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

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Gaiole in Chianti villas

A terrace with wicker furniture, a stone planter with flowers, and a view of vineyards and hills.

1. Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi

Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi
Gaiole in Chianti
10.0 out of 10, Exceptional, (9 reviews)
"Best view in TuscanyIt was all new on the inside and very rustic exterior Beautiful villa!!!Great Host "
United States
Bernard K.
The price is AU$2,923
includes taxes & fees
3 Nov - 4 Nov
Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi
A stone building with a swimming pool, wooden deck, and a tall tree.

2. Villa 'La Petrosa' with Private Pool, Private Garden and Balcony

Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Radda in Chianti
10.0 out of 10, Exceptional, (2 reviews)
"A dream property come true. Breathtaking views, most accommodating hosts, Perfect Tuscan location."
United States
Amber M.
The price is AU$2,389
includes taxes & fees
1 Nov - 2 Nov
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
A stone building with an arched entrance, surrounded by gravel, potted plants, and trees.

3. Villa Montecastello

Villa Montecastello
Monteriggioni
8.0 out of 10, Very good, (3 reviews)
"Amazing stay! Teh apartment is HUGE and GORGEOUS. The whole villa is amazing. The view , unbeatable. The host , super warm. Highly recommend!"
United States
Alvaro
The price is AU$265
includes taxes & fees
16 Oct - 17 Oct
Villa Montecastello
A two-story building with a stone staircase leading to a wooden door. There is a small outdoor table and a potted plant on the porch.

4. Villa Il Signorino

Villa Il Signorino
GREVE IN CHIANTI
9.4 out of 10, Exceptional, (3 reviews)
"Nice place 👌 "
United States
Avi A.
The price is AU$708
includes taxes & fees
18 Oct - 19 Oct
Villa Il Signorino
A landscaped garden with a central fountain, a pool, and a small building with a tiled roof.

5. VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31

VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31
Siena
10.0 out of 10, Exceptional, (1 review)
"We celebrated our 20th Anniversary with 23 guests, all who stayed at the Property. The location and accommodations could not have been better and the staff and property manager were excellent. I would highly recommend staying here for any Tuscany adventures! Thank you so much to the owner and all involved!Ron and Wendy"
United States
Ron M.
The price is AU$11,239
includes taxes & fees
16 Oct - 17 Oct
VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31
A garden with outdoor seating, a shade structure, and a view of the surrounding landscape.

6. Rooster House, cooking classes and opera

Rooster House, cooking classes and opera
Tavarnelle Val di Pesa
The price is AU$213
includes taxes & fees
17 Oct - 18 Oct
Rooster House, cooking classes and opera
A stone building with a tower, surrounded by trees and a garden.

7. Villa Capannina with Private Pool, Wi-Fi and Air Conditioning

Villa Capannina with Private Pool, Wi-Fi and Air Conditioning
Vico dʼArbia
10.0 out of 10, Exceptional, (1 review)
"Lovely house in the Montechiaro property, very close to Siena, but far enough to enjoy the night sky in Tuscany. Communication was great."
United States
Marina O.
The price is AU$1,845
includes taxes & fees
17 Oct - 18 Oct
Villa Capannina with Private Pool, Wi-Fi and Air Conditioning
A rustic stone building with a tower, covered walkways, and a grassy courtyard.

8. Villa Torre Among the Hills of Siena

Villa Torre Among the Hills of Siena
Vico dʼArbia
The price is AU$2,506
includes taxes & fees
17 Oct - 18 Oct
Villa Torre Among the Hills of Siena
A two-story building with balconies, outdoor seating, and potted plants.

9. Artisti del Cavallo Tourism

Artisti del Cavallo Tourism
Foiano della Chiana
8.4 out of 10, Very good, (25 reviews)
"Good house for one night. "
Germany
Heiner
The price is AU$130
includes taxes & fees
29 Oct - 30 Oct
Artisti del Cavallo Tourism
A stone house with a sloped roof, a wooden porch, and a garden with various plants and flowers.

10. Il Poggio dell'Eremita

Il Poggio dell'Eremita
Sinalunga
10.0 out of 10, Exceptional, (73 reviews)
"Fantastic place! Great location. "
Canada
Paul Q.
The price is AU$251
includes taxes & fees
16 Oct - 17 Oct
Il Poggio dell'Eremita
An outdoor patio with a round table and chairs, surrounded by a wooden fence and a large canopy.

11. Villa 'Dimora degli angeli' – An Exclusive Experience in the Heart of Tuscany

Villa 'Dimora degli angeli' – An Exclusive Experience in the Heart of Tuscany
Vaggio
The price is AU$1,548
includes taxes & fees
2 Nov - 3 Nov
Villa 'Dimora degli angeli' – An Exclusive Experience in the Heart of Tuscany
A white shelving unit with various decorative items and framed pictures.

12. Isolotto degli Angeli – Villa with Pool, Hot Tub & Garden in Tuscany

Isolotto degli Angeli – Villa with Pool, Hot Tub & Garden in Tuscany
Vaggio
The price is AU$969
includes taxes & fees
2 Nov - 3 Nov
Isolotto degli Angeli – Villa with Pool, Hot Tub & Garden in Tuscany
A house with a covered patio, a lawn, and potted plants.

13. Villa 'Cascina Gretaio' with Mountain View, Private Pool and Wi-Fi

Villa 'Cascina Gretaio' with Mountain View, Private Pool and Wi-Fi
Reggello
The price is AU$1,083
includes taxes & fees
1 Nov - 2 Nov
Villa 'Cascina Gretaio' with Mountain View, Private Pool and Wi-Fi
An outdoor patio with a table and chairs, surrounded by greenery and a view of distant hills.

14. Luxury Villa in the Florentine hills

Luxury Villa in the Florentine hills
Florence
9.8 out of 10, Exceptional, (151 reviews)
"The villa is a nicely restored rustic home with a beautiful landscape. I would definitely stay there again!"
United States
melissa r.
The price is AU$527
includes taxes & fees
1 Nov - 2 Nov
Luxury Villa in the Florentine hills
An outdoor dining area with a table and chairs, overlooking a historic town with a prominent tower and buildings.

15. Villa Mami: A Tuscan Retreat of Elegance and Charm

Villa Mami: A Tuscan Retreat of Elegance and Charm
Toscana
10.0 out of 10, Exceptional, (1 review)
The price is AU$4,128
includes taxes & fees
18 Oct - 19 Oct
Villa Mami: A Tuscan Retreat of Elegance and Charm
A stone building with a tiled roof, a paved entrance, and potted plants.

16. Antica Filanda 6 - Three Bedroom Villa, Sleeps 6

Antica Filanda 6 - Three Bedroom Villa, Sleeps 6
Arezzo
The price is AU$555
includes taxes & fees
1 Nov - 2 Nov
Antica Filanda 6 - Three Bedroom Villa, Sleeps 6
Terrace/patio

17. Villa Sunset, in the heart of Chianti area

Villa Sunset, in the heart of Chianti area
Greve in Chianti
8.0 out of 10, Very good, (1 review)
"La casa é spaziosa ed accogliente e molto pulita in una posizione e strategica e comoda per visitare Firenze e i borghi della zona. "
Italy
elisa b.
Villa Sunset, in the heart of Chianti area
A stone building with a large arched entrance, potted plants, and outdoor seating.

18. Exclusive Estate | Personal Concierge & Heated Pool

Exclusive Estate | Personal Concierge & Heated Pool
impruneta
10.0 out of 10, Exceptional, (115 reviews)
"We had a great time with the family in impruneta. Caterine - the host - was very friendly and made everything to have a perfect stay in the villa. We can absolutely recommend this villa !"
Germany
Oli P.
The price is AU$1,751
includes taxes & fees
19 Oct - 20 Oct
Exclusive Estate | Personal Concierge & Heated Pool
A residential area with a swimming pool, stone walls, and a view of houses and hills.

19. Holiday Home 'Isola Degli Angeli' with Mountain View, Wi-Fi and Air Conditioning

Holiday Home 'Isola Degli Angeli' with Mountain View, Wi-Fi and Air Conditioning
Vaggio
The price is AU$873
includes taxes & fees
2 Nov - 3 Nov
Holiday Home 'Isola Degli Angeli' with Mountain View, Wi-Fi and Air Conditioning
A covered outdoor patio with a wooden table and chairs, a vase of flowers, and a view of the countryside.

20. Villa Capanna: A Window onto Tuscany

Villa Capanna: A Window onto Tuscany
Vico dʼArbia
The price is AU$2,508
includes taxes & fees
17 Oct - 18 Oct
Villa Capanna: A Window onto Tuscany
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.
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Top Gaiole in Chianti Hotel Reviews

Hotel Chiusarelli

Hotel Chiusarelli

8/10 Good
"It was OK for the price. The breakfast was so so, the parking very small and often full. The building is old and was making weird noises occasionally. The location was excellent: just outside LTZ but very close to all the points of interest."
Victor 4-night trip
Posted 5 hours ago
Hotel Chiusarelli

Find out more about Gaiole in Chianti

Gaiole in Chianti Villas information

Number of reviews
359
Accommodation
1536 Villas
Lowest Price
AU$130
Highest Price
AU$11,239

Frequently asked questions

How much do villas in Gaiole in Chianti cost?
Expect to pay between AU$130 and AU$11,239 per night for villas in Gaiole in Chianti. Whatever your budget, an awesome stay is just clicks away on Expedia. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many villas are there in Gaiole in Chianti?
Pick from 1536 villas in Gaiole in Chianti. Whether you're travelling with the little ones or planning a getaway with some friends, Expedia can help you find the best space for your crew.
What is there to do near my villa in Gaiole in Chianti?
Whatever your tastes or interests, Gaiole in Chianti has loads to keep you entertained. Castle of Brolio, Meleto Castle and Castello di Radda Winery are on most visitors' sightseeing plans. Don't head home without exploring Castello di Albola, Badia a Coltibuono and Il Molino di Grace Winery either. With Expedia's hotel deals in Gaiole in Chianti, you can see more terrific attractions like these with the cash you save.