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 stone building with multiple windows and a chimney.

1. Agriturismo La Ferrozzola

Castellina in Chianti

Ruth

HK$1,145 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$2,381 total

includes taxes & fees

21 Oct - 22 Oct

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

3. The Arch Among the Hills of Castellina

Topina

HK$2,461 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$1,400 total

includes taxes & fees

19 Oct - 20 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$1,596 total

includes taxes & fees

20 Oct - 21 Oct

A bathroom with a white sink, a mirror, and a towel rack.

6. Casa Vacanze Le Case

San Gimignano

Andrew

HK$840 total

includes taxes & fees

2 Nov - 3 Nov

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

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

Toscana

HK$1,552 total

includes taxes & fees

24 Oct - 25 Oct

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

8. 7 min from Cantina Antinori in Chianti Classico | Pool | Casa Sala & Pepe

Tavarnelle Val di Pesa

HK$2,067 total

includes taxes & fees

19 Oct - 20 Oct

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

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

Greve in Chianti

Linda L.

HK$3,184 total

includes taxes & fees

29 Oct - 30 Oct

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

10. 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

19 Oct - 20 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$4,379 total

includes taxes & fees

19 Oct - 20 Oct

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

12. 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$7,285 total

includes taxes & fees

2 Nov - 3 Nov

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

13. 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$2,946 total

includes taxes & fees

15 Nov - 16 Nov

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

14. Ebbio – Villa and Organic Farm in Monteriggioni

Monteriggioni

HK$74,133 total

includes taxes & fees

27 Oct - 28 Oct

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

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

Tavarnelle Val di Pesa

Ramona S.

HK$2,535 total

includes taxes & fees

19 Oct - 20 Oct

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

16. Villa La Stella - Casa per Ferie

Le Cure

Erin

HK$1,133 total

includes taxes & fees

1 Nov - 2 Nov

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

17. THE TOLOMEI - apartment in the heart of the main street

Siena City Centre

Louise B.

A stone building with a courtyard, outdoor seating, and potted plants.

18. Sorbeto Vacation Home

impruneta

Christine F.

HK$2,620 total

includes taxes & fees

21 Oct - 22 Oct

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

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

Gaiole in Chianti

HK$8,959 total

includes taxes & fees

19 Oct - 20 Oct

20. Luce -exclusive Design Loft IN THE Heart OF Florence

Historic Centre of Florence

HK$1,782 total

includes taxes & fees

1 Nov - 2 Nov

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Top Castellina in Chianti Hotel Reviews

Bernini Palace

10/10 Excellent

"Great location walking distance to attractions and great restaurants"

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."

The Social Hub Florence Belfiore

8/10 Good

"Staff is too young and untrained in hospitality to provide a solid experience, felt like student workers with little supervisors there to actually help them. Advertises with free laundry but you can only run one tiny machine at a time and one of them left my laundry smelling worse making me have to double-wash it. All of it gets run through their own app you have to create an account for, just to use a washing machine during your two-night stay. BAD USE OF HIGH TECH. Room was spacious and clean but bathroom shower floods the rest of the floor. Hallways smelled like meals microwaved by the study-abroad students. Interesting concept, solid rooms, poorly executed."

Find out more about Castellina in Chianti