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 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 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.
$1,727 nightly
The price is $1,732
Nov 15 - Nov 16
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.
$1,197 nightly
The price is $1,201
Nov 15 - Nov 16
Total with taxes and fees
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
A landscaped garden with a central fountain, a pool, and a small building with a tiled roof.

3. 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.
$8,447 nightly
The price is $8,447
Nov 11 - Nov 12
Total with taxes and fees
VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31
A covered outdoor patio with a wooden table and chairs, a vase of flowers, and a view of the countryside.

4. Villa Capanna: A Window onto Tuscany

Villa Capanna: A Window onto Tuscany
Vico dʼArbia
$1,654 nightly
The price is $1,658
Nov 13 - Nov 14
Total with taxes and fees
Villa Capanna: A Window onto Tuscany
A rustic stone building with a tower, covered walkways, and a grassy courtyard.

5. Villa Torre Among the Hills of Siena

Villa Torre Among the Hills of Siena
Vico dʼArbia
$1,654 nightly
The price is $1,658
Nov 15 - Nov 16
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.

6. Rooster House, Cooking Classes, and Opera

Rooster House, Cooking Classes, and Opera
Tavarnelle Val di Pesa
$131 nightly
The price is $135
Nov 11 - Nov 12
Total with taxes and fees
Rooster House, Cooking Classes, and Opera
A two-story building with balconies, outdoor seating, and potted plants.

7. 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
$75 nightly
The price is $87
Nov 22 - Nov 23
Total with taxes and fees
Artisti del Cavallo Tourism
A stone building with an arched entrance, surrounded by gravel, potted plants, and trees.

8. 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
$319 nightly
The price is $355
Nov 29 - Nov 30
Total with taxes and fees
Villa Montecastello
A modern outdoor space with a rectangular pool, a wooden bench, and a well-maintained lawn.

9. 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
$1,152 nightly
The price is $1,155
Nov 15 - Nov 16
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.

10. 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)
$2,823 nightly
The price is $2,823
Nov 16 - Nov 17
Total with taxes and fees
Villa Mami: A Tuscan retreat full of elegance and charm
A stone house with a sloped roof, a wooden porch, and a garden with various plants and flowers.

11. Il Poggio dell'Eremita

Il Poggio dell'Eremita
Sinalunga
10.0 out of 10, Exceptional, (74 reviews)
"Fantastic place! Great location. "
Canada
Paul Q.
$163 nightly
The price is $166
Nov 18 - Nov 19
Total with taxes and fees
Il Poggio dell'Eremita
A modern outdoor pool area with a stone structure, a covered seating area, and a view of distant mountains.

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

Isolotto degli Angeli – Villa with Pool, Hot Tub & Garden in Tuscany
Vaggio
$678 nightly
The price is $681
Nov 12 - Nov 13
Total with taxes and fees
Isolotto degli Angeli – Villa with Pool, Hot Tub & Garden in Tuscany
A large estate with a swimming pool, tennis court, and multiple guest rooms.

13. VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36

VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36
Colle Val D'Elsa
$13,149 nightly
The price is $13,149
Nov 29 - Nov 30
Total with taxes and fees
VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36
A stone building with a tower, surrounded by trees and a garden.

14. 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.
$1,219 nightly
The price is $1,223
Nov 12 - Nov 13
Total with taxes and fees
Villa Capannina with Private Pool, Wi-Fi and Air Conditioning
A house with a covered patio, a lawn, and potted plants.

15. Villa 'Cascina Gretaio' with Mountain Views, Private Pool and Wi-Fi

Villa 'Cascina Gretaio' with Mountain Views, Private Pool and Wi-Fi
Reggello
$667 nightly
The price is $673
Nov 12 - Nov 13
Total with taxes and fees
Villa 'Cascina Gretaio' with Mountain Views, Private Pool and Wi-Fi
A two-story house with a tiled roof, a chimney, and a paved driveway leading to a front door.

16. Lovely Villa newly built. Bright & independent

Lovely Villa newly built. Bright & independent
Foiano della Chiana
Lovely Villa newly built. Bright & independent
A multi-story building with a stone pathway leading to the entrance, surrounded by lush greenery and flowering plants.

17. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
Firenze
$15,779 nightly
The price is $15,779
Nov 11 - Nov 12
Total with taxes and fees
VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
A stone building with a large arched entrance, potted plants, and outdoor seating.

18. Premorae - Tenuta corte dell'Angelo - heated pool and concierge service

Premorae - Tenuta corte dell'Angelo - heated pool and concierge service
impruneta
10.0 out of 10, Exceptional, (117 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.
$1,388 nightly
The price is $1,393
Nov 12 - Nov 13
Total with taxes and fees
Premorae - Tenuta corte dell'Angelo - heated pool and concierge service
A pool area with a stone archway, lounge chairs, and a stone wall with greenery behind.

19. Villa with a Pool in Florence / Breakfast, Daily Housekeeping, Air Conditioning, Jacuzzi

Villa with a Pool in Florence / Breakfast, Daily Housekeeping, Air Conditioning, Jacuzzi
Rignano sull'Arno
$5,386 nightly
The price is $5,390
Nov 11 - Nov 12
Total with taxes and fees
Villa with a Pool in Florence / Breakfast, Daily Housekeeping, Air Conditioning, Jacuzzi
A residential area with a swimming pool, stone walls, and a view of houses and hills.

20. 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
$675 nightly
The price is $679
Nov 12 - Nov 13
Total with taxes and fees
Holiday Home 'Isola Degli Angeli' with Mountain View, Wi-Fi and Air Conditioning
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

10/10 Excellent
"Staff are very friendly and helpful. We appreciated the valet parking at no extra charge. Great location and stunning views from the terrace bar. The staff made it one of the best hotels we have stayed at in a very long time. Good value for the price."
Nancy 3-night trip
Posted 13 hours ago
Hotel Athena

Find out more about Gaiole in Chianti

Gaiole in Chianti Villas information

Number of reviews
208
Accommodation
1822 Villas
Lowest Price
$87
Highest Price
$15,779

Frequently asked questions

How much do villas in Gaiole in Chianti cost?
Prices for villas in Gaiole in Chianti range between $87 and $15,779 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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