Roccastrada Vacation Packages
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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.
Top Roccastrada Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Monastero di Cortona Hotel & Spa
Cortona Old Town
Price was CA $3,028, price is now CA $2,242 per person
CA $2,242
per person
Jul 14 - Jul 20
found 18 hours ago
Roundtrip flight included
Toronto (YYZ) to Florence (FLR)
10/10 Exceptional! (271 reviews)
Delightful place to stay in Cortona. Rooms were clean and comfortable, staff attentive and friendly, and breakfasts and drinks nicely done. I’d gladly return.
Reviewed on May 4, 2026
Precise Tale Poggio Alla Sala
Price was CA $5,387, price is now CA $3,785 per person
CA $3,785
per person
Jul 1 - Jul 5
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Florence (FLR)
9.4/10 Exceptional! (131 reviews)
Absolutely amazing! We travel with small children and this accomodation was incredible. The accomodation and staff was 5 star
Reviewed on May 3, 2026
The James Suite Hotel Firenze 1564 - Small Luxury Hotels of the World
Historic Centre of Florence
Price was CA $4,987, price is now CA $3,614 per person
CA $3,614
per person
Jul 1 - Jul 5
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Florence (FLR)
10/10 Exceptional! (17 reviews)
Outstanding hotel and a remarkable experience staying there. The room was large and beautifully decorated as the rest of the hotel. Service was impeccable and friendly. Food was great. Lovely and intimate atmosphere. Attention to details and distinctive effort to attend to our needs. The hotel manager and Lavinia at the front desk stood out, but everybody else was extremely helpful. I hope to return!
Reviewed on Nov 14, 2025
Donati Luxury Tower Suites
Historic Centre of Florence
Price was CA $12,111, price is now CA $8,890 per person
CA $8,890
per person
Jun 23 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Florence (FLR)
9.8/10 Exceptional! (61 reviews)
Fabulous old building but fully refurbished with modern suites. Only 12 suites, all unique with 2 on each floor. Loads of room. Staff fabulous. Only minus point is there’s no bar or restaurant, but it is located within an area that has literally hundreds on its doorstep. Would definitely stay there again.
Reviewed on Apr 23, 2026
Roccastrada Hotel Deals
Hotel Athena
P Mascagni 55 Siena SI
Fully refundableReserve now, pay when you stay
The price is CA $303 per night from Jun 3 to Jun 4
CA $303
CA $342 total
Jun 3 - Jun 4
includes taxes & fees
9.2/10 Wonderful! (1,007 reviews)
Breakfast was great, the hotel staff were wonderful, and the parking was a nice treat.
Reviewed on May 5, 2026
Castello di Velona Resort Thermal SPA & Winery
Località Velona Montalcino SI
Fully refundableReserve now, pay when you stay
The price is CA $910 per night from May 17 to May 18
CA $910
CA $1,017 total
May 17 - May 18
includes taxes & fees
9/10 Wonderful! (346 reviews)
It was amazing!
Reviewed on May 9, 2026
Palazzo Ravizza
Pian dei Mantellini 34 Siena SI
The price is CA $259 per night from Jun 7 to Jun 8
CA $259
CA $293 total
Jun 7 - Jun 8
includes taxes & fees
9.4/10 Exceptional! (794 reviews)
Great place to stay in Siena.
Reviewed on May 8, 2026
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.
What to do in Roccastrada
La Maliosa Farm Experience & Wine Tasting
CA $73
per adult
100% of travellers recommend
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
