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Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

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 NZ$3,096
includes taxes & fees
15 Nov - 16 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
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.
The price is NZ$2,150
includes taxes & fees
15 Nov - 16 Nov
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.
The price is NZ$15,101
includes taxes & fees
13 Dec - 14 Dec
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
The price is NZ$2,965
includes taxes & fees
13 Nov - 14 Nov
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
The price is NZ$2,968
includes taxes & fees
15 Nov - 16 Nov
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
The price is NZ$247
includes taxes & fees
13 Nov - 14 Nov
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
The price is NZ$165
includes taxes & fees
15 Nov - 16 Nov
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
The price is NZ$700
includes taxes & fees
25 Nov - 26 Nov
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
The price is NZ$2,097
includes taxes & fees
15 Nov - 16 Nov
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)
The price is NZ$5,050
includes taxes & fees
17 Nov - 18 Nov
Villa Mami: A Tuscan retreat full of elegance and charm
A modern outdoor pool area with a stone structure, a covered seating area, and a view of distant mountains.

11. 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 NZ$1,217
includes taxes & fees
15 Nov - 16 Nov
Isolotto degli Angeli – Villa with Pool, Hot Tub & Garden in Tuscany
A stone house with a sloped roof, a wooden porch, and a garden with various plants and flowers.

12. Il Poggio dell'Eremita

Il Poggio dell'Eremita
Sinalunga
10.0 out of 10, Exceptional, (74 reviews)
"Fantastic place! Great location. "
Canada
Paul Q.
The price is NZ$302
includes taxes & fees
17 Nov - 18 Nov
Il Poggio dell'Eremita
A house with a covered patio, a lawn, and potted plants.

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

Villa 'Cascina Gretaio' with Mountain Views, Private Pool and Wi-Fi
Reggello
The price is NZ$1,203
includes taxes & fees
13 Nov - 14 Nov
Villa 'Cascina Gretaio' with Mountain Views, Private Pool and Wi-Fi
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.
The price is NZ$2,189
includes taxes & fees
13 Nov - 14 Nov
Villa Capannina with Private Pool, Wi-Fi and Air Conditioning
A large estate with a swimming pool, tennis court, and multiple guest rooms.

15. VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36

VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36
Colle Val D'Elsa
The price is NZ$23,508
includes taxes & fees
13 Dec - 14 Dec
VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36
A multi-story building with a stone pathway leading to the entrance, surrounded by lush greenery and flowering plants.

16. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
Firenze
The price is NZ$28,209
includes taxes & fees
7 Dec - 8 Dec
VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
A stone building with a large arched entrance, potted plants, and outdoor seating.

17. 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.
The price is NZ$2,451
includes taxes & fees
13 Nov - 14 Nov
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.

18. 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
The price is NZ$9,656
includes taxes & fees
13 Nov - 14 Nov
Villa with a Pool in Florence / Breakfast, Daily Housekeeping, Air Conditioning, Jacuzzi
A two-story building with a gravel driveway, a wooden door, and a small garden area with potted plants.

19. Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites

Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites
Montespertoli
10.0 out of 10, Exceptional, (42 reviews)
"Absolutely fabulous! Beautiful location, exceptional host and the Tuscan countryside dream. Room for all 11 of our ladies, dreamy grounds. We all felt like we were living our Eat, Love, Pray best life!"
United States
Krista G.
The price is NZ$2,729
includes taxes & fees
13 Dec - 14 Dec
Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites
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
The price is NZ$1,215
includes taxes & fees
13 Nov - 14 Nov
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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Learn more about Gaiole in Chianti

Medieval stone buildings house family-run wine shops where you can taste Chianti Classico from surrounding vineyards. Join locals at Piazza Ricasoli's cafés before exploring L'Eroica cycling route that winds through nearby hilltop villages.

See all hotels in Gaiole in Chianti
A stone castle with battlements overlooking a lush valley with vineyards.

Frequently Asked Questions

How much do villas in Gaiole in Chianti cost?

Prices for villas in Gaiole in Chianti range between NZ$165 and NZ$28,209 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 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.

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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