A stone building with a clock tower, steps leading up to it, and people walking around.

Castellina in Chianti Holiday Rentals

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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 Castellina in Chianti 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)
"Beautiful view, very clean and everything in great condition. Friendly service. We will definitely stay again."
United States
Frank
The price is S$115
includes taxes & fees
7 Oct - 8 Oct
Mariani Bed & Breakfast
A balcony with a table, chairs, and a bottle of wine, overlooking a vineyard and distant hills.

2. 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 S$192
includes taxes & fees
21 Oct - 22 Oct
Casa Vacanze Squarcialupi
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 S$271
includes taxes & fees
29 Sept - 30 Sept
Riserva di Fizzano Residence
A pool area with lounge chairs and umbrellas, surrounded by greenery and a stone building.

4. 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 S$186
includes taxes & fees
6 Oct - 7 Oct
Residenzia del Sogno
A table with two wine glasses, a bottle, and a book.

5. Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (98 reviews)
"Everything was very clean and modern, working perfect. We didn’t meet anyone from the staff. And it would be nice if they leave some bottle of water for each room. We like the place a lot. People have to consider that it is outside Siena walls and it’s a pretty steep and long distance walk"
United States
María
The price is S$100
includes taxes & fees
12 Oct - 13 Oct
Domus il Palio B&B
A bathroom with a window view of a historic building and a tiled roof.

6. Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (481 reviews)
"Fantastic location and very friendly staff, we will definitely be back"
United Kingdom
Luis
The price is S$158
includes taxes & fees
21 Oct - 22 Oct
Siena Vip
A room with a bed, a leather sofa, and a window with a view of a building outside.

7. Al Mercato B&B

Al Mercato B&B
Siena City Centre
9.0 out of 10, Wonderful, (104 reviews)
"Great location."
Canada
Marie-Christine
The price is S$124
includes taxes & fees
8 Oct - 9 Oct
Al Mercato B&B
A modern lobby with white leather sofas, a glass coffee table, and potted plants.

8. 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 S$127
includes taxes & fees
27 Sept - 28 Sept
ApartHotel Anghel
A hotel room with a bed, a bedside table with a lamp, a potted plant, and a view of the outside through the window.

9. PALAZZO DEL PAPA

PALAZZO DEL PAPA
Siena City Centre
9.6 out of 10, Exceptional, (111 reviews)
"We loved our stay The host made us feel appreciated and really went out of his way to show us the highlight spots to see and where to eat. Thanks you."
Canada
scott
The price is S$278
includes taxes & fees
12 Oct - 13 Oct
PALAZZO DEL PAPA
A white mobile home with blue shutters, a red roof, and a small deck with white chairs.

10. Camping Boschetto Di Piemma

Camping Boschetto Di Piemma
3.0 star property
San Gimignano
8.8 out of 10, Excellent, (89 reviews)
"Great experience, close to a beautiful city and castle on a hill. "
New Zealand
Anonymous traveller
The price is S$73
includes taxes & fees
13 Oct - 14 Oct
Camping Boschetto Di Piemma
A courtyard with a stone statue, a round table, and chairs.

11. Regis Condo

Regis Condo
Siena City Centre
9.4 out of 10, Exceptional, (80 reviews)
"We loved this place; lovely large space, bed was lovely, shower was great. The access to the back garden was an added bonus."
Norway
Ida Christine
The price is S$194
includes taxes & fees
25 Oct - 26 Oct
Regis Condo
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 Castellina in Chianti Hotel Reviews

Plus Florence - Hostel

Plus Florence - Hostel

10/10 Excellent
"Nos gustó mucho las habitaciones privadas"
Yanelys 2-night trip
Posted less than an hour ago
Plus Florence - Hostel

Frequently asked questions

Are there holiday rentals in Castellina in Chianti?

Yes, there are holiday rentals close to the most popular sights in Castellina in Chianti, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Castellina in Chianti speak positively about the countryside and wineries in this destination. Make sure you have time to check out the forests while you're in the area.

What are some of the best holiday rentals that Castellina in Chianti has to offer?

Villa La Stella - Casa per Ferie: This holiday home rental outside Castellina in Chianti is located near the airport, and has a garden, a library and air conditioning to put you at ease in your new surroundings. This holiday rental also comes with free parking to give you added peace of mind.

How many holiday rentals will I find in Castellina in Chianti?

With 27 Expedia holiday rentals, you're guaranteed to find just the right place for your Castellina in Chianti stay.

What’s there to see and do in Castellina in Chianti?

While exploring the area, visit family-friendly sights like Chianti Observatory, or get outside and enjoy nature at Chianti Sculpture Park. While here, City Hall Castellina In Chianti and Castellina Fortress are other places worth a visit.

What’s a holiday rental in Castellina in Chianti like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Castellina in Chianti. Holiday rentals provide amenities such as hot tubs, fire pits and patios so you'll have everything you want. If you're concerned about a sanitised environment, a holiday rental can offer a sense of seclusion away from shared hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a great choice for families.