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

RM619 total

includes taxes & fees

2 Nov - 3 Nov

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

RM756 total

includes taxes & fees

12 Oct - 13 Oct

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

3. Villa Curina Resort

Castelnuovo Berardenga

Deanna

RM593 total

includes taxes & fees

9 Oct - 10 Oct

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

Greve in Chianti

Allison

RM570 total

includes taxes & fees

4 Oct - 5 Oct

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

5. Residenzia del Sogno

Castellina in Chianti

Katherine

RM586 total

includes taxes & fees

6 Oct - 7 Oct

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

6. Terre di Baccio

Greve in Chianti

Gage

RM1,243 total

includes taxes & fees

16 Oct - 17 Oct

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

7. Mariani Bed & Breakfast

Castellina in Chianti

Frank

RM411 total

includes taxes & fees

13 Oct - 14 Oct

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

8. Siena Vip

Siena City Centre

Luis

RM437 total

includes taxes & fees

2 Nov - 3 Nov

An arched brick corridor with gravel flooring, potted plants, and a gate leading to a garden area.

9. Ca' Bianca Tuscany Relais

Siena

Talha

RM1,101 total

includes taxes & fees

8 Oct - 9 Oct

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

10. Villa Cassia di Baccano

Loro Ciuffenna

Ralphvincent

RM657 total

includes taxes & fees

21 Oct - 22 Oct

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

Siena City Centre

"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!!!"

Walter

RM835 total

includes taxes & fees

3 Nov - 4 Nov

A bakery display with pastries and a coffee station.

12. B&B Il Corso

Siena City Centre

Enrique

RM526 total

includes taxes & fees

1 Nov - 2 Nov

An open wooden door leading to an outdoor patio with a table and chairs.

13. Palazzo al Torrione 2

San Gimignano City Centre

Angela

RM613 total

includes taxes & fees

4 Oct - 5 Oct

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

14. Domus il Palio B&B

Ravacciano

Waleska

RM317 total

includes taxes & fees

20 Oct - 21 Oct

15. iConic Wellness Resort

Arezzo

Rheymarie

RM363 total

includes taxes & fees

25 Oct - 26 Oct

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

16. La Locanda di Pietracupa

Tavarnelle Val di Pesa

Isabell

RM783 total

includes taxes & fees

4 Oct - 5 Oct

An outdoor dining area with tables and chairs, covered by umbrellas, overlooking a scenic landscape.

17. B&B La Fonte del Machiavelli

San Casciano in Val di Pesa

James

RM542 total

includes taxes & fees

4 Oct - 5 Oct

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

18. Villa il Fedino

San Casciano in Val di Pesa

Lori

RM1,124 total

includes taxes & fees

13 Oct - 14 Oct

A reception desk with the word "SPORTLAND" prominently displayed.

19. Sportland

Colle di Val d'Elsa

Giorgio

RM210 total

includes taxes & fees

11 Oct - 12 Oct

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

20. Antica Pieve B&B

Tavarnelle Val di Pesa

Jessica

RM662 total

includes taxes & fees

23 Oct - 24 Oct

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Top Gaiole in Chianti Hotel Reviews

Hu Firenze Camping In Town

8/10 Good

"A very well maintained campsite with good amenities and a bustling friendly atmosphere on the whole. The only downside is beyond the control of the campsite and was the bus service into central Florence. Appalling service with infrequent and misleading times. Overall other than the logistics of going to central Florence I would recommend the campsite highly"

Castello di Tornano Wine Resort

10/10 Excellent

"This was a magical place!!! Has a working farm mentality but all the nice touches of an upscale place. Modern bathrooms, updated AC, a pool that was wonderful to relax in after touring some local wineries. Gorgeous terrace area, a bar and some wonderful wines, delicious buffet breakfast, and superb restaurant for dinner!!! Staff also very helpful. Roads are narrow so be cautious in planning your day trips and the dirt road to the castle will leave your car quite dusty! Still- the views were breathtaking and we wished we could stay longer!"

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent

"This was a beautiful hotel! Everything from the room to the amenities to the staff. Most of the amenities are complimentary (sauna, steam room, pool, gym, etc). The staff were very helpful as well. We would absolutely stay here again."

Hotel Mulino di Firenze, WorldHotels Crafted

10/10 Excellent

"From the moment we arrived to the moment we left the staff were fantastic. Lapo, at the front desk, was extremely helpful in making last minute arrangements for anything we needed. The entire staff from the porters, bar tenders, cleaning staff and managers were friendly and accommodating. The property was picturesque and absolutely stunning. We wish we would have stayed more days just to enjoy the property itself. If you're having an afternoon drink on the patio bar or enjoying a scrumptious evening meal in the restaurant you will not be disappointed."

Fattoria di Vegi

10/10 Excellent

"Booked this as a last minute decision to shorten our time in Milan (and fine a place close to Florence on our way to Montepulciano) We only stayed one night, but wish it had been longer. If you are looking for informal luxury, you will find it at this idyllic Tuscan Estate. They are still expanding their amenities to include a gym, tennis court, and Spa (planned for a 2027 open) what they DO offer is a quiet, thoughtful experience. The room was perfection and the restaurant on the property - delicious. There were a few artists there taking advantage of the atelier, or painting on the property. The estate is located an hour’s drive outside of Florence and is well worth the trip if you are looking for a place to relax. We hope to return with more time to enjoy it."

Find out more about Gaiole in Chianti