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Holiday houses in Chiassa

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Popular amenities for Chiassa holiday rentals

Other great holiday rentals in Chiassa

Guest favourite
Apartment in Pogi
4.94 out of 5 average rating, 89 reviews

Borgo Iesolana Suite Superior

RobertRating, 5 stars3 weeks ago
5 Stars – A Tuscan Dream Come True! Our stay at Francesco’s private resort-style retreat in the hills of Tuscany was absolutely magical. The location is stunning—peaceful, picturesque, and the perfect escape into the beauty of the Italian countryside. The rustic room had so much charm and comfort, and the property itself was amazing, with not one but two beautiful pools to relax by. One of the highlights was the on-site restaurant. The free breakfast was far beyond the typical offering—not just muffins, but a full, authentic Italian breakfast that we looked forward to each morning. Dinner was just as impressive, showcasing delicious local flavors and warm hospitality. It was also a great jumping-off point for exploring the region—we took a lovely day trip to Siena with ease. This place is a hidden gem, and we’d return in a heartbeat. Highly recommended for anyone looking to experience the best of Tuscany!
Guest favourite
Condo in San Gimignano
4.93 out of 5 average rating, 118 reviews

Luxury Medieval Tower - Penthouse

RussRating, 5 stars1 month ago
We stayed for 5 night and enjoyed this large, well appointed two story apartment. The place was warm and inviting and was an authentic home to be a unique setting. My family enjoyed the surroundings and there was plenty of restaurants to close from. Be prepared to tackle the 52 steps to the apartment door which my 90 year old mother managed twice a day. Keeps you healthy.
Guest favourite
Condo in Monte San Savino
4.97 out of 5 average rating, 35 reviews

La Foresteria | Casa Bianchini

NicoleRating, 5 stars2 weeks ago
Our stay at Marion’s place was incredible! She was so responsive to all my questions and needs. We stayed in the largest apartment they have and it was so wonderful to have a private bedroom and bathroom for all of our family. The linens were fresh and white and smelled like orange blossoms. We ate one night at the restaurant and the food was delicious! As we were in Tuscany for a wedding, we were not able to eat there again, but would have loved to. The grounds were beautiful and immaculate and the pool so refreshing. Luca was so helpful with anything we needed. If we ever have the opportunity, we will stay there again! Thank you for making our stay so stress-free and lovely!
Top Guest favourite
Condo in Anghiari
4.94 out of 5 average rating, 18 reviews

Agriturismo Reggello - Pendolino

VilmaRating, 5 stars1 week ago
We had a very friendly welcome when we arrived at the destination. The apartment was clean and had everything we needed. The area and surroundings, the yard and the swimming pool were lovely. Thank you!
Guest favourite
Farm stay in Sovicille
4.93 out of 5 average rating, 139 reviews

House at Gianni - Olmo

AmandaRating, 5 starstoday
Perfect get away from the hustle of the big cities. Peaceful, family oriented and very beautiful.
Guest favourite
Apartment in Castelnuovo Berardenga
4.93 out of 5 average rating, 161 reviews

Villa di Geggiano - Perellino Suite

RachelRating, 5 stars1 week ago
This estate is a dream—life changing in all the best ways. From the jasmine-scented gardens and sweeping views of Siena to the beautifully restored guest suites—personally designed by Andrea, an architect and true artist—every detail felt magical. He greeted us so warmly, spent generous time sharing the estate’s history, and even gifted us a bottle of his family’s wine—which was absolutely lovely and made us feel truly welcome. The plunge pool was a refreshing retreat, and the setting was pure tranquility: birdsong, rustling leaves, and golden Tuscan sunsets. Andrea gave us a wonderful tour and shared the story behind his family’s efforts to preserve this incredible place. We adored the gentle Maremma dogs, Fiora and her puppy, Pecorino, who made us feel right at home. We were so impressed with this stay and Andrea’s efforts to preserve this very special place. Every moment here felt like a scene from a film—elegant, peaceful, and filled with soul. We can’t wait to return.
Superhost
Condo in Castelfranco di Sopra
4.83 out of 5 average rating, 252 reviews

House between Firenze, Arezzo, chianti e Siena

Sylvie & AlainRating, 5 stars1 week 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 favorite, this place is a gem! We'll be back!
Guest favourite
Condo in Castelnuovo Berardenga
4.96 out of 5 average rating, 69 reviews

Castello di Orgiale Charme Residenz

ShellRating, 5 stars1 month ago
Property is amazing, host so friendly and helpful… Honestly we spent very little time on the property as we were exploring so much of Tuscany during our stay with the lovely location as our home base. But it was so beautiful to wake to every day and come “home” to late every evening :) During our 6 days, we explored Florence, hung out in Siena, hiked Chianti trails, visiting all over from Monteriggioni to San Gimignano to Volterra… and throughout Val d’Orcia from Montepulciano to Pienza , Pitigliano to Serano… and north to Lucca & Pisa. Just wonderful location :) Thank you so much!

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Chiassa