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

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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
The price is CA $181
CA $211 total
includes taxes & fees
Nov 2 - Nov 3
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 CA $249
CA $274 total
includes taxes & fees
Oct 29 - Oct 30
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
The price is CA $187
CA $212 total
includes taxes & fees
Oct 25 - Oct 26
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
The price is CA $185
CA $210 total
includes taxes & fees
Oct 31 - Nov 1
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 CA $118
CA $136 total
includes taxes & fees
Oct 27 - Oct 28
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, (76 reviews)
"Wonderful place, great location."
United States
Khaled
The price is CA $139
CA $159 total
includes taxes & fees
Nov 6 - Nov 7
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, (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
The price is CA $389
CA $435 total
includes taxes & fees
Oct 31 - Nov 1
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, (494 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 CA $140
CA $161 total
includes taxes & fees
Nov 4 - Nov 5
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.

9. 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 CA $253
CA $285 total
includes taxes & fees
Nov 7 - Nov 8
PALAZZO DEL PAPA
An outdoor dining area with tables and chairs, covered by umbrellas, overlooking a scenic landscape.

10. B&B La Fonte del Machiavelli

B&B La Fonte del Machiavelli
San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (91 reviews)
"The view is unique. Perfect location for a romantic trip."
United States
Stella
The price is CA $163
CA $185 total
includes taxes & fees
Oct 27 - Oct 28
B&B La Fonte del Machiavelli
A table with two wine glasses, a bottle, and a book.

11. 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 CA $98
CA $114 total
includes taxes & fees
Nov 18 - Nov 19
Domus il Palio B&B
A cozy living room with a stone wall, a wine rack, and two sofas.

12. 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 CA $155
CA $170 total
includes taxes & fees
Nov 24 - Nov 25
Villa Cassia di Baccano
A dining area with a table set for two, featuring a view of greenery through a window.

13. 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 CA $187
CA $212 total
includes taxes & fees
Nov 8 - Nov 9
La Locanda di Pietracupa
Pool

14. 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 CA $104
CA $124 total
includes taxes & fees
Nov 16 - Nov 17
iConic Wellness Resort
An arched entrance with a lantern above, flanked by two potted plants.

15. 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 CA $231
CA $260 total
includes taxes & fees
Nov 23 - Nov 24
Villa il Fedino
An aerial view of a hotel with a swimming pool, outdoor seating area, and well-maintained gardens.

16. 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 CA $178
CA $234 total
includes taxes & fees
Oct 27 - Oct 28
Antica Pieve B&B
A stone courtyard with a bench, potted plants, and a building in the background.

17. 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 CA $126
CA $144 total
includes taxes & fees
Nov 24 - Nov 25
Casa di Campagna in Toscana
A traditional stone building with a courtyard, a staircase, and potted plants.

18. 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 CA $145
CA $166 total
includes taxes & fees
Oct 26 - Oct 27
Il Pozzo di Sant'Andrea
A bakery display with pastries and a coffee station.

19. B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (216 reviews)
"Very clean and comfortable, great location and staff"
United States
Heather
The price is CA $103
CA $120 total
includes taxes & fees
Nov 15 - Nov 16
B&B Il Corso
An open wooden door leading to an outdoor patio with a table and chairs.

20. 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 CA $128
CA $188 total
includes taxes & fees
Nov 7 - Nov 8
Palazzo al Torrione 2
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

Poderi Arcangelo

Poderi Arcangelo

10/10 Excellent
"Fantastic experience all around from the the food, the wine, THE VIEWS, and the late October weather gifted us an afternoon poolside. Our room was wonderful and passed every expectation. Five stars!"
Christine 2-night trip
Posted 19 hours ago
Poderi Arcangelo

Find out more about Gaiole in Chianti

Gaiole in Chianti Townhomes information

Number of reviews
1,339
Accommodation
113 Townhomes
Lowest Price
CA $114
Highest Price
CA $435