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$1,141 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$2,364 total

includes taxes & fees

20 Oct - 21 Oct

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

3. The Arch Among the Hills of Castellina

Topina

HK$2,452 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$1,390 total

includes taxes & fees

20 Oct - 21 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$1,585 total

includes taxes & fees

20 Oct - 21 Oct

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

6. Casa Vacanze Le Case

San Gimignano

Andrew

HK$837 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$1,541 total

includes taxes & fees

20 Oct - 21 Oct

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

8. Your nest in the Tuscany countryside

Certaldo - Firenze

HK$2,013 total

includes taxes & fees

15 Oct - 16 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$3,173 total

includes taxes & fees

29 Oct - 30 Oct

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

10. 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$4,356 total

includes taxes & fees

20 Oct - 21 Oct

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

11. 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$1,637 total

includes taxes & fees

18 Oct - 19 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$7,259 total

includes taxes & fees

2 Nov - 3 Nov

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

13. Ebbio – Villa and Organic Farm in Monteriggioni

Monteriggioni

HK$73,868 total

includes taxes & fees

18 Oct - 19 Oct

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

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$3,753 total

includes taxes & fees

15 Oct - 16 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$2,516 total

includes taxes & fees

20 Oct - 21 Oct

A bedroom with a bed, a nightstand, a chair, a wardrobe, and a window with curtains.

16. B&B Liveinflorence Centro Storico

Historic Centre of Florence

Rose S.

HK$1,784 total

includes taxes & fees

3 Nov - 4 Nov

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

17. Villa La Stella - Casa per Ferie

Le Cure

Erin

HK$1,129 total

includes taxes & fees

1 Nov - 2 Nov

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

18. House with views of the Chianti

impruneta

Chase B.

HK$2,370 total

includes taxes & fees

15 Oct - 16 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$8,893 total

includes taxes & fees

18 Oct - 19 Oct

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

20. Wonderful Tuscan farmhouse with large spaces and panoramic views

impruneta

Christine F.

HK$2,610 total

includes taxes & fees

21 Oct - 22 Oct

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Top Castellina in Chianti Hotel Reviews

Grand Hotel Cavour

10/10 Excellent

"They have been very helpful with everything. And arranged several things for us while there"

Hu Firenze Camping In Town

10/10 Excellent

"It was a really nice experience staying at Hu Firenze. It was away from the hustle and bustle of the city and the main tourist areas, while a bus stop right across the street made it easy to get to the city centre. We also got to enjoy a bit of the Tuscan countryside experience. The only issue was that there is another Hu campsite called Hu Certosa, so you need to be careful not to book the wrong one, especially when travelling in a group and everyone is booking separately. This happened to us, but fortunately, the staff allowed my brother to stay with us since our accommodation had an extra bed. However, we had already paid for a tent at Hu Certosa. My recommendation would be to start breakfast earlier than 7:30 a.m. This would allow guests to leave at different times and help avoid long queues at the bus stop."

Find out more about Castellina in Chianti