Casole d'Elsa Country Houses

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Our top choices for Casole d'Elsa country houses

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

1. Relais la Costa - Dimora Storica

Monteriggioni

Doug

P11,087 total

includes taxes & fees

Oct 13 - Oct 14

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

2. Locanda Casalta

Strove

Manfred August

P8,306 total

includes taxes & fees

Oct 5 - Oct 6

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

3. Il Castagnolo Country B&B

San Gimignano

Allan

P8,444 total

includes taxes & fees

Oct 8 - Oct 9

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

4. Tenuta Guardastelle

San Gimignano

Sarah

P17,350 total

includes taxes & fees

Oct 10 - Oct 11

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

5. Borgo della Meliana

Gambassi Terme

Alice

P10,430 total

includes taxes & fees

Oct 8 - Oct 9

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

6. L'Aia di Argia

Monteroni d'Arbia

mario

P5,409 total

includes taxes & fees

Oct 2 - Oct 3

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

7. Podere L'Aquila

Gaiole in Chianti

Heather

P29,020 total

includes taxes & fees

Oct 8 - Oct 9

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

8. 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

P7,329 total

includes taxes & fees

Oct 8 - Oct 9

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Top Casole d'Elsa Hotel Reviews

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."

Castiglion del Bosco, A Rosewood Hotel

10/10 Excellent

"Castiglion del Bosco is truly exquisite, the perfect way to experience Tuscany in luxury while still feeling completely surrounded by nature. The property is impeccable, from the beautiful gardens and grounds to the elegant rooms. Everything feels authentically Italian, refined and incredibly well maintained. The service is exceptional and very personalized. The staff genuinely goes out of their way to make you feel welcome. General Manager Nicola Migheli even greeted us personally upon arrival, which was a lovely touch. We also saw him regularly walking the property with his team, and it was clear how hands-on he is with every detail. One thing to know is that getting in and out requires about 40 minutes on a bumpy dirt road. It wasn’t terrible, but worth mentioning if you plan to explore frequently. That said, this is a hotel you don’t need to leave. It’s a beautiful place to slow down, relax and enjoy Tuscany in a truly special setting. We absolutely loved our 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."

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