Castellina in Chianti Vacation Homes

A stone building with a clock tower, steps leading up to it, and people walking around.

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Our top choices for Castellina in Chianti holiday homes

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

1. Casa Marisa in Castellina in Chianti

Castellina in Chianti

HK$2,456 total

includes taxes & fees

15 Sept - 16 Sept

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

2. The Arch Among the Hills of Castellina

Topina

HK$2,720 total

includes taxes & fees

1 Oct - 2 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$1,444 total

includes taxes & fees

14 Sept - 15 Sept

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

4. Chianti Craft House Badia a Passignano

Tavarnelle Val di Pesa

Oscar O.

HK$1,647 total

includes taxes & fees

15 Sept - 16 Sept

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

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

Toscana

HK$1,601 total

includes taxes & fees

16 Sept - 17 Sept

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

6. Ebbio – Villa and Organic Farm in Monteriggioni

Monteriggioni

HK$76,458 total

includes taxes & fees

8 Oct - 9 Oct

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

7. Farmhouse in Chianti

gaiole in chianti

"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...

Lara W.

HK$4,526 total

includes taxes & fees

14 Sept - 15 Sept

A modern kitchen with white cabinets, a wooden dining table, and a built-in oven.

8. Casa San Martino between Florence and Siena with Pool

Tavarnelle Val di Pesa

HK$6,586 total

includes taxes & fees

21 Sept - 22 Sept

A rustic wall shelf with a 'PALIO' book and various items.

9. THE CASINA OF SANT 'AGOSTINO

Colle di Val d'Elsa

A room with a large sliding glass door leading to a pool area with a view of rolling hills and a distant village.

10. Your nest in the Tuscany countryside

Certaldo - Firenze

HK$2,083 total

includes taxes & fees

16 Sept - 17 Sept

A living room with a dining table, two sofas, a coffee table, and a ceiling fan.

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

Greve in Chianti

Linda L.

HK$3,284 total

includes taxes & fees

14 Sept - 15 Sept

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

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

Castelnuovo Berardenga

Anonymous traveller

HK$3,366 total

includes taxes & fees

14 Sept - 15 Sept

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

13. Casa Vacanze Le Case

San Gimignano

Jackie

HK$1,169 total

includes taxes & fees

20 Sept - 21 Sept

An outdoor patio with a table, chairs, a grill, and a large umbrella.

14. Vernaccia Country House - Agriturismo Apartment with Pool, Garden & Wi-Fi

Tavarnelle Val di Pesa

Ramona S.

HK$2,726 total

includes taxes & fees

6 Oct - 7 Oct

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

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

Gaiole in Chianti

HK$10,657 total

includes taxes & fees

16 Sept - 17 Sept

A stone building with a courtyard, a table with chairs, and a wheelbarrow.

16. House with views of the Chianti

impruneta

Chase B.

HK$2,101 total

includes taxes & fees

17 Sept - 18 Sept

An open doorway leading to an outdoor patio with a wooden table and chairs, a stone floor, and a wooden barrel with bottles.

17. Tuscan Farmhouse with Private Pool & Chianti Vineyard Views - 3 Bedr + AC

Montespertoli

"We found sanctuary at this lovely farmhouse during the July heat wave--refreshing dip in the pool, relaxing dinner in the courtyard, restful sleep in the air-conditioned home. Got up to watch the sunrise over the vineyards, absolutely stunning scenery, and watched three hot air balloons also taking in the sights. Matteo was very welcoming, and we bridged the language barrier with a little help from Google translate. Wished we could have stayed longer!"

Susan A.

HK$3,757 total

includes taxes & fees

14 Oct - 15 Oct

A patio with a table and chairs, an umbrella, and a view of a green fence and plants.

18. Holiday Home 'Sandra House Certaldo' with Private Garden and Wi-Fi

Certaldo

Anonymous traveller

HK$1,126 total

includes taxes & fees

14 Sept - 15 Sept

A stone building with a blue door, a wicker basket, and a clear vase with pink flowers.

19. Vacation Home "Casa di Campagna" with Private Terrace & Wi-Fi

Colle Val d'Elsa

Rupert H.

HK$4,067 total

includes taxes & fees

30 Sept - 1 Oct

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

20. 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$1,701 total

includes taxes & fees

18 Sept - 19 Sept

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Top Castellina in Chianti Hotel Reviews

Bernini Palace

10/10 Excellent

"L’hôtel est très très bien situé au cœur de l’héritage de Florence…. Le personnel est attentif et dévoué…. Les lieux sont propre et accueillant et le petit déjeuner est honnête…. Recommandé sans hésitation Michel de St Bruno Québec Canada"

Villa Neroli

10/10 Excellent

"This is overall a great property in every respect. Highly recommended. The only advice to other visitors is to plan for their lunch and dinner if they want more variety. The hotel restaurant is great and we dined there several times. But there are not many other good choices within walking distance from the hotel."

Find out more about Castellina in Chianti