Mountain Vacations in Chianti Region 2026

Plan, book, travel with confidence
Better together
Save up to CA $4,200 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place

Flight and Mountain hotel deals in Chianti Region

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

Palagina la Dimora

CA $1,820

per person

Sep 26 - Oct 2

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Florence (FLR)

9/10 Wonderful! (353 reviews)

Beautiful to stay in the main house. The breakfasts were great to start the day - really enjoyed sitting around the pool, nice and peaceful with amazing view. Rooms were comfortable. Easy to get out and try local restaurants and visit other places. Only think for us is it could do with a gym - if you're onsite all day, this would have just made the place perfect.

Reviewed on Aug 23, 2026

Don't see what you're looking for?

See all available trips from Columbus to Chianti Region

View all trips

Mountain Hotels in Chianti Region

Castello di Selvole-Adults Only

Localita Selvole, Vagliagli Radda in Chianti SI

39 min drive from Antinori nel Chianti Classico

Stay at this farm stay in Radda in Chianti. Enjoy free parking, an attached winery, and a rooftop terrace. Popular attractions Castello di Albola and Badia a ...

8.4/10 Very good! (18 reviews)

a lovely warm place to stay

"a wonderful agriturismo with welcoming and warm staff. we felt comfortable from the moment we 1st got there and we didn't want to leave."

Reviewed on Dec 30, 2012

Chiusarella Arceno Rentals Club Chianti Villa exclusive Pool Concierge freeWiFi

CASTELNUOVO BERARDENGA Tuscany

59 min drive from Antinori nel Chianti Classico

Book a stay at this family-friendly villa in Castelnuovo Berardenga. Enjoy free WiFi, private pools, and a fitness center. Popular attractions San Felice Winery ...

10/10 Exceptional! (35 reviews)

"Such a beautiful home in a perfect setting, we immediately felt at home. The daily cleaning service was wonderful and friendly. We loved arriving to a fully stocked kitchen, with enough to make a great meal and several snacks throughout our time. I would highly recommend this home!"

Reviewed on Jul 8, 2026

Casa l'Oca, spacious and bright in the heart of Tuscany at the gateway to Chianti.

Ponte Agli Stolli Tuscany

35 min drive from Antinori nel Chianti Classico

Stay at this vacation home in Figline e Incisa Valdarno. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Querciabella and Savignola Winery ...

9/10 Wonderful! (16 reviews)

"Casa muy bien comunicada a mitad de camino de todo. Paraje precioso, la Toscana es maravilloso, así como su comida y su gente. Casa amplia y bien equipada para nuestra familia de cinco, atención de 10 por parte de Valentina y su familia. Con regalo extra ;-). Y una pizzeria a un minuto caminando ..."

Reviewed on Aug 14, 2026

See all 4,903 properties in Chianti Region

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.