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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Cavallari holiday rentals

A kitchen with wooden cabinets, a glass display case, and a dining area with a table and chairs.

1. Mariani Bed & Breakfast

Mariani Bed & Breakfast
Castellina in Chianti
9.8 out of 10, Exceptional, (18 reviews)
"Very nice and quiet neighbourhood. Close to city centre. The host is very kind."
Japan
Chie
The price is ฿2,962
฿3,411 total
includes taxes & fees
7 Oct - 8 Oct
Mariani Bed & Breakfast
A pool area with lounge chairs and umbrellas, surrounded by greenery and a stone building.

2. Residenzia del Sogno

Residenzia del Sogno
Castellina in Chianti
9.6 out of 10, Exceptional, (15 reviews)
"Beautiful and authentic place, lovely couple running the place that care about you and your stay. "
Canada
Katherine
The price is ฿4,278
฿4,859 total
includes taxes & fees
6 Oct - 7 Oct
Residenzia del Sogno
A stone building with a courtyard, a swimming pool, and vineyard fields in the background.

3. Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (39 reviews)
"Great place to stay in Tuscany! Very nice breakfast also!"
United States
Janet
The price is ฿6,646
฿7,387 total
includes taxes & fees
29 Sept - 30 Sept
Riserva di Fizzano Residence
A balcony with a table, chairs, and a bottle of wine, overlooking a vineyard and distant hills.

4. Casa Vacanze Squarcialupi

Casa Vacanze Squarcialupi
Castellina in Chianti
9.0 out of 10, Wonderful, (4 reviews)
"Staff was very helpful. Was a bit bummed the pool was closed as that was part of the reason for choosing the hotel. "
United States
Jeffrey
The price is ฿4,443
฿5,116 total
includes taxes & fees
18 Oct - 19 Oct
Casa Vacanze Squarcialupi
A rectangular swimming pool with a clear blue water surface, surrounded by a brick patio. There are several lounge chairs and umbrellas around the pool area.

5. Villa Rosa Panzano

Villa Rosa Panzano
Greve in Chianti
8.2 out of 10, Very good, (56 reviews)
"A lovely rural B&B with very kind staff."
Canada
Allison
The price is ฿4,157
฿4,725 total
includes taxes & fees
5 Oct - 6 Oct
Villa Rosa Panzano
A restaurant with hanging baskets of greenery, wicker furniture, and a view of the outdoors.

6. Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (79 reviews)
"The stay was great, and the staff were wonderful. "
United States
SYDNEY
The price is ฿9,977
฿11,128 total
includes taxes & fees
25 Sept - 26 Sept
Terre di Baccio
A table with breakfast items and a view of rolling hills.

7. Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Tavarnelle Val di Pesa
8.6 out of 10, Excellent, (121 reviews)
"Front desk was very helpful and very comfortable room. "
United States
Chris
The price is ฿2,444
฿2,764 total
includes taxes & fees
14 Oct - 15 Oct
Chianti Village Morrocco
A dining area with a table set for two, featuring a view of greenery through a window.

8. La Locanda di Pietracupa

La Locanda di Pietracupa
Tavarnelle Val di Pesa
9.6 out of 10, Exceptional, (38 reviews)
"Great place, wonderful restaurant"
Germany
Isabell
The price is ฿5,760
฿6,488 total
includes taxes & fees
26 Sept - 27 Sept
La Locanda di Pietracupa
A stone building with a garden in front.

9. Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (27 reviews)
"What an amazing place. We enjoyed it so much."
United States
Tatevik
The price is ฿5,792
฿6,677 total
includes taxes & fees
28 Sept - 29 Sept
Borgo Argenina
A balcony with a view of rolling hills, a table with a book and a bottle, and a chair.

10. Villa San Filippo

Villa San Filippo
4.0 star property
Barberino Val d'Elsa
8.6 out of 10, Excellent, (53 reviews)
"This place was beautiful, quiet like a picture you’d see in the movies"
Canada
Nadia
The price is ฿3,627
฿4,218 total
includes taxes & fees
28 Sept - 29 Sept
Villa San Filippo
A pool area with two rectangular pools, surrounded by lounge chairs and umbrellas, set against a backdrop of vineyards and tall cypress trees.

11. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (39 reviews)
"Great spot"
Canada
Philippe
The price is ฿5,231
฿7,279 total
includes taxes & fees
1 Oct - 2 Oct
Villa di Sotto
An arched brick corridor with gravel flooring, potted plants, and a gate leading to a garden area.

12. Ca' Bianca Tuscany Relais

Ca' Bianca Tuscany Relais
Siena
10.0 out of 10, Exceptional, (46 reviews)
"Clean room, amazing staff"
Canada
Talha
Ca' Bianca Tuscany Relais
An outdoor dining area with tables and chairs, candles, and a view of palm trees and greenery.

13. Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (101 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
The price is ฿5,081
฿5,665 total
includes taxes & fees
1 Oct - 2 Oct
Palazzo Pacini
An arched entrance with a lantern above, flanked by two potted plants.

14. Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (105 reviews)
"Tha parking was easy on the property. It was within walking distance to the villages with shops, restaurants and cafes. The best part was the staff. The owners were incredibly helpful, friendly and made you feel like family. Breakfast outside was lovely overlooking the hills of Tuscany. We met many people and had lovely conversations with other travelers during breakfast. A gem in Tuscany."
United States
Lori
The price is ฿7,988
฿8,939 total
includes taxes & fees
18 Oct - 19 Oct
Villa il Fedino
A villa with a swimming pool, outdoor seating, and a tennis court.

15. Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (80 reviews)
"Beautiful resort in the hills, lovely and charming room, incredibly spacious."
United States
Deanna
The price is ฿5,729
฿6,455 total
includes taxes & fees
23 Sept - 24 Sept
Villa Curina Resort
A modern lobby with white leather sofas, a glass coffee table, and potted plants.

16. ApartHotel Anghel

ApartHotel Anghel
Siena
8.4 out of 10, Very good, (347 reviews)
"Humming noise in the room. Slow internet. Fine bed. Good location."
Netherlands
Lauro
The price is ฿3,395
฿3,887 total
includes taxes & fees
23 Sept - 24 Sept
ApartHotel Anghel
An outdoor dining area with tables and chairs, covered by umbrellas, overlooking a scenic landscape.

17. B&B La Fonte del Machiavelli

B&B La Fonte del Machiavelli
San Casciano in Val di Pesa
9.2 out of 10, Wonderful, (84 reviews)
"Very pretty B&B! The rooms are super cozy and feels welcoming! The scenery around is just amazing! The pool was very refreshing and the host very nice! The trail to reach the B&B is narrow make sure you have a small car ;)"
Canada
Alexia
The price is ฿3,949
฿4,497 total
includes taxes & fees
6 Oct - 7 Oct
B&B La Fonte del Machiavelli
An aerial view of a hotel with a swimming pool, outdoor seating area, and well-maintained gardens.

18. Antica Pieve B&B

Antica Pieve B&B
Tavarnelle Val di Pesa
9.4 out of 10, Exceptional, (15 reviews)
"Very nice stay here! Great breakfast and coffee every morning. Great location to tour around to different wineries and towns. Free parking. "
Canada
Jessica
The price is ฿4,157
฿5,488 total
includes taxes & fees
12 Oct - 13 Oct
Antica Pieve B&B
A bakery display with pastries and a coffee station.

19. B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (208 reviews)
"We enjoyed our stay very much. Staff was very friendly and offered great advise on places to eat. The rooms had great charm to them. We were delighted with our selection of where to stay."
United States
Enrique
The price is ฿3,857
฿4,396 total
includes taxes & fees
30 Sept - 1 Oct
B&B Il Corso
A spacious indoor area with arched windows, wooden furniture, and hanging plants.

20. Relais Villa Olmo

Relais Villa Olmo
Impruneta
9.4 out of 10, Exceptional, (266 reviews)
"Very friendly and clean."
United States
Mohamed
The price is ฿5,668
฿6,350 total
includes taxes & fees
19 Oct - 20 Oct
Relais Villa Olmo
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 Cavallari Hotel Reviews

Hotel Chiusarelli

Hotel Chiusarelli

8/10 Good
"This hotel is well maintained and delicious breakfast. Great location to walk to everything in Siena"
Christian 2-night trip
Posted 12 hours ago
Hotel Chiusarelli

Find out more about Cavallari

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

  • View our selection of featured holiday rentals in Cavallari
  • Use the map to find apartments and other holiday homes in the Cavallari neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Cavallari while they last

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

Frequently asked questions

Can I find holiday rentals in Cavallari?

Yes, there are holiday rentals close to the most popular sights in Cavallari, 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 Cavallari has to offer?

Borgo Argiano: This holiday home rental outside of Cavallari is located on a river, and has a balcony, a terrace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and kitchenware. You can relax into your holiday with a garden and a library.

How many holiday rentals will I find in Cavallari?

Choose from 3 Expedia holiday rentals in Cavallari for a memorable holiday.

What’s there to see and do in Cavallari?

While exploring the area, visit family-friendly sights like Borgo di Vescine - Tenute di Castelvecchi, or get outside and enjoy nature at Arno River. In the wider area, you’ll find City Hall Castellina In Chianti and Il Molino di Grace Winery.

What’s a holiday rental in Cavallari like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Cavallari. Holiday rentals offer extras such as hot tubs, fire pits and patios so you'll be comfy for your stay. If you're concerned about a sanitised environment, holiday rentals can provide a sense of privacy away from public hotel lifts and busy front desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for families.