A cobblestone street with historic buildings, a wooden chair, and potted plants.

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Casole d'Elsa holiday rentals

A stone building with a tiled roof, a brick pathway, and a small grassy area.

1. Le Mascie Country House

Le Mascie Country House
Casole d'Elsa
9.2 out of 10, Wonderful, (9 reviews)
"We loved our stay. The property is quiet and private but is in close proximity to a small town. Very charming and the pool was an added bonus. "
United States
Misti
The price is 5.353.795 ₫
5.948.066 ₫ total
includes taxes & fees
3 Oct - 4 Oct
Le Mascie Country House
A garden with a stone pathway, wooden benches, and various potted plants.

2. Antico Borgo il Cardino

Antico Borgo il Cardino
San Gimignano
9.4 out of 10, Exceptional, (86 reviews)
"It was perfect for my one night stop before moving on to another location in Toscana."
United States
Craig
The price is 3.975.153 ₫
4.519.896 ₫ total
includes taxes & fees
13 Oct - 14 Oct
Antico Borgo il Cardino
A narrow street with stone buildings, a tower, and an archway.

3. Materia Rooms San Gimignano

Materia Rooms San Gimignano
San Gimignano City Centre
10.0 out of 10, Exceptional, (1 review)
"Fantastic all around experience. The rooms were beautiful and clean and this unique mix of rustic modern Italian styling. Located right in the heart of the old city made it very easy to walk everywhere. The service was fantastic, I was able to message the team and within a minute I got the help and had my questions answered. I’d definitely stay there again."
Canada
Bradley
The price is 3.204.239 ₫
3.671.891 ₫ total
includes taxes & fees
5 Oct - 6 Oct
Materia Rooms San Gimignano
An open wooden door leading to an outdoor patio with a table and chairs.

4. Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (113 reviews)
"They were very helpful to me when I arrived. I difficulty accessing there messages to me. They put me at ease"
United States
Angela
The price is 2.761.523 ₫
3.920.204 ₫ total
includes taxes & fees
15 Oct - 16 Oct
Palazzo al Torrione 2
An interior with stone walls, wooden doors, and a bar area with stools and bottles.

5. Borgo Il Poggiaccio

Borgo Il Poggiaccio
Sovicille
8.8 out of 10, Excellent, (67 reviews)
"I loved the stay here. A great quiet place with an awesome restaurant and unbelievable staff. "
United States
Louie
The price is 3.035.571 ₫
5.429.764 ₫ total
includes taxes & fees
14 Oct - 15 Oct
Borgo Il Poggiaccio
An outdoor dining area with tables and chairs, candles, and a view of palm trees and greenery.

6. Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (102 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
The price is 3.486.470 ₫
3.893.952 ₫ total
includes taxes & fees
31 Oct - 1 Nov
Palazzo Pacini
A stone building with outdoor seating and a view of the countryside.

7. Antico Borgo Poggiarello

Antico Borgo Poggiarello
2.0 star property
Monteriggioni
9.0 out of 10, Wonderful, (20 reviews)
"We had an absolutely wonderful time staying here. Our kids had fun on their playground and my wife and I enjoyed the views, the hospitality. And the entire experience. The food was outstanding. "
United States
James Bakley
The price is 4.452.759 ₫
4.986.288 ₫ total
includes taxes & fees
29 Oct - 30 Oct
Antico Borgo Poggiarello
A compact kitchen with a gas stove, a refrigerator, and a wooden dining table with chairs.

8. Nido con vista

Nido con vista
Radicondoli
The price is 4.505.173 ₫
4.955.690 ₫ total
includes taxes & fees
31 Oct - 1 Nov
Nido con vista
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 Casole d'Elsa Hotel Reviews

Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel

10/10 Excellent
"Castiglion del Bosco is truly exquisite, the perfect way to experience Tuscany in luxury while still feeling completely surrounded by nature. The property is impeccable, from the beautiful gardens and grounds to the elegant rooms. Everything feels authentically Italian, refined and incredibly well maintained. The service is exceptional and very personalized. The staff genuinely goes out of their way to make you feel welcome. General Manager Nicola Migheli even greeted us personally upon arrival, which was a lovely touch. We also saw him regularly walking the property with his team, and it was clear how hands-on he is with every detail. One thing to know is that getting in and out requires about 40 minutes on a bumpy dirt road. It wasn’t terrible, but worth mentioning if you plan to explore frequently. That said, this is a hotel you don’t need to leave. It’s a beautiful place to slow down, relax and enjoy Tuscany in a truly special setting. We absolutely loved our stay!"
Carole 5-night trip
Posted 7 hours ago
Castiglion del Bosco, A Rosewood Hotel

Frequently asked questions

Can I find holiday rentals in Casole d'Elsa?

Yes, there are holiday rentals in Casole d'Elsa close to Terre di Vini, or you can select a more secluded option if you're looking for a relaxing stay. Casole d'Elsa is known for its spas.

How many holiday rentals are there in Casole d'Elsa?

Expedia has 36 holiday rentals for your stay in Casole d'Elsa.

What’s there to see and do in Casole d'Elsa?

Family-friendly attractions include Terre di Vini, whereas Val di Merse is a spot to enjoy the outdoors. Archeological and Collegiate Church Museum and Colle di Val d'Elsa Cathedral are a couple of places you'll find in the wider area.

What’s a holiday rental in Casole d'Elsa like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Casole d'Elsa. Holiday rentals offer extras such as kitchens and laundry facilities so you'll have everything you want. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from public hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for family gatherings.