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Holiday houses in Chiassaia

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Popular amenities for Chiassaia holiday rentals

Other great holiday rentals in Chiassaia

Top Guest favourite
Farm stay in Arezzo
4.97 out of 5 average rating, 230 reviews

Explore nature in the center of Vigneti Chianti

BaileyRating, 5 stars5 days ago
Staying at Agrigreen La Lama was hands down the best Airbnb experience I’ve ever had. From the moment we arrived, Rita welcomed us with such warmth and hospitality that we felt at home. The property is peaceful, beautifully maintained, and full of charm—surrounded by nature and the kind of quiet that soothes the soul. One of the most memorable parts of our stay was getting to cook in Rita’s own home, which she generously opened to us. It was such a unique and personal experience that made us feel truly connected to the space and the spirit of the farm. If you’re looking for a place to slow down, feel grounded, and enjoy genuine hospitality, Rita’s space is an absolute gem. I’m already looking forward to the day I can return.
Guest favourite
Holiday home in Vitignano
4.97 out of 5 average rating, 34 reviews

Podere Vittoria Apartment: Heart of Chianti

CraigRating, 5 stars1 week ago
We absolutely loved this apartment, it was spacious and spotless, with modern bathrooms and the most perfect “farmhouse” kitchen. The view from the apartment and infinity pool was breathtaking. It’s the best Airbnb we have stayed in!
Superhost
Condo in Castelfranco di Sopra
4.83 out of 5 average rating, 250 reviews

House between Firenze, Arezzo, chianti e Siena

Sylvie & AlainRating, 5 stars2 days ago
We were immediately enchanted by this property. Everything here makes up the image that one can have of the beautiful Tuscan countryside. At the top of the hill overlooking the valley, the view is splendid and romantic. The property has been renovated with today's comforts while retaining its soul of yesteryear. You feel good right away, the energy is beneficial, nature, animals, everything is in harmony! The welcome, Oscar's cooking, the superb pool, the shaded terrace, the hearty homemade breakfasts! It's more than a crush, this place is a gem! We'll be back!
Top Guest favourite
Holiday home in Loro Ciuffenna
4.93 out of 5 average rating, 30 reviews

"Gelso" (Mulberry) 2/4p, pool, garden, view

AnnaRating, 5 stars2 days ago
We had a wonderful stay! Information and check-in were super easy thanks to Simone. The property is beautiful! The great pool and the cool house did very well. I can recommend it 100%!
Top Guest favourite
Farm stay in Pian di Scò
4.95 out of 5 average rating, 132 reviews

Agriturismo I Gelsi

GabriellaRating, 5 stars4 days ago
Eva's place is absolute heaven. We stayed for 10 days with our two small children (1 and 4) and had the most wonderful time. The apartment is perfect – beautifully decorated with everything catered for. The outside garden and terrace is great for eating with amazing views. And the pool is also wonderful – we had it to ourselves the whole time we were there. We couldn't recommend this place more! Thank you, Eva and family!
Top Guest favourite
Barn in Castellina in Chianti
5 out of 5 average rating, 26 reviews

Cipressini 2 - pool and amazing views

BrandonRating, 5 stars2 weeks ago
We cannot say enough about how fantastic our stay was. Maybe the most gorgeous property we’ve ever seen - even better than the pictures! Pia was incredibly helpful, sent us a whole printout of recommendations for different restaurants, wineries, and things to do. She is incredibly kind, responsive, and proactive - she thought of everything you may need during your stay and gave us a tour of our home. Waking up in the Tuscan countryside and watching the sun rise over the vineyards was relaxing and beautiful. The sunsets were breathtaking to see over the rolling hills in Chianti. Castellina was a cute little town with fantastic places to eat and panoramic views of the valley. And on top of all that, we made a new friend in the Public Relations Manager, Teo - you can be sure you’ll be greeted with a wagging tail and a happy little smile. Couldn’t recommend this place highly enough!
Top Guest favourite
Apartment in Terranuova Bracciolini
5 out of 5 average rating, 11 reviews

Villa Piandarca-"Sole"-Tuscany-Chianti-pool

NinaRating, 5 stars9 months ago
It was like a dream. It made us consider leaving Germany and stay in The Tuskany. Beautiful surrounding with a very nice pool area and garden with fruit trees, chickens and sweet cats. We felt very comfortable. Everyone was very friendly, helpful and kind. We would recommend Piandarca for 100% and wish to come back soon!
Top Guest favourite
Home in TERRANUOVA BRACCIOLINI,
4.96 out of 5 average rating, 139 reviews

il Fienile - (Typical Tuscan rural accommodation)

ObhiRating, 5 stars2 weeks ago
We really enjoyed our stay, except that it was too short! We will need to return for a longer stay to really allow the peace and calm there to sink in. Special thanks to Mario and his daughter for welcoming us even though we were delayed several hours by the power outage in France’s Alpes-Maritime region, where we were arriving from. The sitting area in the garden has a spectacular view of the surrounding Tuscan hills. Next time, we will make better use of it, including for star-gazing in the clear night sky.

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Arezzo
  5. Chiassaia