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

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Check prices for these dates

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

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 ￥317,926
￥322,165 total
includes taxes & fees
Nov 15 - Nov 16
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 ￥178,350
￥263,286 total
includes taxes & fees
Nov 1 - Nov 2
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 ￥27,787
￥31,095 total
includes taxes & fees
Oct 25 - Oct 26
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 ￥55,637
￥79,305 total
includes taxes & fees
Oct 18 - Oct 19
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 ￥1,150,469
￥1,238,782 total
includes taxes & fees
Oct 20 - Oct 21
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 ￥19,429
￥23,138 total
includes taxes & fees
Oct 17 - Oct 18
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 ￥164,368
￥203,403 total
includes taxes & fees
Oct 17 - Oct 18
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 ￥237,173
￥276,208 total
includes taxes & fees
Oct 17 - Oct 18
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 ￥12,558
￥14,521 total
includes taxes & fees
Oct 23 - Oct 24
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 ￥23,814
￥27,700 total
includes taxes & fees
Oct 19 - Oct 20
Il Poggio dell'Eremita
A patio with a grill, a table, chairs, and a potted plant.

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 ￥170,126
￥170,656 total
includes taxes & fees
Nov 2 - Nov 3
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 ￥106,329
￥106,859 total
includes taxes & fees
Nov 2 - Nov 3
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 ￥107,699
￥119,353 total
includes taxes & fees
Nov 1 - Nov 2
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 ￥35,325
￥58,639 total
includes taxes & fees
Nov 1 - Nov 2
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 ￥353,251
￥484,131 total
includes taxes & fees
Oct 18 - Oct 19
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 ￥38,858
￥61,113 total
includes taxes & fees
Nov 1 - Nov 2
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 ￥172,228
￥197,486 total
includes taxes & fees
Oct 20 - Oct 21
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 ￥95,696
￥96,226 total
includes taxes & fees
Nov 2 - Nov 3
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 ￥238,095
￥277,281 total
includes taxes & fees
Oct 17 - Oct 18
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 4 hours ago
Hotel Chiusarelli

Find out more about Gaiole in Chianti

Gaiole in Chianti Villas information

Number of reviews
359
Accommodation
1841 Villas
Lowest Price
￥14,521
Highest Price
￥1,238,782

Frequently asked questions

How much do villas in Gaiole in Chianti cost?
Prices for villas in Gaiole in Chianti range between ￥14,521 and ￥1,238,782 per night. Whatever your budget, you'll find something that fits the bill with Expedia. These prices were 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?
Gaiole in Chianti has 1841 villas to select from. Find your perfect stay quickly and easily by checking the "Villa" box under the "Property type" tab in our handy filter tool.
Why book your villa in Gaiole in Chianti with Expedia?
We think vacation time shouldn't be complicated, so if you're looking for villas at a nice price, Expedia can help. Save those pennies and opt for an all-inclusive stay, or splurge on a luxury villa to spoil your loved ones. Use our convenient search filters to find an escape in Gaiole in Chianti that suits your needs.
How can I find cheap villas in Gaiole in Chianti?
An excellent way to locate cheap villas in Gaiole in Chianti is with Expedia's filter tool. Narrow your search by star rating, amenities and budget to nab unbeatable rates in only a click or two.
What is there to do near my villa in Gaiole in Chianti?
There are plenty of fantastic things to do in Gaiole in Chianti. Make tracks to leading attractions like Cantalici Winery, Castle of Brolio and Meleto Castle. Badia a Coltibuono, Church of San Sigismondo and PoggioBrandani also appeal to many visitors.