Chiassa Superiore Vacation Rentals

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In two weeks
Sep 19 - Sep 21
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Oct 31 - Nov 2
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Nov 28 - Nov 30
In four months
Dec 26 - Dec 28

Vacation Rentals in Chiassa Superiore

Sun-Soaked Private View Terrace in the Historical Centre of Cortona.
Outdoor dining

Sun-Soaked Private View Terrace in the Historical Centre of Cortona.

9.6 out of 10, Exceptional, (71)
"My husband and I loved our stay here! It was so close to town and the terrace was absolutely stunning. Would definitely stay here again! "
Sun-Soaked Private View Terrace in the Historical Centre of Cortona.
Unwind under the Tuscan sun, La Casina, Pet friendly, family villa in Tuscany.
Outdoor dining

Unwind under the Tuscan sun, La Casina, Pet friendly, family villa in Tuscany.

2.0 out of 10, (1)
Unwind under the Tuscan sun, La Casina, Pet friendly, family villa in Tuscany.
Secluded Villa, private heated Pool, Wi-fi and TV. Secure Payment
Outdoor dining

Secluded Villa, private heated Pool, Wi-fi and TV. Secure Payment

9.2 out of 10, Wonderful, (27)
"Family of 7 adults spent 1 week in beautiful secluded Tuscan farmhouse. Great location for visiting the region - Arezzo short drive. Florence Pisa approx. 1.5 hours. Beautiful hilltop villages, olive groves and vineyards. Quintessential Tuscany!"
Secluded Villa, private heated Pool, Wi-fi and TV. Secure Payment
Castello di Gargonza
Exterior

Castello di Gargonza

3.0 star property
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. "
Castello di Gargonza
17th century farmhouse with private pool and Wi-Fi and air conditioning
Outdoor pool

17th century farmhouse with private pool and Wi-Fi and air conditioning

9.4 out of 10, Exceptional, (37)
"Our host Maurizio, added quite a few extra layers of enjoyment to our stay. A brilliant host who went above and beyond to make our holiday truely memorable! We have invited him to come stay with us when he visits Australia. As for the farm house it’s self, an amazing experience to live like a true Italian. If you want to experience country life, I recommend La Rustica! Thank you Maurizio and Simonetta. ❤️"
17th century farmhouse with private pool and Wi-Fi and air conditioning
Farmhouse in the hills with panoramic view and swimming pool
Pool

Farmhouse in the hills with panoramic view and swimming pool

9.6 out of 10, Exceptional, (71)
"We‘ve spent two wonderful weeks with our two year old daughter and our dog. The house is beautifully located in the hills with no direct neighbours. The view is fantastic and we felt immediately at home in this beautiful house. We had a wonderful time and our hosts were just lovely. (We cannot say anything about the pool - except that it is huge - because we were there out of season in March when the pool was closed.)"
Farmhouse in the hills with panoramic view and swimming pool
Family-friendly Cottage in authentic stone style Swimmingpool Wine Relax Wif
Outdoor pool

Family-friendly Cottage in authentic stone style Swimmingpool Wine Relax Wif

9.2 out of 10, Wonderful, (23)
"Its a nice place but it is on top of a hill with a really small road to it...almost no place to pass another car. When we arrived the host thought we would arrive the day after, so we had to wait for another hour for the key. The house was fine, big enough, nice bedrooms and living room and kitchen is fine. The pool is great! The winery is super and really tastefull! We had a nice vacation."
Family-friendly Cottage in authentic stone style Swimmingpool Wine Relax Wif
Charming Tuscan villa with private pool, wide garden and breathtaking view
Outdoor pool

Charming Tuscan villa with private pool, wide garden and breathtaking view

10.0 out of 10, Exceptional, (123)
"Very clean, big house, nice oven, cozy, amazing view, big pool, close to arezzo and firenze with a very kind owner of the house. "
Charming Tuscan villa with private pool, wide garden and breathtaking view
Charming & Luxury Historic Guest House in the Center of Arezzo ( Tuscany)
Fridge, microwave, oven, stovetop

Charming & Luxury Historic Guest House in the Center of Arezzo ( Tuscany)

10.0 out of 10, Exceptional, (129)
"This place is amazing and was by far the best part of our trip! It was artfully and thoughtfully restored with a huge stone fireplace, large spacious rooms, and beautiful new modern bathrooms with all the extras. Stefano was the best host I have ever stayed with, was on the property to help whenever needed and provided us with many recommendations for restaurants and wineries. We absolutely loved our cooking class with you. Our family will forever fondly remember this trip because of you - and...
Charming & Luxury Historic Guest House in the Center of Arezzo ( Tuscany)
Relais Villa Belpoggio - Residenza d'Epoca
View from property

Relais Villa Belpoggio - Residenza d'Epoca

9.8 out of 10, Exceptional, (35)
"Excellent getaway- beautiful property - great staff - extremely clean - I give it a 100"
$164 nightly
The price is $180
Sep 30 - Oct 1
Total with taxes and fees
Relais Villa Belpoggio - Residenza d'Epoca
Pretty Tuscan House next Anghiari, 8/14 guest,Pool, A.C WI.FI Family LAST WEEK
Outdoor dining

Pretty Tuscan House next Anghiari, 8/14 guest,Pool, A.C WI.FI Family LAST WEEK

10.0 out of 10, Exceptional, (21)
"Fantastic maintained Villa with great layout for a big family. Beautiful surroundings. Staff easy to reach 24/7. Definatly a place to return to."
Pretty Tuscan House next Anghiari, 8/14 guest,Pool, A.C WI.FI Family LAST WEEK
Large stone manor with 8BR and 7BA, extended grounds, large fully-equipped pool.
Dining

Large stone manor with 8BR and 7BA, extended grounds, large fully-equipped pool.

9.4 out of 10, Exceptional, (12)
"Surrounding very nice and quiet. Accomodation very comfortable and huge garden. Large Shilling pool. Everything compiled to have a very nice stay."
Large stone manor with 8BR and 7BA, extended grounds, large fully-equipped pool.
Casa Bacco - private house with a remarkable garden in the centre of Cortona
Outdoor dining

Casa Bacco - private house with a remarkable garden in the centre of Cortona

10.0 out of 10, Exceptional, (8)
"This is a lovely property. Plenty of room. Well equipped with everything you need. The courtyard is a beautiful place for breakfast in the morning and wine in the evening. The flowers planted in the courtyard are beautiful. Please be aware that you must be able to walk up steep hills to get to this property. Of course, pretty much anywhere you go in Cortona is a hill."
Casa Bacco - private house with a remarkable garden in the centre of Cortona
Old Tuscan farmhouse with salt pool, soccer/volleyball field, barbecue
Pool

Old Tuscan farmhouse with salt pool, soccer/volleyball field, barbecue

10.0 out of 10, Exceptional, (43)
"Federica and Giuseppe were wonderful hosts - great communication throughout the stay and always available. The house was immaculate and well presented. The pool and facilities (swing, table tennis, football pitch etc) were superb. Views were incredible and the area was so peaceful. Highly recommend this villa for a restful break!"
Old Tuscan farmhouse with salt pool, soccer/volleyball field, barbecue
Villa Calcinaio - Holiday Country Villa with swimming pool in Cortona
Pool

Villa Calcinaio - Holiday Country Villa with swimming pool in Cortona

9.2 out of 10, Wonderful, (45)
"Great location in Tuscany! tight roads in and out of the property, must it has the most spectacular views around. 3 min. drive to Cortona.The villa is spacious and very accomodating. Just be sure to ask how to use the dishwasher and washing machine. "
Villa Calcinaio - Holiday Country Villa with swimming pool in Cortona
Typical Tuscan Residence near the farm la Vialla
Outdoor spa tub

Typical Tuscan Residence near the farm la Vialla

9.2 out of 10, Wonderful, (11)
"Wir fühlten uns in der Toskana sehr wohl. Die Übergabe war sehr gut und die Vermieterin sehr freundlich. Die Wegbeschreibung könnte etwas genauer sein. Das Geschirr war leider schmutzig. Nachdem wir es gespült hatten, fühlten wir uns wohl. Wetterbedingt war es sehr kalt und feucht in der Wohnung. Wir bekamen auf Nachfrage den Pelletofen angemacht. Für die Pellets hatten wir Zusatzkosten, dass muss man wissen. Ohne Heizung hätte man es nicht ausgehalten. Leider hat es im auch sehr aus dem Ausguss...
Typical Tuscan Residence near the farm la Vialla
Spacious Villa Noble With All the Comfort, Located In A Peaceful Location Arezzo
Outdoor pool

Spacious Villa Noble With All the Comfort, Located In A Peaceful Location Arezzo

10.0 out of 10, Exceptional, (18)
"This worked out really well for our extended family across 3 generations. Lots of space, great amenities, and we loved Arezzo. Liliana is a brilliant host"
Spacious Villa Noble With All the Comfort, Located In A Peaceful Location Arezzo
Beautiful Tuscan Villa with large garden and ample outside space
Outdoor pool, a heated pool

Beautiful Tuscan Villa with large garden and ample outside space

10.0 out of 10, Exceptional, (57)
"Our stay was really nice. The house is wonderful, the pool and the garden also. The kitchen is huge Just right for 8 people. The sight from the pool over the hills is great"
Beautiful Tuscan Villa with large garden and ample outside space
Villa Vallorsaia with private pool, lake view, no neighbors
Pool

Villa Vallorsaia with private pool, lake view, no neighbors

10.0 out of 10, Exceptional, (14)
"We had a joint family holiday and a small wedding towards the end of the week. The location is beautiful and Chiara was very pleasant to communicate with. We recommend the wine tasting! "
$1,364 nightly
The price is $1,364
Sep 4 - Sep 5
Total with taxes and fees
Villa Vallorsaia with private pool, lake view, no neighbors
Exlusive Villa with swimming pool and SPA 18 guests
Pool

Exlusive Villa with swimming pool and SPA 18 guests

10.0 out of 10, Exceptional, (43)
"Perfectly located. The villa fit our extended family quite well. We enjoyed the pool, well equipped central kitchen and the walkable town of Poppi"
Exlusive Villa with swimming pool and SPA 18 guests
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

Find out more about Chiassa Superiore

Everything you need to know about Chiassa Superiore vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chiassa Superiore vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chiassa Superiore vacation 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 low season months. For more hustle and bustle, you may prefer to visit Chiassa Superiore in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $180 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chiassa Superiore rentals

At Expedia, we put the best Chiassa Superiore vacation 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 vacation.

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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Chiassa Superiore?

Yes, there are vacation rentals near popular sights in Chiassa Superiore, or you can go with a more remote option if you're looking for relaxation.

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

Farmhouse in the hills with panoramic view and swimming pool: This vacation home near Chiassa Superiore is located in a rural location and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. Make the most of the 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 Arezzo Equestrian Centre, or get outside and enjoy nature at Piazza Guido Monaco. In the larger area, you’ll find Cathedral of Saints Peter and Donato and Church of Santa Maria della Pieve.

What’s a vacation rental in Chiassa Superiore like?

Vacation rentals are privately owned properties you can stay in for a few weeks or just a few days in Chiassa Superiore. Vacation rentals feature amenities such as WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of safety away from shared hotel elevators and busy front desks while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental a popular choice for families.