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

Search Holiday Rentals in Roccastrada

  • 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

Check prices for these dates

In two weeks
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Roccastrada holiday rentals

Exterior

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 ₹11,529
₹12,902 total
includes taxes & fees
31 Jul - 1 Aug
Country House il Ciliegio
Comfort Apartment, 1 Queen Bed with Sofa bed, Patio, Garden View | Terrace/patio

Podere Cascatelle & Agriletizia

Podere Cascatelle & Agriletizia
Massa Marittima
10.0 out of 10, Exceptional, (2 reviews)
"Ótimo local, limpo, amplo, piscina boa, cascata boa, espaço amplo, adorei o local."
Brazil
Alan Cesar
The price is ₹15,972
₹18,338 total
includes taxes & fees
2 Aug - 3 Aug
Podere Cascatelle & Agriletizia
Premium bedding, down duvets, pillow-top beds, desk

Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (28 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is ₹7,462
₹9,636 total
includes taxes & fees
25 Aug - 26 Aug
Tuscasì Aparthotel
Aerial view

Bosco della Spina

Bosco della Spina
Murlo
9.6 out of 10, Exceptional, (175 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 ₹14,284
₹16,591 total
includes taxes & fees
28 Jul - 29 Jul
Bosco della Spina
Standard Double Room (La Piazza) | Desk, soundproofing, free WiFi, bed sheets

B&B Le Scalette di Piazza

B&B Le Scalette di Piazza
Montalcino
9.4 out of 10, Exceptional, (99 reviews)
"Great location, nice room, and great host!"
United States
Chris
The price is ₹12,897
₹14,626 total
includes taxes & fees
27 Jul - 28 Jul
B&B Le Scalette di Piazza
Seasonal outdoor pool, pool loungers

Residence Arianna

Residence Arianna
Sovicille
9.6 out of 10, Exceptional, (5 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 ₹19,088
₹21,326 total
includes taxes & fees
27 Jul - 28 Jul
Residence Arianna
Exterior

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 ₹7,187
₹8,346 total
includes taxes & fees
27 Jul - 28 Jul
Villa le Camelie Siena
Studio | Terrace/patio

La Dimora di Dida

La Dimora di Dida
Seggiano
The price is ₹6,867
₹7,554 total
includes taxes & fees
28 Jul - 29 Jul
La Dimora di Dida
Exterior

Idolina Guest House

Idolina Guest House
Montalcino
9.6 out of 10, Exceptional, (117 reviews)
"This is a wonderful B&B that is part of the historic district. Sloping uneven floors, which is the charm of having the chance to stay in a piece of history. A very comfortable room, with breakfast at a cafe nearby. Parking option is nearby, just talk with your host who is so helpful. Wonderful location to walk and enjoy all the town has to offer."
United States
Sophie
The price is ₹10,151
₹12,045 total
includes taxes & fees
18 Aug - 19 Aug
Idolina Guest House
Property grounds

Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (96 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 ₹6,827
₹7,949 total
includes taxes & fees
31 Jul - 1 Aug
Domus il Palio B&B
Terrace/patio

Casa di Campagna in Toscana

Casa di Campagna in Toscana
Sovicille
9.4 out of 10, Exceptional, (25 reviews)
"A wonderful stay. "
United States
Sally
The price is ₹12,532
₹14,115 total
includes taxes & fees
6 Aug - 7 Aug
Casa di Campagna in Toscana
1 treatment room, massages

Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.2 out of 10, Wonderful, (92 reviews)
"Our stay at Casanova Panoramic Rooms was absolutely wonderful. The room was beautiful, spotless, and the view was simply breathtaking. The entire check-in process was smooth and welcoming, and having convenient parking made everything even easier. We also loved the restaurant—the food was delicious, and breakfast was excellent. Every part of our stay exceeded our expectations. We would definitely stay here again and highly recommend it to anyone visiting the area."
United States
Anonymous traveller
The price is ₹17,075
₹19,222 total
includes taxes & fees
31 Jul - 1 Aug
Casanova - Panoramic Rooms and Suites
Double Room (Ginevra) | View from room

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 ₹11,690
₹13,298 total
includes taxes & fees
27 Jul - 28 Jul
A Casa Mastacchi
City view from property

Birbo Bike Hospitality

Birbo Bike Hospitality
Siena City Centre
8.0 out of 10, Very good, (17 reviews)
"Beautiful view from our room at the top"
United States
ralph
The price is ₹7,212
₹8,372 total
includes taxes & fees
5 Aug - 6 Aug
Birbo Bike Hospitality
Indoor pool, 2 outdoor pools, pool loungers

Antica Fornace

Antica Fornace
3.0 star property
Grosseto
8.6 out of 10, Excellent, (50 reviews)
"Location fantastica......personale sempre disponibile.....stanze grandi .... Tutto perfetto"
Italy
Stefano
The price is ₹12,936
₹14,592 total
includes taxes & fees
30 Jul - 31 Jul
Antica Fornace
Exterior

Corte Francigena - Apartments

Corte Francigena - Apartments
Montalcino
9.8 out of 10, Exceptional, (10 reviews)
"was such a beautiful location I dont have anything bad to say about it...would definitely go again for a relaxing and tranquil stay - you definitely need a car to get there though and to go around.."
United States
Hanna
The price is ₹15,682
₹18,349 total
includes taxes & fees
26 Aug - 27 Aug
Corte Francigena - Apartments
Aerial view

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 ₹27,669
₹30,656 total
includes taxes & fees
29 Jul - 30 Jul
Dimora Santa Margherita - Boutique Hotel
Front of property – evening/night

Residence Borgo San Lorenzo a Linari

Residence Borgo San Lorenzo a Linari
Sovicille
8.6 out of 10, Excellent, (98 reviews)
"Such a pleasant stay and the staff was incredible. "
United States
Monica
The price is ₹12,140
₹13,903 total
includes taxes & fees
24 Aug - 25 Aug
Residence Borgo San Lorenzo a Linari
Food court

Borgo Il Poggiaccio

Borgo Il Poggiaccio
Sovicille
8.8 out of 10, Excellent, (67 reviews)
"Beautiful place, great position in the countryside, truly relaxing place, wish we could stay longer, definitely will return A***"
United States
Dean
The price is ₹16,170
₹25,583 total
includes taxes & fees
30 Jul - 31 Jul
Borgo Il Poggiaccio
Breakfast, lunch and dinner served

Palazzo Saloni

Palazzo Saloni
Montalcino
10.0 out of 10, Exceptional, (2 reviews)
"Amazing stay! The staff are exceptional- so helpful and kind with every aspect of the stay. The rooms are beautiful and lovely amenities upon arrival. Would definitely go back again!"
United States
Victoria
The price is ₹26,639
₹30,181 total
includes taxes & fees
2 Aug - 3 Aug
Palazzo Saloni
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Roccastrada Hotel Reviews

Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent
"What a wonderful stay right in the cent of siena historic district. really recommend this hotel. Staff are very kind and welcoming."
Suresh 2-night trip
Posted 1 day ago
Grand Hotel Continental Siena – Starhotels Collezione

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:

  • View our selection of featured holiday rentals in Roccastrada
  • Use the map to find apartments and other holiday homes in the Roccastrada neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Roccastrada while they last

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 73 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.