Chiassa Superiore Holiday Rentals

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Our top choices for Chiassa Superiore holiday rentals

Townhouse in Loro Ciuffenna

Villa Cassia di Baccano
9.4 out of 10, Exceptional, (23)
"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is AU$225
includes taxes & fees
7 Jan - 8 Jan 2026
Villa Cassia di Baccano

Townhouse in Arezzo

THE MONNA LISA RESORT
9.6 out of 10, Exceptional, (8)
"Massimiliano was a great host, but we were the only guests and the restaurant was closed. The hotel was basically unmanaged. It should not have been listed as a hotel. "
United States
Bart
The price is AU$215
includes taxes & fees
19 Dec - 20 Dec
THE MONNA LISA RESORT

Townhouse in Monte San Savino

DormiVeglia B&B
10.0 out of 10, Exceptional, (27)
"This was our favourite B&B. The owner Simona was absolutely wonderful. The hot tub in our room was out of this world. If you have the chance to visite this gem…DO IT!!"
Canada
Claude
DormiVeglia B&B

Townhouse in Subbiano

Villa La Ginestra
9.6 out of 10, Exceptional, (5)
"Le charme de l'endroit, l'attention de l'hôte, le confort, le déjeuner delicieux."
Canada
Philippe
Villa La Ginestra

Townhouse in Castiglion Fiorentino

San Michele al Borgo
9.8 out of 10, Exceptional, (9)
"Excellent staff and tasty breakfast!"
United States
Vern
The price is AU$222
includes taxes & fees
11 Dec - 12 Dec
San Michele al Borgo

Townhouse in Arezzo Centro Storico

Cameracaffè Centro
8.6 out of 10, Excellent, (179)
"Great room and wonderful staff. Loved the breakfast from the veranda with both a view of the mountains and the city center. "
United States
Keith
The price is AU$143
includes taxes & fees
15 Dec - 16 Dec
Cameracaffè Centro

Apartment in Città di Castello

Elegant Countryside Retreat
The price is AU$330
includes taxes & fees
10 Jan - 11 Jan 2026
Elegant Countryside Retreat

Townhouse in Anghiari

Locanda del Viandante
9.0 out of 10, Wonderful, (6)
"Smuk beliggenhed - meget autentisk på den gode måde"
Denmark
tina
The price is AU$236
includes taxes & fees
11 Dec - 12 Dec
Locanda del Viandante

Apartment in Arezzo Centro Storico

Deluxe room Cartazucchero in the heart of Arezzo
10.0 out of 10, Exceptional, (2)
"From all the places we stayed during our 13-day trip to Italy, this was by far our favorite. Fabio was incredibly communicative and friendly right from the start, sending us clear instructions on how to get there. He greeted us at the door with such warmth that it truly felt like we were staying with family. The room was spotless, beautifully decorated, and generously stocked with water, cookies, pastries, and other treats. It had the comfort and attention to detail of a hotel, yet the warmth of...
United States
Hector
The price is AU$125
includes taxes & fees
7 Jan - 8 Jan 2026
Deluxe room Cartazucchero in the heart of Arezzo

Apartment in Pergine Valdarno

Casa Vacanze Le Fornaci
9.4 out of 10, Exceptional, (3)
"We absolutely loved our stay at this hotel. The suite was perfect and the restaurant had probably the best food I have had in Tuscany. We definitely plan to stay there again."
United States
Gregory
The price is AU$222
includes taxes & fees
3 Jan - 4 Jan 2026
Casa Vacanze Le Fornaci

Apartment in Montevarchi

Cennano Suite - enter apartment
10.0 out of 10, Exceptional, (3)
"After and before the tourist rushes of Florence. I enjoyed a few very quiet and relaxing days in a beautiful and spacious place. "
Germany
Judith T.
The price is AU$201
includes taxes & fees
26 Dec - 27 Dec
Cennano Suite - enter apartment
10.0 out of 10, Exceptional, (6)
"This place was such a great find! So central and easily reachable. We really enjoyed our stay!"
United States
Julie R.
The price is AU$171
includes taxes & fees
15 Dec - 16 Dec
City / Village Apartment in Cortona with 1 bedrooms sleeps 2
10.0 out of 10, Exceptional, (1)
"Large apartment 4 floors above the town. Easy walking to anywhere in the area. Great shower and large bathroom. Equipped kitchen with big refrigerator. Living room with TV and dining table and couch. Large bedroom with fan. Also, there is a hairdryer and ironing board and iron. You are very close to walk to restaurants and stores, About a mile from the train station up a hill but the hostess helped us with transport.Overall, an excellent stay for my wife and I. (Be aware the room is 4...
United States
aric w.
The price is AU$248
includes taxes & fees
30 Dec - 31 Dec
The window on the tower apartment new castiglion fiorentino

Townhouse in Arezzo Centro Storico

B&B 52cento
8.0 out of 10, Very good, (73)
"Exactly how it is described and very near the train station. Walkable distance to all the things to do around there. I really enjoyed my stay there. "
United States
Maria de Lourdes
The price is AU$162
includes taxes & fees
9 Jan - 10 Jan 2026
B&B 52cento

Apartment in Cortona Old Town

La casa di Laura
10.0 out of 10, Exceptional, (1)
"Best sleep I’ve had in a long time. Very quiet area. Beautiful views. Absolutely gorgeous. Water and coffee were provided. Clean. Bruno was very patient with us with the language barrier. We also had trouble getting to the place because we were not getting service on our phone till we connected to WiFi. Bruno met us and showed us where to park after showing us the way to the apartment. Very steep climb up to the apartment from the parking area, but Cortona is overall steep. You will climb up...
United States
Angie F.
The price is AU$296
includes taxes & fees
11 Dec - 12 Dec
La casa di Laura

Apartment in Arezzo Centro Storico

Living suite Verdeconiglio in the heart of Arezzo
10.0 out of 10, Exceptional, (1)
"It was a beautiful and quiet part of town and was very close to everything. The property manager spoke pretty good English which made everything much easier. It is a beautiful comforting and clean stay in the heart of Arezzo. Thank you. Era una zona bellissima e tranquilla della città, vicinissima a tutto. Il gestore parlava un ottimo inglese, il che ha reso tutto molto più semplice. È stato un soggiorno splendido, confortevole e pulito nel cuore di Arezzo. Grazie."
United States
Andrew T.
The price is AU$156
includes taxes & fees
7 Jan - 8 Jan 2026
Living suite Verdeconiglio in the heart of Arezzo
9.8 out of 10, Exceptional, (35)
"Excellent getaway- beautiful property - great staff - extremely clean - I give it a 100"
United Kingdom
Mona
The price is AU$271
includes taxes & fees
11 Dec - 12 Dec
Relais Villa Belpoggio - Residenza d'Epoca

Townhouse in Arezzo Centro Storico

Allegra Toscana - Affittacamere Guest house
7.0 out of 10, Good, (16)
"Great location in Arezzo, easy and simple to find and access. Everything was exactly as we needed although we did not need to stay long."
United Kingdom
Justin
Allegra Toscana - Affittacamere Guest house

Apartment in Arezzo Centro Storico

Deluxe room Chocolate in the heart of Arezzo
The price is AU$125
includes taxes & fees
8 Jan - 9 Jan 2026
Deluxe room Chocolate in the heart of Arezzo

Holiday Home in Castiglion fibocchi

Casa Da Vinci for two
8.0 out of 10, Very good, (1)
"Sauber gemütlich, nette Atmosphäre Einrichtung ist ausreichend."
Germany
Perdita I.
The price is AU$122
includes taxes & fees
6 Jan - 7 Jan 2026
Casa Da Vinci for two
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.
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Top Chiassa Superiore Hotel Reviews

Find out more about Chiassa Superiore

Everything you need to know about Chiassa Superiore holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chiassa Superiore holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chiassa Superiore holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Chiassa Superiore holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chiassa Superiore. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chiassa Superiore holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chiassa Superiore holiday rentals we have selected for you start as low as AU$222 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Chiassa Superiore rentals

At Expedia, we put the best Chiassa Superiore holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chiassa Superiore rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chiassa Superiore holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chiassa Superiore. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Farmhouse in the hills with panoramic view and swimming pool: This holiday home rental outside of Chiassa Superiore is located in a rural location, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of garden in this rental home to help you unwind.

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

While exploring the area, visit family-friendly sights like Aboca Museum, 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.