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

Holiday Homes in Gaiole in Chianti

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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Gaiole in Chianti holiday homes

A swimming pool with a colorful inflatable ring and a water fountain.

1. Farmhouse in Chianti

Farmhouse in Chianti
gaiole in chianti
9.8 out of 10, Exceptional, (6 reviews)
"This location provided our blended family an authentic experience in a small village on top of a mountain in Chianti. The house is surrounded by olive groves and wine grapes. The pool was great and the village, literally less than a city block up the road. Folks are incredibly friendly and helpful. Two of the rooms had their own bathrooms and the other two share a bathroom. There is a common kitchen for cooking and eating. We cooked most nights and ate on the outside terrace. Allesandra is a...
United States
Lara W.
The price is €507
includes taxes & fees
27 Sept - 28 Sept
Farmhouse in Chianti
A dining area with a table and chairs, a sofa, and large windows with curtains.

2. 'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi

'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi
Gaiole in Chianti
The price is €1,893
includes taxes & fees
27 Sept - 28 Sept
'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi
A stone building with a gated entrance, terracotta pots with flowers, and a staircase leading up to the door.

3. UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK

UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
Ruffoli
9.2 out of 10, Wonderful, (24 reviews)
"This is truly a unique and special property providing incredible value . One of the most beautiful views in a spectacular setting hidden away in the Tuscan hills above Panzano. A perfect location for day trips to vinyards, restaurants and the Chianti area. Our apartment was extremely well appointed and beautifully decorated. Spacious and varied outdoor sitting areas and patios with a very nice pool area. Our hostess Babette was extremely accomodating and informative which added to our overall...
Canada
James
The price is €164
includes taxes & fees
15 Sept - 16 Sept
UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
A dining area with a brick archway, wooden dining table, chairs, and a chandelier.

4. Holiday Home 'Poggio Loccano' with Private Garden and Balcony

Holiday Home 'Poggio Loccano' with Private Garden and Balcony
Montevarchi
The price is €289
includes taxes & fees
15 Sept - 16 Sept
Holiday Home 'Poggio Loccano' with Private Garden and Balcony
A garden pathway leading to a stone building with a brick wall, a pergola, and a small brick structure in the background.

5. Villa 'La Tinaia Il Sole Verde' with Shared Pool and Wi-Fi

Villa 'La Tinaia Il Sole Verde' with Shared Pool and Wi-Fi
Bucine
10.0 out of 10, Exceptional, (2 reviews)
"Upon arrival Guido had everything prepared for us. A bottle of his amazing wine that he makes along with 2 wine glasses we’re waiting on the farmhouse table. The home had 2 very comfortable bedrooms and a bathroom along with a living room and kitchen. Front porch overlooks the stunning Tuscany fields. The swimming pool was refreshing and everything was beyond perfect. This location was everything and more. The hosts were so helpful. I will come back her again..make sure to take time for the...
United States
Marianne H.
The price is €385
includes taxes & fees
15 Sept - 16 Sept
Villa 'La Tinaia Il Sole Verde' with Shared Pool and Wi-Fi
A clear blue pool with a view of green hills and a distant building.

6. Casale Rosennano Apartment – Shared Garden, Wi-Fi, Medieval Setting

Casale Rosennano Apartment – Shared Garden, Wi-Fi, Medieval Setting
Rosennano
The price is €383
includes taxes & fees
20 Sept - 21 Sept
Casale Rosennano Apartment – Shared Garden, Wi-Fi, Medieval Setting
A rectangular swimming pool with a wooden deck and metal railing, surrounded by a grassy area with trees and a clear sky.

7. Holiday Home "Limonaia" with Shared Pool, Communal Garden and Wi-Fi

Holiday Home "Limonaia" with Shared Pool, Communal Garden and Wi-Fi
Castelnuovo Berardenga
10.0 out of 10, Exceptional, (1 review)
"Pros: The view and unique traditional apartment. Cons: -"
United States
Anonymous traveller
The price is €370
includes taxes & fees
15 Sept - 16 Sept
Holiday Home "Limonaia" with Shared Pool, Communal Garden and Wi-Fi
A modern hotel room with a flat-screen TV displaying 'NETFLIX', a jacuzzi, and a neon sign.

8. Love Nest Siena: Romantic Suite with SPA & Jacuzzi

Love Nest Siena: Romantic Suite with SPA & Jacuzzi
Toscana
The price is €180
includes taxes & fees
16 Sept - 17 Sept
Love Nest Siena: Romantic Suite with SPA & Jacuzzi
A swimming pool with a wooden deck, a tree with red leaves, and a building with a beige facade.

9. Holiday Home 'Il Piccolo Rifugio' with Private Pool, Garden and Wi-Fi

Holiday Home 'Il Piccolo Rifugio' with Private Pool, Garden and Wi-Fi
Figline Valdarno
The price is €105
includes taxes & fees
1 Oct - 2 Oct
Holiday Home 'Il Piccolo Rifugio' with Private Pool, Garden and Wi-Fi
A view through a wooden door of a courtyard with stone walls and potted plants.

10. Chianti Craft House Badia a Passignano

Chianti Craft House Badia a Passignano
Tavarnelle Val di Pesa
10.0 out of 10, Exceptional, (12 reviews)
"Very historic venue, with amazing views"
United States
Oscar O.
The price is €173
includes taxes & fees
15 Sept - 16 Sept
Chianti Craft House Badia a Passignano
An outdoor patio with a wooden pergola, a sofa, a table, and chairs.

11. Blue villa surrounded by greenery between Arezzo Florence and Siena

Blue villa surrounded by greenery between Arezzo Florence and Siena
TERRANUOVA BRACCIOLINI
The price is €187
includes taxes & fees
1 Oct - 2 Oct
Blue villa surrounded by greenery between Arezzo Florence and Siena
A covered patio with a wooden table and chairs, stone walls, and a view of a garden.

12. Villa 'Il Fienile Il Sole Verde' with Shared Pool and Wi-Fi

Villa 'Il Fienile Il Sole Verde' with Shared Pool and Wi-Fi
Bucine
10.0 out of 10, Exceptional, (4 reviews)
"Pros: Guido og Angela var helt fantastiske værter og deres medhjælper sørgede godt for os med friske grøntsager fra haven. Poolen var perfekt og altid ren og pæn. For os var det helt perfekt vi kun var to familier og at der var ro Cons: Vi har ingen kritik punkter ☺️"
Denmark
Anonymous traveller
The price is €415
includes taxes & fees
20 Sept - 21 Sept
Villa 'Il Fienile Il Sole Verde' with Shared Pool and Wi-Fi
A swimming pool with lounge chairs, a tiled deck, and surrounding trees.

13. Villa 'La Stalla Il Sole Verde' with Shared Pool, Wi-Fi, Pets Allowed

Villa 'La Stalla Il Sole Verde' with Shared Pool, Wi-Fi, Pets Allowed
Bucine
The price is €403
includes taxes & fees
10 Oct - 11 Oct
Villa 'La Stalla Il Sole Verde' with Shared Pool, Wi-Fi, Pets Allowed
A stone building with a gravel path, outdoor seating, and greenery.

14. The Arch Among the Hills of Castellina

The Arch Among the Hills of Castellina
Topina
The price is €299
includes taxes & fees
1 Oct - 2 Oct
The Arch Among the Hills of Castellina
A brick building with a garden, a metal fence, and a clear sky.

15. Casa Marisa in Castellina in Chianti

Casa Marisa in Castellina in Chianti
Castellina in Chianti
The price is €270
includes taxes & fees
20 Sept - 21 Sept
Casa Marisa in Castellina in Chianti
A building with a stone facade, a door, a window, and a patio area with chairs and a table.

16. Peaceful corner with garden between Chianti and Crete, very close to Old Town

Peaceful corner with garden between Chianti and Crete, very close to Old Town
Casetta
The price is €110
includes taxes & fees
21 Sept - 22 Sept
Peaceful corner with garden between Chianti and Crete, very close to Old Town
A modern kitchen with a tiled backsplash, a dining area with a table and chairs, and a staircase with a plant shelf.

17. Little cozy house

Little cozy house
Loro Ciuffenna
The price is €92
includes taxes & fees
15 Sept - 16 Sept
Little cozy house
A brick building with a sliding glass door entrance, a large potted plant, and two smaller potted plants outside.

18. GuestHost - Charming studio of 40 sqm can accommodate up to 3 people, located on the ground floor (rise to access) of a refined period building with breathtaking views of the Sienese countryside. The property is located in a historic area, at the door of

GuestHost - Charming studio of 40 sqm can accommodate up to 3 people, located on the ground floor (rise to access) of a refined period building with breathtaking views of the Sienese countryside. The property is located in a historic area, at the door of
Siena
The price is €167
includes taxes & fees
23 Sept - 24 Sept
GuestHost - Charming studio of 40 sqm can accommodate up to 3 people, located on the ground floor (rise to access) of a refined period building with breathtaking views of the Sienese countryside. The property is located in a historic area, at the door of
A living room with a dining table, two sofas, a coffee table, and a ceiling fan.

19. casagreve - stylish house in Tuscan village - breathtaking view from its terrace

casagreve - stylish house in Tuscan village - breathtaking view from its terrace
Greve in Chianti
10.0 out of 10, Exceptional, (10 reviews)
"This was my favorite stay during our travels throughout Italy. Restaurants on the square or dining out on the lovely balcony. We had a wonderful stay here. Perfect location for dayctrips to Sienna and Florence, bike riding through Tuscany, . Great hosts as well!"
United States
Linda L.
casagreve - stylish house in Tuscan village - breathtaking view from its terrace
A stone building with a courtyard, a table with chairs, and a wheelbarrow.

20. House with views of the Chianti

House with views of the Chianti
impruneta
10.0 out of 10, Exceptional, (4 reviews)
"My wife and I stayed here for our honeymoon and have already talked about returning here for an anniversary. This house was clean, charming and located in a beautiful area. The views from the property are stunning."
United States
Chase B.
The price is €240
includes taxes & fees
27 Sept - 28 Sept
House with views of the Chianti
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

10/10 Excellent
"Excellent location. Easy parking and helpful staff."
Tracy 1-night trip
Posted 1 day ago
Hotel Chiusarelli

Find out more about Gaiole in Chianti

Gaiole in Chianti Holiday Homes information

Number of reviews
12
Accommodation
1555 Holiday Homes
Lowest Price
€128
Highest Price
€128