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

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Check prices for these dates

Next weekend
9 Oct - 11 Oct
In two weeks
16 Oct - 18 Oct
In one month
30 Oct - 1 Nov
In two months
27 Nov - 29 Nov

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 £115
includes taxes & fees
2 Nov - 3 Nov
L' Eroico
A pool area with two rectangular pools, surrounded by lounge chairs and umbrellas, set against a backdrop of vineyards and tall cypress trees.

2. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (40 reviews)
"Great spot"
Canada
Philippe
The price is £140
includes taxes & fees
12 Oct - 13 Oct
Villa di Sotto
A villa with a swimming pool, outdoor seating, and a tennis court.

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 £102
includes taxes & fees
10 Oct - 11 Oct
Villa Curina Resort
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.

4. 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 £106
includes taxes & fees
4 Oct - 5 Oct
Villa Rosa Panzano
A pool area with lounge chairs and umbrellas, surrounded by greenery and a stone building.

5. 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 £109
includes taxes & fees
6 Oct - 7 Oct
Residenzia del Sogno
A restaurant with hanging baskets of greenery, wicker furniture, and a view of the outdoors.

6. 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 £240
includes taxes & fees
21 Oct - 22 Oct
Terre di Baccio
A kitchen with wooden cabinets, a glass display case, and a dining area with a table and chairs.

7. 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 £76
includes taxes & fees
13 Oct - 14 Oct
Mariani Bed & Breakfast
A bathroom with a window view of a historic building and a tiled roof.

8. Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (484 reviews)
"Fantastic location and very friendly staff, we will definitely be back"
United Kingdom
Luis
The price is £81
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.

9. 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 £204
includes taxes & fees
8 Oct - 9 Oct
Ca' Bianca Tuscany Relais
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, (26 reviews)
"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is £122
includes taxes & fees
21 Oct - 22 Oct
Villa Cassia di Baccano
A hotel room with a bed, a bedside table with a lamp, a potted plant, and a view of the outside through the window.

11. PALAZZO DEL PAPA

PALAZZO DEL PAPA
Siena City Centre
9.6 out of 10, Exceptional, (114 reviews)
"The setup was more like a guest house/Bed and Breakfast. It was impeccably clean and newly renovated, which made it very cozy and comfortable. Everything needed was provided. The location was half a block from the Piazza del Campo. And last but not least, Hamza was one of the most welcoming and gracious hosts imaginable, directing us to a magical Trattoria, Pappei’s, that felt like you were visiting your own Nonna! Wonderful!!!"
United States
Walter
The price is £169
includes taxes & fees
2 Nov - 3 Nov
PALAZZO DEL PAPA
A bakery display with pastries and a coffee station.

12. B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (211 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 £97
includes taxes & fees
1 Nov - 2 Nov
B&B Il Corso
An open wooden door leading to an outdoor patio with a table and chairs.

13. Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (113 reviews)
"They were very helpful to me when I arrived. I difficulty accessing there messages to me. They put me at ease"
United States
Angela
The price is £114
includes taxes & fees
4 Oct - 5 Oct
Palazzo al Torrione 2
A table with two wine glasses, a bottle, and a book.

14. Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (99 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 £59
includes taxes & fees
20 Oct - 21 Oct
Domus il Palio B&B
Pool

15. 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 £67
includes taxes & fees
25 Oct - 26 Oct
iConic Wellness Resort
A dining area with a table set for two, featuring a view of greenery through a window.

16. 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 £138
includes taxes & fees
4 Oct - 5 Oct
La Locanda di Pietracupa
An outdoor dining area with tables and chairs, covered by umbrellas, overlooking a scenic landscape.

17. B&B La Fonte del Machiavelli

B&B La Fonte del Machiavelli
San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (87 reviews)
"Beautiful location, beautiful rooms. Host is very friendly and accommodating."
Australia
James
The price is £94
includes taxes & fees
1 Nov - 2 Nov
B&B La Fonte del Machiavelli
An arched entrance with a lantern above, flanked by two potted plants.

18. Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (105 reviews)
"Tha parking was easy on the property. It was within walking distance to the villages with shops, restaurants and cafes. The best part was the staff. The owners were incredibly helpful, friendly and made you feel like family. Breakfast outside was lovely overlooking the hills of Tuscany. We met many people and had lovely conversations with other travelers during breakfast. A gem in Tuscany."
United States
Lori
The price is £190
includes taxes & fees
8 Oct - 9 Oct
Villa il Fedino
A reception desk with the word "SPORTLAND" prominently displayed.

19. Sportland

Sportland
Colle di Val d'Elsa
7.2 out of 10, Good, (5 reviews)
"Struttura essenziale ed economica "
Italy
Giorgio
The price is £39
includes taxes & fees
4 Oct - 5 Oct
Sportland
An aerial view of a hotel with a swimming pool, outdoor seating area, and well-maintained gardens.

20. 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 £123
includes taxes & fees
22 Oct - 23 Oct
Antica Pieve B&B
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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