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

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 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$2,945
includes taxes & fees
6 Oct - 7 Oct
Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi
An outdoor patio with a wooden table and chairs, a hanging lantern, and a view of the surrounding landscape.

2. Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi

Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi
Gaiole in Chianti
8.0 out of 10, Very good, (1 review)
"Pros: La casa è sita in una posizione super tranquilla in mezzo al verde e alla natura. Tutto è curato alla perfezione. Nota di merito per il verde e i fiori e per la gentilezza dei proprietari. Cons: La posizione che è un pregio per qualcuno per altri potrebbe non esserlo. In effetti per arrivare al podere ci sono 2 km di strada bianca molto stretta. Una volta arrivati si è però ripagati ampiamente del piccolo disagio!"
Italy
Anonymous traveller
The price is NZ$2,305
includes taxes & fees
6 Oct - 7 Oct
Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi
An outdoor patio with a wooden pergola, a table set for breakfast, and a view of the surrounding garden.

3. Villa Bellavista - Homelike Villas

Villa Bellavista - Homelike Villas
Montegonzi
Villa Bellavista - Homelike Villas
A stone building with a swimming pool, wooden deck, and a tall tree.

4. 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 NZ$3,616
includes taxes & fees
4 Oct - 5 Oct
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
A stone building with an arched entrance, surrounded by gravel, potted plants, and trees.

5. 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$332
includes taxes & fees
3 Oct - 4 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.

6. 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 NZ$915
includes taxes & fees
29 Sept - 30 Sept
Villa Il Signorino
A garden with outdoor seating, a shade structure, and a view of the surrounding landscape.

7. Rooster House, cooking classes and opera

Rooster House, cooking classes and opera
Tavarnelle Val di Pesa
The price is NZ$263
includes taxes & fees
29 Sept - 30 Sept
Rooster House, cooking classes and opera
A covered outdoor patio with a wooden table and chairs, a vase of flowers, and a view of the countryside.

8. Villa Capanna: A Window onto Tuscany

Villa Capanna: A Window onto Tuscany
Vico dʼArbia
The price is NZ$3,445
includes taxes & fees
17 Oct - 18 Oct
Villa Capanna: A Window onto Tuscany
A rustic stone building with a tower, covered walkways, and a grassy courtyard.

9. Villa Torre Among the Hills of Siena

Villa Torre Among the Hills of Siena
Vico dʼArbia
The price is NZ$3,445
includes taxes & fees
17 Oct - 18 Oct
Villa Torre Among the Hills of Siena
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, (70 reviews)
"Fantastic place! Great location. "
Canada
Paul Q.
The price is NZ$311
includes taxes & fees
7 Oct - 8 Oct
Il Poggio dell'Eremita
An outdoor patio with a table and chairs, surrounded by greenery and a view of distant hills.

11. Luxury Villa in the Florentine hills

Luxury Villa in the Florentine hills
Florence
9.8 out of 10, Exceptional, (150 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 NZ$744
includes taxes & fees
29 Sept - 30 Sept
Luxury Villa in the Florentine hills
A landscaped garden with a central fountain, a pool, and a small building with a tiled roof.

12. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32

VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32
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$14,106
includes taxes & fees
29 Sept - 30 Sept
VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32
A brick building with a gravel courtyard, a staircase, and potted plants.

13. GuestHost - Porta Romana Elegant House with Private Parking!

GuestHost - Porta Romana Elegant House with Private Parking!
Siena
9.0 out of 10, Wonderful, (4 reviews)
"Excellent location 15 mi minute walk to the center of town. Towels and linens were fresh and fragrant. On site parking was super convenient because of limited parking around the town. The property manager was immediately available by phone and delivered an extra blanket which in 5 minutes of our request."
United States
Kathleen M.
The price is NZ$630
includes taxes & fees
5 Oct - 6 Oct
GuestHost - Porta Romana Elegant House with Private Parking!
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
The price is NZ$1,457
includes taxes & fees
29 Sept - 30 Sept
Villa 'Cascina Gretaio' with Mountain View, Private Pool and Wi-Fi
An outdoor dining area with tables and chairs, surrounded by greenery and a view of trees and hills.

15. Villa with Pool - Two Bedrooms

Villa with Pool - Two Bedrooms
Rignano sull'Arno (Florence)
The price is NZ$408
includes taxes & fees
18 Oct - 19 Oct
Villa with Pool - Two Bedrooms

16. My Exclusive Italy - Classic Suite in a Luxury Wine Estate

My Exclusive Italy - Classic Suite in a Luxury Wine Estate
Rignano sull'Arno
The price is NZ$803
includes taxes & fees
16 Oct - 17 Oct
My Exclusive Italy - Classic Suite in a Luxury Wine Estate

17. 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$1,152
includes taxes & fees
26 Oct - 27 Oct
Isolotto degli Angeli – Villa with Pool, Hot Tub & Garden in Tuscany

18. Villa Sunset, in the heart of Chianti

Villa Sunset, in the heart of Chianti
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

19. My Exclusive Italy - Exclusive Suite with view in a Luxury Wine Estate

My Exclusive Italy - Exclusive Suite with view in a Luxury Wine Estate
Rignano sull'Arno
The price is NZ$951
includes taxes & fees
20 Oct - 21 Oct
My Exclusive Italy - Exclusive Suite with view in a Luxury Wine Estate
An outdoor dining area with a table and chairs, overlooking a historic town with a prominent tower and buildings.

20. 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 NZ$5,314
includes taxes & fees
18 Oct - 19 Oct
Villa Mami: A Tuscan Retreat of Elegance and Charm
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

Fattoria di Vegi

Fattoria di Vegi

10/10 Excellent
"10/10 - we loved every bit of our stay at Fattoria di Vegi. The hotel is beautiful with great views across the Tuscan hills, an amazing pool, the rooms and decor are wonderful and we also loved the food at the restaurant. We would highly recommend this hotel to anybody visiting the area and will definitely be coming back."
Matthew 1-night trip
Posted 3 hours ago
Fattoria di Vegi

Find out more about Gaiole in Chianti

Gaiole in Chianti Villas information

Number of reviews
244
Accommodation
1552 Villas
Lowest Price
NZ$263
Highest Price
NZ$14,106

Frequently asked questions

How much do villas in Gaiole in Chianti cost?
Prices for villas in Gaiole in Chianti range between NZ$263 and NZ$14,106 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 1552 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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