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

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Check prices for these dates

Next weekend
2 Oct - 4 Oct
In two weeks
9 Oct - 11 Oct
In one month
23 Oct - 25 Oct
In two months
20 Nov - 22 Nov

Our top choices for Gaiole in Chianti town houses

Exterior

1. L' Eroico

L' Eroico
Gaiole in Chianti
10.0 out of 10, Exceptional, (15 reviews)
"Monica is a very gracious host. We very much enjoyed our stay. The village is also very quaint and within walking distance. We appreciate the hospitality and highly recommend staying here if you’re coming to the area."
United States
Angela
The price is SAR 593
SAR 686 total
includes taxes & fees
20 Oct - 21 Oct
L' Eroico
Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers

2. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (39 reviews)
"Great spot"
Canada
Philippe
The price is SAR 590
SAR 821 total
includes taxes & fees
1 Oct - 2 Oct
Villa di Sotto
Aerial view

3. Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (80 reviews)
"Beautiful resort in the hills, lovely and charming room, incredibly spacious."
United States
Deanna
The price is SAR 647
SAR 729 total
includes taxes & fees
4 Oct - 5 Oct
Villa Curina Resort
Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, sun loungers

4. Residenzia del Sogno

Residenzia del Sogno
Castellina in Chianti
9.6 out of 10, Exceptional, (15 reviews)
"Beautiful and authentic place, lovely couple running the place that care about you and your stay. "
Canada
Katherine
The price is SAR 470
SAR 535 total
includes taxes & fees
27 Sep - 28 Sep
Residenzia del Sogno
Outdoor pool

5. Villa Rosa Panzano

Villa Rosa Panzano
Greve in Chianti
8.2 out of 10, Very good, (56 reviews)
"A lovely rural B&B with very kind staff."
Canada
Allison
The price is SAR 466
SAR 530 total
includes taxes & fees
5 Oct - 6 Oct
Villa Rosa Panzano
Lounge

6. Mariani Bed & Breakfast

Mariani Bed & Breakfast
Castellina in Chianti
9.8 out of 10, Exceptional, (18 reviews)
"Very nice and quiet neighbourhood. Close to city centre. The host is very kind."
Japan
Chie
The price is SAR 326
SAR 375 total
includes taxes & fees
8 Oct - 9 Oct
Mariani Bed & Breakfast
Property grounds

7. Ca' Bianca Tuscany Relais

Ca' Bianca Tuscany Relais
Siena
10.0 out of 10, Exceptional, (46 reviews)
"Clean room, amazing staff"
Canada
Talha
The price is SAR 1,204
SAR 1,341 total
includes taxes & fees
28 Sep - 29 Sep
Ca' Bianca Tuscany Relais
Free daily buffet breakfast

8. Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (79 reviews)
"The stay was great, and the staff were wonderful. "
United States
SYDNEY
The price is SAR 1,187
SAR 1,323 total
includes taxes & fees
25 Sep - 26 Sep
Terre di Baccio
Property grounds

9. Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (98 reviews)
"Everything was very clean and modern, working perfect. We didn’t meet anyone from the staff. And it would be nice if they leave some bottle of water for each room. We like the place a lot. People have to consider that it is outside Siena walls and it’s a pretty steep and long distance walk"
United States
María
The price is SAR 253
SAR 295 total
includes taxes & fees
22 Oct - 23 Oct
Domus il Palio B&B
Breakfast meal

10. B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (208 reviews)
"We enjoyed our stay very much. Staff was very friendly and offered great advise on places to eat. The rooms had great charm to them. We were delighted with our selection of where to stay."
United States
Enrique
The price is SAR 433
SAR 493 total
includes taxes & fees
25 Oct - 26 Oct
B&B Il Corso
Exterior

11. Villa le Camelie Siena

Villa le Camelie Siena
Petriccio
8.6 out of 10, Excellent, (8 reviews)
"Nice for the price. Would stay there again."
United States
Mark
The price is SAR 369
SAR 423 total
includes taxes & fees
4 Oct - 5 Oct
Villa le Camelie Siena
Room amenity

12. Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (481 reviews)
"Fantastic location and very friendly staff, we will definitely be back"
United Kingdom
Luis
The price is SAR 407
SAR 465 total
includes taxes & fees
21 Oct - 22 Oct
Siena Vip
Lobby

13. Villa Cassia di Baccano

Villa Cassia di Baccano
Loro Ciuffenna
9.4 out of 10, Exceptional, (26 reviews)
"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is SAR 486
SAR 706 total
includes taxes & fees
10 Oct - 11 Oct
Villa Cassia di Baccano
Double Room | Minibar, desk, blackout drapes, WiFi (free)

14. PALAZZO DEL PAPA

PALAZZO DEL PAPA
Siena City Centre
9.6 out of 10, Exceptional, (111 reviews)
"Fantastic location, walkable to everything, very clean & Hamza was a great host with lots of tips on what to see & where to eat"
United Kingdom
Diane
The price is SAR 728
SAR 818 total
includes taxes & fees
15 Oct - 16 Oct
PALAZZO DEL PAPA
Exterior

15. Il Pozzo di Sant'Andrea

Il Pozzo di Sant'Andrea
Siena
9.8 out of 10, Exceptional, (16 reviews)
"Great host, lovely place near Siena"
United Kingdom
Prem
The price is SAR 381
SAR 437 total
includes taxes & fees
21 Oct - 22 Oct
Il Pozzo di Sant'Andrea
Breakfast, lunch and dinner served

16. La Locanda di Pietracupa

La Locanda di Pietracupa
Tavarnelle Val di Pesa
9.6 out of 10, Exceptional, (38 reviews)
"Great place, wonderful restaurant"
Germany
Isabell
The price is SAR 620
SAR 699 total
includes taxes & fees
25 Oct - 26 Oct
La Locanda di Pietracupa
Interior

17. Villa Fontis Rapolano

Villa Fontis Rapolano
Rapolano Terme
10.0 out of 10, Exceptional, (1 review)
"Bella struttura, nuova, pulita in posizione comoda"
Italy
Barbara
The price is SAR 317
SAR 366 total
includes taxes & fees
27 Sep - 28 Sep
Villa Fontis Rapolano
Outdoor dining

18. B&B La Fonte del Machiavelli

B&B La Fonte del Machiavelli
San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (85 reviews)
"Beautiful location, beautiful rooms. Host is very friendly and accommodating."
Australia
James
The price is SAR 416
SAR 475 total
includes taxes & fees
13 Oct - 14 Oct
B&B La Fonte del Machiavelli
Superior Double Room, Ensuite, City View | Egyptian cotton sheets, premium bedding, down comforters, minibar

19. B&B Palazzo del Magnifico

B&B Palazzo del Magnifico
Siena City Centre
9.8 out of 10, Exceptional, (73 reviews)
"Wonderful place, great location."
United States
Khaled
The price is SAR 429
SAR 490 total
includes taxes & fees
19 Oct - 20 Oct
B&B Palazzo del Magnifico
Standard Double Room | Bathroom | Deep soaking tub, rainfall showerhead, free toiletries, hair dryer

20. Piazza Paradiso Accomodation

Piazza Paradiso Accomodation
Siena City Centre
9.2 out of 10, Wonderful, (160 reviews)
"Great location and lovely staff!"
United States
Dawn
The price is SAR 392
SAR 448 total
includes taxes & fees
5 Oct - 6 Oct
Piazza Paradiso Accomodation
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

Radisson Blu Hotel, Florence

Radisson Blu Hotel, Florence

10/10 Excellent
"Perfect Stay as expected, clean hotel, extremely attentive and friendly staff. Shuttle service to town was extremely helpful and easy to use."
Mateusz 1-night trip
Posted 9 hours ago
Radisson Blu Hotel, Florence