Gaiole in Chianti Town Houses

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

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Our top choices for Gaiole in Chianti town houses

A stone building with a yellow sign reading "b&b erioico".

1. L' Eroico

Gaiole in Chianti

Angela

HK$1,490 total

includes taxes & fees

17 Sept - 18 Sept

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

Castelnuovo Berardenga

Philippe

HK$1,388 total

includes taxes & fees

21 Sept - 22 Sept

A villa with a swimming pool, outdoor seating, and a tennis court.

3. Villa Curina Resort

Castelnuovo Berardenga

Mary

HK$1,573 total

includes taxes & fees

13 Sept - 14 Sept

A kitchen with wooden cabinets, a glass display case, and a dining area with a table and chairs.

4. Mariani Bed & Breakfast

Castellina in Chianti

Chie

HK$816 total

includes taxes & fees

9 Sept - 10 Sept

A pool area with lounge chairs and umbrellas, surrounded by greenery and a stone building.

5. Residenzia del Sogno

Castellina in Chianti

Katherine

HK$1,161 total

includes taxes & fees

21 Sept - 22 Sept

A table with two wine glasses, a bottle, and a book.

6. Domus il Palio B&B

Ravacciano

Alissia

HK$628 total

includes taxes & fees

1 Oct - 2 Oct

A restaurant with hanging baskets of greenery, wicker furniture, and a view of the outdoors.

7. Terre di Baccio

Greve in Chianti

SYDNEY

HK$2,661 total

includes taxes & fees

25 Sept - 26 Sept

A staircase with a wooden handrail, a potted plant, and a chair in a hallway.

8. Villa Fontis Rapolano

Rapolano Terme

Barbara

HK$823 total

includes taxes & fees

14 Sept - 15 Sept

A bathroom with a window view of a historic building and a tiled roof.

9. Siena Vip

Siena City Centre

Luis

HK$991 total

includes taxes & fees

9 Sept - 10 Sept

A building with a sign reading 'Villa Le Camelie' and multiple flags.

10. Villa le Camelie Siena

Petriccio

Mark

HK$765 total

includes taxes & fees

9 Sept - 10 Sept

A room with a bed, a leather sofa, and a window with a view of a building outside.

11. Al Mercato B&B

Siena City Centre

Marie-Christine

HK$775 total

includes taxes & fees

5 Oct - 6 Oct

A traditional stone building with a courtyard, a staircase, and potted plants.

12. Il Pozzo di Sant'Andrea

Siena

Prem

HK$949 total

includes taxes & fees

5 Oct - 6 Oct

An aerial view of a hotel with a swimming pool, outdoor seating area, and well-maintained gardens.

13. Antica Pieve B&B

Tavarnelle Val di Pesa

Jessica

HK$1,311 total

includes taxes & fees

28 Sept - 29 Sept

A cozy living room with a stone wall, a wine rack, and two sofas.

14. Villa Cassia di Baccano

Loro Ciuffenna

Ralphvincent

HK$2,122 total

includes taxes & fees

27 Sept - 28 Sept

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

Siena City Centre

Alana

HK$815 total

includes taxes & fees

11 Sept - 12 Sept

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

Siena City Centre

Diane

HK$2,276 total

includes taxes & fees

3 Oct - 4 Oct

A room with a white wardrobe, a glass-top table, a chair, and a large ornate mirror.

17. B&B Palazzo del Magnifico

Siena City Centre

Khaled

HK$1,113 total

includes taxes & fees

24 Sept - 25 Sept

A dining area with a table set for two, featuring a view of greenery through a window.

18. La Locanda di Pietracupa

Tavarnelle Val di Pesa

Isabell

HK$1,550 total

includes taxes & fees

9 Sept - 10 Sept

A view from a window overlooking a cityscape with terracotta rooftops and a prominent dome structure in the distance.

19. A Casa Mastacchi

Siena City Centre

Christina

HK$1,171 total

includes taxes & fees

10 Sept - 11 Sept

An arched entrance with a lantern above, flanked by two potted plants.

20. Villa il Fedino

San Casciano in Val di Pesa

"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...

Nilesh

HK$2,205 total

includes taxes & fees

3 Oct - 4 Oct

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Top Gaiole in Chianti Hotel Reviews

Villa Olmi Firenze

10/10 Excellent

"Amazing stay a perfect escape from Florence"

"Villa Torre in Chianti" Vrbo Vacation Rental of the Year 2026- 8 bedrooms A/C

10/10 Excellent

"WOW! What a beautiful place and awesome hosts! 15 of us traveled to celebrate several birthdays, to enjoy, to discover the area, eat well and create new experiences. For all of these I used the experience and recommendations of Jacopo and Beatrice. We maintained communication for 3 months, and everything turned out perfect! They are the perfect hosts and this is a perfect house whether you want to rest or use it as a base with a large group. The villa(house) is large, with plenty of to do's, with a nice pool and quiet surroundings. The pictures are accurate and the dinners from Beatrice are amazing. Do not hesitate to stay on this place, to pay for the villa and the experiences, and to work together with Jacopo and Beatrice for the perfect celebration and vacation. Don't skip taking a tour of local wineries and eating in one of the local restaurants. 100% Recommended!!"

Find out more about Gaiole in Chianti