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
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

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
$85 nightly
The price is $96
Oct 16 - Oct 17
Total with taxes and fees
Country House il Ciliegio
A wooden interior with a glass-enclosed shower, large windows, and a wooden floor.

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
$80 nightly
The price is $90
Oct 23 - Oct 24
Total with taxes and fees
Agriturismo Benvenuti
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.

3. Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (31 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
$66 nightly
The price is $76
Nov 4 - Nov 5
Total with taxes and fees
Tuscasì Aparthotel
An aerial view of a historic stone building complex with a swimming pool, surrounded by lush greenery and vineyards.

4. Bosco della Spina

Bosco della Spina
Murlo
9.6 out of 10, Exceptional, (183 reviews)
"Lovely stay! I would highly recommend this hotel. The indoor pool was just so enjoyable after a day out sightseeing. "
United Kingdom
Lizl
$89 nightly
The price is $106
Nov 1 - Nov 2
Total with taxes and fees
Bosco della Spina
A restaurant with tables and wicker chairs, large windows, and a view of buildings and greenery.

5. Palazzo Saloni

Palazzo Saloni
Montalcino
10.0 out of 10, Exceptional, (11 reviews)
"Excellent location to tour wine country montalcino."
United States
Michael
$247 nightly
The price is $283
Nov 11 - Nov 12
Total with taxes and fees
Palazzo Saloni
A spacious hotel room with a large bed, a sitting area with chairs, and a view through an arched doorway to another room.

6. La Terrazza Sul Campo Rooming House

La Terrazza Sul Campo Rooming House
Siena City Centre
9.8 out of 10, Exceptional, (251 reviews)
"Great stay. Thanks for the hospitality and kindness."
United Kingdom
Agnieszka
$96 nightly
The price is $110
Nov 3 - Nov 4
Total with taxes and fees
La Terrazza Sul Campo Rooming House
A wine cellar with stone walls, wine racks, and tables with glasses and candles.

7. Il Battistero Siena - Residenza d'Epoca

Il Battistero Siena - Residenza d'Epoca
Siena City Centre
9.6 out of 10, Exceptional, (222 reviews)
"The room was so unique and convenient for everything we wanted to do. Wish we could have spent more than one night!"
United States
Kellie
$132 nightly
The price is $150
Nov 5 - Nov 6
Total with taxes and fees
Il Battistero Siena - Residenza d'Epoca
A wooden door with a metal handle, a brick archway, a staircase, and a flower pot on the wall.

8. 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
$85 nightly
The price is $102
Oct 27 - Oct 28
Total with taxes and fees
Idolina Guest House
A dining table with a bottle of wine, two wine glasses, a candle, and a vase with flowers.

9. B&B Le Scalette di Piazza

B&B Le Scalette di Piazza
Montalcino
9.4 out of 10, Exceptional, (105 reviews)
"Great location. Staff was accommodating and very helpful."
Canada
François
$117 nightly
The price is $133
Oct 14 - Oct 15
Total with taxes and fees
B&B Le Scalette di Piazza
A hotel room with a bed, a bedside table with a lamp, a potted plant, and a view of the outside through the window.

10. PALAZZO DEL PAPA

PALAZZO DEL PAPA
Siena City Centre
9.6 out of 10, Exceptional, (116 reviews)
"Hamza is so helpful!! Finding the property is a little tricky, but he helped every step of the way! He also provided excellent dining suggestions and a great cooking class!"
United States
Charles
$168 nightly
The price is $189
Nov 10 - Nov 11
Total with taxes and fees
PALAZZO DEL PAPA
A table set with breakfast items on a balcony overlooking a historic town.

11. Residenza d'Epoca Palazzo Borghesi

Residenza d'Epoca Palazzo Borghesi
Siena City Centre
9.6 out of 10, Exceptional, (132 reviews)
"We had a great experience Property is perfectly located."
United States
Roman
$153 nightly
The price is $172
Nov 4 - Nov 5
Total with taxes and fees
Residenza d'Epoca Palazzo Borghesi
A bakery display with pastries and a coffee station.

12. B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (214 reviews)
"We enjoyed our stay very much. Staff was very friendly and offered great advise on places to eat. The rooms had great charm to them. We were delighted with our selection of where to stay."
United States
Enrique
$82 nightly
The price is $95
Nov 9 - Nov 10
Total with taxes and fees
B&B Il Corso
A large estate with multiple buildings, a swimming pool, and a well-maintained garden.

13. Dimora Santa Margherita - Boutique Hotel

Dimora Santa Margherita - Boutique Hotel
Cinigiano
8.2 out of 10, Very good, (12 reviews)
"We had a great time at this place. The room was spectacular and the views were some of the best on this entire trip. We would definitely come back. The only thing that we didn’t love was the menu at the restaurant is quite limited and there were not many things on the menu that appealed to us, as we were looking for more traditional Tuscan food. Breakfast was great and very traditional. The staff was fantastic and very helpful. Loved it."
Canada
Nicole
$337 nightly
The price is $373
Oct 25 - Oct 26
Total with taxes and fees
Dimora Santa Margherita - Boutique Hotel
A poolside area with two glasses of water, candles, and a stone pathway.

14. Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.2 out of 10, Wonderful, (101 reviews)
"Great location and lovely pool. Rooms were large but the place is definitely dated. Breakfast was decent with a lot of options. Parking wasn’t all that great but nevertheless on the property itself"
Canada
Sunil
$170 nightly
The price is $192
Oct 12 - Oct 13
Total with taxes and fees
Casanova - Panoramic Rooms and Suites
A couple seated at a table with drinks, overlooking a pool area with lounge chairs and umbrellas.

15. Fattoria Maremmana

Fattoria Maremmana
4.0 star property
Grosseto
8.0 out of 10, Very good, (11 reviews)
"Staff very friendly and helpful. Very quiet stay as we visited at the beginning of the slow season. "
United States
James
Fattoria Maremmana
Outdoor pool

16. Residence Arianna

Residence Arianna
Sovicille
9.6 out of 10, Exceptional, (9 reviews)
"The place is excellent! The owner and her daughter extremely friendly and kind! They helped us with everything we needed. I will definitely stay here again. I highly recommend this place!"
United States
Violeta
$125 nightly
The price is $141
Nov 11 - Nov 12
Total with taxes and fees
Residence Arianna
A bathroom with a window view of a historic building and a tiled roof.

17. Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (488 reviews)
"Great location right in the heart of everything and next to an escalator that takes you to the main plaza. Very comfortable bed, friendly staff. Convenient parking option very close by."
United States
Heather
$111 nightly
The price is $127
Nov 2 - Nov 3
Total with taxes and fees
Siena Vip
A rectangular pool with a metal ladder, surrounded by wooden lounge chairs and a stone deck.

18. Corte Francigena - Apartments

Corte Francigena - Apartments
Montalcino
9.8 out of 10, Exceptional, (19 reviews)
"The unit is very clean, awesome breakfast, beautiful view"
Canada
Ivan
$96 nightly
The price is $114
Nov 11 - Nov 12
Total with taxes and fees
Corte Francigena - Apartments
An outdoor swimming pool with a wooden pergola, lounge chairs, and a stone wall backdrop.

19. Guild Living Siena Senior Resort & Residence

Guild Living Siena Senior Resort & Residence
Scacciapensieri
8.8 out of 10, Excellent, (55 reviews)
"Amazing! Thank you!"
United Kingdom
Lucy
$128 nightly
The price is $145
Nov 1 - Nov 2
Total with taxes and fees
Guild Living Siena Senior Resort & Residence
A stone courtyard with a bench, potted plants, and a building in the background.

20. 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
$101 nightly
The price is $115
Nov 8 - Nov 9
Total with taxes and fees
Casa di Campagna in Toscana
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

Hotel Italia

Hotel Italia

10/10 Excellent
"We stayed here for three nights and absolutely loved it. The hotel is charming, convenient and comfortable. Breakfast was very good, with a nice choice of foods, and the lounge/bar is a great place to relax. The staff were very helpful with directions and bookings. We would gladly stay here again."
Ralph 2-night trip
Posted 14 hours ago
Hotel Italia

Find out more about Roccastrada

Everything you need to know about Roccastrada vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Roccastrada vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Roccastrada vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Roccastrada vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Roccastrada. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Roccastrada in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $32 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Roccastrada rentals

At Expedia, we put the best Roccastrada vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Roccastrada rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Roccastrada vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Roccastrada. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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.

What are some of the best vacation home rentals that Roccastrada has to offer?

Casa Viale Italia - homely house with direct access to the sandy beach: This vacation home rental near Roccastrada is located near the beach and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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.