Roccastrada Vacations from $801

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Your Roccastrada Vacation

When you choose a Roccastrada vacation package, it's all about letting go and enjoying your getaway to the fullest. Discover the sights and sounds of this exciting city knowing that all the travel planning has been organized before you go. If taking in sights is part of the program during your trip to Roccastrada, stop by top attractions like Podere Ristella Vineyards and Winery, I Canaloni del Torrente Farma and Castello del Belagaio. Expedia will help you escape your daily routine. Tailor your vacation to Roccastrada to suit your travel style, whatever that may be.

The Latest Roccastrada vacation packages

Price found within the past 48 hours. Click for updated prices.
The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $1,304, price is now $801 per person
$801
per person
Oct 31 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.6/10 Exceptional! (469 reviews)
The hotel is located a 25 min walk away from the heart of Florence so very easy to access the main attractions within the city. The hotel itself is immaculate and the staff are extremely helpful with dealing with any questions you may have. Being able to access the spa everyday for 1 and 30 minutes is an excellent perk as the facilities are well worth a visit, you are also able to book massages for an extra fee. The breakfast also gives a variety of options to start each day and the room itself is spacious, with the shower particularly being very comfortable.

Reviewed on Aug 13, 2025

L'Andana

L'Andana

5 out of 5
Save 100% on your flight
Price was $3,172, price is now $1,995 per person
$1,995
per person
Sep 25 - Oct 1
found 5 hours ago
Roundtrip flight included
New York (JFK) to Florence (FLR)
9.4/10 Exceptional! (79 reviews)
What an amazing place I hope to get back here next year again everybody was super nice. Property was super nice. It is quite relaxing. Great food apparently a great wine as well but I don’t drink. I highly recommend anybody to go.

Reviewed on Jul 5, 2025

Arte' Boutique Hotel

Arte' Boutique Hotel

4 out of 5
Historic Centre of Florence
Price was $1,417, price is now $1,005 per person
$1,005
per person
Nov 1 - Nov 5
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Florence (FLR)
9.8/10 Exceptional! (283 reviews)
Staff were really friendly, including making sure we were attended to even during a blackout

Reviewed on Aug 10, 2025

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $2,060, price is now $1,151 per person
$1,151
per person
Oct 12 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,005 reviews)
Our stay was lovely, very comfortable, small but good choice of breakfast. Beds were comfy and room was clean when we arrived and cleaned everyday. I would only suggest maybe for a shower curtains as when we had a shower the bathroom floor would be all wet, but easily to clean. And just a note on how to use the phone if we need to call reception but overall the hotel facilities and the staff were brilliant if i could give more then 5 stars i would.

Reviewed on Aug 19, 2025

Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was $1,743, price is now $980 per person
$980
per person
Oct 7 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,005 reviews)
The room that we used for 5 nights was filthy.and dusty. The shower was very small, barely squeeze in. The interior was outdated with only one point to recharge phones and the cupboards were broken. The door to the room required force to open and close. Location is convenient close to transport.

Reviewed on Aug 23, 2025

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Discover the most popular places to visit in Roccastrada

I Canaloni del Torrente Farma

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.

I Canaloni del Torrente Farma

Castello del Belagaio

You can find out about the history of Roccastrada with a trip to Castello del Belagaio. Discover the area's countryside and wineries.

Castello del Belagaio

What to do in Roccastrada

Rocca di Frassinello Winery: Tour & Wine Tasting in Tuscany

Rocca di Frassinello Winery: Tour & Wine Tasting in Tuscany

$41
per adult
Rocca di Frassinello Winery: Tour & Wine Tasting in Tuscany
See all activities in Roccastrada

Roccastrada Hotel Deals

Hotel Athena

Hotel Athena

4 out of 5
P Mascagni 55, Siena, SI
Fully refundable
$167 nightly
The price is $190 total per night from Aug 28 to Aug 29
$190 total
Aug 28 - Aug 29
Total with taxes and fees
9.2/10 Wonderful! (1,004 reviews)
"Excellent staff who are always on standby for anything that you need."

Reviewed on Aug 23, 2025

Hotel Athena
Palazzo Ravizza

Palazzo Ravizza

4 out of 5
Pian dei Mantellini 34, Siena, SI
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $140 total per night from Aug 26 to Aug 27
$140 total
Aug 26 - Aug 27
Total with taxes and fees
9.2/10 Wonderful! (689 reviews)
Just beautiful
"The building, the views, the staff, the food, everything was just incredible. It was so quiet we felt like we were the only people there until we went for breakfast and realised there were others in the hotel. The view from the our room at the back of the hotel over the Tuscan hills will live with ..."

Reviewed on Aug 9, 2025

Palazzo Ravizza
NH Siena

NH Siena

4 out of 5
Piazza La Lizza 1, Siena, SI
Fully refundableReserve now, pay when you stay
$121 nightly
The price is $139 total per night from Aug 28 to Aug 29
$139 total
Aug 28 - Aug 29
Total with taxes and fees
8.2/10 Very Good! (993 reviews)
"Everything good !"

Reviewed on Aug 11, 2025

NH Siena
See all 4,971 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.

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Frequently asked questions

How much does a Roccastrada vacation package cost?
You can snap up a vacation package to this top destination from $801 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?
October, November and December are the best times to look for cheap Roccastrada vacation packages. Opting to travel in less busy months means you can typically find better prices on accommodations and flights.
How many days is enough for Roccastrada?
With a well-planned schedule, you can easily tick off the top Roccastrada sights in a few days. But if you'd like to venture off the beaten track or go on day trips, consider 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 when to get away: Check your calendar and get packing. Your preferred time of year and the type of activities available will also help you decide when to visit Roccastrada.
  2. Budget wisely: In addition to the cost of your stay, you'll need to consider other expenses too. These include transportation, food and flights. Also, put aside some extra funds for unexpected costs that may crop up during your trip to Roccastrada.
  3. Use our trip planning tool to explore Roccastrada: Research every part of your trip to Roccastrada with this handy planner. Invite your friends and family to collaborate on a group getaway, search for hotels or things to do and make bookings.
  4. Work out your trip length: Think about how much time you'd like to spend exploring Roccastrada. Plan your days so you can get to all the attractions and experiences you're interested in without rushing.
  5. Bundle your bookings: With your travel dates in order, you can combine your flights, hotels, car rental and more into a customized Roccastrada vacation package.
  6. Book any day trips or activities: Now to the fun part — organizing everything you want to see and do. Browse some of the best things to do in Roccastrada and reserve your tickets early to save time (and maybe some spending money too!).

Does Expedia offer Book Now, Pay Later Roccastrada vacation packages?
Secure your ideal getaway to Roccastrada with our Book Now, Pay Later vacations. No need to scrimp and save or wait until your next paycheck — we've partnered with online lender Affirm to offer you flexibility with your finances. Our vacation packages with payment plans allow you to spread the cost across 3, 6 or 12 months. With no late payment fees or extra charges, it's easy to stay on budget and snap up cheap deals while they last.

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Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.