Castellina in Chianti Vacation Rentals

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Check prices for these dates

Tonight
Dec 13 - Dec 14
Tomorrow
Dec 14 - Dec 15
Next weekend
Dec 19 - Dec 21
In two weeks
Dec 26 - Dec 28

Our top choices for Castellina in Chianti vacation rentals

Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, sun loungers
Residenzia del Sogno

Townhouse in Castellina in Chianti

Residenzia del Sogno
9.8 out of 10, Exceptional, (14)
"Beautiful and authentic place, lovely couple running the place that care about you and your stay. "
Canada
Katherine
The price is NT$4,328
NT$4,907 total
includes taxes & fees
Jan 3 - 2026/1/4
Residenzia del Sogno
Seasonal outdoor pool
Agriturismo La Ferrozzola

Vacation Home in Castellina in Chianti

Agriturismo La Ferrozzola
9.4 out of 10, Exceptional, (9)
"Very nice agriturismo. "
United States
Ruth
Agriturismo La Ferrozzola
Panoramic Apartment, Hill View (4) | Terrace/patio
Casa Vacanze Squarcialupi

Apartment in Castellina in Chianti

Casa Vacanze Squarcialupi
8.0 out of 10, Very Good, (2)
"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 NT$3,784
NT$4,383 total
includes taxes & fees
Dec 15 - Dec 16
Casa Vacanze Squarcialupi
Chalet | In-room safe, cribs/infant beds, bed sheets
Hu Firenze Camping In Town

Camping in Florence

Hu Firenze Camping In Town
8.8 out of 10, Excellent, (1611)
"It was a grt place to stay"
United States
Sunitha
Hu Firenze Camping In Town
Premier Apartment | Private kitchen | Coffee/tea maker, electric kettle
My Guest In Florence

Townhouse in Historic Centre of Florence

My Guest In Florence
9.0 out of 10, Wonderful, (125)
"My kids and I had a wonderful stay. The apartment was very nice and clean. Directions for checking in were clear and the staff was very helpful. "
United States
Susie
My Guest In Florence
Food and drink
San Giuliano Inn - Adults Only

Townhouse in Historic Centre of Florence

San Giuliano Inn - Adults Only
10.0 out of 10, Exceptional, (405)
"Great inn. "
United States
Carol
The price is NT$3,424
NT$4,207 total
includes taxes & fees
Dec 14 - Dec 15
San Giuliano Inn - Adults Only
32-inch Smart TV with digital channels, TV, streaming services
B&B Il Corso

Townhouse in Siena City Centre

B&B Il Corso
9.8 out of 10, Exceptional, (191)
"Safe, clean, close to all attractions"
Canada
Carlo
B&B Il Corso
Birthday party area
Siena Vip

Townhouse in Siena City Centre

Siena Vip
9.2 out of 10, Wonderful, (422)
"A great location!"
Canada
Cheryl
Siena Vip
Lobby lounge
ApartHotel Anghel

Apartment in Siena

ApartHotel Anghel
8.4 out of 10, Very Good, (335)
"Would recommend staying here and will hopefully be back!"
Canada
Lisa
The price is NT$2,079
NT$2,434 total
includes taxes & fees
Dec 22 - Dec 23
ApartHotel Anghel
Exterior
PALAZZO DEL PAPA

Townhouse in Siena City Centre

PALAZZO DEL PAPA
9.6 out of 10, Exceptional, (96)
"Hamza was so wonderful and accommodating, would definitely stay here again!"
United States
Elise
The price is NT$3,953
NT$4,495 total
includes taxes & fees
Dec 16 - Dec 17
PALAZZO DEL PAPA
Bar (on property)
Il Battistero Siena - Residenza d'Epoca

Residence in Siena City Centre

Il Battistero Siena - Residenza d'Epoca
9.6 out of 10, Exceptional, (192)
"Great location and friendly staff. "
United States
Parissa
Il Battistero Siena - Residenza d'Epoca
Suite | Premium bedding, Select Comfort beds, minibar, in-room safe
La Terrazza Sul Campo Rooming House

Residence in Siena City Centre

La Terrazza Sul Campo Rooming House
9.8 out of 10, Exceptional, (239)
"Huge room! Great location "
Canada
karen
La Terrazza Sul Campo Rooming House
Grand Apartment with Garden | Private kitchen | Full-size fridge, microwave, oven, stovetop
Regis Condo

Apartment in Siena City Centre

Regis Condo
9.4 out of 10, Exceptional, (65)
"This was one of our favorite stays in Italy. It was spacious, clean, and in a great part of the city."
United States
Ben
Regis Condo
Balcony
Palazzo al Torrione 2

Townhouse in San Gimignano City Centre

Palazzo al Torrione 2
9.2 out of 10, Wonderful, (107)
"Truly a gem! Our room was beautiful with a lovely view. It is very close to the main road and restaurants. Definitely opt in for the breakfast it was absolutely delicious. "
United States
Leasly
The price is NT$2,946
NT$4,340 total
includes taxes & fees
Dec 15 - Dec 16
Palazzo al Torrione 2
Seasonal outdoor pool, open 8 AM to 8 PM, pool umbrellas, sun loungers
Tenuta Sant'Ilario

Townhouse in Gambassi Terme

Tenuta Sant'Ilario
9.4 out of 10, Exceptional, (33)
"Amazing location and property! Owner and staff super nice! I am sure we will be back!"
Australia
Ilaria
Tenuta Sant'Ilario
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

Bernini Palace

Bernini Palace

10/10 Excellent
"Beautiful. Great location and staff."
Sally 3-night trip
Posted 1 day ago
Bernini Palace

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:

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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 vacation rentals in Castellina in Chianti?

Yes, you can find vacation rentals near the most popular attractions in Castellina in Chianti, or you can go with a more remote option if you're looking for relaxation. 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 vacation home rentals in Castellina in Chianti?

QK Costa58 Home Tower: This vacation home rental outside Castellina in Chianti is located in the historical district and offers a terrace, air-conditioning, and daily housekeeping to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

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

With 29 Expedia vacation rentals, you're sure 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 Borgo di Vescine - Tenute di Castelvecchi, or get outside and enjoy nature at Chianti Sculpture Park. While here, City Hall Castellina In Chianti and Buondonno Winery are other places worth a visit.

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

A vacation rental is a private property you can stay in for several days or longer in Castellina in Chianti. Vacation rentals provide amenities like kitchens and laundry facilities so you'll have everything you want. If you're concerned about a sanitized environment, a vacation rental can provide a sense of seclusion away from shared hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a great option for family gatherings.