Chiassa Superiore Holiday Rentals

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Holiday Rentals in Chiassa Superiore

Sun-Soaked Private View Terrace in the Historical Centre of Cortona.
9.8 out of 10, Exceptional, 55 reviews
"Great comfortable apt. with spectacular terrace"
Sun-Soaked Private View Terrace in the Historical Centre of Cortona.
Charming & Luxury Historic Guest House in the Center of Arezzo ( Tuscany)
10.0 out of 10, Exceptional, 101 reviews
"Stephano goes out of his way to make his guests feel at home. The place was comfortable and spotless. We enjoyed getting to know our host and his city. The kitchen is well appointed with a well stocked wine rack. Read through the reviews, they are accurate! Comfortable bedding, lovely surroundings and, oh yes, a wonderful bakery across the street. Highly recommended!"
Charming & Luxury Historic Guest House in the Center of Arezzo ( Tuscany)
Charming Tuscan villa with private pool, wide garden and breathtaking view
10.0 out of 10, Exceptional, 109 reviews
"The moment we pulled up to Casa Fontaine, our reaction was "Wow." The amenities were great, the property beautiful and the weather cooperated. We visited the surrounding villages, hiked trails and enjoyed reading by the pool Gianfranco was the ultimate host, so helpful in all aspects of our visit. Thank you."
Charming Tuscan villa with private pool, wide garden and breathtaking view
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Castello di Gargonza
3.0 star property
9.0 out of 10, Wonderful, 33 reviews
"Beautiful area and friendly staff. We stayed here several years ago and were so excited to return."
The price is NZ$385
per night
11 Jun - 12 Jun
Castello di Gargonza
Casa Bacco - private house with a remarkable garden in the centre of Cortona
Casa Bacco - private house with a remarkable garden in the centre of Cortona
Traditional stone cottage in rural, tranquil and quiet location built in 1799
10.0 out of 10, Exceptional, 31 reviews
"property and hosts were great. the drive down to it was an experience not to miss. you could hear a pin drop if it wasn't for the birds songs all day. thank you John and Diana for a brill time. 11 stars 🌟"
Traditional stone cottage in rural, tranquil and quiet location built in 1799
"Villa Stefania" Old Tuscan Farmhouse - Great View on Cortona
10.0 out of 10, Exceptional, 56 reviews
"Where to even begin? We loved everything about our stay. Stefania was wonderful, and responsive to our many questions before we even arrived. Upon arrival, it felt like a dream. The Villa is beautiful, private, and expansive. The property is huge, with lots of olive trees, fig trees, and places for the kids to play and explore. And not to mention the stunning pool, which overlooks the most incredible views of Cortona. We were pleased to find a ping pong table, and just absolutely loved the pool...
"Villa Stefania" Old Tuscan Farmhouse - Great View on Cortona
Ultra Stunning 2 Br Apt In Tuscany, With Pool, Stoned Arch And Wooden Beams.
9.8 out of 10, Exceptional, 40 reviews
"Wow, wow, wow. This property delivered on so many fronts! It was even better than we anticipated. Next year we plan to stay here for 2 weeks. The view was spectacular, location was excellent. Lucia was a perfect host!"
Ultra Stunning 2 Br Apt In Tuscany, With Pool, Stoned Arch And Wooden Beams.
Villa Calcinaio - Holiday Country Villa with swimming pool in Cortona
9.4 out of 10, Exceptional, 40 reviews
"Just on the slope nestled between Cortona city and the Calcinaio church, the location was perfect for us. We enjoyed the serenity of no one immediately around us while only being a very short drive from the city walls. (Admittedly, we could have walked, but driving was easier!) Taking day trips to various Tuscan cities and sights was wonderfully served by the central location."
Villa Calcinaio - Holiday Country Villa with swimming pool in Cortona
Secluded Villa, private heated Pool, Wi-fi and TV. Secure Payment
9.6 out of 10, Exceptional, 14 reviews
"We enjoyed a lovely week in Val di Chiana in this beautiful remote spot. The hosts helped us to find the property when we first got there. The house is great. There were some issues with the water supply but they responded to the problem very promptly."
Secluded Villa, private heated Pool, Wi-fi and TV. Secure Payment
17th century farmhouse with private pool and Wi-Fi and air conditioning
9.4 out of 10, Exceptional, 32 reviews
"This property is located approx 5km from the beautiful town of Arezzo. There is a bus every hour, daily, from Tregozanno, where the property is actually located, to Arezzo. It is very rustic and in a beautiful setting. So relaxing. And, because it’s not right in town, the best of both worlds. There are no restaurants in Tregozanno but there is a great butcher and deli/mini market. There is also a pharmacy and bar! Maurizio, the owner lives next door and is the loveliest, most helpful human being...
17th century farmhouse with private pool and Wi-Fi and air conditioning
House consists of a "two-room" and a "trilocale", Valdarno Aretino
10.0 out of 10, Exceptional, 45 reviews
"This is a well contained villa with a beautiful garden surrounding the property. As a group of friends we enjoyed all the comforts of the property including the swimming pool. Spent relaxing times in the porch beside the kitchen. The bedrooms are well furnished and clean. The kitchen is well equipped. The hosts Santa and Giovanni are lovely and stocked the kitchen with complimentary essentials and drinks. They also provided some vegetables from their allotment which was very kind of them. We...
House consists of a "two-room" and a "trilocale", Valdarno Aretino
Casale Chiesina. Villa in Tuscany for the EXCLUSIVE USE of the guest.
10.0 out of 10, Exceptional, 5 reviews
"Highly recommended for the view, the pergola, the pool and all other amenities. We had a great and peaceful time. Just as we imagined Tuscany."
Casale Chiesina. Villa in Tuscany for the EXCLUSIVE USE of the guest.
Relais Villa Belpoggio - Residenza d'Epoca
9.8 out of 10, Exceptional, 31 reviews
"Excellent getaway- beautiful property - great staff - extremely clean - I give it a 100"
The price is NZ$290
per night
17 Jun - 18 Jun
Relais Villa Belpoggio - Residenza d'Epoca
Farmhouse in the Tuscan countryside
10.0 out of 10, Exceptional, 11 reviews
"A huge apartment, with all the home comforts, in a stunning rural setting. It would benefit from fans in the bedrooms, which did get very hot, but everything else was amazing."
Farmhouse in the Tuscan countryside
NEW!!! Fenice, Tuscan Villa, Private pool, stunning scenery, WIFI, chef option!
10.0 out of 10, Exceptional, 21 reviews
"Absolutely superb hosts. Nothing was too much trouble. We had two delicious meals cooked by Linda and we left with her homemade limoncello and olive oil. Peaceful, beautiful grounds with wonderful walks straight from the house. Tennis club 5 min drive away, and a local train station that whisked us off to Florence for the day. Don't miss Snoopy's gelato in the local town. This holiday was a 5* experience."
NEW!!! Fenice, Tuscan Villa, Private pool, stunning scenery, WIFI, chef option!
Farmhouse in the hills with panoramic view and swimming pool
9.6 out of 10, Exceptional, 58 reviews
"A super holiday. The location is superb with many places of interest within a 1 hour drive. Pool was maintained well and clean. We had a great 2 weeks."
Farmhouse in the hills with panoramic view and swimming pool
Giglio Dorato is an antique restored stone farmhouse with indipendent apartments
Giglio Dorato is an antique restored stone farmhouse with indipendent apartments
Mansion - Arezzo
9.4 out of 10, Exceptional, 16 reviews
"Arezzo proved to be a great jumping off point for a number of our favourite destinations in central Italy. We returned to Firenze and Siena and visited, for the first time, Arezzo, Anghiari and San Marino, all of which were in easy reach. The accommodation was perfect in every way for us. A quiet spot, conveniently close to Arezzo and the essential shops for a self-catering holiday. The rooms were nicely appointed and the accommodation included almost everything necessary for our stay, including...
Mansion - Arezzo
Villa Primula - Holiday Rental in Cortona, Tuscany
9.6 out of 10, Exceptional, 45 reviews
"A great villa for a 3 generation group; lovely pool and garden with plenty of outside furniture. Cafes, shops and transport are within walking distance. Spacious rooms and well equipped kitchen. Owner very helpful."
Villa Primula - Holiday Rental in Cortona, Tuscany
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See all available properties in Chiassa Superiore
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Chiassa Superiore you may be interested in

Relais La Torre
9.0 out of 10, Wonderful, 31 reviews
"Gorgeous property, lovely Tuscan experience and wonderful people. They did an exceptional job restoring such an old property. Quiet, peaceful and lovely experience. "
The price is NZ$249
per night
13 Jun - 14 Jun
Relais La Torre
Monastero di Cortona Hotel & Spa
5.0 star property
10.0 out of 10, Exceptional, 171 reviews
"What a beautiful place. Staff was amazing, so helpful in every way. Lovely breakfasts in the garden. Their bartender fixes some incredible cocktails and the one night we had dinner in the hotel restaurant, everything was delicious. A word of advice: If you’re driving, insist on a SMALL rental car. Cortona is full of tiny curvy cobblestone streets some of which you must drive through to get to and from the hotel. We were offered an upgrade to a Jeep with the turning radius of a semi truck and...
The price is NZ$558
per night
1 Jul - 2 Jul
Monastero di Cortona Hotel & Spa
Il Borro - Relais & Châteaux
9.2 out of 10, Wonderful, 60 reviews
"Il Borro is absolute luxury as only the Ferragamo family could do without being ostentatious. The service is also commensurate. "
The price is NZ$1,028
per night
21 Jun - 22 Jun
Il Borro - Relais & Châteaux
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Chiassa Superiore holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Chiassa Superiore. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Chiassa Superiore. Seeing all the best attractions is bound to make you fall in love with Chiassa Superiore. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Chiassa Superiore short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Chiassa Superiore?

Yes, there are holiday rentals close to the most popular sights in Chiassa Superiore, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Chiassa Superiore has to offer?

STONE HOUSE IN THE HEART OF TUSCANY WITH LARGE GARDEN AND SWIMMING POOL: This holiday home rental outside of Chiassa Superiore is located in the mountains, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of garden in this rental home to help you unwind.

How many holiday rentals are there in Chiassa Superiore?

With 5 Expedia holiday rentals, you're guaranteed to find just the right place for your Chiassa Superiore stay.

What’s there to see and do in Chiassa Superiore?

While exploring the area, visit family-friendly sights like Arezzo Equestrian Centre, or get outside and enjoy nature at Piazza Guido Monaco. In the wider area, you’ll find Castelnuovo di Subbiano and Cathedral of Saints Peter and Donato.

What’s a holiday rental in Chiassa Superiore like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chiassa Superiore. Holiday rentals provide amenities such as WiFi and washers and dryers so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can offer a sense of privacy away from shared hotel lifts and busy concierge desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for a family trip or a small group gathering.

Recent reviews of Chiassa Superiore properties
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