Holiday Rentals in Chiassa Superiore

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Check prices for these dates

In two weeks
19 Dec - 21 Dec
In two months
30 Jan - 1 Feb
In three months
27 Feb - 1 Mar
In four months
27 Mar - 29 Mar

Holiday Rentals in Chiassa Superiore

Lobby lounge
Villa Cassia di Baccano

Villa Cassia di Baccano

Loro Ciuffenna
9.4 out of 10, Exceptional, (23)
"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is €135
includes taxes & fees
9 Dec - 10 Dec
Villa Cassia di Baccano
Classic Double or Twin Room, 1 Double Bed
THE MONNA LISA RESORT

THE MONNA LISA RESORT

Arezzo
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 €123
includes taxes & fees
19 Dec - 20 Dec
THE MONNA LISA RESORT
Daily buffet breakfast (EUR 10 per person)
DormiVeglia B&B

DormiVeglia B&B

Monte San Savino
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
Free daily cooked-to-order breakfast
San Michele al Borgo

San Michele al Borgo

Castiglion Fiorentino
9.8 out of 10, Exceptional, (9)
"Excellent staff and tasty breakfast!"
United States
Vern
The price is €132
includes taxes & fees
9 Dec - 10 Dec
San Michele al Borgo
Balcony
Cameracaffè Centro

Cameracaffè Centro

Arezzo Centro Storico
8.6 out of 10, Excellent, (178)
"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 €91
includes taxes & fees
15 Dec - 16 Dec
Cameracaffè Centro
Exterior
Castello di Gargonza

Castello di Gargonza

3.0 star property
Monte San Savino
9.2 out of 10, Wonderful, (39)
"All of the hotel staff did an outstanding job. Our room had everything we needed and the restaurant was great. Breakfast was exceptional. Special shoutout to Neri, the owner, for taking such good care of us. "
United States
Diane
Castello di Gargonza
View from property
Relais Villa Belpoggio - Residenza d'Epoca

Relais Villa Belpoggio - Residenza d'Epoca

Loro Ciuffenna
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 €155
includes taxes & fees
5 Dec - 6 Dec
Relais Villa Belpoggio - Residenza d'Epoca
Fridge, microwave, oven, stovetop
Cennano Suite - enter apartment

Cennano Suite - enter apartment

Montevarchi
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 €117
includes taxes & fees
23 Dec - 24 Dec
Cennano Suite - enter apartment
Property grounds
La casa di Laura

La casa di Laura

Cortona Old Town
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 €200
includes taxes & fees
4 Jan - 5 Jan 2026
La casa di Laura
Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas
Villa La Ginestra

Villa La Ginestra

Subbiano
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
1 bedroom, travel cot, free WiFi
City / Village Apartment in Cortona with 1 bedrooms sleeps 2

City / Village Apartment in Cortona with 1 bedrooms sleeps 2

Cortona Old Town
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 €98
includes taxes & fees
5 Dec - 6 Dec
City / Village Apartment in Cortona with 1 bedrooms sleeps 2
Property grounds
Deluxe room Cartazucchero in the heart of Arezzo

Deluxe room Cartazucchero in the heart of Arezzo

Arezzo Centro Storico
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 €86
includes taxes & fees
9 Dec - 10 Dec
Deluxe room Cartazucchero in the heart of Arezzo
Outdoor dining
Apartment "La Finestra sul Fiume" with Private Terrace

Apartment "La Finestra sul Fiume" with Private Terrace

Subbiano
10.0 out of 10, Exceptional, (3)
"Pros: Tutto molto pulito, il proprietario si è rivelata una persona gentilissima e molto disponibile"
Italy
Anonymous traveller
The price is €85
includes taxes & fees
9 Dec - 10 Dec
Apartment "La Finestra sul Fiume" with Private Terrace
Fridge, oven, stovetop, electric kettle
The window on the tower apartment new castiglion fiorentino

The window on the tower apartment new castiglion fiorentino

Castiglion fiorentino
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 €144
includes taxes & fees
5 Dec - 6 Dec
The window on the tower apartment new castiglion fiorentino
Front of property
Locanda Antico Borgo

Locanda Antico Borgo

Civitella in Val di Chiana
9.2 out of 10, Wonderful, (20)
"What an absolutely beautiful stay, in a stunning place. Our host was attentive and kind, and the food was wonderful. The hotel and rooms were spotlessly clean, and particularly for my needs on a road trip with my 18 year old son, the accommodation offering two adjoining bedrooms was perfect, and we could park outside. Also very good value in my opinion. I would definitely return, it’s also ideal for couples and I would love to bring my wife here. "
United Kingdom
Mr Andy
Locanda Antico Borgo
Business centre
Allegra Toscana - Affittacamere Guest house

Allegra Toscana - Affittacamere Guest house

Arezzo Centro Storico
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
Dining
Zero Point

Zero Point

San Giovanni Valdarno
8.0 out of 10, Very good, (3)
"Sehr freundliche Vermieter, hat alles super funktioniert."
Germany
Familie K.
The price is €177
includes taxes & fees
5 Dec - 6 Dec
Zero Point
1 bedroom, desk, iron/ironing board, WiFi
Cortona Shabby Chic House<br>(Independent & balcony)

Cortona Shabby Chic House<br>(Independent & balcony)

Cortona Old Town
10.0 out of 10, Exceptional, (3)
"Greatly enjoyed staying here. Beautiful place and beautiful town! Thank you!"
United States
Erin
The price is €120
includes taxes & fees
8 Dec - 9 Dec
Cortona Shabby Chic House<br>(Independent & balcony)
Exterior
Sanniccolo'20 - Historic Residence

Sanniccolo'20 - Historic Residence

Arezzo Centro Storico
10.0 out of 10, Exceptional, (1)
"We stayed in the apartment for two nights with a family of four. The apartment is in a great location that is walkable to all the main areas of Arezzo. Close to shops and restaurants and the main piazza. The apartment was clean and plenty of room for a family of four. The communication was great and very easy to locate the apartment from the train station and enter the building. We loved our stay and would definitely stay again."
United States
Tony V.
The price is €158
includes taxes & fees
28 Dec - 29 Dec
Sanniccolo'20 - Historic Residence
Terrace/patio
Casa Vacanze Le Fornaci

Casa Vacanze Le Fornaci

Pergine Valdarno
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 €127
includes taxes & fees
3 Jan - 4 Jan 2026
Casa Vacanze Le Fornaci
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

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

10/10 Excellent
"Our arrival experience was less than stellar for a warm welcome to property. Front desk associate was very cold and accusatory of the situation we encountered outside of the property. We have traveled extensively and I expected better arrival experience. It all changed for the better when we finally got to our amazing suite and befriending two amazing individuals in the hotel bar. The roof top suite was absolutely amazing! The room is quiet, private and much larger than described on the site. We absolutely loved the room and the privacy. The rooftop suite is the best in the house! Claudio in the bar and Salvatore the sommelier are stellar to guests, they turned around the entire experience! I let them know what had happened upon arrival and they immediately got the GM to reach out to us. Lara, the GM is amazing and quickly made our experience turn into something so special, as we wanted! She is an incredible woman and turned our stay into an incredible experience! The breakfast is nothing less than wonderful and the service in their restaurants are so attentive and the food was delicious. Hands down, I would love to go back again. They certainly made things right by making our romantic stay, exactly what I wanted. They made us feel heard and valued and welcomed at this once in a lifetime experience. We made friends that we will cherish and memories that we will never forget! Claudio, Lara and Salvatore really made our stay exactly what we needed and wanted! "
heather 2-night trip
Posted 11 days ago
Monastero di Cortona Hotel & Spa

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, apart-hotels, 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 favorite 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 depends 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 €127 per night. Entering your travel dates in the search wizard you might find 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.