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Check prices for these dates

In two weeks
15 May - 17 May
In two months
26 Jun - 28 Jun
In three months
24 Jul - 26 Jul
In four months
21 Aug - 23 Aug

Our top choices for Castellina in Chianti holiday rentals

Aerial view

Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.8 out of 10, Exceptional, (25 reviews)
"Perfect location on the top of a hill surrounded by the beautiful vineyards of Chianti. Enjoy the view by the pool or the fabulous sunset with a glass of wine. The staff were friendly and the restaurant was 5 star. I highly recommend a stay to fulfill all your Tuscan dreams. "
United States
Eileen
The price is ฿6,546
฿7,276 total
includes taxes & fees
17 May - 18 May
Riserva di Fizzano Residence
Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, pool loungers

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 ฿3,813
฿4,346 total
includes taxes & fees
28 Apr - 29 Apr
Residenzia del Sogno
Garden

Villa Cristina

Villa Cristina
Castellina in Chianti
7.8 out of 10, Good, (39 reviews)
"Arnaque absolue par rapport aux photos. Sdb salle moisi partout, wc jaune de calcaire. Aucune isolation phonique. Photos ne correspondent pas Chambre dans garage hauteur sous planfond nulle obligé de se baisser."
France
pascal
The price is ฿2,933
฿3,377 total
includes taxes & fees
16 May - 17 May
Villa Cristina
Lounge

Mariani Bed & Breakfast

Mariani Bed & Breakfast
Castellina in Chianti
9.8 out of 10, Exceptional, (17 reviews)
"Very nice and quiet neighbourhood. Close to city centre. The host is very kind."
Japan
Chie
The price is ฿3,422
฿3,915 total
includes taxes & fees
25 May - 26 May
Mariani Bed & Breakfast
Panoramic Apartment (2) | Terrace/patio

Casa Vacanze Squarcialupi

Casa Vacanze Squarcialupi
Castellina in Chianti
8.8 out of 10, Excellent, (3 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 ฿4,817
฿5,525 total
includes taxes & fees
28 Apr - 29 Apr
Casa Vacanze Squarcialupi
Property amenity

hu Firenze Certosa camping in town

hu Firenze Certosa camping in town
Impruneta
8.2 out of 10, Very good, (68 reviews)
"Wonderful staff and great amenities!"
Canada
Chenjin
The price is ฿1,639
฿1,916 total
includes taxes & fees
3 May - 4 May
hu Firenze Certosa camping in town
City view from property

Boboli Living

Boboli Living
Historic Centre of Florence
8.4 out of 10, Very good, (5 reviews)
"The room was perfect, the location is near to all main attractions of the city and is 15 minutes away from the train station."
United States
Rustinko
The price is ฿6,484
฿7,586 total
includes taxes & fees
29 Apr - 30 Apr
Boboli Living
Property amenity

Camping Village Il Poggetto.

Camping Village Il Poggetto.
3.0 star property
Rignano sull'Arno
8.0 out of 10, Very good, (68 reviews)
"Pet friendly and clean"
United Kingdom
Nancy
The price is ฿2,162
฿2,491 total
includes taxes & fees
28 Apr - 29 Apr
Camping Village Il Poggetto.
Suite | Premium bedding, Select Comfort beds, minibar, in-room safe

La Terrazza Sul Campo Rooming House

La Terrazza Sul Campo Rooming House
Siena City Centre
9.8 out of 10, Exceptional, (241 reviews)
"My first time in Siena and this Rooming House turned out to be a great choice. The view onto the piazza is a real bonus, as is the great location in the heart of the city. The host was lovely and a great communicator. The room itself was fantastic and spacious. I would recommend it and will book again. "
United Kingdom
Jeffrey William
The price is ฿3,735
฿4,259 total
includes taxes & fees
12 May - 13 May
La Terrazza Sul Campo Rooming House
Lobby lounge

ApartHotel Anghel

ApartHotel Anghel
Siena
8.4 out of 10, Very good, (338 reviews)
"Would recommend staying here and will hopefully be back!"
Canada
Lisa
The price is ฿3,179
฿3,648 total
includes taxes & fees
17 May - 18 May
ApartHotel Anghel
Breakfast meal

B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (200 reviews)
"Excellent B&B, very helpful host"
United States
Anushya
The price is ฿3,853
฿4,389 total
includes taxes & fees
29 Apr - 30 Apr
B&B Il Corso
Double Room | Minibar, desk, blackout curtains, free WiFi

PALAZZO DEL PAPA

PALAZZO DEL PAPA
Siena City Centre
9.6 out of 10, Exceptional, (100 reviews)
"Fantastic location, walkable to everything, very clean & Hamza was a great host with lots of tips on what to see & where to eat"
United Kingdom
Diane
The price is ฿6,433
฿7,227 total
includes taxes & fees
29 Apr - 30 Apr
PALAZZO DEL PAPA
Room amenity

Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (435 reviews)
"Nice place!"
United States
Pavel
The price is ฿4,690
฿5,310 total
includes taxes & fees
24 May - 25 May
Siena Vip
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

25hours Hotel Florence Piazza San Paolino

25hours Hotel Florence Piazza San Paolino

10/10 Excellent
"The breakfast was great each morning. The bar and restaurant were phenomenal. The staff was friendly and attentive. "
Benjamin 2-night trip
Posted 2 hours ago
25hours Hotel Florence Piazza San Paolino

Find out more about Castellina in Chianti

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

  • View our selection of featured holiday rentals in Castellina in Chianti
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Look no further and take a look at our great range of rental properties in Castellina in Chianti!

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 Sentierelsa Trail. While here, City Hall Castellina In Chianti and Buondonno Winery 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.