Roccastrada Vacation Rentals from $52: Search Short-Term Rentals

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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

Roccastrada

Maaike

$83 nightly

Nov 3 - Nov 4

Total with taxes and fees

A glass-enclosed structure with a wooden deck, surrounded by various plants and a garden.

2. Agriturismo Benvenuti

Roccastrada

"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."

Ivano

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

Sovicille

Sergey

$72 nightly

Nov 20 - Nov 21

Total with taxes and fees

A narrow hallway with a wooden bench, a radiator, and a wooden cabinet.

4. Il Battistero Siena - Residenza d'Epoca

Siena City Centre

Kellie

$103 nightly

Nov 9 - Nov 10

Total with taxes and fees

A courtyard with outdoor seating, a building with multiple windows, and a stone wall.

5. Palazzo Saloni

Montalcino

Michael

$280 nightly

Nov 3 - Nov 4

Total with taxes and fees

A table set with breakfast items on a balcony overlooking a historic town.

6. Residenza d'Epoca Palazzo Borghesi

Siena City Centre

Suelina

$140 nightly

Nov 4 - Nov 5

Total with taxes and fees

A table with two wine glasses, a bottle, and a book.

7. Domus il Palio B&B

Ravacciano

Leo

$69 nightly

Nov 18 - Nov 19

Total with taxes and fees

A wooden door with a metal handle, a brick archway, a staircase, and a flower pot on the wall.

8. Idolina Guest House

Montalcino

Jaiden

$82 nightly

Nov 27 - Nov 28

Total with taxes and fees

An aerial view of a historic stone building complex with a swimming pool, surrounded by lush greenery and vineyards.

9. Bosco della Spina

Murlo

Amir

$89 nightly

Nov 1 - Nov 2

Total with taxes and fees

A narrow street with buildings on either side, featuring arched windows and a pedestrian walkway.

10. B&B Il Corso

Siena City Centre

Heather

$73 nightly

Nov 22 - Nov 23

Total with taxes and fees

A bathroom with a window view of a historic building and a tiled roof.

11. Siena Vip

Siena City Centre

Jacob

$100 nightly

Oct 28 - Oct 29

Total with taxes and fees

A historic building with a clock tower, arched windows, and a shop selling souvenirs.

12. PALAZZO DEL PAPA

Siena City Centre

Charles

$180 nightly

Nov 7 - Nov 8

Total with taxes and fees

A dining table with a bottle of wine, two wine glasses, a candle, and a vase with flowers.

13. B&B Le Scalette di Piazza

Montalcino

Morris

$119 nightly

Nov 6 - Nov 7

Total with taxes and fees

A room with a white wardrobe, a glass-top table, a chair, and a large ornate mirror.

14. B&B Palazzo del Magnifico

Siena City Centre

Khaled

$94 nightly

Nov 12 - Nov 13

Total with taxes and fees

A spacious hotel room with a large bed, a sitting area with chairs, and a view through an arched doorway to another room.

15. La Terrazza Sul Campo Rooming House

Siena City Centre

Agnieszka

A large estate with multiple buildings, a swimming pool, and a well-maintained garden.

16. Dimora Santa Margherita - Boutique Hotel

Cinigiano

"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."

Nicole

A stone-walled room with a fireplace, a hot tub, candles, and a tray with snacks.

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

San Quirico d'Orcia

Elena

$122 nightly

Nov 8 - Nov 9

Total with taxes and fees

A pool area with lounge chairs and umbrellas, surrounded by tall cypress trees and a view of distant hills.

18. Casanova - Panoramic Rooms and Suites

San Quirico d'Orcia

DANIELA

$170 nightly

Oct 29 - Oct 30

Total with taxes and fees

A rectangular pool with a metal ladder, surrounded by wooden lounge chairs and a stone deck.

19. Corte Francigena - Apartments

Montalcino

Ivan

$101 nightly

Nov 1 - Nov 2

Total with taxes and fees

An outdoor swimming pool with a wooden pergola, lounge chairs, and a stone wall backdrop.

20. Guild Living Siena Senior Resort & Residence

Scacciapensieri

"We booked this last - minute and were really impressed with the whole experience. The property and grounds are beautiful. Staff was so friendly and helpful. The rooms were well appointed and quiet. Beds were too firm for our liking, but it was easy to overlook as the entire stay was really great. Good options in the restaurant too. The block of hotel rooms is in a retirement resort, which I think is a wonderful idea! Very much enjoyed our stay. We had a car and parking was free."

Heidi

$96 nightly

Nov 4 - Nov 5

Total with taxes and fees

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Top Roccastrada Hotel Reviews

Hotel Minerva

10/10 Excellent

"Clean, great breakfast, lovely view!"

Castello di Velona Resort Thermal SPA & Winery

10/10 Excellent

"Stayed at the hotel for our honeymoon and it was an incredible experience. The view is simply breathtaking and the castle is extremely charming. Food (breakfast and diner) and wine at the restaurants are high quality, inspired and locally sourced, though expensive. Their Brunello is VERY good. The thermal spa experience is unique in the region and is awsome, especially during the fall season when it is cooler outside. The room was super clean and the staff was very helpful throughout the entire week, and we felt welcomed at any time of day. 15 min by car from Montalcino, strongly recommend to rent a car since it is slightly remote. Overall 9.5/10, strongly recommend for a special occasion."

Hotel Italia

10/10 Excellent

"We stayed at this basic but nice 3-star hotel just one night while visiting Siena. We had a room for 3 for my wife and I and our adult daughter. The hotel was easy walking distance from the train/bus station. It's kind of weird because you enter an indoor shopping area across the street from the station and then go up about 6 banks of escalators to get up the hillside. Then the hotel is just a block away. One of the AC units didn't work but friendly staff helped start the other one. All staff were very friendly and spoke English. Easy walk a few blocks into the old city. Wonderful breakfast!!! We were able to leave our bags for most of the day while we explored the city prior to leaving on the bus again. I would definitely stay again."

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 $52 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.

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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.

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.

Roccastrada Vacation Rentals

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Check prices for these dates

Our top choices for Roccastrada vacation rentals

1. Country House il Ciliegio

2. Agriturismo Benvenuti

3. Tuscasì Aparthotel

4. Il Battistero Siena - Residenza d'Epoca

5. Palazzo Saloni

6. Residenza d'Epoca Palazzo Borghesi

7. Domus il Palio B&B

8. Idolina Guest House

9. Bosco della Spina

10. B&B Il Corso

11. Siena Vip

12. PALAZZO DEL PAPA

13. B&B Le Scalette di Piazza

14. B&B Palazzo del Magnifico

15. La Terrazza Sul Campo Rooming House

16. Dimora Santa Margherita - Boutique Hotel

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

18. Casanova - Panoramic Rooms and Suites

19. Corte Francigena - Apartments

20. Guild Living Siena Senior Resort & Residence

Find vacation rentals that suit your style

Top Roccastrada Hotel Reviews

Hotel Minerva

Find out more about Roccastrada

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