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

Roccastrada Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Roccastrada vacation 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 NT$2,842
NT$3,199 total
includes taxes & fees
Nov 2 - Nov 3
Country House il Ciliegio
A wooden door with a metal handle, a brick archway, a staircase, and a flower pot on the wall.

2. Idolina Guest House

Idolina Guest House
Montalcino
9.6 out of 10, Exceptional, (118 reviews)
"A truly special place!"
United States
Jaiden
The price is NT$2,839
NT$3,414 total
includes taxes & fees
Nov 25 - Nov 26
Idolina Guest House
An aerial view of a historic stone building complex with a swimming pool, surrounded by lush greenery and vineyards.

3. Bosco della Spina

Bosco della Spina
Murlo
9.6 out of 10, Exceptional, (188 reviews)
"Very peaceful and scenic. Wish we had stayed longer."
United States
Amir
Bosco della Spina
A restaurant with tables and wicker chairs, large windows, and a view of buildings and greenery.

4. Palazzo Saloni

Palazzo Saloni
Montalcino
10.0 out of 10, Exceptional, (14 reviews)
"Excellent location to tour wine country montalcino."
United States
Michael
The price is NT$8,371
NT$9,572 total
includes taxes & fees
Dec 1 - Dec 2
Palazzo Saloni
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.

5. Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (33 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is NT$2,018
NT$2,693 total
includes taxes & fees
Nov 20 - Nov 21
Tuscasì Aparthotel
A stone courtyard with a bench, potted plants, and a building in the background.

6. 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 NT$2,711
NT$3,091 total
includes taxes & fees
Nov 15 - Nov 16
Casa di Campagna in Toscana
A dining table with a bottle of wine, two wine glasses, a candle, and a vase with flowers.

7. B&B Le Scalette di Piazza

B&B Le Scalette di Piazza
Montalcino
9.4 out of 10, Exceptional, (106 reviews)
"We had a great stay in this conveniently located property. The breakfast was good with many options and staff to assist."
Canada
Morris
The price is NT$3,869
NT$4,402 total
includes taxes & fees
Nov 8 - Nov 9
B&B Le Scalette di Piazza
A rectangular pool with a metal ladder, surrounded by wooden lounge chairs and a stone deck.

8. Corte Francigena - Apartments

Corte Francigena - Apartments
Montalcino
9.6 out of 10, Exceptional, (22 reviews)
"The unit is very clean, awesome breakfast, beautiful view"
Canada
Ivan
The price is NT$3,936
NT$4,621 total
includes taxes & fees
Nov 3 - Nov 4
Corte Francigena - Apartments
A poolside area with two glasses of water, candles, and a stone pathway.

9. Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.0 out of 10, Wonderful, (104 reviews)
"The variety at the buffet was really good and the coffee machines made really good coffee. The site itself was very nice and well maintained. The problem with this place is the reception for arrival and departure, no service and fast to dismiss you."
Canada
DANIELA
The price is NT$5,820
NT$6,548 total
includes taxes & fees
Nov 18 - Nov 19
Casanova - Panoramic Rooms and Suites
A traditional stone building with a courtyard, a staircase, and potted plants.

10. 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
Il Pozzo di Sant'Andrea
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
"Our 6 night stay was absolutely fantastic. Palazzo Ravizza is a treasure on every level, from the hotel itself to the wonderful staff. An extra special thank you goes out to Frederica who was extremely kind to us. As importantly, she was there when we needed her. This was our second visit to Palazzo Ravizza and we definitely plan on returning."
William 6-night trip
Posted 7 hours ago
Palazzo Ravizza

Find out more about Roccastrada

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

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Frequently asked questions

Can I find vacation rentals in Roccastrada?

Yes, we give you a choice of vacation rentals close to well known points of interest in Roccastrada, or you can choose a secluded option if you're looking for a relaxing stay.

How many vacation rentals are there in Roccastrada?

Choose from 77 Expedia vacation rentals in Roccastrada for a memorable vacation.

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 vacation rental in Roccastrada like?

Vacation rentals are private properties where you can stay for several days or longer in Roccastrada. Vacation rentals provide amenities like kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about cleanliness, vacation rentals can provide a sense of privacy away from shared hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental a great option for family trips or small group gatherings.