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

Find 5 Star Hotels in Roccastrada from $99

  • Upfront pricing

    Our total price for your stay includes taxes and fees

  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check availability on Roccastrada 5 Star Hotels

Tonight
Sep 7 - Sep 8
Tomorrow
Sep 8 - Sep 9
This weekend
Sep 11 - Sep 13
Next weekend
Sep 18 - Sep 20

Our top choices for Roccastrada 5-star hotels

An interior with a grand arched ceiling, a large clock, and a central round table with chairs.
An outdoor dining setup with a table set for two, surrounded by candles and greenery, with a historic building in the background.
A grand hallway with high ceilings, ornate columns, and a central chandelier. There are seating areas with tables and chairs, and a large potted plant in the middle.
A spacious lobby with a high ceiling, ornate columns, and a central chandelier. There are multiple seating areas with chairs and tables, and a large potted plant in the center.

1. Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione
Siena City Centre
United States
Lisa
$623 nightly
$697 total
Sep 14 - Sep 15
Total with taxes and fees
Grand Hotel Continental Siena – Starhotels Collezione
A stone building with a pool overlooking a mountainous landscape.
A dining area with a table and chairs, a vase with flowers, and a view of the countryside through an arched window.
A terrace with stone walls, potted plants, and outdoor furniture overlooking a valley with a river and distant hills during sunset.

2. Castello di Velona Resort Thermal SPA & Winery

Castello di Velona Resort Thermal SPA & Winery
Montalcino
United States
Song
$765 nightly
$853 total
Sep 27 - Sep 28
Total with taxes and fees
Castello di Velona Resort Thermal SPA & Winery
A stone-walled room with a large arched doorway, a sofa, a table with a vase, and a view of the landscape.
An open archway leading to a kitchen with a wooden ceiling, a hanging lantern, and a tiled backsplash.
A villa with a swimming pool, surrounded by lush greenery and a view of distant hills.
An aerial view of a villa with a swimming pool, terraced gardens, and a stone pathway.

3. Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel
Montalcino
United States
Talib
$2,376 nightly
$2,625 total
Oct 8 - Oct 9
Total with taxes and fees
Castiglion del Bosco, A Rosewood Hotel
A pool with a modern water feature and a stone structure.
A wicker dining table set with breakfast items, a vase of flowers, and a scenic view.
A buffet table with various desserts and a long dining area with tables and chairs.
An indoor swimming pool with clear glass walls, a tiled floor, and a stone wall with a mosaic pattern.

4. Mercure Petriolo Siena Terme Spa Hotel

Mercure Petriolo Siena Terme Spa Hotel
Civitella Paganico
United States
Mike
$92 nightly
$101 total
Sep 8 - Sep 9
Total with taxes and fees
Mercure Petriolo Siena Terme Spa Hotel
A serene infinity pool with lounge chairs and umbrellas, surrounded by natural scenery and a clear view of distant mountains.
A rustic dining area with brick walls, hanging plants, and candle-lit tables.
A bathroom with a bathtub, a chandelier, and a view of the outdoors.
A cozy living room with a fireplace, elegant furniture, and a chandelier.

5. Borgo Santo Pietro

Borgo Santo Pietro
Chiusdino
United States
Rachel
$1,373 nightly
$1,521 total
Sep 8 - Sep 9
Total with taxes and fees
Borgo Santo Pietro
A bed with white bedding and a decorative headboard with a floral pattern.
An aerial view of a historic building with a central tower, surrounded by lush greenery and a swimming pool.
A dining area with a wooden table set for four, surrounded by bamboo chairs.
A covered outdoor seating area with benches and tables, a pathway, and a view of a garden and pool.

6. Hotel Certosa Di Maggiano

Hotel Certosa Di Maggiano
Siena
United States
Tulsi
$529 nightly
$594 total
Sep 23 - Sep 24
Total with taxes and fees
Hotel Certosa Di Maggiano
A wooden deck with a white outdoor seating area, a pergola, and a view of the sea.
A hotel room with a bed, a green blanket, white curtains, a TV, and a view of the beach.
A coastal hotel with multiple buildings, a beach, and a mountainous backdrop.

7. The Sense Experience Resort - Preferred Hotels & Resorts

The Sense Experience Resort - Preferred Hotels & Resorts
Follonica
Canada
Carl
$208 nightly
$235 total
Oct 4 - Oct 5
Total with taxes and fees
The Sense Experience Resort - Preferred Hotels & Resorts
A hotel with a pool, outdoor seating, and a mountainous backdrop.
A bedroom with a stone archway, a bed, a chair, a table, and a window with curtains.
A cozy living room with a stone wall, wooden beams, a sofa, a coffee table, and a view through open doors.
An aerial view of a large estate with a central building surrounded by manicured gardens, a swimming pool, and a fountain.

8. Castello di Casole, A Belmond Hotel, Tuscany

Castello di Casole, A Belmond Hotel, Tuscany
Casole d'Elsa
United States
sarah
$1,974 nightly
$2,174 total
Sep 28 - Sep 29
Total with taxes and fees
Castello di Casole, A Belmond Hotel, Tuscany
A pool with a tree in the center, surrounded by a deck and a view of hills in the background.
A bar area with green walls, wooden stools, and a bar counter.
A table set for dining with a scenic view of hills in the background.

9. La Posta Hotel & Thermal Spa

La Posta Hotel & Thermal Spa
San Quirico d'Orcia
United States
Anna
$462 nightly
$514 total
Sep 11 - Sep 12
Total with taxes and fees
La Posta Hotel & Thermal Spa
A couple in a hot spring with a large rock formation in the background.
A hotel with a large building, a pool, and a landscaped garden.
A person in a white robe standing in a bamboo garden.
A restaurant with a bar area, dining tables, and chairs, with a view of the outdoors.

10. ADLER Thermae

ADLER Thermae
San Quirico d'Orcia
United States
Nataliya
$1,089 nightly
$1,204 total
Sep 18 - Sep 19
Total with taxes and fees
ADLER Thermae
A spacious lounge area with a high ceiling, ornate chandelier, and a variety of seating options including sofas and armchairs.
An indoor water feature with a brick archway and a view to the outside.
A large, multi-story building surrounded by lush greenery and fields.
A pool area with lounge chairs and umbrellas, surrounded by lush greenery and hills in the background.

11. L'Andana

L'Andana
Castiglione della Pescaia
United States
Aleksandr
$439 nightly
$494 total
Oct 4 - Oct 5
Total with taxes and fees
L'Andana
A rectangular swimming pool surrounded by a well-maintained lawn, with several lounge chairs and umbrellas.
A beach with two blue umbrellas and lounge chairs facing the sea.
A modern living room with a white sofa, a glass coffee table, and a view of the outdoors.
A table with two wine glasses and a bottle of champagne on a balcony overlooking a scenic view of the sea and greenery.

12. Gallia Palace Hotel

Gallia Palace Hotel
Castiglione della Pescaia
United States
Steven
$327 nightly
$371 total
Sep 22 - Sep 23
Total with taxes and fees
Gallia Palace Hotel
A stone wall with a view of rolling hills and mountains.
An outdoor dining area with tables and chairs, a flower arrangement, and a view of the countryside.
A stone building with a swimming pool, lounge chairs, and umbrellas.
A large stone castle with multiple towers, surrounded by vineyards and cypress trees.

13. Castello Banfi - Il Borgo - Relais et Chateaux

Castello Banfi - Il Borgo - Relais et Chateaux
Montalcino
United States
Jason
$1,563 nightly
$1,731 total
Sep 8 - Sep 9
Total with taxes and fees
Castello Banfi - Il Borgo - Relais et Chateaux
A pool area with a clear blue pool, surrounded by lounge chairs and umbrellas, with trees and flowers around.
A large, modern resort with multiple buildings, a swimming pool, and lush greenery.
A table with a meal, a glass of orange juice, and a view of the sea and boats.

14. Cala del Porto Punta Ala

Cala del Porto Punta Ala
Castiglione della Pescaia
United Kingdom
Shailesh
$370 nightly
$418 total
Sep 19 - Sep 20
Total with taxes and fees
Cala del Porto Punta Ala
A coastal hotel with a beach view, a modern building with a glass roof, and lush greenery.
A modern hotel room with a bed, a desk, a chair, a TV, and a balcony with red umbrellas.
A sunlit outdoor seating area with lounge chairs and a table, overlooking a beach with boats and hills in the distance.
A dining table with a white plate of appetizers, two wine glasses, and a bottle of wine.

15. Cala Beach Resort

Cala Beach Resort
Castiglione della Pescaia
United States
Christian
$637 nightly
$713 total
Oct 1 - Oct 2
Total with taxes and fees
Cala Beach Resort
A narrow street with a building featuring a tiled roof and a circular window.
A courtyard with a fountain, a gazebo, and a building with a dome.
A dining area with tables set for service, a chandelier, and wall-mounted candelabras.
An outdoor dining area with tables and chairs, a covered section, and a scenic view of hills and vineyards.

16. La Bagnaia Golf Resort

La Bagnaia Golf Resort
Murlo
Canada
Eric
La Bagnaia Golf Resort

17. Castel Porrona Relais & Spa

Castel Porrona Relais & Spa
Cinigiano
Finland
Joona
Castel Porrona Relais & Spa
A dining area with a long table set for breakfast, featuring bread, pastries, and fruit.
A cozy living area with wicker sofas, a coffee table, and a brick wall.
A view of a countryside landscape with rolling hills, a swimming pool, and a building with a tiled roof.
A restaurant with brick arches, wooden tables, and a piano.

18. Agriturismo San Fabiano

Agriturismo San Fabiano
Monteroni d'Arbia
United States
James
Agriturismo San Fabiano
Save an average of 15% on thousands of hotels when you're signed in

Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Roccastrada.
Hotel Athena

Hotel Athena

P Mascagni 55 Siena SI
$277 nightly
$310 total
Sep 8 - Sep 9
Total with taxes and fees
9.4/10 Exceptional! (1,011 reviews)
Hotel Athena
Four Points by Sheraton Siena

Four Points by Sheraton Siena

Via Antonio Lombardi 41 Siena SI
$199 nightly
$224 total
Sep 27 - Sep 28
Total with taxes and fees
8.8/10 Excellent! (603 reviews)
Four Points by Sheraton Siena
Fattoria La Principina Hotel & Congress

Fattoria La Principina Hotel & Congress

Via Dei Girasoli, 1 (Via del Tarabuso) Grosseto GR
$85 nightly
$99 total
Oct 8 - Oct 9
Total with taxes and fees
8.4/10 Very Good! (194 reviews)
Fattoria La Principina Hotel & Congress
Still don't see what you're looking for?
See all properties in Roccastrada.
You can also use these popular filters to refine your search.
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.

Learn more about Roccastrada

Hike through the dramatic rock formations of I Canaloni del Torrente Farma, where natural pools invite summer swimming between towering canyon walls. Medieval history comes alive at Sassoforte Castle, while nearby Podere Ristella offers wine tastings showcasing Tuscan varietals grown on sun-drenched slopes.

See all hotels in Roccastrada
A rural landscape with rolling hills, vineyards, and scattered buildings.

Top Roccastrada Hotel Reviews

The Sense Experience Resort - Preferred Hotels & Resorts

The Sense Experience Resort - Preferred Hotels & Resorts

10/10 Excellent
"Great property, classy, staff crew are professionals. Egor is great. Staff remembers from year to year. Management is awesome and helpful all the time The manager Sylvia is a friendly and helpful. All over staff, front desk, waiters, cleaners, managements, and bellboys are the best of the best. Only missing thing in this hotel is a Gym , but they do some classes, but gym is needed to make it as a cherry on the top. Breakfast is great , dinners are lovely. We keep going there every year."
NIMAT 1-night trip
Posted 7 hours ago
The Sense Experience Resort - Preferred Hotels & Resorts
Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent
"Great location, beautiful rooms, wonderful staff!"
Lisa 1-night trip
Posted 10 days ago
Grand Hotel Continental Siena – Starhotels Collezione
Castello di Velona Resort Thermal SPA & Winery

Castello di Velona Resort Thermal SPA & Winery

10/10 Excellent
"This property was amazing from the moment we booked. Chiara was extremely helpful with looking into horseback riding and other tours for us. I made a mistake in booking and she caught it and corrected it before we even arrived. She was great. Additionally, the room was beautiful and really clean. The food was delicious and every waitstaff that we encountered was polite and attentive--it could not have been a better experience."
Amy 2-night trip
Posted 1 month ago
Castello di Velona Resort Thermal SPA & Winery
Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel

10/10 Excellent
"Best hotel ever."
Ray 2-night trip
Posted 2 months ago
Castiglion del Bosco, A Rosewood Hotel

Find out more about Roccastrada

There's nothing wrong with enjoying the finer things in life. Add further luxury on your next trip to Roccastrada by treating yourself to the best of the best when it comes to accommodation. It's an ideal fusion. There's no reason to delay a getaway to Roccastrada any longer. You'll join the multitudes of vacationers who have made Roccastrada so fashionable in the last few seasons. You can also expect excellent customer service from these hotels, so get ready to kick back and indulge. Don't wait any longer. Our 5-star hotels in Roccastrada are the perfect places to relax in during your next chunk of time off.

Book the Best Roccastrada 5-Star Hotels

You'll have a fantastic time at one of these 5-star hotels. Top-notch service, delicious meals, and personalized service are all at your fingertips. You're sure to find exactly the accommodation you need. You can also look forward to an outstanding experience and fantastic customer care, so get ready to kick back and indulge. What kind of amenities will make your stay a wonderful one? 24-hour room service, so you can order that berry tart in the wee hours of the morning? A reflexology treatment that will leave you feeling like a million bucks? Butler services? No matter what you want on a perfect getaway, you're bound to find it here. Don't want to take our word for it? Explore our listings and pick the perfect accommodation for your needs.

You won't sleep and order room service the entire time, though. We hear you. From doing a bit of shopping to embracing the great outdoors, you'll never be bored on this retreat. No matter what's on your agenda, the 5-star hotels in Roccastrada are the perfect place to rest up after an exciting day.

Your Getaway Starts Today

The results are in, and Roccastrada 5-star hotels are the place to be when you book your next vacation. If you've been dreaming about a vacation set here, then go ahead and book it. Expedia can help you land a great deal on accommodation. Your great getaway is just a mouse-click away. Opt for one of our Roccastrada 5-star hotels today and decompress in the lap of luxury tomorrow.

Explore a world of travel with Expedia