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

Villas in Gaiole in Chianti

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

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.
$1,729 nightly
The price is $1,733
Nov 16 - Nov 17
Total with taxes and fees
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
7.4 out of 10, Good, (3 reviews)
"RUN as fast as you can. Booked this place and left hours after. Here is why:1. It is actually part of a commune. Numerous other building that don't appear in pictures or description on VRBO2. There are 2 separate units. One up, One down. Require separate entrance3. Downstairs bathroom flooded. Owner admits to a broken pipe in the wall, so says use the other 2 upstairs. So, go outside, upstairs, unlock the door to use the bathroom in the middle of the night? We decide to sleep upstairs with the...
United States
JIm B.
$1,198 nightly
The price is $1,202
Nov 2 - Nov 3
Total with taxes and fees
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
$167 nightly
The price is $187
Oct 31 - Nov 1
Total with taxes and fees
Villa Montecastello
A landscaped garden with a central fountain, a pool, and a small building with a tiled roof.

4. 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.
$7,850 nightly
The price is $7,850
Oct 31 - Nov 1
Total with taxes and fees
VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31
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.

5. Villa Il Signorino

Villa Il Signorino
GREVE IN CHIANTI
9.4 out of 10, Exceptional, (3 reviews)
"Nice place 👌 "
United States
Avi A.
$498 nightly
The price is $503
Nov 1 - Nov 2
Total with taxes and fees
Villa Il Signorino
A stone building with a tower, surrounded by trees and a garden.

6. 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.
$1,220 nightly
The price is $1,224
Nov 2 - Nov 3
Total with taxes and fees
Villa Capannina with Private Pool, Wi-Fi and Air Conditioning
A rustic stone building with a tower, covered walkways, and a grassy courtyard.

7. Villa Torre Among the Hills of Siena

Villa Torre Among the Hills of Siena
Vico dʼArbia
$1,655 nightly
The price is $1,660
Nov 2 - Nov 3
Total with taxes and fees
Villa Torre Among the Hills of Siena
A garden with outdoor seating, a shade structure, and a view of the surrounding landscape.

8. Rooster House, Cooking Classes, and Opera

Rooster House, Cooking Classes, and Opera
Tavarnelle Val di Pesa
$143 nightly
The price is $146
Nov 2 - Nov 3
Total with taxes and fees
Rooster House, Cooking Classes, and Opera
A stone house with a sloped roof, a wooden porch, and a garden with various plants and flowers.

9. Il Poggio dell'Eremita

Il Poggio dell'Eremita
Sinalunga
10.0 out of 10, Exceptional, (74 reviews)
"Fantastic place! Great location. "
Canada
Paul Q.
$177 nightly
The price is $179
Nov 10 - Nov 11
Total with taxes and fees
Il Poggio dell'Eremita
A two-story building with balconies, outdoor seating, and potted plants.

10. 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
$78 nightly
The price is $90
Nov 4 - Nov 5
Total with taxes and fees
Artisti del Cavallo Tourism
A modern outdoor space with a rectangular pool, a wooden bench, and a well-maintained lawn.

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
$1,153 nightly
The price is $1,156
Nov 4 - Nov 5
Total with taxes and fees
Villa 'Dimora degli angeli' – An Exclusive Experience in the Heart of Tuscany
An outdoor dining area with a table and chairs, overlooking a historic town with a prominent tower and buildings.

12. Villa Mami: A Tuscan retreat full of elegance and charm

Villa Mami: A Tuscan retreat full of elegance and charm
Toscana
10.0 out of 10, Exceptional, (1 review)
$3,057 nightly
The price is $3,057
Nov 3 - Nov 4
Total with taxes and fees
Villa Mami: A Tuscan retreat full of elegance and charm
A modern house with a swimming pool, outdoor seating, and a view of mountains.

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

Isolotto degli Angeli – Villa with Pool, Hot Tub & Garden in Tuscany
Vaggio
$787 nightly
The price is $790
Nov 2 - Nov 3
Total with taxes and fees
Isolotto degli Angeli – Villa with Pool, Hot Tub & Garden in Tuscany
A house with a covered patio, a lawn, and potted plants.

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

Villa 'Cascina Gretaio' with Mountain View, Private Pool and Wi-Fi
Reggello
$680 nightly
The price is $686
Nov 3 - Nov 4
Total with taxes and fees
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.

15. Luxury Villa in the Florentine hills

Luxury Villa in the Florentine hills
Florence
9.8 out of 10, Exceptional, (152 reviews)
"The villa is a nicely restored rustic home with a beautiful landscape. I would definitely stay there again!"
United States
melissa r.
$366 nightly
The price is $372
Nov 1 - Nov 2
Total with taxes and fees
Luxury Villa in the Florentine hills
A covered outdoor patio with a wooden table and chairs, a vase of flowers, and a view of the countryside.

16. Villa Capanna: A Window onto Tuscany

Villa Capanna: A Window onto Tuscany
Vico dʼArbia
$1,655 nightly
The price is $1,660
Nov 2 - Nov 3
Total with taxes and fees
Villa Capanna: A Window onto Tuscany
A stone building with a large arched entrance, potted plants, and outdoor seating.

17. 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.
$1,074 nightly
The price is $1,079
Nov 1 - Nov 2
Total with taxes and fees
Exclusive Estate | Personal Concierge & Heated Pool
A residential area with a swimming pool, stone walls, and a view of houses and hills.

18. 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
$742 nightly
The price is $746
Nov 2 - Nov 3
Total with taxes and fees
Holiday Home 'Isola Degli Angeli' with Mountain View, Wi-Fi and Air Conditioning
A covered balcony with a brick railing, a bench, and a view of lush greenery.

19. Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany

Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
Certaldo - Firenze
2.0 out of 10, (1 review)
"House is very nice and clean , but not equipped for rental, kitchen is poorly equipped, towels are like napkins , no toilet paper, no soap , nothing "
United States
Kelly C.
$1,296 nightly
The price is $1,296
Nov 3 - Nov 4
Total with taxes and fees
Villa in the Heart of Chianti — Peace, Views, and Authentic 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 Athena

Hotel Athena

8/10 Good
"Hotel was fine, the staff need to communicate through what port to enter to avoid ZTL fine!! We got fined since we didn’t know. A lady staff was kind enough to email police department not to fine but it didn’t work. The hotel is on the edge of the ZTL zone and you need to enter through “San Marco” port!!"
ALLEN 2-night trip
Posted 1 day ago
Hotel Athena

Find out more about Gaiole in Chianti

Gaiole in Chianti Villas information

Number of reviews
362
Accommodation
1822 Villas
Lowest Price
$90
Highest Price
$7,850

Frequently asked questions

How much do villas in Gaiole in Chianti cost?
Prices for villas in Gaiole in Chianti range between $90 and $7,850 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 1822 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.

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