Gaiole in Chianti Vacation Packages
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Your Gaiole in Chianti Vacation
When a city getaway is calling, answer it with a Gaiole in Chianti vacation package. The neighborhood of Badia Coltibuono, which is great for families, nature and walking, makes an excellent base for your adventures. Any trip to Gaiole in Chianti needs a well-crafted itinerary. Fill yours with famous sights like Castle of Brolio, Meleto Castle and Castello di Albola. Whoever you're going away with and whether your budget is big or small, your dream Gaiole in Chianti vacation is only clicks away with Expedia.
Top Gaiole in Chianti Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Villa Pitiana
Price was CA $2,098, price is now CA $1,622 per person
CA $1,622
per person
Jul 14 - Jul 20
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Florence (FLR)
8.6/10 Excellent! (148 reviews)
Great for staty with family and kids
Great breakfast
You need to drive allot if you want to visit Firenze
Excellent fiendly staff
Reviewed on Jun 22, 2024
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 1 day ago
Roundtrip flight included
Toronto (YYZ) to Florence (FLR)
10/10 Exceptional! (271 reviews)
Everything was perfect. Customer service was everything. The classic room itself is slightly small, but a lovely big bathroom, and we were hoping for a view but understandably that would be the deluxe room. We used the spa amenities and it was pretty good for the price - recommended after a day or two of walking up and down the steep hills. Overall we will stay again. It was a beautiful hotel with lovely people working there, filled with so much history.
Reviewed on May 9, 2026
Borgo Scopeto Wine & Country Relais
Price was CA $3,575, price is now CA $2,725 per person
CA $2,725
per person
Jul 14 - Jul 20
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Florence (FLR)
9.2/10 Wonderful! (194 reviews)
This hotel is absolutely gorgeous. The staff, food and grounds are fantastic. Can’t recommend more! Big thanks to Luka and Giuseppe for making our stay so special. Great wine tasting and delicious wine recommendations. Won’t disappoint
Reviewed on Sep 2, 2025
Hotel Borgo San Luigi
Price was CA $3,034, price is now CA $2,342 per person
CA $2,342
per person
Jul 14 - Jul 20
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Florence (FLR)
9.2/10 Wonderful! (419 reviews)
Beautiful property very well maintained. Relaxing, private, quiet and extremely beautiful setting. Rooms were well appointed with nice terraces out front. Staff were very professional and attended to your every need. Slightly disappointed with the food at dinner but the breakfast was good and had an assortment of choices.
Reviewed on Apr 28, 2026
Gaiole in Chianti Hotel Deals
Castello di Spaltenna- Small Luxury Hotels of the World
Via Spaltenna 13 Gaiole in Chianti SI
Fully refundableReserve now, pay when you stay
The price is CA $580 per night from Jun 2 to Jun 3
CA $580
CA $655 total
Jun 2 - Jun 3
includes taxes & fees
9.6/10 Exceptional! (263 reviews)
Hotel located in a gorgeous mountain settings, the views absolutely stunning, the food was ok, fresh and decent choices on the menu. Room was very clean, but moldy smell was still in the room. The service was excellent. Spa i was not impressed at all. Chlorine smell inside the facility, average massage ...
Reviewed on Apr 28, 2026
Ultimo Mulino Wellness Country Hotel
Localita La Ripresa di Vistareni Gaiole in Chianti SI
Fully refundableReserve now, pay when you stay
The price is CA $263 per night from May 26 to May 27
CA $263
CA $302 total
May 26 - May 27
includes taxes & fees
8.8/10 Excellent! (151 reviews)
Stunning
Reviewed on Apr 27, 2026
Agriturismo San Sano
Località San Sano Gaiole in Chianti SI
The price is CA $135 per night from May 18 to May 19
CA $135
CA $155 total
May 18 - May 19
includes taxes & fees
10/10 Exceptional! (87 reviews)
This place is amazing. Wonderful drive to the hotel and the solitude is so great. The breakfast was amazing. Staff was very friendly for our stay. Definitely go back.
Reviewed on May 7, 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.
Discover the most popular places to visit in Gaiole in Chianti
Medieval Tower of Barbischio
Find out about the history of Gaiole in Chianti when you take a trip to Medieval Tower of Barbischio. Discover the beautiful countryside in this walkable area, or enjoy its local tours.
Church of San Sigismondo
After visiting Church of San Sigismondo, make a plan to see the other sights and activities in Gaiole in Chianti. Discover the beautiful countryside in this walkable area, or enjoy its local tours.
What to do in Gaiole in Chianti
Siena, San Gimignano, Monteriggioni & Chianti from Florence
CA $74
per adult
86% of travellers recommend
Florence: San Gimignano, Siena, Monteriggioni, Chianti & Lunch with Wine
CA $128
per adult
88% of travellers recommend
Chianti Half Day Wine Tour from Florence
CA $40
per adult
88% 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.
