Chianti Region Country Houses

A vineyard with rows of grapevines, a house surrounded by trees, and a road with vehicles.

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Our top choices for Chianti Region country houses

A swimming pool area with lounge chairs and umbrellas, surrounded by a landscaped garden and a hilly backdrop.

1. Palagina Il Borgo Agricolo

Figline e Incisa Valdarno

Casey

A terrace with stone arches, green plants, and a table set for dining with a scenic mountain view.

2. Podere L'Aquila

Gaiole in Chianti

Heather

includes taxes & fees

5 Oct - 6 Oct

3. Palazzo Tiglio - A Small Luxury Hotels of the World

Bucine

David

includes taxes & fees

1 Nov - 2 Nov

A traditional villa with multiple terracotta-tiled roofs, surrounded by lush greenery and trees.

4. Relais de Ricci

Impruneta

includes taxes & fees

2 Nov - 3 Nov

An outdoor patio with a stone table, a plate of food, a glass of red drink, and a sunflower.

5. Cappannelle Country House Tuscany

Castiglion Fibocchi

includes taxes & fees

22 Oct - 23 Oct

A stone building with a swimming pool, surrounded by trees and a view of the landscape.

6. Relais la Costa - Dimora Storica

Monteriggioni

Doug

includes taxes & fees

28 Oct - 29 Oct

A stone building with a swimming pool, outdoor seating, and trees.

7. Il Castagnolo Country B&B

San Gimignano

Allan

includes taxes & fees

4 Oct - 5 Oct

A stone building with a staircase leading to a second floor, a small garden area, and a red brick courtyard.

8. Locanda Casalta

Strove

Manfred August

includes taxes & fees

5 Oct - 6 Oct

A table with a bottle of wine, two glasses, and a plate of food on a balcony overlooking a historic cityscape.

9. Tenuta Guardastelle

San Gimignano

Sarah

includes taxes & fees

10 Oct - 11 Oct

A cellar with wine racks, a wooden table, and barrels.

10. CASALE DI VALLE DIMORA STORICA

Vinci

Delsy Alejandra

includes taxes & fees

5 Oct - 6 Oct

A large estate with three main buildings, a swimming pool, and well-maintained gardens.

11. Borgo della Meliana

Gambassi Terme

Alice

includes taxes & fees

3 Oct - 4 Oct

A dining area with a table set for four, chairs, a television mounted on the wall, and a cabinet with glass doors.

12. L'Aia di Argia

Monteroni d'Arbia

mario

includes taxes & fees

4 Oct - 5 Oct

A balcony with a table set for two, overlooking a calm river and lush greenery.

13. Fattoria di Maiano

Fiesole

"Our first visit to Tuscany and this was a beautiful location. We had the 3 bedroom apartment and it was so much space. Full kitchen with terrace, living room with TV if you want it, views of the Tuscan countryside from the windows. We had breakfast on sight each day, dinner a few times. Fresh and local ingredients. I loved walking through the property seeing the animals and in the trails through the woods. Only 5km outside of Florence, it's a great location to still do the touristy things in...

Charlotte

includes taxes & fees

2 Nov - 3 Nov

A pool with a wooden deck and lounge chairs, surrounded by trees and hills in the background.

14. Fattoria Pieve a Salti

Montalcino

Marko

includes taxes & fees

1 Nov - 2 Nov

A swimming pool with a stone wall and a bench, surrounded by lights.

15. Cordella in Montalcino Wine Resort

Montalcino

Marcelo

includes taxes & fees

14 Oct - 15 Oct

A stone building with a pool, surrounded by trees and outdoor seating.

16. Fattorie di Celli

Poppi

Samuel

includes taxes & fees

11 Oct - 12 Oct

A poolside area with lounge chairs and umbrellas, overlooking a scenic landscape.

17. Laqua Vineyard

Terricciola

nocham

includes taxes & fees

27 Oct - 28 Oct

A hot tub with stone steps leading up to it, under a pergola, with a view of distant hills.

18. Tenuta Castellare di Tonda

Montaione

"The reception was extremely helpful with all our queries even before we got to the property and really helped make sure we had a comfortable stay. The apartment came with amazing views and the basic necessities. The pool was a very nice size and kept clean for us to enjoy. We also booked a horse riding lesson which was with a great instructor and I’d highly recommend a ride if you have the time. Thanks for the hospitality! "

Shifnaz

includes taxes & fees

8 Oct - 9 Oct

A stone villa with a swimming pool, surrounded by lush gardens and flowering plants.

19. Borgo in Montalbano by Secret Hills

Larciano

includes taxes & fees

18 Oct - 19 Oct

A swimming pool with lounge chairs and umbrellas, surrounded by greenery and trees.

20. Country House Podere Casorbica

Cortona

Kristie

includes taxes & fees

4 Oct - 5 Oct

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Top Chianti Region Hotel Reviews

Hotel Toscana Ambassador

8/10 Good

"Close to train station"

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent

"From the moment we checked in, This place was a Gem. From the friendly and helpful staff to the beautiful grounds, we were so impressed. Its hard to put into words how wonderful this Hotel is. The food, and drinks were incredible. We also celebrated my wife's birthday at this resort and they did a very special dinner for us to enjoy. Along with Campaign and a personalized Birthday dessert. Special thanks to Noamie (hope i got that right). She was absolutely wonderful. I could go on forever about this Resort. So easy to explore the region while calling this a comfortable landing spot. Can't thank the team enough for a wonderful stay."

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."

Hu Norcenni Girasole Village

10/10 Excellent

"My family and I had such a great time. Such a kid friendly place and at check in they even had a little playground while you waiting and gave the kids bubbles. So great to be in nature and all of the amenities were lovely. The waterparks that were padded on the ground were genius and we did a family wine tasting which was such a lovely memory. Our stay was so nice with the deck and the grocery store is so affordable for dinners in. Love love love! My toddler played all day and there were so many times we got to relax because they had everything that we wanted or needed right on property."

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