A stone castle with battlements overlooking a lush valley with vineyards.

Gaiole in Chianti Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Gaiole in Chianti vacation homes

A stone building with a tiled roof, surrounded by greenery and a large terracotta pot.

1. Agriturismo La Ferrozzola

Agriturismo La Ferrozzola
Castellina in Chianti
9.4 out of 10, Exceptional, (9 reviews)
"Very nice agriturismo. "
United States
Ruth
The price is CA $180
CA $204 total
includes taxes & fees
Nov 16 - Nov 17
Agriturismo La Ferrozzola
A stone building with a wooden door and window, surrounded by a stone wall and a gravel path.

2. Apartment in Chianti With Pool ID 513

Apartment in Chianti With Pool ID 513
Casole d'Elsa
The price is CA $379
CA $421 total
includes taxes & fees
Nov 16 - Nov 17
Apartment in Chianti With Pool ID 513
A rustic stone building with a brick pathway leading to a wooden door.

3. Apartment in Chianti With Pool ID 455

Apartment in Chianti With Pool ID 455
Casole d'Elsa
The price is CA $559
CA $618 total
includes taxes & fees
Nov 16 - Nov 17
Apartment in Chianti With Pool ID 455
A rustic stone building with a covered patio area, a small table, and a door.

4. Apartment in Chianti With Pool ID 3939

Apartment in Chianti With Pool ID 3939
Casole d'Elsa
The price is CA $559
CA $618 total
includes taxes & fees
Nov 16 - Nov 17
Apartment in Chianti With Pool ID 3939
A rustic stone building with a tiled roof, surrounded by lush greenery and a clear sky.

5. Apartment in Chianti With Pool ID 450

Apartment in Chianti With Pool ID 450
Casole d'Elsa
The price is CA $559
CA $618 total
includes taxes & fees
Nov 18 - Nov 19
Apartment in Chianti With Pool ID 450
A rustic stone building with a tiled roof, surrounded by lush greenery and a clear sky.

6. Country House a Casole d Elsa ID 451

Country House a Casole d Elsa ID 451
Casole d'Elsa
The price is CA $759
CA $838 total
includes taxes & fees
Nov 16 - Nov 17
Country House a Casole d Elsa ID 451
A stone building with a pool and outdoor seating, surrounded by greenery and a view of distant mountains.

7. Casa Vacanze Le Case

Casa Vacanze Le Case
San Gimignano
9.6 out of 10, Exceptional, (14 reviews)
"The property was perfect and the host was so nice and helpful. We would definitely stay there again."
United States
Andrew
Casa Vacanze Le Case
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Gaiole in Chianti Hotel Reviews

Salvadonica - Borgo del Chianti

Salvadonica - Borgo del Chianti

10/10 Excellent
"Excelente servicio."
Alejandro 2-night trip
Posted 2 days ago
Salvadonica - Borgo del Chianti

Find out more about Gaiole in Chianti

Gaiole in Chianti Vacation Homes information

Number of reviews
9
Accommodation
1602 Vacation Homes
Lowest Price
CA $204
Highest Price
CA $838