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

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Roccastrada holiday rentals

Exterior

1. 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 ₹8,586
₹9,665 total
includes taxes & fees
9 Oct - 10 Oct
Country House il Ciliegio
Sauna, body treatments, hot stone massages, body wraps, body scrubs

2. Agriturismo Benvenuti

Agriturismo Benvenuti
Roccastrada
6.0 out of 10, (3 reviews)
"La stanza era molto grande e tranquilla. C'è anche un giardino abbastanza ampio a disposizione esclusiva di ogni camera/appartamento. Estrema cortesia. Ovviamente si è in aperta campagna, non in vicinanza del mare o dentro un borgo, ma in auto si raggiungo facilmente molte località interessanti del luogo. Su alcuni particolari, potrebbe essere tenuto un po' meglio, ma nel complesso ha un ottimo rapporto qualità/prezzo per la zona."
Italy
Ivano
The price is ₹7,257
₹9,301 total
includes taxes & fees
1 Oct - 2 Oct
Agriturismo Benvenuti
Comfort Apartment, 1 Queen Bed with Sofa bed, Patio, Garden View | Terrace/patio

3. Podere Cascatelle & Agriletizia

Podere Cascatelle & Agriletizia
Massa Marittima
10.0 out of 10, Exceptional, (3 reviews)
"Great for families, convenient parking and facilities, very tranquil."
United States
Ciarán
The price is ₹5,249
₹6,545 total
includes taxes & fees
30 Sept - 1 Oct
Podere Cascatelle & Agriletizia
Breakfast, lunch and dinner served

4. Palazzo Saloni

Palazzo Saloni
Montalcino
10.0 out of 10, Exceptional, (5 reviews)
"Excellent boutique hotel with a very welcoming staff. Rooms were wonderful. Location was terrific - very easy short walk to restaurants in town. Would highly recommend"
United States
BRIAN
The price is ₹36,999
₹41,802 total
includes taxes & fees
12 Sept - 13 Sept
Palazzo Saloni
Exterior

5. Corte Francigena - Apartments

Corte Francigena - Apartments
Montalcino
9.8 out of 10, Exceptional, (13 reviews)
"The apartments and pool are fantastic. The location and breakfast boxes are perfect. The only real complaint was the parking lot was difficult to manage even in a smaller SUV. Staff were extremely communicative and made everything very easy for us."
United States
Ryan
The price is ₹14,983
₹17,584 total
includes taxes & fees
5 Oct - 6 Oct
Corte Francigena - Apartments
Seasonal outdoor pool, pool loungers

6. Residence Arianna

Residence Arianna
Sovicille
9.8 out of 10, Exceptional, (7 reviews)
"We had a 4 night’s stay here and used it as our base for tours around Toscany. It is located in a quiet area outside Siena. The apartment was nice and clean. We used the kitchen for minor cooking and that worked well. There is a supermarket close by and small restaurants in the town. The AC was working great. The host was very keen to share information on good places to see and was eager to make our stay as pleasant as possible. The breakfast was very nice and they also have a restaurant where...
Denmark
Gitte Harrits
The price is ₹12,949
₹14,574 total
includes taxes & fees
17 Sept - 18 Sept
Residence Arianna
Seasonal outdoor pool, open 8:00 AM to 7:30 PM, pool umbrellas

7. Casale Vigna Carbona

Casale Vigna Carbona
Gavorrano
10.0 out of 10, Exceptional, (1 review)
"Cosa scrivere su questo magnifico angolo della maremma. Posto stupendo immerso nella natura, pulizia delle camere impeccabile così come la piscina se poi ci metti anche la cordialità di Luigi e di sua figlia Agnese padroni di casa impeccabili direi che non potevo scegliere posto migliore. Bravi, bravi , bravi "
Italy
Gennaro
The price is ₹8,118
₹13,616 total
includes taxes & fees
26 Sept - 27 Sept
Casale Vigna Carbona
Standard Double Room (La Piazza) | Desk, soundproofing, free WiFi, bed sheets

8. B&B Le Scalette di Piazza

B&B Le Scalette di Piazza
Montalcino
9.4 out of 10, Exceptional, (101 reviews)
"Great location. Staff was accommodating and very helpful."
Canada
François
The price is ₹12,297
₹13,967 total
includes taxes & fees
1 Oct - 2 Oct
B&B Le Scalette di Piazza
Aerial view

9. Bosco della Spina

Bosco della Spina
Murlo
9.6 out of 10, Exceptional, (178 reviews)
"Lovely stay! I would highly recommend this hotel. The indoor pool was just so enjoyable after a day out sightseeing. "
United Kingdom
Lizl
The price is ₹10,651
₹12,598 total
includes taxes & fees
5 Oct - 6 Oct
Bosco della Spina
Premium bedding, down duvets, pillow-top beds, desk

10. Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (29 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is ₹7,561
₹9,751 total
includes taxes & fees
26 Sept - 27 Sept
Tuscasì Aparthotel
1 treatment room, massages

11. Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.2 out of 10, Wonderful, (94 reviews)
"Very good accommodation in the heart of Val’d’Orcia. Reasonably priced"
Finland
Jarkko
The price is ₹15,920
₹17,953 total
includes taxes & fees
17 Sept - 18 Sept
Casanova - Panoramic Rooms and Suites
Front of property

12. Idolina Guest House

Idolina Guest House
Montalcino
9.6 out of 10, Exceptional, (118 reviews)
"Felt like home. The central kitchen / coffee area felt like home."
United States
Bradley
The price is ₹13,621
₹15,865 total
includes taxes & fees
23 Sept - 24 Sept
Idolina Guest House
Aerial view

13. Dimora Santa Margherita - Boutique Hotel

Dimora Santa Margherita - Boutique Hotel
Cinigiano
8.2 out of 10, Very good, (11 reviews)
"The place was great! Food from their was amazing but also a bit expensive. Poolarea was so beautiful and the view was amazing! Only negative thing is that the wine tasting is not in hotel, need to take own car drive for that. Also the last 2km was sand road, which was not that good shape."
Finland
Anonymous traveller
The price is ₹31,519
₹34,891 total
includes taxes & fees
5 Oct - 6 Oct
Dimora Santa Margherita - Boutique Hotel
Terrace/patio

14. Casa di Campagna in Toscana

Casa di Campagna in Toscana
Sovicille
9.6 out of 10, Exceptional, (27 reviews)
"A wonderful stay. "
United States
Sally
The price is ₹11,618
₹13,111 total
includes taxes & fees
8 Oct - 9 Oct
Casa di Campagna in Toscana
Front of property – evening/night

15. Residence Borgo San Lorenzo a Linari

Residence Borgo San Lorenzo a Linari
Sovicille
8.6 out of 10, Excellent, (99 reviews)
"Such a pleasant stay and the staff was incredible. "
United States
Monica
The price is ₹11,597
₹13,306 total
includes taxes & fees
21 Sept - 22 Sept
Residence Borgo San Lorenzo a Linari
Food court

16. Borgo Il Poggiaccio

Borgo Il Poggiaccio
Sovicille
8.8 out of 10, Excellent, (67 reviews)
"I loved the stay here. A great quiet place with an awesome restaurant and unbelievable staff. "
United States
Louie
The price is ₹12,812
₹14,645 total
includes taxes & fees
29 Sept - 30 Sept
Borgo Il Poggiaccio
Interior entrance

17. Residence Il Boschetto

Residence Il Boschetto
Grosseto
8.6 out of 10, Excellent, (8 reviews)
"The house is gorgeous! The area is very nice and the amenities were great! "
United States
Enrique
The price is ₹8,074
₹9,212 total
includes taxes & fees
6 Oct - 7 Oct
Residence Il Boschetto
Seasonal outdoor pool, pool umbrellas, pool loungers

18. BeVedetta - Relais & Glamping - Adult Only

BeVedetta - Relais & Glamping - Adult Only
Scarlino
10.0 out of 10, Exceptional, (12 reviews)
"Loved it here!!!"
United States
Nina
The price is ₹20,295
₹22,325 total
includes taxes & fees
2 Oct - 3 Oct
BeVedetta - Relais & Glamping - Adult Only
Exterior

19. Il Pozzo di Sant'Andrea

Il Pozzo di Sant'Andrea
Siena
9.8 out of 10, Exceptional, (16 reviews)
"Great host, lovely place near Siena"
United Kingdom
Prem
The price is ₹9,935
₹11,370 total
includes taxes & fees
5 Oct - 6 Oct
Il Pozzo di Sant'Andrea
Daily continental breakfast for a fee

20. Residenza d'Epoca Palazzo Borghesi

Residenza d'Epoca Palazzo Borghesi
Siena City Centre
9.6 out of 10, Exceptional, (130 reviews)
"The room was very impressive with a large Chandelier. The breakfast was Delicious and the staff very very nice and helpful"
United States
Peggy
The price is ₹28,279
₹31,548 total
includes taxes & fees
29 Sept - 30 Sept
Residenza d'Epoca Palazzo Borghesi
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.
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Top Roccastrada Hotel Reviews

Castello di Velona Resort Thermal SPA & Winery

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!"
Ruth 3-night trip
Posted 4 hours ago
Castello di Velona Resort Thermal SPA & Winery

Find out more about Roccastrada

Holiday Rentals in Roccastrada

Search for holiday rentals in Roccastrada on Expedia.co.uk! You can easily find your home rentals, villas, holiday apartments in Roccastrada using one of the methods below:

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Look no further and take a look at our great range of rental properties in Roccastrada!

Frequently asked questions

Can I find holiday rentals in Roccastrada?

Yes, there are holiday rentals close to the most popular sights in Roccastrada, or you can select a more secluded option if you're looking for a relaxing stay.

How many holiday rentals are there in Roccastrada?

Choose from 80 Expedia holiday rentals in Roccastrada for a memorable holiday.

What’s there to see and do in Roccastrada?

I Canaloni del Torrente Farma and Val di Merse are a couple of lovely local spots to get outside and enjoy nature. Podere Ristella Vineyards and Winery and Castello del Belagaio are other places to visit while you're in town.

What’s a holiday rental in Roccastrada like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Roccastrada. Holiday rentals provide amenities such as WiFi and washers and dryers so your stay will be comfortable. If you're concerned about cleanliness, a holiday rental can provide a sense of seclusion away from shared hotel lifts and busy concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for small groups.