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

Gaiole in Chianti Town Houses

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Check prices for these dates

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

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
$126 nightly
The price is $148
Nov 14 - Nov 15
Total with taxes and fees
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
$164 nightly
The price is $181
Oct 29 - Oct 30
Total with taxes and fees
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, (81 reviews)
"Beautiful resort in the hills, lovely and charming room, incredibly spacious."
United States
Deanna
$135 nightly
The price is $153
Oct 27 - Oct 28
Total with taxes and fees
Villa Curina Resort
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
$119 nightly
The price is $136
Nov 1 - Nov 2
Total with taxes and fees
Residenzia del Sogno
An arched entrance with a lantern above, flanked by two potted plants.

5. 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
$165 nightly
The price is $186
Nov 23 - Nov 24
Total with taxes and fees
Villa il Fedino
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
$89 nightly
The price is $102
Oct 30 - Oct 31
Total with taxes and fees
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, (81 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
$281 nightly
The price is $313
Oct 30 - Oct 31
Total with taxes and fees
Terre di Baccio
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, (495 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
$100 nightly
The price is $115
Nov 2 - Nov 3
Total with taxes and fees
Siena Vip
A table with two wine glasses, a bottle, and a book.

9. Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (100 reviews)
"Very nice place. Nice people, clean and just nice"
Denmark
Leo
$70 nightly
The price is $81
Nov 18 - Nov 19
Total with taxes and fees
Domus il Palio B&B
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
$112 nightly
The price is $123
Nov 24 - Nov 25
Total with taxes and fees
Villa Cassia di Baccano
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, (92 reviews)
"The view is unique. Perfect location for a romantic trip."
United States
Stella
$116 nightly
The price is $132
Oct 26 - Oct 27
Total with taxes and fees
B&B La Fonte del Machiavelli
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
$176 nightly
The price is $198
Nov 25 - Nov 26
Total with taxes and fees
PALAZZO DEL PAPA
A bakery display with pastries and a coffee station.

13. B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (217 reviews)
"Very clean and comfortable, great location and staff"
United States
Heather
$74 nightly
The price is $85
Nov 9 - Nov 10
Total with taxes and fees
B&B Il Corso
A stone courtyard with a bench, potted plants, and a building in the background.

14. 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
$86 nightly
The price is $98
Nov 25 - Nov 26
Total with taxes and fees
Casa di Campagna in Toscana
A room with a white wardrobe, a glass-top table, a chair, and a large ornate mirror.

15. B&B Palazzo del Magnifico

B&B Palazzo del Magnifico
Siena City Centre
9.8 out of 10, Exceptional, (76 reviews)
"Wonderful place, great location."
United States
Khaled
$94 nightly
The price is $108
Nov 9 - Nov 10
Total with taxes and fees
B&B Palazzo del Magnifico
A building with a sign reading 'Villa Le Camelie' and multiple flags.

16. 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
$76 nightly
The price is $89
Oct 26 - Oct 27
Total with taxes and fees
Villa le Camelie Siena
A dining area with a table set for two, featuring a view of greenery through a window.

17. La Locanda di Pietracupa

La Locanda di Pietracupa
Tavarnelle Val di Pesa
9.4 out of 10, Exceptional, (40 reviews)
"Great place, wonderful restaurant"
Germany
Isabell
$134 nightly
The price is $151
Nov 8 - Nov 9
Total with taxes and fees
La Locanda di Pietracupa
An aerial view of a hotel with a swimming pool, outdoor seating area, and well-maintained gardens.

18. 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
$148 nightly
The price is $167
Oct 26 - Oct 27
Total with taxes and fees
Antica Pieve B&B
A garden with a stone pathway, wooden benches, and various potted plants.

19. Antico Borgo il Cardino

Antico Borgo il Cardino
San Gimignano
9.4 out of 10, Exceptional, (88 reviews)
"friendly staff, gorgeous property"
United States
Heidi
$133 nightly
The price is $151
Oct 30 - Oct 31
Total with taxes and fees
Antico Borgo il Cardino
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
$86 nightly
The price is $99
Oct 26 - Oct 27
Total with taxes and fees
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

Castello di Tornano Wine Resort

Castello di Tornano Wine Resort

10/10 Excellent
"Beautiful property, stunning views. Remote location and we did have a little trouble finding it! This was our favorite stay and highlight from our Italian vacation! Loved the wine and complimentary breakfast. Really enjoyed our time in this castle!"
Ramon 3-night trip
Posted 6 hours ago
Castello di Tornano Wine Resort

Find out more about Gaiole in Chianti

Gaiole in Chianti Town Houses information

Number of reviews
773
Accommodation
113 Town Houses
Lowest Price
$81
Highest Price
$313

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