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

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Check prices for these dates

Next weekend
16 Oct - 18 Oct
In two weeks
23 Oct - 25 Oct
In one month
6 Nov - 8 Nov
In two months
4 Dec - 6 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 500
SAR 584 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 430
SAR 490 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)
The price is SAR 630
SAR 693 total
includes taxes & fees
12 Oct - 13 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
9.6 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 498
SAR 564 total
includes taxes & fees
10 Oct - 11 Oct
Residenzia del Sogno
A rectangular swimming pool with a clear blue water surface, surrounded by a brick patio. There are several lounge chairs and umbrellas around the pool area.

5. Villa Rosa Panzano

Villa Rosa Panzano
Greve in Chianti
8.2 out of 10, Very good, (57 reviews)
"A lovely rural B&B with very kind staff."
Canada
Allison
The price is SAR 505
SAR 573 total
includes taxes & fees
11 Oct - 12 Oct
Villa Rosa Panzano
A kitchen with wooden cabinets, a glass display case, and a dining area with a table and chairs.

6. 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 327
SAR 377 total
includes taxes & fees
14 Oct - 15 Oct
Mariani Bed & Breakfast
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 1,096
SAR 1,222 total
includes taxes & fees
16 Oct - 17 Oct
Terre di Baccio
A bakery display with pastries and a coffee station.

8. B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (214 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 308
SAR 356 total
includes taxes & fees
4 Nov - 5 Nov
B&B Il Corso
A bathroom with a window view of a historic building and a tiled roof.

9. Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (487 reviews)
"Great location right in the heart of everything and next to an escalator that takes you to the main plaza. Very comfortable bed, friendly staff. Convenient parking option very close by."
United States
Heather
The price is SAR 418
SAR 477 total
includes taxes & fees
2 Nov - 3 Nov
Siena Vip
An arched brick corridor with gravel flooring, potted plants, and a gate leading to a garden area.

10. 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 901
SAR 1,008 total
includes taxes & fees
12 Oct - 13 Oct
Ca' Bianca Tuscany Relais
An outdoor dining area with tables and chairs, covered by umbrellas, overlooking a scenic landscape.

11. B&B La Fonte del Machiavelli

B&B La Fonte del Machiavelli
San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (88 reviews)
"Beautiful location, beautiful rooms. Host is very friendly and accommodating."
Australia
James
The price is SAR 436
SAR 496 total
includes taxes & fees
15 Oct - 16 Oct
B&B La Fonte del Machiavelli
A dining area with a table set for two, featuring a view of greenery through a window.

12. 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 513
SAR 581 total
includes taxes & fees
9 Nov - 10 Nov
La Locanda di Pietracupa
A view of a traditional European town with stone buildings, a church with a bell tower, and a tiled roof.

13. Birbo Bike Hospitality

Birbo Bike Hospitality
Siena City Centre
8.2 out of 10, Very good, (18 reviews)
"Beautiful view from our room at the top"
United States
ralph
The price is SAR 352
SAR 404 total
includes taxes & fees
9 Nov - 10 Nov
Birbo Bike Hospitality
A hotel room with a bed, a bedside table with a lamp, a potted plant, and a view of the outside through the window.

14. PALAZZO DEL PAPA

PALAZZO DEL PAPA
Siena City Centre
9.6 out of 10, Exceptional, (116 reviews)
The price is SAR 679
SAR 764 total
includes taxes & fees
3 Nov - 4 Nov
PALAZZO DEL PAPA
A cozy living room with a stone wall, a wine rack, and two sofas.

15. Villa Cassia di Baccano

Villa Cassia di Baccano
Loro Ciuffenna
9.4 out of 10, Exceptional, (27 reviews)
The price is SAR 520
SAR 573 total
includes taxes & fees
13 Oct - 14 Oct
Villa Cassia di Baccano
Pool

16. iConic Wellness Resort

iConic Wellness Resort
Arezzo
8.8 out of 10, Excellent, (40 reviews)
"Beautiful and peaceful resort! Hope to return soon❤️"
United States
Rheymarie
The price is SAR 279
SAR 332 total
includes taxes & fees
25 Oct - 26 Oct
iConic Wellness Resort
An aerial view of a hotel with a swimming pool, outdoor seating area, and well-maintained gardens.

17. Antica Pieve B&B

Antica Pieve B&B
Tavarnelle Val di Pesa
9.4 out of 10, Exceptional, (15 reviews)
"Very nice stay here! Great breakfast and coffee every morning. Great location to tour around to different wineries and towns. Free parking. "
Canada
Jessica
The price is SAR 478
SAR 627 total
includes taxes & fees
22 Oct - 23 Oct
Antica Pieve B&B
A room with a bed, a leather sofa, and a window with a view of a building outside.

18. Al Mercato B&B

Al Mercato B&B
Siena City Centre
9.0 out of 10, Wonderful, (105 reviews)
"Great location."
Canada
Marie-Christine
The price is SAR 232
SAR 309 total
includes taxes & fees
8 Nov - 9 Nov
Al Mercato B&B
A room with a white wardrobe, a glass-top table, a chair, and a large ornate mirror.

19. B&B Palazzo del Magnifico

B&B Palazzo del Magnifico
Siena City Centre
9.8 out of 10, Exceptional, (74 reviews)
The price is SAR 361
SAR 414 total
includes taxes & fees
4 Nov - 5 Nov
B&B Palazzo del Magnifico
A view from a window overlooking a rural landscape with fields and a distant mountain range.

20. B&B Palazzo Tortoli

B&B Palazzo Tortoli
San Gimignano City Centre
9.2 out of 10, Wonderful, (66 reviews)
"In the center of town overlooking a plaza (other rooms overlook the valley). Multiple museums, and dining and shopping options within very easy walking distance. The town and surroundings are beautiful."
United States
Harold
The price is SAR 481
SAR 551 total
includes taxes & fees
19 Oct - 20 Oct
B&B Palazzo Tortoli
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

Hu Firenze Camping In Town

Hu Firenze Camping In Town

10/10 Excellent
"Loved the place. Our cabin was perfect & it’s right on a bus line into town."
Debra 2-night trip
Posted 1 hour ago
Hu Firenze Camping In Town