Gaiole in Chianti Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$1,300 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

Top hotels in Gaiole in Chianti

Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World

5 out of 5
Via Spaltenna 13 Gaiole in Chianti SI
Fully refundableReserve now, pay when you stay
The price is S$606 per night from 6 May to 7 May
S$606
6 May - 7 May
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 28 Apr, 2026

Castello di Spaltenna- Small Luxury Hotels of the World
Ultimo Mulino Wellness Country Hotel

Ultimo Mulino Wellness Country Hotel

4 out of 5
Localita La Ripresa di Vistareni Gaiole in Chianti SI
Fully refundableReserve now, pay when you stay
The price is S$171 per night from 11 May to 12 May
S$171
11 May - 12 May
includes taxes & fees
8.8/10 Excellent! (150 reviews)
Stunning

Reviewed on 27 Apr, 2026

Ultimo Mulino Wellness Country Hotel
Agriturismo San Sano

Agriturismo San Sano

3 out of 5
Località San Sano Gaiole in Chianti SI
Fully refundableReserve now, pay when you stay
The price is S$135 per night from 4 May to 5 May
S$135
4 May - 5 May
includes taxes & fees
10/10 Exceptional! (86 reviews)
The staff is amazing ! Lorena and Matteo are exceptional, always willing to help. Very clean, beautiful views and really good breakfast

Reviewed on 26 Apr, 2026

Agriturismo San Sano
See all 8,388 properties in Gaiole in Chianti
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

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.

Church of San Sigismondo

What to do in Gaiole in Chianti

Florence: San Gimignano, Siena, Monteriggioni, Chianti & Lunch with Wine

Florence: San Gimignano, Siena, Monteriggioni, Chianti & Lunch with Wine

S$119
per adult
88% of travellers recommend
Florence: San Gimignano, Siena, Monteriggioni, Chianti & Lunch with Wine
Florence Day Trip: Medieval Villages & Cooking Class

Florence Day Trip: Medieval Villages & Cooking Class

S$209
per adult
86% of travellers recommend
Florence Day Trip: Medieval Villages & Cooking Class
Full-Day Chianti Bike Tour from Siena

Full-Day Chianti Bike Tour from Siena

S$98
per adult
100% of travellers recommend
Full-Day Chianti Bike Tour from Siena
See all activities in Gaiole in Chianti

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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.