Gaiole in Chianti Vacation Homes

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

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Our top choices for Gaiole in Chianti holiday homes

A dining area with a table and chairs, a sofa, and large windows with curtains.

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

Gaiole in Chianti

HK$8,959 total

includes taxes & fees

20 Oct - 21 Oct

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

2. Farmhouse in Chianti

gaiole in chianti

"We absolutely loved the pool and the view. The pool with a deep end and color changing light was our highlight. The hosts were very friendly, helpful and always available if needed, since they live upstairs in the same house. Still, they never complained about us being loud. Everything was perfectly clean, the pool was cleaned regularly during our stay. The road to the property might be rough, but the view is beautiful. Also, we were gifted some delicious wine."

Johanna K.

HK$4,388 total

includes taxes & fees

20 Oct - 21 Oct

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

Ruffoli

"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...

James

HK$1,400 total

includes taxes & fees

20 Oct - 21 Oct

A stone building with multiple windows and a chimney.

4. Agriturismo La Ferrozzola

Castellina in Chianti

Ruth

HK$1,145 total

includes taxes & fees

8 Nov - 9 Nov

A dining area with a brick archway, wooden dining table, chairs, and a chandelier.

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

Montevarchi

HK$2,946 total

includes taxes & fees

2 Nov - 3 Nov

A swimming pool with a wooden deck, a tree with red leaves, and a building with a beige facade.

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

Figline Valdarno

HK$968 total

includes taxes & fees

5 Nov - 6 Nov

A brick building with a garden, a metal fence, and a clear sky.

7. Casa Marisa in Castellina in Chianti

Castellina in Chianti

HK$2,381 total

includes taxes & fees

20 Oct - 21 Oct

A covered patio with a wooden table and chairs, stone walls, and a view of a garden.

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

Bucine

Anonymous traveller

HK$3,496 total

includes taxes & fees

20 Oct - 21 Oct

A swimming pool with lounge chairs, a tiled deck, and surrounding trees.

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

Bucine

HK$3,237 total

includes taxes & fees

20 Oct - 21 Oct

A modern hotel room with a flat-screen TV displaying 'NETFLIX', a jacuzzi, and a neon sign.

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

Toscana

HK$1,552 total

includes taxes & fees

20 Oct - 21 Oct

A garden pathway leading to a stone building with a brick wall, a pergola, and a small brick structure in the background.

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

Bucine

"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...

Marianne H.

HK$3,396 total

includes taxes & fees

20 Oct - 21 Oct

A building with a stone facade, a door, a window, and a patio area with chairs and a table.

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

Casetta

HK$864 total

includes taxes & fees

2 Nov - 3 Nov

A stone building with a gravel path, outdoor seating, and greenery.

13. The Arch Among the Hills of Castellina

Topina

HK$2,461 total

includes taxes & fees

2 Nov - 3 Nov

A modern kitchen with a tiled backsplash, a dining area with a table and chairs, and a staircase with a plant shelf.

14. Little cozy house

Loro Ciuffenna

HK$776 total

includes taxes & fees

20 Oct - 21 Oct

A view through a wooden door of a courtyard with stone walls and potted plants.

15. Chianti Craft House Badia a Passignano

Tavarnelle Val di Pesa

Oscar O.

HK$1,477 total

includes taxes & fees

20 Oct - 21 Oct

A gated entrance with a number plaque, a pathway leading to a building, and a parked vehicle.

16. Tuscan House: Spacious, Traditional Tuscan Apartment with Plenty of Outdoor Space and Breakfast Included

Monteroni d'Arbia

HK$1,041 total

includes taxes & fees

25 Oct - 26 Oct

A rustic building with a brick facade, a small arched window, and a door.

17. Cozy Tuscan-style apartment Suitable for families. Pets allowed

Toscana

"This refurbished cottage is a hidden gem, surrounded by fruit trees on a hillside facing Siena. You’ll need a car — it s about a 5-minute drive on a steep, narrow, winding road to get to the stores by the freeway. The cottage was bigger than we were expecting, with a small but well-equipped kitchen. The host turned on the AC in anticipation of our arrival. There are two bedrooms on the main floor with AC, and a fourth bed in a loft."

Shanti R.

HK$1,649 total

includes taxes & fees

21 Oct - 22 Oct

A pool area with lounge chairs and umbrellas, surrounded by stone buildings and greenery.

18. Casa Vacanze Le Case

San Gimignano

Andrew

HK$840 total

includes taxes & fees

2 Nov - 3 Nov

A rectangular swimming pool with a wooden deck and metal railings, surrounded by a grassy area with trees and a clear sky.

19. Holiday Home 'Fienile' with Shared Pool, Garden and Wi-Fi

Castelnuovo Berardenga

Anonymous traveller

HK$5,715 total

includes taxes & fees

2 Nov - 3 Nov

A rustic villa with a garden, a pond, and a mountainous backdrop.

20. Ebbio – Villa and Organic Farm in Monteriggioni

Monteriggioni

HK$74,133 total

includes taxes & fees

27 Oct - 28 Oct

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Top Gaiole in Chianti Hotel Reviews

Hu Firenze Camping In Town

10/10 Excellent

"On a bien aimé notre séjour. C’était très propre partout. Notre cabine était parfaite. Votre équipe s’est bien occupée de nous. Et nous avons eu un très bon service. Nous le recommandons. Et le restaurant et le service était très bon aussi. Nous avons trouvé très pratique de pouvoir acheter nos excursions au camping et d’avoir le transport pour les excursions directement du camping c’était bien pratique et zéro stress à essayer de trouver le groupe au centre ville."

Hotel Casolare Le Terre Rosse

10/10 Excellent

"Great Family run hotel with friendly staff. Perfectly located to explore Tuscany.. we visited Sienna, Certaldo, Volterra, Sam Gimignano and Livorno on the coast. There is a walkable (5mins) winery called Il Colombaio which I would highly recommended. The breakfast buffet was fabulous."

Find out more about Gaiole in Chianti