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

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Check prices for these dates

Next weekend
18 Sep - 20 Sep
In two weeks
25 Sep - 27 Sep
In one month
9 Oct - 11 Oct
In two months
6 Nov - 8 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 ฿5,409
฿6,256 total
includes taxes & fees
17 Sept - 18 Sept
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, (39 reviews)
"Great spot"
Canada
Philippe
The price is ฿5,293
฿5,823 total
includes taxes & fees
21 Sept - 22 Sept
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, (77 reviews)
"Beautiful property"
Canada
Mary
The price is ฿5,866
฿6,606 total
includes taxes & fees
13 Sept - 14 Sept
Villa Curina Resort
A kitchen with wooden cabinets, a glass display case, and a dining area with a table and chairs.

4. Mariani Bed & Breakfast

Mariani Bed & Breakfast
Castellina in Chianti
9.8 out of 10, Exceptional, (17 reviews)
"Very nice and quiet neighbourhood. Close to city centre. The host is very kind."
Japan
Chie
The price is ฿2,972
฿3,422 total
includes taxes & fees
10 Sept - 11 Sept
Mariani Bed & Breakfast
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 ฿4,293
฿4,875 total
includes taxes & fees
22 Sept - 23 Sept
Residenzia del Sogno
A table with two wine glasses, a bottle, and a book.

6. Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (97 reviews)
"Rooms were clean and spacious ! Happy there was a good blow dryer in the room and a heated towel rack. Staff were very friendly and helpful . Would stay again !"
Canada
Alissia
The price is ฿2,259
฿2,638 total
includes taxes & fees
1 Oct - 2 Oct
Domus il Palio B&B
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, (79 reviews)
"The stay was great, and the staff were wonderful. "
United States
SYDNEY
The price is ฿10,011
฿11,165 total
includes taxes & fees
25 Sept - 26 Sept
Terre di Baccio
A staircase with a wooden handrail, a potted plant, and a chair in a hallway.

8. 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 ฿3,003
฿3,457 total
includes taxes & fees
10 Sept - 11 Sept
Villa Fontis Rapolano
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, (478 reviews)
"Fantastic location and very friendly staff, we will definitely be back"
United Kingdom
Luis
The price is ฿3,803
฿4,336 total
includes taxes & fees
28 Sept - 29 Sept
Siena Vip
A building with a sign reading 'Villa Le Camelie' and multiple flags.

10. 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 ฿3,285
฿3,766 total
includes taxes & fees
21 Sept - 22 Sept
Villa le Camelie Siena
A room with a bed, a leather sofa, and a window with a view of a building outside.

11. Al Mercato B&B

Al Mercato B&B
Siena City Centre
9.0 out of 10, Wonderful, (102 reviews)
"Great location."
Canada
Marie-Christine
Al Mercato B&B
A traditional stone building with a courtyard, a staircase, and potted plants.

12. 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 ฿3,481
฿3,982 total
includes taxes & fees
5 Oct - 6 Oct
Il Pozzo di Sant'Andrea
An aerial view of a hotel with a swimming pool, outdoor seating area, and well-maintained gardens.

13. Antica Pieve B&B

Antica Pieve B&B
Tavarnelle Val di Pesa
9.4 out of 10, Exceptional, (14 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 ฿4,171
฿5,506 total
includes taxes & fees
28 Sept - 29 Sept
Antica Pieve B&B
A cozy living room with a stone wall, a wine rack, and two sofas.

14. Villa Cassia di Baccano

Villa Cassia di Baccano
Loro Ciuffenna
9.4 out of 10, Exceptional, (25 reviews)
"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is ฿5,503
฿7,584 total
includes taxes & fees
7 Oct - 8 Oct
Villa Cassia di Baccano
An outdoor café with tables and chairs under umbrellas, a stone building with green shutters, and a sign that reads "POSTERIA".

15. B&B Dei Rossi

B&B Dei Rossi
Siena City Centre
8.2 out of 10, Very good, (18 reviews)
"Wonderful stay. Large room, shared kitchen and great location to shops and restaurants. A lot of stairs, but it comes with a beautiful view. "
Canada
Alana
The price is ฿3,097
฿3,560 total
includes taxes & fees
22 Sept - 23 Sept
B&B Dei Rossi
A hotel room with a bed, a bedside table with a lamp, a potted plant, and a view of the outside through the window.

16. PALAZZO DEL PAPA

PALAZZO DEL PAPA
Siena City Centre
9.6 out of 10, Exceptional, (111 reviews)
"Fantastic location, walkable to everything, very clean & Hamza was a great host with lots of tips on what to see & where to eat"
United Kingdom
Diane
The price is ฿8,541
฿9,548 total
includes taxes & fees
3 Oct - 4 Oct
PALAZZO DEL PAPA
A room with a white wardrobe, a glass-top table, a chair, and a large ornate mirror.

17. B&B Palazzo del Magnifico

B&B Palazzo del Magnifico
Siena City Centre
9.8 out of 10, Exceptional, (73 reviews)
"Wonderful place, great location."
United States
Khaled
The price is ฿4,108
฿4,671 total
includes taxes & fees
24 Sept - 25 Sept
B&B Palazzo del Magnifico
A dining area with a table set for two, featuring a view of greenery through a window.

18. La Locanda di Pietracupa

La Locanda di Pietracupa
Tavarnelle Val di Pesa
9.6 out of 10, Exceptional, (38 reviews)
"Great place, wonderful restaurant"
Germany
Isabell
The price is ฿5,779
฿6,510 total
includes taxes & fees
21 Sept - 22 Sept
La Locanda di Pietracupa
A view from a window overlooking a cityscape with terracotta rooftops and a prominent dome structure in the distance.

19. A Casa Mastacchi

A Casa Mastacchi
Siena City Centre
7.8 out of 10, Good, (29 reviews)
"Christiana was the perfect hostess. Accommodations were quaint. Rooms and common areas were spotless. Breakfast and cafe were amazing. A true gem located in the heart of Siena. Close to shops, restaurants, and enotecas. I highly recommend you stay. "
United States
Christina
The price is ฿4,331
฿4,917 total
includes taxes & fees
10 Sept - 11 Sept
A Casa Mastacchi
An arched entrance with a lantern above, flanked by two potted plants.

20. Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (103 reviews)
"This is an excellent property. Very historic, rustic and with great views across the Tuscan landscapes. Lorenzo and his mother were super duper hosts who took great care of us. The property dates back to 1380 and the rooms are decorated with choicest artifacts that adds greatly to the experience. The location is fantastic too with the local market and restaurants in easy walking reach. The breakfast service is fabulous with many choices and Lorenzo himself is great chef as well! Highly recommend...
United States
Nilesh
The price is ฿8,274
฿9,254 total
includes taxes & fees
3 Oct - 4 Oct
Villa il Fedino
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

Villa Scacciapensieri Boutique Hotel

Villa Scacciapensieri Boutique Hotel

10/10 Excellent
"The staff were very friendly and helpful. The bar service is the best."
Harley 1-night trip
Posted 10 hours ago
Villa Scacciapensieri Boutique Hotel

Find out more about Gaiole in Chianti

Gaiole in Chianti Town Houses information

Number of reviews
1,315
Accommodation
113 Town Houses
Lowest Price
฿2,638
Highest Price
฿11,165