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

Search Vacation Homes in Castellina in Chianti

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
18 Sep - 20 Sep
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Castellina in Chianti vacation homes

TV

1. Casa Marisa in Castellina in Chianti

Casa Marisa in Castellina in Chianti
Castellina in Chianti
The price is AED 921
AED 1,152 total
includes taxes & fees
6 Sep - 7 Sep
Casa Marisa in Castellina in Chianti
Outdoor dining

2. The Arch Among the Hills of Castellina

The Arch Among the Hills of Castellina
Topina
The price is AED 1,229
AED 1,395 total
includes taxes & fees
6 Sep - 7 Sep
The Arch Among the Hills of Castellina
Exterior detail

3. 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, (24 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 344
AED 686 total
includes taxes & fees
2 Sep - 3 Sep
UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
Interior

4. 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 533
AED 781 total
includes taxes & fees
4 Sep - 5 Sep
Chianti Craft House Badia a Passignano
Spa

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

Love Nest Siena: Romantic Suite with SPA & Jacuzzi
Toscana
The price is AED 384
AED 704 total
includes taxes & fees
6 Sep - 7 Sep
Love Nest Siena: Romantic Suite with SPA & Jacuzzi
Outdoor pool

6. Farmhouse in Chianti

Farmhouse in Chianti
gaiole in chianti
9.8 out of 10, Exceptional, (6 reviews)
"This location provided our blended family an authentic experience in a small village on top of a mountain in Chianti. The house is surrounded by olive groves and wine grapes. The pool was great and the village, literally less than a city block up the road. Folks are incredibly friendly and helpful. Two of the rooms had their own bathrooms and the other two share a bathroom. There is a common kitchen for cooking and eating. We cooked most nights and ate on the outside terrace. Allesandra is a...
United States
Lara W.
The price is AED 1,728
AED 2,135 total
includes taxes & fees
2 Sep - 3 Sep
Farmhouse in Chianti
Property grounds

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

country house with garden ,pool,children's play area ,Tuscany,15 from Florence
Toscana
9.8 out of 10, Exceptional, (83 reviews)
"The hostess Sonia was fabulous."
United States
Kim
The price is AED 580
AED 921 total
includes taxes & fees
2 Sep - 3 Sep
country house with garden ,pool,children's play area ,Tuscany,15 from Florence
Interior

8. Casa San Martino between Florence and Siena with Pool

Casa San Martino between Florence and Siena with Pool
Tavarnelle Val di Pesa
The price is AED 2,808
AED 3,081 total
includes taxes & fees
21 Sep - 22 Sep
Casa San Martino between Florence and Siena with Pool
Exterior

9. Vana Hills House - Three Bedroom House, Sleeps 8

Vana Hills House - Three Bedroom House, Sleeps 8
Monteriggioni
The price is AED 358
AED 1,019 total
includes taxes & fees
4 Sep - 5 Sep
Vana Hills House - Three Bedroom House, Sleeps 8
Living area

10. Casagreve - Stilvolles Haus am Hauptplatz - Wunderbarer Blick von der Terrasse

Casagreve - Stilvolles Haus am Hauptplatz - Wunderbarer Blick von der Terrasse
Greve in Chianti
Casagreve - Stilvolles Haus am Hauptplatz - Wunderbarer Blick von der Terrasse
Interior

11. THE CASINA OF SANT 'AGOSTINO

THE CASINA OF SANT 'AGOSTINO
Colle di Val d'Elsa
The price is AED 512
AED 649 total
includes taxes & fees
4 Sep - 5 Sep
THE CASINA OF SANT 'AGOSTINO
Interior

12. Fornace di Bonazza - wonderful house among the Chianti hills

Fornace di Bonazza - wonderful house among the Chianti hills
Tavarnelle Val di Pesa
10.0 out of 10, Exceptional, (2 reviews)
"Great property and home!"
United States
Anonymous traveler
Fornace di Bonazza - wonderful house among the Chianti hills
Outdoor pool

13. Casa Vacanze Le Case

Casa Vacanze Le Case
San Gimignano
9.4 out of 10, Exceptional, (12 reviews)
"Wonderful. Beautiful property, the views were amazing,and it was so clean. A10 out of 10. "
United States
Jackie
The price is AED 465
AED 532 total
includes taxes & fees
17 Sep - 18 Sep
Casa Vacanze Le Case
Pool

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

Holiday Home "Limonaia" with Shared Pool, Communal Garden and Wi-Fi
Castelnuovo Berardenga
10.0 out of 10, Exceptional, (1 review)
"Pros: The view and unique traditional apartment. Cons: -"
United States
Anonymous traveler
The price is AED 1,302
AED 1,574 total
includes taxes & fees
2 Sep - 3 Sep
Holiday Home "Limonaia" with Shared Pool, Communal Garden and Wi-Fi
Interior

15. '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 4,617
AED 4,998 total
includes taxes & fees
8 Sep - 9 Sep
'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi
Outdoor dining

16. House with views of the Chianti

House with views of the Chianti
impruneta
10.0 out of 10, Exceptional, (4 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 299
AED 990 total
includes taxes & fees
2 Sep - 3 Sep
House with views of the Chianti
Outdoor dining

17. 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 1,048
AED 1,279 total
includes taxes & fees
1 Oct - 2 Oct
Vernaccia Country House - Agriturismo Apartment with Pool, Garden & Wi-Fi
Outdoor dining

18. Holiday Home 'Sandra House Certaldo' with Private Garden and Wi-Fi

Holiday Home 'Sandra House Certaldo' with Private Garden and Wi-Fi
Certaldo
10.0 out of 10, Exceptional, (1 review)
"Pros: Die familiäre Aufnahme und Unterstützung war sehr angenehm."
Germany
Anonymous traveler
The price is AED 515
AED 528 total
includes taxes & fees
2 Sep - 3 Sep
Holiday Home 'Sandra House Certaldo' with Private Garden and Wi-Fi
Interior

19. 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 1,194
AED 2,231 total
includes taxes & fees
8 Sep - 9 Sep
Tuscan Farmhouse with Private Pool & Chianti Vineyard Views - 3 Bedr + AC
Exterior detail

20. 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

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
The price is AED 428
AED 817 total
includes taxes & fees
23 Sep - 24 Sep
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
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Castellina in Chianti Hotel Reviews

Grand Hotel Cavour

Grand Hotel Cavour

10/10 Excellent
"Excellent location!"
tigist 3-night trip
Posted less than an hour ago
Grand Hotel Cavour

Explore a world of travel with Expedia