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

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Check prices for these dates

Next weekend
30 Oct - 1 Nov
In two weeks
6 Nov - 8 Nov
In one month
20 Nov - 22 Nov
In two months
18 Dec - 20 Dec

Our top choices for Gaiole in Chianti town houses

A stone building with a yellow sign reading "b&b erioico".

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 485
SAR 567 total
includes taxes & fees
2 Nov - 3 Nov
L' Eroico
A villa with a swimming pool, outdoor seating, and a tennis court.

2. 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 543
SAR 615 total
includes taxes & fees
24 Oct - 25 Oct
Villa Curina Resort
A pool area with two rectangular pools, surrounded by lounge chairs and umbrellas, set against a backdrop of vineyards and tall cypress trees.

3. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (40 reviews)
"Great spot"
Canada
Philippe
The price is SAR 629
SAR 692 total
includes taxes & fees
21 Oct - 22 Oct
Villa di Sotto
A pool area with lounge chairs and umbrellas, surrounded by greenery and a stone building.

4. Residenzia del Sogno

Residenzia del Sogno
Castellina in Chianti
9.8 out of 10, Exceptional, (16 reviews)
"Beautiful and authentic place, lovely couple running the place that care about you and your stay. "
Canada
Katherine
The price is SAR 497
SAR 564 total
includes taxes & fees
23 Oct - 24 Oct
Residenzia del Sogno
A kitchen with wooden cabinets, a glass display case, and a dining area with a table and chairs.

5. Mariani Bed & Breakfast

Mariani Bed & Breakfast
Castellina in Chianti
9.8 out of 10, Exceptional, (18 reviews)
"Beautiful view, very clean and everything in great condition. Friendly service. We will definitely stay again."
United States
Frank
The price is SAR 339
SAR 389 total
includes taxes & fees
21 Oct - 22 Oct
Mariani Bed & Breakfast
A room with a white wardrobe, a glass-top table, a chair, and a large ornate mirror.

6. B&B Palazzo del Magnifico

B&B Palazzo del Magnifico
Siena City Centre
9.8 out of 10, Exceptional, (75 reviews)
"Wonderful place, great location."
United States
Khaled
The price is SAR 366
SAR 419 total
includes taxes & fees
7 Nov - 8 Nov
B&B Palazzo del Magnifico
A restaurant with hanging baskets of greenery, wicker furniture, and a view of the outdoors.

7. Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (80 reviews)
"Amazing property and room, only issue is it’s very understaffed so it’s hard to get anything without chasing down workers. They also don’t stay on the property so after like 11pm you’re on your own. Besides that it was a wonderful location and very peaceful."
United States
Gage
The price is SAR 1,095
SAR 1,222 total
includes taxes & fees
6 Nov - 7 Nov
Terre di Baccio
An outdoor dining area with tables and chairs, covered by umbrellas, overlooking a scenic landscape.

8. B&B La Fonte del Machiavelli

B&B La Fonte del Machiavelli
San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (90 reviews)
"Beautiful location, beautiful rooms. Host is very friendly and accommodating."
Australia
James
The price is SAR 436
SAR 496 total
includes taxes & fees
25 Oct - 26 Oct
B&B La Fonte del Machiavelli
A bakery display with pastries and a coffee station.

9. B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (215 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 276
SAR 321 total
includes taxes & fees
2 Nov - 3 Nov
B&B Il Corso
A cozy living room with a stone wall, a wine rack, and two sofas.

10. Villa Cassia di Baccano

Villa Cassia di Baccano
Loro Ciuffenna
9.4 out of 10, Exceptional, (27 reviews)
"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is SAR 432
SAR 476 total
includes taxes & fees
21 Oct - 22 Oct
Villa Cassia di Baccano
A bathroom with a window view of a historic building and a tiled roof.

11. Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (491 reviews)
"Very friendly staff and great location close to the center of town. Breakfast was a nice touch and just what we needed to start the day. Would recommend!"
United States
Jacob
The price is SAR 418
SAR 477 total
includes taxes & fees
3 Nov - 4 Nov
Siena Vip
A hotel room with a bed, a bedside table with a lamp, a potted plant, and a view of the outside through the window.

12. PALAZZO DEL PAPA

PALAZZO DEL PAPA
Siena City Centre
9.6 out of 10, Exceptional, (117 reviews)
"Hamza is so helpful!! Finding the property is a little tricky, but he helped every step of the way! He also provided excellent dining suggestions and a great cooking class!"
United States
Charles
The price is SAR 679
SAR 764 total
includes taxes & fees
3 Nov - 4 Nov
PALAZZO DEL PAPA
A table with two wine glasses, a bottle, and a book.

13. Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (100 reviews)
"Place was great, beautiful, modern, well maintained and staff was very helpful. I didn’t like that it is far from everything, far from train station, not too many options for food in the vicinity."
United States
Waleska
The price is SAR 249
SAR 290 total
includes taxes & fees
25 Oct - 26 Oct
Domus il Palio B&B
A dining area with a table set for two, featuring a view of greenery through a window.

14. La Locanda di Pietracupa

La Locanda di Pietracupa
Tavarnelle Val di Pesa
9.6 out of 10, Exceptional, (39 reviews)
"Great place, wonderful restaurant"
Germany
Isabell
The price is SAR 507
SAR 574 total
includes taxes & fees
15 Nov - 16 Nov
La Locanda di Pietracupa
Pool

15. iConic Wellness Resort

iConic Wellness Resort
Arezzo
8.8 out of 10, Excellent, (41 reviews)
"Beautiful and peaceful resort! Hope to return soon❤️"
United States
Rheymarie
The price is SAR 279
SAR 332 total
includes taxes & fees
16 Nov - 17 Nov
iConic Wellness Resort
A stone courtyard with a bench, potted plants, and a building in the background.

16. Casa di Campagna in Toscana

Casa di Campagna in Toscana
Sovicille
9.6 out of 10, Exceptional, (27 reviews)
"A wonderful stay. "
United States
Sally
The price is SAR 348
SAR 396 total
includes taxes & fees
15 Nov - 16 Nov
Casa di Campagna in Toscana
An arched entrance with a lantern above, flanked by two potted plants.

17. Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (108 reviews)
"Food was amazing, we love how quiet and relaxing it was"
United States
Justyna
The price is SAR 811
SAR 909 total
includes taxes & fees
21 Oct - 22 Oct
Villa il Fedino
An open wooden door leading to an outdoor patio with a table and chairs.

18. Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (114 reviews)
"Great location, beautiful room with a terrace and the best breakfast we had in Italy! "
United States
Angel
The price is SAR 343
SAR 504 total
includes taxes & fees
17 Nov - 18 Nov
Palazzo al Torrione 2
A building with a sign reading 'Villa Le Camelie' and multiple flags.

19. 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 306
SAR 353 total
includes taxes & fees
21 Oct - 22 Oct
Villa le Camelie Siena
A staircase with a wooden handrail, a potted plant, and a chair in a hallway.

20. 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 323
SAR 372 total
includes taxes & fees
28 Oct - 29 Oct
Villa Fontis Rapolano
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 location amazing place"
Rodolfo 1-night trip
Posted less than an hour ago
La Certosa di Pontignano