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Our top choices for Cavallari hotels

1. Hotel Palazzo San niccolò & Spa

Hotel Palazzo San niccolò & Spa
4.0 star property
Radda in Chianti
9.2 out of 10, Wonderful, (198 reviews)
"Great stay!"
United States
Afeefa
The price is AU$126
includes taxes & fees
1 Dec - 2 Dec
Hotel Palazzo San niccolò & Spa

2. Palazzo Leopoldo Dimora Storica & Spa

Palazzo Leopoldo Dimora Storica & Spa
4.0 star property
Radda in Chianti
9.2 out of 10, Wonderful, (306 reviews)
"Very helpful and friendly staff, beautiful and spacious room, and wonderful location in the most lovely town in Tuscany. We loved our stay!"
Canada
Elizabeth
The price is AU$179
includes taxes & fees
1 Dec - 2 Dec
Palazzo Leopoldo Dimora Storica & Spa

3. Belvedere di San Leonino

Belvedere di San Leonino
4.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (211 reviews)
"Brautiful scenery, convenient location. Parking was great."
Canada
Kevork
The price is AU$181
includes taxes & fees
12 Nov - 13 Nov
Belvedere di San Leonino

4. Hotel Villa San Giorgio

Hotel Villa San Giorgio
3.0 star property
Poggibonsi
9.0 out of 10, Wonderful, (116 reviews)
"Very buetifull hotel with magnificent view on Tuscany hills. Very kind staff, clean room and Very good breakfast."
United States
Arik
The price is AU$96
includes taxes & fees
8 Nov - 9 Nov
Hotel Villa San Giorgio

5. Hotel Casafrassi

Hotel Casafrassi
4.0 star property
Castellina in Chianti
8.2 out of 10, Very good, (249 reviews)
"Absolutely loved our stay here. The property is beautiful and the staff are lovely. The best value stay we had on our Italy trip. Can hear the horses whilst lying by the pool and the house has a very friendly ginger cat too!"
United Kingdom
Stuart
The price is AU$105
includes taxes & fees
18 Nov - 19 Nov
Hotel Casafrassi

6. Castello di Fonterutoli Wine Resort

Castello di Fonterutoli Wine Resort
Castellina in Chianti
9.4 out of 10, Exceptional, (234 reviews)
"The staff and experience staying at Castello Di Fonterutoli was amazing! Everyone was so kind and welcoming! Cannot wait to go back☺️"
United States
Micaela
The price is AU$254
includes taxes & fees
8 Nov - 9 Nov
Castello di Fonterutoli Wine Resort

7. La Certosa di Pontignano - Place of Charme

La Certosa di Pontignano - Place of Charme
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (581 reviews)
"Great location amazing place"
United States
Rodolfo
The price is AU$115
includes taxes & fees
9 Nov - 10 Nov
La Certosa di Pontignano - Place of Charme

8. Hotel Ristorante La Dama nella Vigna

Hotel Ristorante La Dama nella Vigna
Monteriggioni
9.4 out of 10, Exceptional, (59 reviews)
"Beautiful and excellent. Great stay."
United States
Amanda
The price is AU$157
includes taxes & fees
23 Nov - 24 Nov
Hotel Ristorante La Dama nella Vigna

9. Villa San Lucchese

Villa San Lucchese
4.0 star property
Poggibonsi
9.4 out of 10, Exceptional, (360 reviews)
"Very nice"
United Kingdom
James
The price is AU$165
includes taxes & fees
8 Nov - 9 Nov
Villa San Lucchese

10. Park Hotel Chianti

Park Hotel Chianti
4.0 star property
Tavarnelle Val di Pesa
9.0 out of 10, Wonderful, (282 reviews)
"The staff are very helpful and kind."
Canada
Manuel
The price is AU$101
includes taxes & fees
24 Nov - 25 Nov
Park Hotel Chianti

11. Castello La Leccia

Castello La Leccia
Castellina in Chianti
10.0 out of 10, Exceptional, (127 reviews)
"Gorgeous castle/hotel in a divinely beautiful setting. Beautiful views, excellent staff, and fabulous food!!! Great location for day trips as well. Would highly recommend!!!"
United States
Susan
The price is AU$245
includes taxes & fees
13 Nov - 14 Nov
Castello La Leccia

12. Hotel Toscana Ambassador

Hotel Toscana Ambassador
4.0 star property
Poggibonsi
8.0 out of 10, Very good, (379 reviews)
"Close to train station"
Canada
Marian
The price is AU$99
includes taxes & fees
8 Dec - 9 Dec
Hotel Toscana Ambassador

13. Albergo Il Colombaio

Albergo Il Colombaio
3.0 star property
Castellina in Chianti
8.4 out of 10, Very good, (66 reviews)
"I was a little hesitant about staying outside a "major city," but I'm so glad we did. Very cute hotel and room. It was a short walk to the local town, which had lots of options for dinner and chianti tasting. "
United States
Christine
The price is AU$241
includes taxes & fees
9 Nov - 10 Nov
Albergo Il Colombaio

14. Dievole Wine Resort

Dievole Wine Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (219 reviews)
"This stay was absolutely perfect. The staff is amazing and we had a great time! The food is also great!"
Norway
Magdalena
The price is AU$429
includes taxes & fees
16 Nov - 17 Nov
Dievole Wine Resort

15. Tenuta CorteDomina

Tenuta CorteDomina
Radda in Chianti
9.8 out of 10, Exceptional, (149 reviews)
"Wonderful property with a breathtaking view! They restored the property but kept the rustic feel."
United States
piyanut
The price is AU$347
includes taxes & fees
10 Nov - 11 Nov
Tenuta CorteDomina

16. Hotel Il Piccolo Castello

Hotel Il Piccolo Castello
4.0 star property
Monteriggioni
8.6 out of 10, Excellent, (369 reviews)
"Good value"
Canada
Frank
The price is AU$189
includes taxes & fees
12 Nov - 13 Nov
Hotel Il Piccolo Castello

17. Hotel Borgo di Cortefreda Relais - Place of Charme

Hotel Borgo di Cortefreda Relais - Place of Charme
4.0 star property
Tavarnelle Val di Pesa
9.4 out of 10, Exceptional, (531 reviews)
"It was a beautiful place. Location was perfect to travel around. It was very clean. Restaurant is decent and food was good. Breakfast was ok."
United States
Rahul
The price is AU$148
includes taxes & fees
29 Nov - 30 Nov
Hotel Borgo di Cortefreda Relais - Place of Charme

18. Hotel Borgo San Luigi

Hotel Borgo San Luigi
4.0 star property
Monteriggioni
9.2 out of 10, Wonderful, (456 reviews)
"It was definitely a place we will return too."
United States
JOHN
The price is AU$191
includes taxes & fees
8 Nov - 9 Nov
Hotel Borgo San Luigi

19. Albergo Del Chianti

Albergo Del Chianti
3.0 star property
Greve in Chianti
8.6 out of 10, Excellent, (218 reviews)
"Ideal place to stay if visiting Greve, perfect location and very helpful staff"
United States
David
The price is AU$227
includes taxes & fees
8 Nov - 9 Nov
Albergo Del Chianti

20. Borgo Vescine

Borgo Vescine
5.0 star property
Radda in Chianti
9.6 out of 10, Exceptional, (250 reviews)
"The staff was amazing and incredibly kind."
United States
Natalie
The price is AU$748
includes taxes & fees
8 Nov - 9 Nov
Borgo Vescine
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.

Top Cavallari Hotel Reviews

Frequently Asked Questions

What is the best area to stay in Cavallari?

The best area to stay in Cavallari is around the historic centre, particularly near Piazza del Duomo and the surrounding streets.


This area is the heart of Cavallari, offering a blend of historic architecture and modern comforts. You'll find a pedestrian-friendly environment with narrow cobbled streets leading to charming squares, boutique shops, and traditional Tuscan eateries. The Piazza del Duomo, with its impressive cathedral, serves as a central landmark and a popular meeting point.


Couples looking for a romantic and cultured escape will find this area particularly appealing. You're within easy walking distance of art galleries, renowned restaurants, and wine bars. Strolling through the streets in the evening, hand-in-hand, creates a memorable experience, with many hotels offering intimate settings and beautiful views.


For those who appreciate convenience and a touch of luxury, consider the hotels slightly outside the immediate pedestrian-only zone but still within a 5-10 minute walk of Piazza del Duomo. These often provide easier access for vehicles and may offer amenities like private parking or larger grounds, while still keeping you close to all the main attractions.

When is the best time to go to Cavallari?

The best time to visit Cavallari, Tuscany, is during the spring (April to June) and autumn (September to October) months.


During spring, the countryside is lush and green, and the weather is pleasantly mild, making it ideal for exploring the rolling hills and vineyards. You'll find fewer crowds compared to the peak summer season, allowing for a more relaxed experience. It's a great time for couples to enjoy scenic drives and outdoor activities like leisurely walks through olive groves.


Autumn also offers excellent weather, with comfortable temperatures and the beautiful colours of the harvest season. This period is superb for those interested in food and wine, as many local festivals celebrate the grape and olive harvests.

Can I cancel my hotel reservation on Expedia?

You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if cancelled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Cavallari.

How can I save on a hotel booking in Cavallari with Expedia?

One Key™—Expedia’s free travel rewards program—gives you instant access to discounts with Member Prices on Cavallari hotels. Plus, you’ll earn OneKeyCash™* on eligible bookings to use on future trips. Booking an Expedia hotel and flight package is another great way to save, where bundling can result in significant savings. *Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

How much is the nightly rate for a hotel in Cavallari?

Prices for hotels in Cavallari often vary, but you can find a great deal from AU$95 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for our cheapest rates.

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