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 traditional interior with stone arches, a staircase, and a cozy seating area with a table.

1. Agriturismo La Ferrozzola

Castellina in Chianti

Ruth

HK$1,139 total

includes taxes & fees

8 Nov - 9 Nov

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

2. Casa Marisa in Castellina in Chianti

Castellina in Chianti

HK$2,367 total

includes taxes & fees

2 Nov - 3 Nov

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

3. The Arch Among the Hills of Castellina

Topina

HK$2,236 total

includes taxes & fees

2 Nov - 3 Nov

A stone building with a gated entrance, terracotta pots with flowers, and a staircase leading up to the door.

4. 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$1,392 total

includes taxes & fees

28 Oct - 29 Oct

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

5. Chianti Craft House Badia a Passignano

Tavarnelle Val di Pesa

Oscar O.

HK$1,587 total

includes taxes & fees

20 Nov - 21 Nov

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

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

Toscana

HK$1,543 total

includes taxes & fees

2 Nov - 3 Nov

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

7. Casa Vacanze Le Case

San Gimignano

Andrew

HK$796 total

includes taxes & fees

2 Nov - 3 Nov

An outdoor patio with a table, chairs, and a view of a landscape.

8. country house with garden ,pool,children's play area ,Tuscany,15 from Florence

Toscana

Kim

HK$1,271 total

includes taxes & fees

2 Nov - 3 Nov

A room with a view of a vineyard through an arched window, a bottle of wine, and a plate of fruit.

9. 7 min from Cantina Antinori in Chianti Classico | Pool | Casa Sala & Pepe

Tavarnelle Val di Pesa

HK$2,054 total

includes taxes & fees

2 Nov - 3 Nov

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

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

Greve in Chianti

Linda L.

HK$3,165 total

includes taxes & fees

29 Oct - 30 Oct

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

11. 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$4,353 total

includes taxes & fees

30 Oct - 31 Oct

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

12. 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$2,954 total

includes taxes & fees

15 Nov - 16 Nov

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

13. Ebbio – Villa and Organic Farm in Monteriggioni

Monteriggioni

HK$73,684 total

includes taxes & fees

29 Oct - 30 Oct

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

14. Casa San Martino between Florence and Siena with Pool

Tavarnelle Val di Pesa

"Pros: Wat hebben we een heerlijke tijd gehad in dit prachtige vakantiehuis in Barberino Tavarnelle! De ligging is fantastisch: rustig, sfeervol en helemaal ondergedompeld in de mooie Toscaanse omgeving. Het huis is comfortabel en van alles voorzien wat je nodig hebt voor een ontspannen verblijf. Met name de airco tijdens warme dagen was erg fijn. Een extra groot compliment voor Susanna. Ze is ontzettend gastvrij, vriendelijk en betrokken, en denkt echt met je mee. Ze was bovendien heel...

Anonymous traveller

HK$7,241 total

includes taxes & fees

3 Nov - 4 Nov

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

15. A cozy, Tuscan-style apartment perfect 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$1,639 total

includes taxes & fees

28 Oct - 29 Oct

A garden with various plants and flowers, a pathway, and a swing set.

16. Apartment House with garden Tuscany Chianti , Florence 15km.

Toscana

Robert M.

HK$1,376 total

includes taxes & fees

2 Nov - 3 Nov

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

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

Tavarnelle Val di Pesa

Ramona S.

HK$2,461 total

includes taxes & fees

1 Nov - 2 Nov

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

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

Gaiole in Chianti

HK$7,423 total

includes taxes & fees

2 Nov - 3 Nov

A stone building with a sign reading "VIA DI CALZOLERIA".

19. IL TOLOMEI - new apartment in the middle of the main street

Siena City Centre

Louise B.

A terrace with a table set for breakfast, a chair, and a large umbrella.

20. Villa La Stella - Casa per Ferie

Le Cure

Erin

HK$1,126 total

includes taxes & fees

1 Nov - 2 Nov

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Top Castellina in Chianti Hotel Reviews

Hotel Paris

10/10 Excellent

"Very good place. Loved it"

aparto Florence Manifattura

8/10 Good

"L'endroit est propre et très pratique que ce soit la localisation, le parking, les facilités interne. Il y avait un problème avec le wi-fi qui n'était pas disponible. Nos données entraient mal également et aucune facilités pour palier à ce problème qui a duré les 3 jours de notre présence...."

The Social Hub Florence Belfiore

10/10 Excellent

"Unbelievably great hotel.... Modern , new, fresh....the room was very modern and clean....the rooftop is a huge huge space with portions open to the public and separate pool area for guests only....spectacular views from the rooftop....the poolside lounge beds for two was very relaxing..the pool is a long architectural masterpiece...the hotel has so many special lounges for guests only where you can relax .....the hotel is located right next to the tram train that takes you directly to the train station and all the downtown areas....the hotel has security 24-7 monitoring who goes up the elevators..."

Find out more about Castellina in Chianti