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
11 Sep - 13 Sep
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Roccastrada holiday rentals

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

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 2.794.567 ₫
3.135.017 ₫ total
includes taxes & fees
31 Aug - 1 Sept
Country House il Ciliegio
A dining table with a bottle of wine, two wine glasses, a candle, and a vase with flowers.

2. B&B Le Scalette di Piazza

B&B Le Scalette di Piazza
Montalcino
9.4 out of 10, Exceptional, (100 reviews)
"Great location. Staff was accommodating and very helpful."
Canada
François
The price is 3.543.056 ₫
4.019.408 ₫ total
includes taxes & fees
9 Sept - 10 Sept
B&B Le Scalette di Piazza
A view from a window overlooking a cityscape with terracotta rooftops and a prominent dome structure in the distance.

3. A Casa Mastacchi

A Casa Mastacchi
Siena City Centre
7.8 out of 10, Good, (29 reviews)
"Christiana was the perfect hostess. Accommodations were quaint. Rooms and common areas were spotless. Breakfast and cafe were amazing. A true gem located in the heart of Siena. Close to shops, restaurants, and enotecas. I highly recommend you stay. "
United States
Christina
The price is 3.263.655 ₫
3.712.006 ₫ total
includes taxes & fees
27 Aug - 28 Aug
A Casa Mastacchi
A bakery display with pastries and a coffee station.

4. B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (206 reviews)
"Lovely B&B right in the heart of Siena. Pierre was incredibly helpful and kept me up to date prior to my arrival with suggestions for dining out, shopping and bars. Would highly recommend"
United Kingdom
Katherine
The price is 3.086.879 ₫
3.517.552 ₫ total
includes taxes & fees
28 Aug - 29 Aug
B&B Il Corso
A covered outdoor seating area with wicker furniture, a table, and potted plants.

5. Fattoria San Lorenzo - Apartments

Fattoria San Lorenzo - Apartments
Grosseto
8.8 out of 10, Excellent, (30 reviews)
"Great, clean, and beautiful place."
United States
Aimee
The price is 3.653.353 ₫
4.110.239 ₫ total
includes taxes & fees
18 Sept - 19 Sept
Fattoria San Lorenzo - Apartments
A traditional stone building with a courtyard, a staircase, and potted plants.

6. 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 3.102.579 ₫
3.534.822 ₫ total
includes taxes & fees
3 Sept - 4 Sept
Il Pozzo di Sant'Andrea
An interior with stone walls, wooden doors, and a bar area with stools and bottles.

7. 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 4.154.422 ₫
6.735.100 ₫ total
includes taxes & fees
14 Sept - 15 Sept
Borgo Il Poggiaccio
A bathroom with a window view of a historic building and a tiled roof.

8. Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (476 reviews)
"Fantastic location and very friendly staff, we will definitely be back"
United Kingdom
Luis
The price is 2.982.393 ₫
3.402.617 ₫ total
includes taxes & fees
28 Aug - 29 Aug
Siena Vip
A stone fountain with a light-up base, surrounded by grass and trees, with a building in the background.

9. Fattoria Pian di Rocca

Fattoria Pian di Rocca
Castiglione della Pescaia
9.6 out of 10, Exceptional, (33 reviews)
"Great place to stay. Very clean, close to town, great breakfast. "
Canada
Jose Pedro
The price is 3.050.541 ₫
3.477.489 ₫ total
includes taxes & fees
20 Sept - 21 Sept
Fattoria Pian di Rocca
A spacious living area with a dining table, red chairs, and a small round table. Large windows provide natural light and views of greenery outside.

10. 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 2.903.855 ₫
3.285.730 ₫ total
includes taxes & fees
1 Sept - 2 Sept
Residence Il Boschetto
A stone courtyard with a bench, potted plants, and a building in the background.

11. 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 3.480.733 ₫
3.920.295 ₫ total
includes taxes & fees
2 Sept - 3 Sept
Casa di Campagna in Toscana
A wooden door with a metal handle, a brick archway, a staircase, and a flower pot on the wall.

12. Idolina Guest House

Idolina Guest House
Montalcino
9.6 out of 10, Exceptional, (117 reviews)
"Felt like home. The central kitchen / coffee area felt like home."
United States
Bradley
The price is 2.551.151 ₫
3.050.236 ₫ total
includes taxes & fees
8 Sept - 9 Sept
Idolina Guest House
A bedroom with a bed, bedside table, and a window with a view of greenery.

13. La Coroncina Lodging

La Coroncina Lodging
Siena
10.0 out of 10, Exceptional, (43 reviews)
"Fantastic place, and I highly recommend it."
United States
Hassan
The price is 3.242.446 ₫
3.688.676 ₫ total
includes taxes & fees
27 Aug - 28 Aug
La Coroncina Lodging
A modern lobby with white leather sofas, a glass coffee table, and potted plants.

14. ApartHotel Anghel

ApartHotel Anghel
Siena
8.4 out of 10, Very good, (344 reviews)
"Great stay highly recommend!!"
United States
jon
The price is 2.445.495 ₫
2.812.030 ₫ total
includes taxes & fees
2 Sept - 3 Sept
ApartHotel Anghel
A bedroom with a bed, a bedside table, a TV mounted on the wall, and a sliding glass door leading to a balcony with a view of greenery and hills.

15. 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 1.961.389 ₫
2.554.246 ₫ total
includes taxes & fees
28 Aug - 29 Aug
Tuscasì Aparthotel
A stone-walled room with a large bathtub, a fireplace, and a set of stone steps leading to the tub.

16. Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso

Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
San Quirico d'Orcia
9.0 out of 10, Wonderful, (49 reviews)
"Our stay was great. "
United States
Elena
The price is 3.299.141 ₫
3.751.041 ₫ total
includes taxes & fees
27 Aug - 28 Aug
Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
A table with two wine glasses, a bottle, and a book.

17. Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (97 reviews)
"Rooms were clean and spacious ! Happy there was a good blow dryer in the room and a heated towel rack. Staff were very friendly and helpful . Would stay again !"
Canada
Alissia
The price is 2.101.492 ₫
2.433.626 ₫ total
includes taxes & fees
6 Sept - 7 Sept
Domus il Palio B&B
An aerial view of a historic stone building complex with a swimming pool, surrounded by lush greenery and vineyards.

18. Bosco della Spina

Bosco della Spina
Murlo
9.6 out of 10, Exceptional, (177 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 3.967.286 ₫
4.607.984 ₫ total
includes taxes & fees
23 Sept - 24 Sept
Bosco della Spina
A building with a sign reading 'Villa Le Camelie' and multiple flags.

19. Villa le Camelie Siena

Villa le Camelie Siena
Petriccio
8.6 out of 10, Excellent, (8 reviews)
"Nice for the price. Would stay there again."
United States
Mark
The price is 2.108.401 ₫
2.441.339 ₫ total
includes taxes & fees
27 Aug - 28 Aug
Villa le Camelie Siena
A bedroom with a bed, wooden floor, and two bedside lamps.

20. Guest House All'83

Guest House All'83
Grosseto
9.6 out of 10, Exceptional, (5 reviews)
"La camera spaziosa"
Italy
Orlando
The price is 2.354.921 ₫
2.681.902 ₫ total
includes taxes & fees
30 Aug - 31 Aug
Guest House All'83
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

Palazzo Ravizza

Palazzo Ravizza

10/10 Excellent
"quiet place for stay"
XUESHENG 1-night trip
Posted 1 hour ago
Palazzo Ravizza

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.