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$1,232 total

includes taxes & fees

2 Nov - 3 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$2,377 total

includes taxes & fees

11 Oct - 12 Oct

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

3. The Arch Among the Hills of Castellina

Topina

HK$2,465 total

includes taxes & fees

3 Nov - 4 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$1,398 total

includes taxes & fees

13 Oct - 14 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$1,594 total

includes taxes & fees

9 Oct - 10 Oct

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

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

Toscana

HK$1,550 total

includes taxes & fees

18 Oct - 19 Oct

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

7. Casa Vacanze Le Case

San Gimignano

Andrew

HK$841 total

includes taxes & fees

2 Nov - 3 Nov

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$2,023 total

includes taxes & fees

11 Oct - 12 Oct

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

9. 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$1,652 total

includes taxes & fees

8 Oct - 9 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$4,380 total

includes taxes & fees

11 Oct - 12 Oct

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$3,163 total

includes taxes & fees

7 Nov - 8 Nov

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

12. Ebbio – Villa and Organic Farm in Monteriggioni

Monteriggioni

HK$74,006 total

includes taxes & fees

9 Oct - 10 Oct

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

13. 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$7,412 total

includes taxes & fees

7 Nov - 8 Nov

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

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

Toscana

Robert M.

A brick building with a sliding glass door entrance, a large potted plant, and two smaller potted plants outside.

15. GuestHost - Charming studio of 40 sqm can accommodate up to 3 people, located on the ground floor (rise to access) of a refined period building with breathtaking views of the Sienese countryside. The property is located in a historic area, at the door of

Siena

HK$1,526 total

includes taxes & fees

9 Oct - 10 Oct

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

16. 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.

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

17. B&B Liveinflorence Centro Storico

Historic Centre of Florence

Rose S.

HK$1,805 total

includes taxes & fees

3 Nov - 4 Nov

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

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

Tavarnelle Val di Pesa

Ramona S.

HK$2,531 total

includes taxes & fees

8 Oct - 9 Oct

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

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

Castelnuovo Berardenga

Anonymous traveller

HK$3,228 total

includes taxes & fees

12 Oct - 13 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$2,209 total

includes taxes & fees

23 Oct - 24 Oct

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Top Castellina in Chianti Hotel Reviews

Bernini Palace

10/10 Excellent

"Alexandro and Lorenzo were fantastic! Extremely helpful and gracious!"

Hotel Paris

8/10 Good

"The staff at Hotel Paris are wonderful, very welcoming and helpful. The good : we were in a nice large, clean room. The reason I took off a star, the noise from the street is substantial so something to be aware of if you are a light sleeper like myself. We only stayed there one night, so I didn’t bother inquiring if an interior, potentially quieter, room was available. This hotel was walkable to the train station and an easy to walk into Florence to see the sights. We did not have the breakfast there so cannot comment on it."

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