A stone building with a clock tower, steps leading up to it, and people walking around.

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Castellina in Chianti vacation homes

A stone building with multiple windows and a chimney.

1. Agriturismo La Ferrozzola

Agriturismo La Ferrozzola
Castellina in Chianti
9.4 out of 10, Exceptional, (9 reviews)
"Very nice agriturismo. "
United States
Ruth
The price is AED 471
AED 535 total
includes taxes & fees
8 Nov - 9 Nov
Agriturismo La Ferrozzola
A brick building with a garden, a metal fence, and a clear sky.

2. Casa Marisa in Castellina in Chianti

Casa Marisa in Castellina in Chianti
Castellina in Chianti
The price is AED 890
AED 1,112 total
includes taxes & fees
19 Oct - 20 Oct
Casa Marisa in Castellina in Chianti
A stone building with a gravel path, outdoor seating, and greenery.

3. The Arch Among the Hills of Castellina

The Arch Among the Hills of Castellina
Topina
The price is AED 988
AED 1,149 total
includes taxes & fees
2 Nov - 3 Nov
The Arch Among the Hills of Castellina
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

UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
Ruffoli
9.2 out of 10, Wonderful, (27 reviews)
"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...
Canada
James
The price is AED 333
AED 654 total
includes taxes & fees
19 Oct - 20 Oct
UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
A view through a wooden door of a courtyard with stone walls and potted plants.

5. Chianti Craft House Badia a Passignano

Chianti Craft House Badia a Passignano
Tavarnelle Val di Pesa
10.0 out of 10, Exceptional, (12 reviews)
"Very historic venue, with amazing views"
United States
Oscar O.
The price is AED 515
AED 745 total
includes taxes & fees
18 Oct - 19 Oct
Chianti Craft House Badia a Passignano
A pool area with lounge chairs and umbrellas, surrounded by stone buildings and greenery.

6. Casa Vacanze Le Case

Casa Vacanze Le Case
San Gimignano
9.6 out of 10, Exceptional, (14 reviews)
"The property was perfect and the host was so nice and helpful. We would definitely stay there again."
United States
Andrew
The price is AED 338
AED 392 total
includes taxes & fees
2 Nov - 3 Nov
Casa Vacanze Le Case
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

Love Nest Siena: Romantic Suite with SPA & Jacuzzi
Toscana
The price is AED 408
AED 725 total
includes taxes & fees
18 Oct - 19 Oct
Love Nest Siena: Romantic Suite with SPA & Jacuzzi
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

Your nest in the Tuscany countryside
Certaldo - Firenze
Your nest in the Tuscany countryside
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

casagreve - stylish house in Tuscan village - breathtaking view from its terrace
Greve in Chianti
10.0 out of 10, Exceptional, (11 reviews)
"This was my favorite stay during our travels throughout Italy. Restaurants on the square or dining out on the lovely balcony. We had a wonderful stay here. Perfect location for dayctrips to Sienna and Florence, bike riding through Tuscany, . Great hosts as well!"
United States
Linda L.
The price is AED 1,318
AED 1,487 total
includes taxes & fees
29 Oct - 30 Oct
casagreve - stylish house in Tuscan village - breathtaking view from its terrace
A swimming pool with a colorful inflatable ring and a water fountain.

10. Farmhouse in Chianti

Farmhouse in Chianti
gaiole in chianti
9.8 out of 10, Exceptional, (6 reviews)
"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."
Germany
Johanna K.
The price is AED 1,668
AED 2,049 total
includes taxes & fees
18 Oct - 19 Oct
Farmhouse in Chianti
A rustic building with a brick facade, a small arched window, and a door.

11. Cozy Tuscan-style apartment Suitable for families. Pets allowed

Cozy Tuscan-style apartment Suitable for families. Pets allowed
Toscana
10.0 out of 10, Exceptional, (2 reviews)
"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."
United States
Shanti R.
The price is AED 618
AED 770 total
includes taxes & fees
18 Oct - 19 Oct
Cozy Tuscan-style apartment Suitable for families. Pets allowed
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

Casa San Martino between Florence and Siena with Pool
Tavarnelle Val di Pesa
10.0 out of 10, Exceptional, (2 reviews)
"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...
Netherlands
Anonymous traveler
The price is AED 3,138
AED 3,402 total
includes taxes & fees
2 Nov - 3 Nov
Casa San Martino between Florence and Siena with Pool
A rustic villa with a garden, a pond, and a mountainous backdrop.

13. Ebbio – Villa and Organic Farm in Monteriggioni

Ebbio – Villa and Organic Farm in Monteriggioni
Monteriggioni
The price is AED 34,597
AED 34,617 total
includes taxes & fees
18 Oct - 19 Oct
Ebbio – Villa and Organic Farm in Monteriggioni
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

Tuscan Farmhouse with Private Pool & Chianti Vineyard Views - 3 Bedr + AC
Montespertoli
10.0 out of 10, Exceptional, (1 review)
"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!"
United States
Susan A.
The price is AED 494
AED 1,376 total
includes taxes & fees
15 Nov - 16 Nov
Tuscan Farmhouse with Private Pool & Chianti Vineyard Views - 3 Bedr + AC
An outdoor patio with a table, chairs, a grill, and a large umbrella.

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

Vernaccia Country House - Agriturismo Apartment with Pool, Garden & Wi-Fi
Tavarnelle Val di Pesa
10.0 out of 10, Exceptional, (1 review)
"Das Objekt liegt zwischen Florenz und Siena umgeben von Olivenbäumen. Die Lage ist perfekt für Ausflüge."
Germany
Ramona S.
The price is AED 961
AED 1,184 total
includes taxes & fees
18 Oct - 19 Oct
Vernaccia Country House - Agriturismo Apartment with Pool, Garden & Wi-Fi
A bedroom with a bed, a nightstand, a chair, a wardrobe, and a window with curtains.

16. B&B Liveinflorence Centro Storico

B&B Liveinflorence Centro Storico
Historic Centre of Florence
9.6 out of 10, Exceptional, (11 reviews)
"Great location, excellent value for money. "
United States
Rose S.
The price is AED 618
AED 836 total
includes taxes & fees
3 Nov - 4 Nov
B&B Liveinflorence Centro Storico
A terrace with a table set for breakfast, a chair, and a large umbrella.

17. Villa La Stella - Casa per Ferie

Villa La Stella - Casa per Ferie
Le Cure
8.6 out of 10, Excellent, (268 reviews)
"Great location with a beautiful view."
United States
Erin
The price is AED 415
AED 490 total
includes taxes & fees
1 Nov - 2 Nov
Villa La Stella - Casa per Ferie
A stone building with a courtyard, a table with chairs, and a wheelbarrow.

18. House with views of the Chianti

House with views of the Chianti
impruneta
10.0 out of 10, Exceptional, (5 reviews)
"My wife and I stayed here for our honeymoon and have already talked about returning here for an anniversary. This house was clean, charming and located in a beautiful area. The views from the property are stunning."
United States
Chase B.
The price is AED 271
AED 1,123 total
includes taxes & fees
28 Oct - 29 Oct
House with views of the Chianti
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

'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi
Gaiole in Chianti
The price is AED 3,815
AED 4,183 total
includes taxes & fees
18 Oct - 19 Oct
'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi
A stone building with a courtyard, outdoor seating, and potted plants.

20. Sorbeto Vacation Home

Sorbeto Vacation Home
impruneta
9.6 out of 10, Exceptional, (27 reviews)
"Lovely area. Charming house. "
United States
Christine F.
The price is AED 321
AED 1,223 total
includes taxes & fees
21 Oct - 22 Oct
Sorbeto Vacation Home
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Castellina in Chianti Hotel Reviews

Bernini Palace

Bernini Palace

8/10 Good
"This was once one of the grand hotels of Florence. The Grand Dame of hotels. It is like a walk back in time. Sadly once you leave the beautiful lobby and the Bar area you can see that the hotel no longer has the 5 star quality. Things are not updated or kept up to par. The hotel needs an up date, the rooms need to be cleaned up, the turn down service needs to be updated, alot of things need to be updated. I could go on but i would rather focus on the front desk and the welcome crew who were amazing. The front desk very professional and very friendly and helpful. With a little update this could once again be a grand hotel"
Darlyne 3-night trip
Posted 4 hours ago
Bernini Palace

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