Roccastrada Vacations from ¥181,239

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The Latest Roccastrada Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Villa Neroli

Villa Neroli

Coverciano
¥181,239
per person
Nov 13 - Nov 17
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Florence (FLR)
9.6/10 Exceptional! (659 reviews)
This is overall a great property in every respect. Highly recommended. The only advice to other visitors is to plan for their lunch and dinner if they want more variety. The hotel restaurant is great and we dined there several times. But there are not many other good choices within walking distance from the hotel.

Reviewed on Sep 10, 2026

Hotel Certosa Di Maggiano

Hotel Certosa Di Maggiano

¥215,183
per person
Nov 13 - Nov 17
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Florence (FLR)
10/10 Exceptional! (215 reviews)
Everything was amazing! Staff was incredibly helpful.

Reviewed on Aug 27, 2026

Dimora Palanca Boutique & SPA

Dimora Palanca Boutique & SPA

Historic Centre of Florence
¥223,402
per person
Nov 13 - Nov 17
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Florence (FLR)
9.2/10 Wonderful! (69 reviews)
The accommodation very much complimented our wonderful experience and love for Florence. Our room, the connected amenities and the wonderful attentive service made our trip very memorable.

Reviewed on Sep 7, 2026

Villa Tolomei Hotel & Resort

Villa Tolomei Hotel & Resort

Oltrarno
¥205,123
per person
Nov 13 - Nov 17
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Florence (FLR)
8.8/10 Excellent! (431 reviews)
Il Pelagone Hotel & Golf Resort Toscana

Il Pelagone Hotel & Golf Resort Toscana

¥189,182
per person
Nov 13 - Nov 17
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Pisa (PSA)
8.8/10 Excellent! (23 reviews)

Find the Best Roccastrada Vacation Packages

Roccastrada Hotel Deals

Hotel Athena

Hotel Athena

P Mascagni 55 Siena SI
Fully refundableReserve now, pay when you stay
¥43,146
¥48,353 total
Sep 30 - Oct 1
includes taxes & fees
9.4/10 Exceptional! (1,013 reviews)
"Overall okay hotel. It’s meant more to come in during the morning while explore and out all day. Rooms are small and you can hear everything that’s going on in the hallway and in othe rooms (e.g., crying baby at 3am). Reception staff (Simone) was helpful and bartender (Lucas) was super nice. View ..."

Reviewed on Sep 10, 2026

Hotel Athena
Castello di Velona Resort Thermal SPA & Winery

Castello di Velona Resort Thermal SPA & Winery

Località Velona Montalcino SI
Fully refundableReserve now, pay when you stay
¥117,481
¥131,013 total
Sep 27 - Sep 28
includes taxes & fees
9/10 Wonderful! (370 reviews)
"Staying here was a wonderful and truly unique experience. The only reason I’m giving it 4 stars instead of 5 was because of the challenges we had with the air conditioning in our room. That said, the staff really did make an effort to find a workaround for us. While it wasn’t a perfect solution, ..."

Reviewed on Sep 9, 2026

Castello di Velona Resort Thermal SPA & Winery
Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

Banchi Di Sopra 85 Siena SI
Fully refundableReserve now, pay when you stay
¥95,700
¥107,054 total
Sep 14 - Sep 15
includes taxes & fees
9.2/10 Wonderful! (627 reviews)
"All the staff in the hotel were very helpful and we would like to stay there again."

Reviewed on Sep 8, 2026

Grand Hotel Continental Siena – Starhotels Collezione
See all 5,148 properties in Roccastrada
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.

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.
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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.
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What to do in Roccastrada

Porto Santo Stefano: Giglio & Giannutri Mini Cruise and Meal

Porto Santo Stefano: Giglio & Giannutri Mini Cruise and Meal

¥20,401
per adult
Porto Santo Stefano: Giglio & Giannutri Mini Cruise and Meal
Welcome to Casale del bosco

Welcome to Casale del bosco

¥6,465
per adult
Welcome to Casale del bosco
La Maliosa Farm Experience & Wine Tasting

La Maliosa Summer Farm Experience & Wine Tasting

¥8,346
per adult
100% of travellers recommend
La Maliosa Summer Farm Experience & Wine Tasting
See all activities in Roccastrada

Frequently asked questions

How much does a Roccastrada vacation package cost?
You can snap up a vacation package to this top destination from ¥181,239 on Expedia. However, how much your vacation to Roccastrada costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Roccastrada?
To pick up cheap Roccastrada vacation packages, organize your trip outside of peak periods such as public holidays. You'll generally find better availability and lower prices for hotels and flights.
How many days is enough for Roccastrada?
With a well-organized travel plan, you can easily tick off the main Roccastrada attractions in a handful of days. But if you'd like to venture off the beaten track or go on day trips, think about booking your Roccastrada vacation for longer.
How to find the best Roccastrada package deals?
Use Expedia's handy filters to find some fabulous Roccastrada package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or look for Roccastrada package deals in the off-season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to book your vacation package well in advance.
Is it cheaper to book a Roccastrada vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking accommodations and flights separately. Better still, you can customize your Roccastrada trip to fit your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Roccastrada?
If you're planning a spur-of-the-moment Roccastrada vacation, browse our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can land incredible deals on your hotels and flights by booking well in advance.
How to plan a trip to Roccastrada?
  1. Choose your travel dates: What you plan to do in Roccastrada and your favorite season will help you decide when to go.
  2. Calculate your budget: Ensure you have enough money to pay for everything from meals and transportation to airfares and activities. Your accommodations will probably be the biggest expense during your trip to Roccastrada.
  3. Determine how many days away: Start by making a list of all the attractions you want to experience in Roccastrada. Then, estimate how long you'll need for each, as well as any travel time.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to choose a Roccastrada vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.