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

1. Casa Marisa in Castellina in Chianti

Castellina in Chianti

HK$2,432 total

includes taxes & fees

20 Sept - 21 Sept

2. The Arch Among the Hills of Castellina

Topina

HK$2,693 total

includes taxes & fees

1 Oct - 2 Oct

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$1,385 total

includes taxes & fees

22 Sept - 23 Sept

4. Chianti Craft House Badia a Passignano

Tavarnelle Val di Pesa

Oscar O.

HK$1,648 total

includes taxes & fees

24 Sept - 25 Sept

5. Ebbio – Villa and Organic Farm in Monteriggioni

Monteriggioni

HK$75,695 total

includes taxes & fees

8 Oct - 9 Oct

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

Toscana

HK$1,585 total

includes taxes & fees

20 Sept - 21 Sept

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$4,426 total

includes taxes & fees

27 Sept - 28 Sept

8. Your nest in the Tuscany countryside

Certaldo - Firenze

HK$2,062 total

includes taxes & fees

19 Sept - 20 Sept

9. Casa San Martino between Florence and Siena with Pool

Tavarnelle Val di Pesa

"Pros: Wir hatten eine rundum wunderschöne Zeit in diesem tollen Ferienhaus! Das Haus ist mit sehr viel Liebe zum Detail eingerichtet, modern, gemütlich und bestens ausgestattet. Selbst in den Zimmern standen frische Blumen - eine wunderschöne Aufmerksamkeit. Man fühlt sich vom ersten Moment an willkommen. Es hat uns wirklich an nichts gefehlt. Ein ganz besonderes Lob geht an unsere Gastgeberin Susanna. Sie ist unglaublich herzlich, freundlich und hilfsbereit. Sie war jederzeit für uns da. Wir...

Anonymous traveller

HK$6,520 total

includes taxes & fees

28 Sept - 29 Sept

10. Casa Vacanze Le Case

San Gimignano

Jackie

HK$1,114 total

includes taxes & fees

22 Sept - 23 Sept

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

Greve in Chianti

Linda L.

HK$3,152 total

includes taxes & fees

25 Sept - 26 Sept

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

Castelnuovo Berardenga

Anonymous traveller

HK$3,437 total

includes taxes & fees

21 Sept - 22 Sept

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

Tavarnelle Val di Pesa

Ramona S.

HK$2,699 total

includes taxes & fees

6 Oct - 7 Oct

14. 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$3,719 total

includes taxes & fees

14 Oct - 15 Oct

15. Ocabianca Holiday Home with Private Terrace, Wi-Fi and Air Conditioning

Casole d'Elsa

"Pros: Das Haus ist liebevoll eingerichtet, hat zwei schöne Bäder und eine wunderbare schattige Terrasse, von der man ins Grüne schaut, tagsüber ab und zu die Schafe nebenan und abends die Wildschweine hören kann. Das Haus liegt sehr ruhig in einem abgeschiedenen Weiler. Es sind ausreichend Liegestühle vorhanden, um im Garten zu entspannen. Die Klimaanlage im Haus funktioniert bestens. Besonders hervorzuheben sind die sehr herzlichen und hilfsbereiten Vermieter, die auch in dem kleinen Ort wohnen...

Anonymous traveller

HK$4,670 total

includes taxes & fees

12 Oct - 13 Oct

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

Gaiole in Chianti

HK$10,538 total

includes taxes & fees

23 Sept - 24 Sept

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$1,684 total

includes taxes & fees

19 Sept - 20 Sept

18. House with views of the Chianti

impruneta

Chase B.

HK$2,170 total

includes taxes & fees

23 Sept - 24 Sept

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

Casetta

HK$955 total

includes taxes & fees

21 Sept - 22 Sept

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

Colle Val d'Elsa

Rupert H.

HK$3,664 total

includes taxes & fees

30 Sept - 1 Oct

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Top Castellina in Chianti Hotel Reviews

Hotel Santa Maria Novella

10/10 Excellent

"Amazing and historical place to stay! Loved everything about it, including the amazing location, helpful stuff, and the historical building."

The Social Hub Florence Belfiore

10/10 Excellent

"Really liked the the social hub! Pool was cool, and an excellent refresh after a long day in the hot sun. The free laundry (with an app) was incredibly helpful and appreciated after traveling across Italy. Beds were comfy, and AC was enough to keep as cool. Asked for extra towels one day and had them delivered to the room within 5 minutes. Would stay again!"

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