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

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Our top choices for Roccastrada hotels

A swimming pool with lounge chairs and umbrellas, surrounded by brick flooring and a hedge.
A rustic interior with exposed wooden beams, a central island with seating, and a stone wall.
A spa area with two hot tubs, a decorative bowl with candles, and a person in a robe.
A bedroom with a stone wall, a bed with white linens, a wooden chair, a desk with a computer, and a window with curtains.

1. La Melosa Resort & Spa - Adults Only

La Melosa Resort & Spa - Adults Only
Roccastrada
Australia
Gillian
CA $112
CA $128 total
includes taxes & fees
Oct 8 - Oct 9
La Melosa Resort & Spa - Adults Only
An outdoor dining area with stone buildings, tables with orange tablecloths, and string lights.
A view through a window of a mountainous landscape with autumn foliage and a house in the distance.
A dining table set with wine glasses and a vase with flowers, a fireplace with a fire, and a stone wall.
A gazebo with a stone wall and a lamp post in a park setting.

2. Historic Farmhouse Casa del Chiodo

Historic Farmhouse Casa del Chiodo
Roccastrada
United States
Ian
CA $139
CA $156 total
includes taxes & fees
Sep 22 - Sep 23
Historic Farmhouse Casa del Chiodo
A historic stone building with multiple windows and a courtyard.
A breakfast buffet with various food items and beverages, set in a room with stone walls and a large window.
A stone staircase leading to an arched doorway, surrounded by stone walls and potted plants.
An outdoor patio with stone arches, terracotta flooring, and tables set for dining.

3. Agriturismo Tenuta di Montemassi La Fattoria

Agriturismo Tenuta di Montemassi La Fattoria
Roccastrada
United States
Alice
CA $143
CA $161 total
includes taxes & fees
Sep 20 - Sep 21
Agriturismo Tenuta di Montemassi La Fattoria
A spacious dining area with a large table and chairs, stone walls, and a view of the mountains.
A balcony with two wooden chairs overlooking a vineyard and distant mountains.
A swimming pool with a view of a valley and mountains.
A room with a large window overlooking a vineyard and mountains. There is a stone wall and a wooden shelf with wine bottles and glasses.

4. Valdonica Winery & Vineyard Residence

Valdonica Winery & Vineyard Residence
Roccastrada
United Kingdom
Tim
CA $205
CA $231 total
includes taxes & fees
Sep 27 - Sep 28
Valdonica Winery & Vineyard Residence
A courtyard with stone steps leading to a small building, surrounded by lush greenery and stone buildings in the background.
A rectangular pool with lounge chairs and umbrellas, surrounded by a brick patio.
A cozy kitchen with a brick ceiling, wooden furniture, and a dining area with a table set for breakfast.
A hotel with a swimming pool, surrounded by greenery and adjacent to a road.

5. Country House il Ciliegio

Country House il Ciliegio
Roccastrada
Netherlands
Maaike
CA $117
CA $131 total
includes taxes & fees
Oct 16 - Oct 17
Country House il Ciliegio
A group of people dining at a table with a view of a valley and mountains.
A long table set for a formal outdoor event, surrounded by a vineyard.
A garden with a wooden chair and a table, surrounded by a stone wall and a wooden fence.
A bedroom with a bed, a desk with a bottle and glasses, a red cabinet, and a view of the outdoors.

6. Valdonica Winery - Chill in Nature Lodge

Valdonica Winery - Chill in Nature Lodge
Roccastrada
CA $256
CA $284 total
includes taxes & fees
Sep 20 - Sep 21
Valdonica Winery - Chill in Nature Lodge
A swimming pool with a view of a hilltop castle.
A kitchen with wooden cabinets, a tiled backsplash, and a dining table with a fruit bowl.
A courtyard with a stone column, potted plants, and a view of a hilltop castle.
An outdoor patio with a pergola, tables, chairs, and a view of rolling hills.

7. Agriturismo Podere Ristella - Wine&Food

Agriturismo Podere Ristella - Wine&Food
Roccastrada
Italy
eugenio
CA $107
CA $153 total
includes taxes & fees
Oct 9 - Oct 10
Agriturismo Podere Ristella - Wine&Food
A modern living room with a sofa, a coffee table, a TV on a wooden cabinet, and a large potted plant.
A fruit basket with apples, pears, bananas, and cherries.
A modern bathroom with a glass shower enclosure, a sink, a toilet, and a window providing natural light.
A bedroom with a bed, a nightstand, a wall-mounted lamp, a window with a view, and a ceiling light fixture.

8. Le Vie del Mare Camere

Le Vie del Mare Camere
Ribolla
CA $162
CA $178 total
includes taxes & fees
Oct 2 - Oct 3
Le Vie del Mare Camere
A wooden interior with a glass-enclosed shower, large windows, and a wooden floor.
A living room with a wooden ceiling, a sofa, a dining table with chairs, a television, and a cabinet.
A small, modern house with a sliding glass door, surrounded by lush greenery and a well-maintained garden.
A pathway leading to a building with a stone-tiled entrance and a wooden door.

9. Agriturismo Benvenuti

Agriturismo Benvenuti
Roccastrada
Italy
Ivano
CA $106
CA $136 total
includes taxes & fees
Oct 8 - Oct 9
Agriturismo Benvenuti
A pool with a modern water feature and a stone structure.
An indoor swimming pool with clear glass walls, a tiled floor, and a stone wall with a mosaic pattern.
A buffet table with various desserts and a long dining area with tables and chairs.
A wicker dining table set with breakfast items, a vase of flowers, and a scenic view.

10. Mercure Petriolo Siena Terme Spa Hotel

Mercure Petriolo Siena Terme Spa Hotel
Civitella Paganico
United States
Mike
CA $120
CA $132 total
includes taxes & fees
Sep 17 - Sep 18
Mercure Petriolo Siena Terme Spa Hotel
A stone building with a tiled roof, a paved pathway, and a well-maintained garden.
A stone building with a pool, lounge chairs, and a garden with flowers.
A stone building with a wooden deck and white lounge chairs.
A dining area with white tables and chairs, a large mirror, and a wine bottle on one table.

11. Podere Brizio

Podere Brizio
Montalcino
United States
Aseem
CA $313
CA $357 total
includes taxes & fees
Oct 11 - Oct 12
Podere Brizio
A table with a glass of white wine, a metal pitcher, and a wooden board with various cheeses and cured meats.
A hotel room with a bed, a sofa, a table with a vase of flowers, a TV, and a window with a view.
A kitchen with a buffet setup, including a variety of food items and glassware.
A poolside area with lounge chairs, a table with wine glasses and a bottle, and a view of a mountainous landscape.

12. SI Montalcino Hotel

SI Montalcino Hotel
Montalcino
Canada
Sam
CA $135
CA $186 total
includes taxes & fees
Sep 29 - Sep 30
SI Montalcino Hotel
A swimming pool with a waterfall feature, large windows, and a lounge chair.
A covered patio with a table and chairs, a small garden, and a building in the background.
A narrow corridor with a wooden ceiling and a tiled floor, leading to a door at the end.
An aerial view of a property with a swimming pool, manicured lawns, and a variety of trees.

13. Montebelli Agriturismo & Country Hotel

Montebelli Agriturismo & Country Hotel
Gavorrano
Canada
Jean-Olivier
CA $128
CA $150 total
includes taxes & fees
Oct 15 - Oct 16
Montebelli Agriturismo & Country Hotel
A bedroom with a bed, a chair, a table, and a stone wall.
An outdoor patio with stone walls, a pergola, and a table set for dining.
An underground wine cellar with wooden tables, wine bottles, and a piano.
A piano with sheet music, an easel with a drawing, and a wine bottle in a stone-walled room.

14. Dimora delle Muse

Dimora delle Muse
Montalcino
United States
Bradley N.
CA $293
CA $336 total
includes taxes & fees
Sep 18 - Sep 19
Dimora delle Muse
An aerial view of a historic town with stone buildings, a prominent church, and a castle-like structure with a sign reading "Castello di Monteverde."
A room with a wooden bench, potted plants, framed artwork, and a view of the outside.
A stone building with a brick archway and a tall cypress tree in front.
An outdoor patio with terracotta-tiled flooring, metal tables and chairs, potted plants, and a view of the sea.

15. Hotel Vecchia Oliviera

Hotel Vecchia Oliviera
Montalcino
United States
Roy
CA $235
CA $271 total
includes taxes & fees
Oct 16 - Oct 17
Hotel Vecchia Oliviera
A person serving food at a table with various dishes and a wine rack in the background.
A living room with a red sofa, a coffee table with magazines, a lamp, and a framed botanical display on the wall.
A building with a brick archway entrance, a wooden door, and a sign indicating 'Palazzo Lucchini.'
A bedroom with a single bed, a wooden desk, a window with a view, and a door leading to a bathroom.

16. Palazzo Lucchini

Palazzo Lucchini
Montalcino
CA $550
CA $621 total
includes taxes & fees
Sep 16 - Sep 17
Palazzo Lucchini
A hot tub with a view of a historic building and mountains.
A staircase with stone steps leading to a room with a large window, wooden beams on the ceiling, and a stone wall.
A brick-walled bar with wooden shelves stocked with bottles, tables, and chairs.
A bedroom with a large window overlooking a castle, a bed, and a mirror on the wall.

17. Drogheria & Locanda Franci

Drogheria & Locanda Franci
Montalcino
United States
Peter
CA $267
CA $310 total
includes taxes & fees
Sep 16 - Sep 17
Drogheria & Locanda Franci
A stone building with a stone staircase, surrounded by lush greenery and a stone pathway.
A bedroom with a large bed, wooden beams on the ceiling, a nightstand with a lamp, and framed pictures on the wall.
A stone building with a swimming pool, white lounge chairs, and a white umbrella.
A spacious living area with leather armchairs, a wooden cabinet with glass doors, and a red carpet.

18. Le Ragnaie

Le Ragnaie
Montalcino
United States
Douglas
CA $170
CA $203 total
includes taxes & fees
Sep 28 - Sep 29
Le Ragnaie
A room with a bed, a chair, a view through an open window, and a white dresser with bottles and glasses.
A hotel room with a bed, a nightstand with bottles, a chair, and a wardrobe.
A courtyard with a stone wall, a small pond, and a waterfall. There are trees and plants around, and a building in the background.
A stone building with the name "Albergoggiardino" above the entrance. Inside, there is a chandelier, a clock, and a blue chair.

19. Albergo Giardino

Albergo Giardino
Montalcino
United Kingdom
Norma
CA $141
CA $168 total
includes taxes & fees
Oct 15 - Oct 16
Albergo Giardino
A poolside area with lounge chairs, a table with drinks, and a view of hills.
A four-poster bed with a bench, stone flooring, and a stone wall.
A room with a large window, a door, and a view of a landscape.
An open door leading to a patio with a view of the countryside, a table with plants, and a television on a wooden cabinet.

20. Capanna Suites

Capanna Suites
Montalcino
United States
Michael
CA $646
CA $727 total
includes taxes & fees
Oct 9 - Oct 10
Capanna Suites
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Stay near popular Roccastrada attractions

I Canaloni del Torrente Farma

8.0/10 (1 review)
Commune with nature and explore the great outdoors at I Canaloni del Torrente Farma during your travels in Roccastrada. Discover the area's countryside and spas.
See properties

Podere Ristella Vineyards and Winery

You can enjoy a tasting or tour at Podere Ristella Vineyards and Winery during your travels to Roccastrada. Wander the gardens or discover the area's countryside.
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Castello del Belagaio

9.0/10 (2 reviews)
You can find out about the history of Roccastrada with a trip to Castello del Belagaio. Discover the area's countryside and wineries.
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Sassoforte Castle

9.0/10 (2 reviews)
You can find out about the history of Roccastrada with a visit to Sassoforte Castle. While you're in the area, wander around the natural setting.
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Church of San Nicola

8.0/10 (1 review)
After visiting Church of San Nicola, make a plan to see the other sights and activities in Roccastrada. Visit the spas in this relaxing area, or simply enjoy its wineries.
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Castello di Torniella

After visiting Castello di Torniella, make a plan to see the other sights and activities in Torniella.
See properties

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

Villa Scacciapensieri Boutique Hotel

Villa Scacciapensieri Boutique Hotel

10/10 Excellent
"Just loved it!! This is a great place!!!"
Daniel 3-night trip
Posted 10 hours ago
Villa Scacciapensieri Boutique Hotel
Palazzo Ravizza

Palazzo Ravizza

10/10 Excellent
"This property was in a great location, clean with large rooms and beautiful views. Staff was extremely helpful and breakfast was wonderful!"
Sherri 1-night trip
Posted 12 hours ago
Palazzo Ravizza
Grand Hotel Bastiani

Grand Hotel Bastiani

10/10 Excellent
"Clean room/ hotel, and v.convenient.Good b/fast"
Gary 1-night trip
Posted 13 hours ago
Grand Hotel Bastiani
The Sense Experience Resort - Preferred Hotels & Resorts

The Sense Experience Resort - Preferred Hotels & Resorts

10/10 Excellent
"Le site est très bien entretenu. Belle plage et bon cocktail."
Stéphanie 3-night trip
Posted 19 hours ago
The Sense Experience Resort - Preferred Hotels & Resorts
Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel

10/10 Excellent
"Very warm and friendly service."
Abdel 2-night trip
Posted 2 days ago
Castiglion del Bosco, A Rosewood Hotel
Hotel Chiusarelli

Hotel Chiusarelli

10/10 Excellent
"Excellent location. Easy parking and helpful staff."
Tracy 1-night trip
Posted 2 days ago
Hotel Chiusarelli
Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent
"Excellent location. Even though a walking only area, easy walk. Great service and breakfast was delicious. My only complaint is the included breakfast was only for 1 person."
Brittany 1-night trip
Posted 3 days ago
Grand Hotel Continental Siena – Starhotels Collezione
Hotel Italia

Hotel Italia

8/10 Good
"Clean, well maintained property that you’ll feel safe spending the night."
Shaji 1-night trip
Posted 3 days ago
Hotel Italia
Hotel Athena

Hotel Athena

10/10 Excellent
"We had a wonderful stay at Hotel Athena in Siena. The service was exceptional, the staff were warm, welcoming and genuinely helpful throughout our visit. The location was fantastic for exploring Siena, with everything within walking distance, while the hotel itself provided a comfortable and relaxing place to come back to after a day of exploring. We also loved the beautiful views from the terrace which was the perfect spot to unwind with a drink and take in the scenery. Sunset was especially beautiful and I would recommend calling the terrace staff themselves to reserve your seat. They are VERY busy up there so please exercise patience and kindness to the server and bartender as they work so hard to get your orders to you as quickly as possible. Self parking our car was a huge bonus as we rented a vehicle to explore Tuscany. A lovely hotel, a great location and wonderful service. We would happily stay here again when visiting Siena!"
stacy 3-night trip
Posted 3 days ago
Hotel Athena

More cheap stays in Roccastrada

Cannon d'Oro

Cannon d'Oro

Via Montanini 28 Siena SI
CA $133
CA $155 total
Sep 28 - Sep 29
includes taxes & fees
7.8/10 Good! (258 reviews)
Cannon d'Oro
Piccolo Hotel Etruria

Piccolo Hotel Etruria

Via delle Donzelle, 3 Siena SI
CA $158
CA $182 total
Sep 20 - Sep 21
includes taxes & fees
7.8/10 Good! (437 reviews)
Piccolo Hotel Etruria
Albergo Centrale

Albergo Centrale

Via Cecco Angiolieri 26 Siena SI
CA $214
CA $244 total
Oct 16 - Oct 17
includes taxes & fees
8.8/10 Excellent! (108 reviews)
Albergo Centrale
Torre del Fuggisole

Torre del Fuggisole

Via di Fieravecchia 7 Siena SI
CA $238
CA $270 total
Oct 11 - Oct 12
includes taxes & fees
10/10 Exceptional! (49 reviews)
Torre del Fuggisole
Porta Pispini Residence

Porta Pispini Residence

Via Baldassarre Peruzzi 33 Siena SI
Get rates
9.4/10 Exceptional! (23 reviews)
Porta Pispini Residence
Hotel Massa Vecchia

Hotel Massa Vecchia

Massa Vecchia, 23 Massa Marittima GR
Get rates
8.6/10 Excellent! (11 reviews)
Hotel Massa Vecchia

Frequently asked questions

What is the best area to stay in Roccastrada?
The best area to stay in Roccastrada is within the hilltop town itself for a classic Tuscan village experience, or in the surrounding countryside for a more secluded retreat.Staying directly in Roccastrada town provides a genuine insight into local life. You'll find a selection of local shops, a few traditional eateries, and the historic Rocca Aldobrandesca, offering lovely views of the Maremma region. It's a small, walkable town, superb for those who appreciate a slower pace and want to experience an authentic Tuscan community.For couples seeking a romantic and tranquil escape, the countryside immediately surrounding Roccastrada offers numerous agriturismi and renovated farmhouses. These properties often feature private pools, expansive gardens, and offer opportunities for wine tasting or cooking classes. You're typically a short drive from the main town, allowing for both seclusion and convenient access to local amenities.
What are the best hotels in Roccastrada that travellers recommend?
For an excellent hotel in Roccastrada that travellers highly recommend, consider La Melosa Resort & Spa - Adults Only.This 4-star resort, with an outstanding 9.4 rating, offers a luxurious experience. Guests frequently highlight the beautiful, clean rooms. The resort features a refreshing outdoor pool with comfortable sun loungers and a convenient poolside bar. For relaxation, there is a Turkish bath or hammam, and the premium bedding ensures a comfortable stay.
What are the best family hotels in Roccastrada?
For family-friendly accommodation in Roccastrada, consider the Agriturismo Tenuta di Montemassi La Fattoria, Valdonica Winery & Vineyard Residence, and B&B Podere Camaiano.The 3-star Agriturismo Tenuta di Montemassi La Fattoria, with an impressive 9.6 rating, is an excellent choice for families. It offers complimentary cots, highchairs, and sofa beds, and connecting rooms are available. Guests can also benefit from free rollaway extra beds and a complimentary buffet breakfast.The Valdonica Winery & Vineyard Residence, rated 9.4, also caters well to families, providing free cots and sofa beds. Guests can enjoy complimentary breakfast, free self-parking, and free WiFi. Pets are also welcome to stay free of charge.Another highly-rated option is the B&B Podere Camaiano, which boasts a superb 10.0 rating. This property offers complimentary cots, a free buffet breakfast, and free WiFi. Like Valdonica, it also provides free self-parking and allows pets to stay without charge.
What are the best spa hotels in Roccastrada?
For an excellent spa experience in Roccastrada, consider La Melosa Resort & Spa - Adults Only or Valdonica Winery & Vineyard Residence.The 4-star La Melosa Resort & Spa - Adults Only, rated 9.4, offers a full-service spa with a wide array of treatments including facial treatments, body treatments, body scrubs, manicures, and pedicures. Guests can also enjoy couples' treatment rooms, massage services, a sauna, a hot tub, a steam room, and a Turkish bath or hammam. Guests frequently comment on the beautiful and clean rooms.Valdonica Winery & Vineyard Residence, with an impressive 9.4 rating, also features a full-service spa that is available daily, offering relaxing massage services. This hotel provides free breakfast, free WiFi, free toiletries, and complimentary self-parking. Pets are also welcome to stay free of charge.
What hotels in Roccastrada offer free breakfast?
For hotels in Roccastrada that offer complimentary breakfast, consider the Valdonica Winery & Vineyard Residence, B&B da Nada Locanda Toscana, B&B Podere Camaiano, and Agriturismo Tenuta di Montemassi La Fattoria.The Valdonica Winery & Vineyard Residence, with an exceptional rating of 9.4, provides free breakfast and also allows pets to stay free of charge. Guests can also benefit from free self-parking and complimentary WiFi.Another excellent option is the B&B da Nada Locanda Toscana, which also boasts a 9.4 rating. This establishment offers free buffet breakfast and free WiFi, ensuring a comfortable start to your day.The B&B Podere Camaiano stands out with a superb 10.0 rating. Here, guests can enjoy a free buffet breakfast, along with free WiFi, free self-parking, and the convenience of pets staying free.Finally, the 3-star Agriturismo Tenuta di Montemassi La Fattoria, rated 9.6, provides a free buffet breakfast. Additional amenities include free WiFi, free toiletries, and complimentary parking nearby, making it a well-rounded choice.
What are the top pet-friendly hotels in Roccastrada?
For top pet-friendly hotels in Roccastrada, consider the B&B Podere Camaiano, Agriturismo Tenuta di Montemassi La Fattoria, and Valdonica Winery & Vineyard Residence.B&B Podere Camaiano stands out with an exceptional 10.0 rating, offering free accommodation for pets, complimentary breakfast, free WiFi, and free self-parking.The 3-star Agriturismo Tenuta di Montemassi La Fattoria, with a 9.6 rating, permits dogs and provides free buffet breakfast.Another excellent choice is the Valdonica Winery & Vineyard Residence, rated 9.4. This residence welcomes both dogs and cats, allows pets to stay for free, and offers complimentary breakfast, free self-parking, and free WiFi.The B&B da Nada Locanda Toscana, with a 9.4 rating, also welcomes both dogs and cats, and provides complimentary breakfast, including a buffet option, along with free WiFi.
What are the best budget hotels in Roccastrada?
For a budget-friendly hotel in Roccastrada, consider the Agriturismo Tenuta di Montemassi La Fattoria.This 3-star agriturismo, with an impressive 9.6 rating, offers a wonderful stay with several complimentary features. Guests can enjoy free WiFi, a free breakfast buffet, and free toiletries. For those travelling with infants, a free crib is available. Additionally, both nearby and on-site self-parking are free, adding to the convenience for those arriving by car.
What are the most romantic hotels in Roccastrada for couples?
For a romantic getaway in Roccastrada, consider the delightful La Melosa Resort & Spa - Adults Only or the charming Valdonica Winery & Vineyard Residence.The 4-star La Melosa Resort & Spa - Adults Only, with an exceptional rating of 9.4, is designed for couples seeking relaxation and pampering. It features a full-service spa with a hot tub, sauna, steam room, and even couples' treatment rooms for shared massages and body treatments. Guests can also enjoy the outdoor pool with sun loungers and a poolside bar, great for a tranquil afternoon together.Another wonderful option is the Valdonica Winery & Vineyard Residence, which also boasts an impressive rating of 9.4. This residence offers complimentary breakfast and free WiFi, making for a comfortable stay. Many rooms include a balcony, providing a lovely spot for couples to enjoy the views.
When is the best time to go to Roccastrada?
The best time to go to Roccastrada is during the spring (April to June) and autumn (September to October) months. These periods offer the most pleasant weather for exploring the Maremma region.During spring, the countryside around Roccastrada is lush and green, with wildflowers in bloom, making it a beautiful time for scenic drives and enjoying the natural beauty. Temperatures are comfortably mild, typically ranging from 15°C to 25°C, superb for outdoor activities like hiking or visiting local vineyards without the intense summer heat.Autumn also provides excellent conditions, with comfortable temperatures similar to spring, usually between 18°C and 26°C. This season is particularly appealing for those interested in food and wine, as it coincides with the grape harvest and olive picking. You'll find many local festivals celebrating these traditions, offering a genuine taste of Tuscan life.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Roccastrada.
How much is the nightly rate at a Roccastrada hotel?
Prices for hotels in Roccastrada often vary, but you can find a great deal from CA $128 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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