A stone castle with battlements overlooking a lush valley with vineyards.

Holiday Homes in Gaiole in Chianti

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Our top choices for Gaiole in Chianti holiday homes

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

'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi
Gaiole in Chianti
The price is €1,465
includes taxes & fees
3 Dec - 4 Dec
'Casa Vacanze Chianti Summer' with Pool, Garden & Wi-Fi

2. 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 €475
includes taxes & fees
3 Nov - 4 Nov
Farmhouse in Chianti

3. 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 €130
includes taxes & fees
8 Nov - 9 Nov
Agriturismo La Ferrozzola

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, (28 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 €156
includes taxes & fees
4 Nov - 5 Nov
UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK

5. Holiday Home 'Il Piccolo Rifugio' with Private Pool, Garden and Wi-Fi

Holiday Home 'Il Piccolo Rifugio' with Private Pool, Garden and Wi-Fi
Figline Valdarno
The price is €110
includes taxes & fees
5 Nov - 6 Nov
Holiday Home 'Il Piccolo Rifugio' with Private Pool, Garden and Wi-Fi

6. Holiday Home 'Poggio Loccano' with Private Garden and Balcony

Holiday Home 'Poggio Loccano' with Private Garden and Balcony
Montevarchi
The price is €334
includes taxes & fees
3 Nov - 4 Nov
Holiday Home 'Poggio Loccano' with Private Garden and Balcony

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

Siena Love Nest: Romantic Suite with Spa & Jacuzzi
Toscana
The price is €170
includes taxes & fees
3 Nov - 4 Nov
Siena Love Nest: Romantic Suite with Spa & Jacuzzi

8. Casa Marisa in Castellina in Chianti

Casa Marisa in Castellina in Chianti
Castellina in Chianti
The price is €270
includes taxes & fees
4 Nov - 5 Nov
Casa Marisa in Castellina in Chianti

9. The Arch Among the Hills of Castellina

The Arch Among the Hills of Castellina
Topina
The Arch Among the Hills of Castellina

10. Villa 'La Stalla Il Sole Verde' with Shared Pool, Wi-Fi, Pets Allowed

Villa 'La Stalla Il Sole Verde' with Shared Pool, Wi-Fi, Pets Allowed
Bucine
The price is €403
includes taxes & fees
3 Dec - 4 Dec
Villa 'La Stalla Il Sole Verde' with Shared Pool, Wi-Fi, Pets Allowed

11. A peaceful spot with a garden between Chianti and Crete, near the old town

A peaceful spot with a garden between Chianti and Crete, near the old town
Casetta
The price is €94
includes taxes & fees
9 Nov - 10 Nov
A peaceful spot with a garden between Chianti and Crete, near the old town

12. Villa 'Il Fienile Il Sole Verde' with Shared Pool and Wi-Fi

Villa 'Il Fienile Il Sole Verde' with Shared Pool and Wi-Fi
Bucine
10.0 out of 10, Exceptional, (4 reviews)
"Pros: Guido og Angela var helt fantastiske værter og deres medhjælper sørgede godt for os med friske grøntsager fra haven. Poolen var perfekt og altid ren og pæn. For os var det helt perfekt vi kun var to familier og at der var ro Cons: Vi har ingen kritik punkter ☺️"
Denmark
Anonymous traveller
The price is €415
includes taxes & fees
3 Dec - 4 Dec
Villa 'Il Fienile Il Sole Verde' with Shared Pool and Wi-Fi

13. Villa 'La Tinaia Il Sole Verde' with Shared Pool and Wi-Fi

Villa 'La Tinaia Il Sole Verde' with Shared Pool and Wi-Fi
Bucine
10.0 out of 10, Exceptional, (2 reviews)
"Upon arrival Guido had everything prepared for us. A bottle of his amazing wine that he makes along with 2 wine glasses we’re waiting on the farmhouse table. The home had 2 very comfortable bedrooms and a bathroom along with a living room and kitchen. Front porch overlooks the stunning Tuscany fields. The swimming pool was refreshing and everything was beyond perfect. This location was everything and more. The hosts were so helpful. I will come back her again..make sure to take time for the...
United States
Marianne H.
The price is €403
includes taxes & fees
3 Dec - 4 Dec
Villa 'La Tinaia Il Sole Verde' with Shared Pool and Wi-Fi

14. Chianti Craft House Badia a Passignano

Chianti Craft House Badia a Passignano
Tavarnelle Val di Pesa
10.0 out of 10, Exceptional, (13 reviews)
"Very historic venue, with amazing views"
United States
Oscar O.
The price is €164
includes taxes & fees
3 Nov - 4 Nov
Chianti Craft House Badia a Passignano

15. Ebbio – Villa and Organic Farm in Monteriggioni

Ebbio – Villa and Organic Farm in Monteriggioni
Monteriggioni
Ebbio – Villa and Organic Farm in Monteriggioni

16. Holiday Home 'Fienile' with Shared Pool, Garden and Wi-Fi

Holiday Home 'Fienile' with Shared Pool, Garden and Wi-Fi
Castelnuovo Berardenga
8.0 out of 10, Very good, (1 review)
"Pros: Posto meraviglioso. Bellissima location e bellissimo panorama Cons: Un po' più di cura e pulizia nella zona piscina. Jacuzzi chiusa e pensavamo di trovarla aperta"
Italy
Anonymous traveller
The price is €648
includes taxes & fees
3 Nov - 4 Nov
Holiday Home 'Fienile' with Shared Pool, Garden and Wi-Fi

17. Tuscan House: Spacious Traditional Apartment with a Large Outdoor Area and Breakfast Included

Tuscan House: Spacious Traditional Apartment with a Large Outdoor Area and Breakfast Included
Monteroni d'Arbia
The price is €128
includes taxes & fees
6 Nov - 7 Nov
Tuscan House: Spacious Traditional Apartment with a Large Outdoor Area and Breakfast Included

18. A cozy, Tuscan-style apartment perfect for families. Pets Allowed

A cozy, Tuscan-style apartment perfect 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 €171
includes taxes & fees
3 Nov - 4 Nov
A cozy, Tuscan-style apartment perfect for families. Pets Allowed

19. 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 €91
includes taxes & fees
3 Nov - 4 Nov
Casa Vacanze Le Case

20. 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.
casagreve - stylish house in Tuscan village - breathtaking view from its terrace
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 Gaiole in Chianti Hotel Reviews

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Gaiole in Chianti Holiday Homes information

Number of reviews
76
Accommodation
1501 Holiday Homes
Lowest Price
€91
Highest Price
€1,465