Roccastrada Vacation Packages 2026 from $1,166

Roccastrada flight + hotel vacation packages

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

Aurum Firenze

Historic Centre of Florence

$1,166

per person

Jul 13 - Jul 19

found 2 hours ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Florence (FLR)

Free WiFi in public areas and a safe deposit box are available at this hotel. Enjoy the free buffet breakfast each morning. Staff at the 24-hour front desk can provide around-the-clock assistance.

Aurum Uffizi

Historic Centre of Florence

$1,168

per person

Jul 13 - Jul 19

found 2 hours ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Florence (FLR)

Free WiFi in public areas, a terrace, and a garden are available at this hotel. Enjoy the free buffet breakfast each morning. A snack bar/deli and a safe deposit box are also provided.

Hotel La Scaletta Al Ponte Vecchio

Historic Centre of Florence

$1,635

per person

Jul 13 - Jul 19

found 2 hours ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Florence (FLR)

This hotel features a restaurant, a rooftop terrace, and a bar/lounge. WiFi in public areas is free. A coffee shop, a terrace, and dry cleaning are also on offer.

The Moon Boutique Hotel & Spa

Historic Centre of Florence

$1,581

per person

Jul 13 - Jul 19

found 2 hours ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Florence (FLR)

This hotel features a full-service spa and a bar/lounge. WiFi in public areas is free. Self parking, a snack bar/deli, and express check-out are also offered.

Hotel degli Orafi

Historic Centre of Florence

$1,635

per person

Jul 13 - Jul 19

found 2 hours ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Florence (FLR)

This hotel features a rooftop terrace and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A terrace, a garden, and a snack bar/deli are also on offer.

Top Roccastrada hotels deals

Hotel Athena

P Mascagni 55 Siena SI

Free Cancellation

Reserve now, pay when you stay

$219 nightly

$247 total

Jun 3 - Jun 4

Total with taxes and fees

This hotel features a restaurant, a rooftop terrace, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free valet parking. Free self parking, a terrace, and a snack bar/deli are also offered.

Pet friendly

Parking included

Grand Hotel Continental Siena – Starhotels Collezione

Banchi Di Sopra 85 Siena SI

Free Cancellation

Reserve now, pay when you stay

$540 nightly

$606 total

Jun 18 - Jun 19

Total with taxes and fees

This hotel features a restaurant and 2 bars/lounges. Families will appreciate the onsite laundry facilities and in-room childcare. WiFi in public areas is free.

Pet friendly

Free WiFi

Castello di Velona Resort Thermal SPA & Winery

Località Velona Montalcino SI

Free Cancellation

Reserve now, pay when you stay

$647 nightly

$724 total

May 20 - May 21

Total with taxes and fees

This luxury hotel features an attached winery, a full-service spa, and hot springs. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and free valet parking. Enjoy the 2 outdoor pools and free perks like cooked-to-order breakfast and free self parking.

Pool

Hot Tub

Palazzo Ravizza

Pian dei Mantellini 34 Siena SI

Free Cancellation

Reserve now, pay when you stay

$146 nightly

$166 total

Jun 15 - Jun 16

Total with taxes and fees

This hotel features free WiFi in public areas, concierge services, and self parking. A terrace, a garden, and a library are also on offer.

Pet friendly

Free WiFi

Hotel Executive

Via Nazareno Orlandi 32 Siena SI

Free Cancellation

Reserve now, pay when you stay

$92 nightly

$107 total

Jun 7 - Jun 8

Total with taxes and fees

A restaurant and a bar/lounge are featured at this hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and airport shuttle. Free self parking, a garden, and a snack bar/deli are also offered.

Pet friendly

Parking included

Castiglion del Bosco, A Rosewood Hotel

Localita Castiglion del Bosco Montalcino SI

Free Cancellation

Reserve now, pay when you stay

$2,164 nightly

$2,392 total

May 27 - May 28

Total with taxes and fees

This luxury hotel features a golf course, an attached winery, and a full-service spa. There's fun for all ages with a children's club and an arcade/game room, and in-room childcare is an added bonus. Enjoy a meal in one of the 2 restaurants and free perks like valet parking and WiFi in public areas.

Pool

Spa

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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.

Popular places to visit

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.

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.

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.

Frequently asked questions

How much are vacation packages to Roccastrada?

With vacation packages being sold from just $1,166, you won't need to max out the credit card to travel to Roccastrada. Travelocity is here to help. Bundle flights, hotels and tours into a package and score some fantastic discounts. The more you book, the greater the savings.

How long should my Roccastrada vacation be?

On average, people stay 4 nights in Roccastrada. Although, that might not be sufficient time for you. If your aim is to see some of the region's hidden treasures, why not add another night or two to your itinerary?

Where can I get the best vacation package deals for Roccastrada?

There are amazing Roccastrada package deals to snap up with Travelocity. Did you know we partner with 400 airlines and 1,000,000 properties across the globe? Keep this in mind the next time you're ready to tick another destination off your travel bucket list.

Why should I book my Roccastrada vacation bundle with Travelocity?

You'll not only enjoy big savings, but you'll also have access to our 24/7 customer support, excellent service and a Price Match Guarantee. Explore every nook-and-cranny across the world, discover lesser-known sights and make unforgettable memories — we'll take care of the important details.

Will I save money on my Roccastrada car rental if I bundle it with hotels and flights?

Sure can — bundle your flight, hotel and car into a Roccastrada vacation package and you can save plenty. With so much to see in and around Roccastrada, having your own wheels will come in handy. Once you've settled into the driver's seat, hit the wide open road and cruise toward St. Peters Basilica, an unmissable attraction about 100 mi from Roccastrada.

What is the best time of year to go to Roccastrada?

If you really want to wander wisely, is a great time to do it. That's when hotel rates tumble. By way of comparison, prices skyrocket around . May, June and July are the most popular times to head to Roccastrada, so expect snaking queues for tourist attractions. Rather travel outside high season? You'll find thinner crowds during October, November and December.

Which airport is best for Roccastrada?

One of the most convenient options is Peretola Airport (FLR), which you'll find 55 mi north of the hustle and bustle of downtown Roccastrada. You can also land at Galileo Galilei Airport (PSA), 60 mi away from central Roccastrada).

What is there to do in Roccastrada?

There is a certain magic as you stroll through the streets of Roccastrada. I Canaloni del Torrente Farma and Podere Ristella Vineyards and Winery are just two renowned sights that entice visitors to this wonderful city, so put them on your to-do list.

Where should I stay when visiting Roccastrada?

Many people choose to spend their nights at the Valdonica Winery And Vineyard Residence. It's a terrific base for your Roccastrada vacation.