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

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Check prices for these dates

Next weekend
14 Aug - 16 Aug
In two weeks
21 Aug - 23 Aug
In one month
4 Sep - 6 Sep
In two months
2 Oct - 4 Oct

Our top choices for Gaiole in Chianti town houses

Exterior

1. L' Eroico

L' Eroico
Gaiole in Chianti
10.0 out of 10, Exceptional, (14 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 519
SAR 606 total
includes taxes & fees
9 Aug - 10 Aug
L' Eroico
Terrace/patio

2. Casa di Campagna in Toscana

Casa di Campagna in Toscana
Sovicille
9.4 out of 10, Exceptional, (25 reviews)
"A wonderful stay. "
United States
Sally
The price is SAR 493
SAR 556 total
includes taxes & fees
6 Aug - 7 Aug
Casa di Campagna in Toscana
Exterior

3. 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 422
SAR 482 total
includes taxes & fees
3 Sep - 4 Sep
Il Pozzo di Sant'Andrea
Standard Double Room | Bathroom | Deep soaking tub, rainfall showerhead, free toiletries, hair dryer

4. 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 308
SAR 356 total
includes taxes & fees
6 Aug - 7 Aug
Piazza Paradiso Accomodation
Double Room | Minibar, desk, blackout drapes, WiFi (free)

5. PALAZZO DEL PAPA

PALAZZO DEL PAPA
Siena City Centre
9.6 out of 10, Exceptional, (110 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 693
SAR 780 total
includes taxes & fees
8 Aug - 9 Aug
PALAZZO DEL PAPA
Superior Double Room, Ensuite, City View | Egyptian cotton sheets, premium bedding, down comforters, minibar

6. B&B Palazzo del Magnifico

B&B Palazzo del Magnifico
Siena City Centre
9.8 out of 10, Exceptional, (72 reviews)
"Wonderful place, great location."
United States
Khaled
The price is SAR 411
SAR 469 total
includes taxes & fees
19 Aug - 20 Aug
B&B Palazzo del Magnifico
Room amenity

7. Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (472 reviews)
"It’s very close to the historical center but feels quiet and like you are separate from it. I loved our stay"
United States
David
The price is SAR 430
SAR 491 total
includes taxes & fees
5 Aug - 6 Aug
Siena Vip
City view from property

8. Birbo Bike Hospitality

Birbo Bike Hospitality
Siena City Centre
8.0 out of 10, Very Good, (17 reviews)
"Beautiful view from our room at the top"
United States
ralph
The price is SAR 460
SAR 523 total
includes taxes & fees
9 Aug - 10 Aug
Birbo Bike Hospitality
Double Room (Ginevra) | View from room

9. A Casa Mastacchi

A Casa Mastacchi
Siena City Centre
7.8 out of 10, Good, (29 reviews)
"Christiana was the perfect hostess. Accommodations were quaint. Rooms and common areas were spotless. Breakfast and cafe were amazing. A true gem located in the heart of Siena. Close to shops, restaurants, and enotecas. I highly recommend you stay. "
United States
Christina
The price is SAR 475
SAR 540 total
includes taxes & fees
20 Aug - 21 Aug
A Casa Mastacchi
Property grounds

10. Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (97 reviews)
"Rooms were clean and spacious ! Happy there was a good blow dryer in the room and a heated towel rack. Staff were very friendly and helpful . Would stay again !"
Canada
Alissia
The price is SAR 256
SAR 299 total
includes taxes & fees
11 Aug - 12 Aug
Domus il Palio B&B
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 314
SAR 363 total
includes taxes & fees
7 Aug - 8 Aug
Villa le Camelie Siena
Property grounds

12. Ca' Bianca Tuscany Relais

Ca' Bianca Tuscany Relais
Siena
10.0 out of 10, Exceptional, (45 reviews)
"Clean room, amazing staff"
Canada
Talha
The price is SAR 1,014
SAR 1,133 total
includes taxes & fees
17 Aug - 18 Aug
Ca' Bianca Tuscany Relais
Exterior

13. Antico Borgo il Cardino

Antico Borgo il Cardino
San Gimignano
9.4 out of 10, Exceptional, (84 reviews)
"It was perfect for my one night stop before moving on to another location in Toscana."
United States
Craig
The price is SAR 696
SAR 787 total
includes taxes & fees
6 Aug - 7 Aug
Antico Borgo il Cardino
Triple Room, Balcony, City View | Desk, iron/ironing board (on request), WiFi (free), bed sheets

14. Al Mercato B&B

Al Mercato B&B
Siena City Centre
9.0 out of 10, Wonderful, (102 reviews)
"Great location."
Canada
Marie-Christine
The price is SAR 295
SAR 380 total
includes taxes & fees
19 Aug - 20 Aug
Al Mercato B&B
Interior

15. 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 312
SAR 360 total
includes taxes & fees
7 Aug - 8 Aug
Villa Fontis Rapolano
Aerial view

16. Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (73 reviews)
"Beautiful property"
Canada
Mary
The price is SAR 597
SAR 674 total
includes taxes & fees
9 Aug - 10 Aug
Villa Curina Resort
Courtyard

17. Fontelunga Hotel & Villas

Fontelunga Hotel & Villas
Foiano della Chiana
10.0 out of 10, Exceptional, (7 reviews)
"We loved our stay here! The hosts and staff were super warm and friendly. Breakfast had a wide choice and we liked the evening drinks set up too! The hotel doggies were definitely a highlight ☺️ we’d love to come back!"
United Kingdom
Shelby
The price is SAR 1,196
SAR 1,333 total
includes taxes & fees
31 Aug - 1 Sep
Fontelunga Hotel & Villas
Balcony

18. Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (109 reviews)
"Great location, beautiful room with a terrace and the best breakfast we had in Italy! "
United States
Angel
The price is SAR 396
SAR 566 total
includes taxes & fees
4 Sep - 5 Sep
Palazzo al Torrione 2
Comfort Apartment, 1 Bedroom (Le Viole) | Terrace/patio

19. Affittacamere Le Ginestre

Affittacamere Le Ginestre
San Gimignano City Centre
7.8 out of 10, Good, (6 reviews)
"Spacious. Clean. Quite. Air conditioned. Comfort. The View. The best. "
United States
Jorge
The price is SAR 454
SAR 521 total
includes taxes & fees
5 Aug - 6 Aug
Affittacamere Le Ginestre
La Torre Grossa | In-room safe, desk, laptop workspace, WiFi (free)

20. Materia Rooms San Gimignano

Materia Rooms San Gimignano
San Gimignano City Centre
The price is SAR 378
SAR 438 total
includes taxes & fees
6 Aug - 7 Aug
Materia Rooms San Gimignano
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

Castello di Tornano Wine Resort

Castello di Tornano Wine Resort

10/10 Excellent
"Beautiful one of a kind property. Great attentive staff all meals available. Clean and quiet."
Richard 2-night trip
Posted 2 hours ago
Castello di Tornano Wine Resort