Castellina in Chianti Vacation Rentals

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Check prices for these dates

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

Our top choices for Castellina in Chianti vacation 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 NT$6,334
NT$7,041 total
includes taxes & fees
May 17 - May 18
Riserva di Fizzano Residence
Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, sun 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 NT$4,357
NT$4,940 total
includes taxes & fees
May 7 - May 8
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 NT$2,871
NT$3,306 total
includes taxes & fees
May 16 - May 17
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 NT$3,350
NT$3,832 total
includes taxes & fees
May 25 - May 26
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 NT$4,715
NT$5,408 total
includes taxes & fees
May 5 - May 6
Casa Vacanze Squarcialupi
Property entrance

Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (100 reviews)
"This is a lovely gem. Includes parking which is hard to find. Family owned and its a truly beautiful place. Breakfast was amazing as well!! Recommend!! "
United States
rose
The price is NT$7,768
NT$8,692 total
includes taxes & fees
May 4 - May 5
Villa il Fedino
Breakfast meal

B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (201 reviews)
"Excellent B&B, very helpful host"
United States
Anushya
The price is NT$3,771
NT$4,296 total
includes taxes & fees
May 13 - May 14
B&B Il Corso
Breakfast, lunch, dinner served; Regional cuisine

La Locanda di Pietracupa

La Locanda di Pietracupa
Barberino Tavarnelle
9.4 out of 10, Exceptional, (36 reviews)
"Great place, wonderful restaurant"
Germany
Isabell
The price is NT$5,253
NT$5,926 total
includes taxes & fees
May 6 - May 7
La Locanda di Pietracupa
Daily continental breakfast (EUR 20 per person)

Residenza d'Epoca Palazzo Borghesi

Residenza d'Epoca Palazzo Borghesi
Siena City Centre
9.6 out of 10, Exceptional, (123 reviews)
"Excellent location on heart of Siena .. staff were lovely"
United Kingdom
Thomas
The price is NT$8,713
NT$9,732 total
includes taxes & fees
May 14 - May 15
Residenza d'Epoca Palazzo Borghesi
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 NT$3,648
NT$4,160 total
includes taxes & fees
May 12 - May 13
La Terrazza Sul Campo Rooming House
Double Room | Minibar, desk, blackout drapes, 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 NT$6,611
NT$7,420 total
includes taxes & fees
May 3 - May 4
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 NT$4,590
NT$5,197 total
includes taxes & fees
May 29 - May 30
Siena Vip
City view

Regis Condo

Regis Condo
Siena City Centre
9.4 out of 10, Exceptional, (69 reviews)
"Adequate basic clean room in a beautiful area."
United States
Margaret
The price is NT$4,058
NT$4,611 total
includes taxes & fees
May 18 - May 19
Regis Condo
Exterior

Antico Borgo il Cardino

Antico Borgo il Cardino
San Gimignano
9.4 out of 10, Exceptional, (82 reviews)
"It was perfect for my one night stop before moving on to another location in Toscana."
United States
Craig
The price is NT$4,608
NT$5,253 total
includes taxes & fees
May 3 - May 4
Antico Borgo il Cardino
Terrace/patio

Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (99 reviews)
"A nice blend of old world charm and modern conveniences. It is far from "
United States
John
The price is NT$3,877
NT$4,338 total
includes taxes & fees
May 17 - May 18
Palazzo Pacini
Superior Double Room, 1 Queen Bed, Private Bathroom, City View | Egyptian cotton sheets, premium bedding, down comforters, minibar

B&B Palazzo del Magnifico

B&B Palazzo del Magnifico
Siena City Centre
9.8 out of 10, Exceptional, (64 reviews)
"Excellent host and location!"
United States
Kimberly
B&B Palazzo del Magnifico
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 NT$2,956
NT$3,399 total
includes taxes & fees
May 17 - May 18
ApartHotel Anghel
Exterior

Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (22 reviews)
"It is an amazing location nested among wineries and rolling hills. If you like a quiet and sophisticated location this is your ideal place. You will need a car to move around but, you will be rewarded by the view and the opportunities for wine tastings and small villages visits. "
United States
Massimo
The price is NT$7,991
NT$9,085 total
includes taxes & fees
May 3 - May 4
Borgo Argenina
Deluxe Apartment | Premium bedding, down comforters, in-room safe, desk

Borgo Argiano

Borgo Argiano
Castelnuovo Berardenga
10.0 out of 10, Exceptional, (77 reviews)
"Very comfortable stay. "
United States
Victor
Borgo Argiano
Deluxe Room, Patio | Frette Italian sheets, premium bedding, minibar, in-room safe

Tenuta Sant'Ilario

Tenuta Sant'Ilario
Gambassi Terme
9.4 out of 10, Exceptional, (35 reviews)
"Amazing location and property! Owner and staff super nice! I am sure we will be back!"
Australia
Ilaria
The price is NT$4,434
NT$4,988 total
includes taxes & fees
May 18 - May 19
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

IQ Hotel Firenze

IQ Hotel Firenze

8/10 Good
"Eggs were too wet, everything else great. At times air conditioning was on 23 but room was cold - seemed difficult to regulate Would be so nice if swimming pool was heated or if there was a hot tub"
Paula 5-night trip
Posted 2 hours ago
IQ Hotel Firenze

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?

Villa La Stella - Casa per Ferie: This vacation 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 vacation rental also comes with free parking to give you added peace of mind.

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

With 27 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 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 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.