total

includes taxes & fees

Nov 7 - Nov 8

15. P.zadelSale Grosseto: Standard Queen Room

Grosseto

￥11,672 total

includes taxes & fees

Nov 11 - Nov 12

An outdoor patio with tables and chairs, surrounded by greenery and a view of distant hills.

16. Podere Belsogno-camera Lavanda

Montalcino

Johannes S.

￥23,519 total

includes taxes & fees

Nov 9 - Nov 10

A terrace with a table set for breakfast, overlooking a mountainous landscape.

17. Il Borghetto - The House on Elba, Rooftop Terrace with Panoramic Views

Castelnuovo dell'Abate

"Il Borghetto is a renovated house in the little village of Castelnuovo dell'Abate, one of the medieval hilltop villages in the UNESCO world heritage-listed Val D'Orcia. It is charming and the beds are very comfortable, but be prepared to take luggage up a steep street to the front door and then steep stairs to both bedrooms. Each bedroom is on a different floor so there is considerable privacy. The piece de la resistance is the rooftop terrace, with 180 degree panoramic views over the valley and...

Judith F.

￥27,586 total

includes taxes & fees

Nov 12 - Nov 13

A stone building with a sign reading 'Ramos'.

18. Holiday Home 'Il Cerreto – Casa Rosmarino' with Private Garden, Wi-Fi & Air Conditioning

Massa Marittima

￥53,377 total

includes taxes & fees

Nov 7 - Nov 8

A wooden structure with a sign that reads "Happy Holidays." It has multiple shelves with potted plants and flowers.

19. Romantico monolocale in casale

Rispescia

￥20,160 total

includes taxes & fees

Nov 7 - Nov 8

A building with a stone facade, a door, a window, and a patio area with chairs and a table.

20. A peaceful spot with a garden between Chianti and Crete, near the old town

Casetta

￥16,092 total

includes taxes & fees

Nov 9 - Nov 10

View all 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 reviews in Roccastrada

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

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....

Nita Marie

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

B&B da Nada Locanda Toscana

Roccastrada

10/10 Excellent

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

Valdonica Winery & Vineyard Residence

Roccastrada

10/10 Excellent

Josh

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

Castello Banfi - Il Borgo - Relais et Chateaux

Montalcino

10/10 Excellent

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 Excellent

KEDARNATH

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

Villa Le Prata - Residenza del Vescovo

Montalcino

10/10 Excellent

Valentin Y.

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

Relais Le Macine di Stigliano

Sovicille

10/10 Excellent

Nicholas

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

Dimora delle Muse

Montalcino

10/10 Excellent

Anonymous traveler

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

Palazzo Saloni

Montalcino

10/10 Excellent

My husband and I spent 6 fabulous nights here. From the moment I made the reservation, I felt in good hands with great communication about any question I had. The front desk can assist with wine excursions, spa, cooking class and even are connected with a nice local gym you can attend for a small fee. We rented a car and it is a big bonus that this property has on-site parking included in the rate. The Palazzo is located in a prime location, also easy to get in and out which can be tricky in...

Laura

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

Podere Brizio

Montalcino

10/10 Excellent

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

Hotel Certosa Di Maggiano

Siena

10/10 Excellent

Anonymous traveler

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 Excellent

Suelina

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

Capanna Suites

Montalcino

10/10 Excellent

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

Torre del Fuggisole

Siena City Centre

10/10 Excellent

Charles

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 Excellent

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

Castello Di Vicarello

Cinigiano

10/10 Excellent

hala

Search Vacation Homes in Roccastrada

Change your mind

Treat yourself

Be picky

Find vacation rentals that suit your style

Check prices for these dates

Our top choices for Roccastrada vacation homes

1. Farmhouse "Casa Girasole" with Private Pool, Terraces & Wi-Fi

2. Detached house with a garden, just a few minutes from the Abbey of San Galgano

3. Villa Pianosa, Botri dei Lumachi

4. Villa Giglio, Botri dei Lumachi

5. Farmhouse 'Le Gerlette - La Stalla' with Shared Pool, Wi-Fi and Air Conditioning

6. Exclusive Stone Tower.

7. The Gelda house, relax with a view

8. Podere Cagnesi: Relaxation in the Heart of Nature

9. Holiday Home 'La Nobiltà Del Tempo' with Balcony and Wi-Fi

10. The Casetta di Brunello, quiet and breathtaking views

11. Tuscan House: Spacious Traditional Apartment with a Large Outdoor Area and Breakfast Included

12. A Nest with a View - A Romantic Getaway Within the City Walls

13. A typical Tuscan country house

14. Alice's House, charm and relaxation

15. P.zadelSale Grosseto: Standard Queen Room

16. Podere Belsogno-camera Lavanda

17. Il Borghetto - The House on Elba, Rooftop Terrace with Panoramic Views

18. Holiday Home 'Il Cerreto – Casa Rosmarino' with Private Garden, Wi-Fi & Air Conditioning

19. Romantico monolocale in casale

20. A peaceful spot with a garden between Chianti and Crete, near the old town

Learn more about Roccastrada

Top reviews in Roccastrada

Historic Farmhouse Casa del Chiodo

10/10 Excellent