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Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Chiaveretto holiday rentals

Lobby lounge
Villa Cassia di Baccano

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 ฿3,762
฿4,138 total
includes taxes & fees
6 Jan - 7 Jan 2026
Villa Cassia di Baccano
Classic Double or Twin Room, 1 Double Bed | Premium bedding, down duvets, pillow-top beds, minibar
THE MONNA LISA RESORT

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 ฿4,642
฿5,326 total
includes taxes & fees
1 Jan - 2 Jan 2026
THE MONNA LISA RESORT
Balcony
Dolce Rosa Centro Storico

Dolce Rosa Centro Storico

Dolce Rosa Centro Storico
Sansepolcro
9.6 out of 10, Exceptional, (13)
"Ottimo rapporto qualità prezzo camera carina... un unico neo mancavano i tappi di vasca e bidet..."
Italy
Sergio
Dolce Rosa Centro Storico
Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas
Villa La Ginestra

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
Exterior
Locanda Guidi

Locanda Guidi

Locanda Guidi
Sansepolcro
9.0 out of 10, Wonderful, (2)
"No one in reception on arrival or departure. Only one small bottle of water in the room. ID cards left in the entry hall with no supervision. Very nice room, excellent location, very clean but totally lacking in "accoglienza"."
Ireland
Michael
Locanda Guidi
Balcony
Cameracaffè Centro

Cameracaffè Centro

Cameracaffè Centro
Arezzo Centro Storico
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 ฿2,829
฿3,332 total
includes taxes & fees
18 Jan - 19 Jan 2026
Cameracaffè Centro
Daily buffet breakfast (EUR 10 per person)
DormiVeglia B&B

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

San Michele al Borgo
Castiglion Fiorentino
9.8 out of 10, Exceptional, (9)
"Excellent staff and tasty breakfast!"
United States
Vern
The price is ฿3,860
฿4,393 total
includes taxes & fees
8 Jan - 9 Jan 2026
San Michele al Borgo
Lunch, dinner served; Italian cuisine, garden views
Locanda del Viandante

Locanda del Viandante

Locanda del Viandante
Anghiari
9.0 out of 10, Wonderful, (6)
"Smuk beliggenhed - meget autentisk på den gode måde"
Denmark
tina
The price is ฿4,492
฿4,942 total
includes taxes & fees
5 Jan - 6 Jan 2026
Locanda del Viandante
Luxury Room, Jetted Tub, City View | Free WiFi, bed sheets
B&B 52cento

B&B 52cento

B&B 52cento
Arezzo Centro Storico
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 ฿2,516
฿2,987 total
includes taxes & fees
8 Jan - 9 Jan 2026
B&B 52cento
Terrace/patio
Casa Vacanze Le Fornaci

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 ฿4,126
฿4,649 total
includes taxes & fees
3 Jan - 4 Jan 2026
Casa Vacanze Le Fornaci
Business centre
Allegra Toscana - Affittacamere Guest house

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
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 Chiaveretto Hotel Reviews

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

10/10 Excellent
"Everything was perfect! Would like to give this Property a 6 Star rating. The staff made you feel like royalty!!"
Sabrina 4-night trip
Posted 8 days ago
Monastero di Cortona Hotel & Spa

Find out more about Chiaveretto

Search for holiday rentals in Chiaveretto on Expedia! You can easily find your home rentals, villas, holiday apartments in Chiaveretto using one of the methods below:

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Look no further and take a look at our great range of rental properties in Chiaveretto!

Frequently asked questions

Can I find holiday rentals in Chiaveretto?

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

What’s there to see and do in Chiaveretto?

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 Casa Vasari House Museum and Cathedral of Saints Peter and Donato.

What’s a holiday rental in Chiaveretto like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chiaveretto. Holiday rentals feature amenities such as kitchens and laundry facilities so you'll have everything you need. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from shared hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great choice for families.