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 AED 513
AED 598 total
includes taxes & fees
5 Aug - 6 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 AED 482
AED 543 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 AED 413
AED 471 total
includes taxes & fees
1 Sep - 2 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 AED 307
AED 355 total
includes taxes & fees
5 Aug - 6 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 AED 678
AED 763 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 AED 423
AED 482 total
includes taxes & fees
9 Aug - 10 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 AED 421
AED 480 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 AED 414
AED 472 total
includes taxes & fees
11 Aug - 12 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 AED 469
AED 533 total
includes taxes & fees
5 Aug - 6 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 AED 250
AED 292 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 AED 307
AED 355 total
includes taxes & fees
5 Aug - 6 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 AED 992
AED 1,108 total
includes taxes & fees
20 Aug - 21 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 AED 681
AED 770 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 AED 288
AED 371 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 AED 308
AED 356 total
includes taxes & fees
5 Aug - 6 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 AED 597
AED 673 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 AED 1,170
AED 1,304 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 AED 388
AED 553 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 AED 444
AED 509 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 AED 370
AED 428 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

La Certosa di Pontignano

La Certosa di Pontignano

10/10 Excellent
"Great property with unique setting being an old monastery. We thought we had booked a room with A/C but there wasn’t. They moved us to a room with A/C at no additional cost."
Frederic 4-night trip
Posted 3 hours ago
La Certosa di Pontignano