Castellina in Chianti Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Nov 17 - Nov 18
Tomorrow
Nov 18 - Nov 19
This weekend
Nov 21 - Nov 23
Next weekend
Nov 28 - Nov 30

Vacation Rentals in Castellina in Chianti

Seasonal outdoor pool
Agriturismo La Ferrozzola

Agriturismo La Ferrozzola

Castellina in Chianti
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

Casa Vacanze Squarcialupi

Castellina in Chianti
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 ￥17,404
￥20,223 total
includes taxes & fees
Nov 26 - Nov 27
Casa Vacanze Squarcialupi
Outdoor dining
La Misura, cottage with garden and swimming pool on the hills of Chianti

La Misura, cottage with garden and swimming pool on the hills of Chianti

Castellina in Chianti
10.0 out of 10, Exceptional, (2)
"What a beautiful stay in the enchanting Tuscan countryside! Every detail was attended to and we could not have felt more at home. We can only dream of returning sometime!"
United States
Jami B.
La Misura, cottage with garden and swimming pool on the hills of Chianti
Fridge, oven, stovetop, coffee/tea maker
Apartment 'Poggio Della Capannina Di Castellina in Chianti' with Private Garden and Wi-Fi

Apartment 'Poggio Della Capannina Di Castellina in Chianti' with Private Garden and Wi-Fi

Castellina in Chianti
The price is ￥11,829
￥20,433 total
includes taxes & fees
Nov 23 - Nov 24
Apartment 'Poggio Della Capannina Di Castellina in Chianti' with Private Garden and Wi-Fi
Food and drink
San Giuliano Inn - Adults Only

San Giuliano Inn - Adults Only

Historic Centre of Florence
10.0 out of 10, Exceptional, (402)
"Great location - we loved it!"
United States
Julian
San Giuliano Inn - Adults Only
Deluxe Double Room (1° floor) | Egyptian cotton sheets, premium bedding, down comforters
Sette Angeli Rooms

Sette Angeli Rooms

Historic Centre of Florence
8.8 out of 10, Excellent, (633)
"I loved this place and the stuff was very kind <3 "
United Kingdom
romina
The price is ￥11,872
￥15,214 total
includes taxes & fees
Nov 23 - Nov 24
Sette Angeli Rooms
Bar (on property)
Il Battistero Siena - Residenza d'Epoca

Il Battistero Siena - Residenza d'Epoca

Siena City Centre
9.6 out of 10, Exceptional, (188)
"Great location and friendly staff. "
United States
Parissa
The price is ￥23,220
￥26,260 total
includes taxes & fees
Nov 18 - Nov 19
Il Battistero Siena - Residenza d'Epoca
Birthday party area
Siena Vip

Siena Vip

Siena City Centre
9.2 out of 10, Wonderful, (418)
"A great location!"
Canada
Cheryl
The price is ￥15,587
￥17,864 total
includes taxes & fees
Nov 19 - Nov 20
Siena Vip
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, (239)
"Huge room! Great location "
Canada
karen
La Terrazza Sul Campo Rooming House
Exterior
PALAZZO DEL PAPA

PALAZZO DEL PAPA

Siena City Centre
9.6 out of 10, Exceptional, (96)
"Hamza was so wonderful and accommodating, would definitely stay here again!"
United States
Elise
The price is ￥19,205
￥21,844 total
includes taxes & fees
Nov 18 - Nov 19
PALAZZO DEL PAPA
32-inch Smart TV with digital channels, TV, streaming services
B&B Il Corso

B&B Il Corso

Siena City Centre
9.8 out of 10, Exceptional, (188)
"Safe, clean, close to all attractions"
Canada
Carlo
B&B Il Corso
Grand Apartment with Garden | Private kitchen | Full-size fridge, microwave, oven, stovetop
Regis Condo

Regis Condo

Siena City Centre
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
Lobby lounge
ApartHotel Anghel

ApartHotel Anghel

Siena
8.4 out of 10, Very Good, (331)
"Would recommend staying here and will hopefully be back!"
Canada
Lisa
The price is ￥10,547
￥12,320 total
includes taxes & fees
Nov 18 - Nov 19
ApartHotel Anghel
Balcony
Palazzo al Torrione 2

Palazzo al Torrione 2

San Gimignano City Centre
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 ￥13,558
￥20,302 total
includes taxes & fees
Nov 20 - Nov 21
Palazzo al Torrione 2
City view from property
Soggiorno Battistero

Soggiorno Battistero

Historic Centre of Florence
8.8 out of 10, Excellent, (376)
"Great room with views of baptistery and historic center "
United States
Julio
The price is ￥16,526
￥20,692 total
includes taxes & fees
Nov 27 - Nov 28
Soggiorno Battistero
Seasonal outdoor pool, open 8 AM to 8 PM, pool umbrellas, sun loungers
Tenuta Sant'Ilario

Tenuta Sant'Ilario

Gambassi Terme
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
Outdoor pool, pool umbrellas, sun loungers
Chianti Village Morrocco

Chianti Village Morrocco

3.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (108)
"Front desk was very helpful and very comfortable room. "
United States
Chris
Chianti Village Morrocco
Apartment, 2 Bedrooms | 2 bedrooms, premium bedding, down comforters, in-room safe
Terre di Baccio

Terre di Baccio

Greve in Chianti
9.8 out of 10, Exceptional, (71)
"Great hotel in a beautiful location with fantastic staff. "
United Kingdom
Mark
The price is ￥103,923
￥115,034 total
includes taxes & fees
Nov 24 - Nov 25
Terre di Baccio
Terrace/patio
Numa Palazzo San Niccolò

Numa Palazzo San Niccolò

Historic Centre of Florence
9.4 out of 10, Exceptional, (173)
"The hotel is a great base for visiting Florence, in a slightly quieter neighbourhood but still plenty of food and drink options nearby and all the big attractions are a walkable distance away. The room was clean and the staff was friendly and helpful. "
United Kingdom
Michelle
The price is ￥13,389
￥16,883 total
includes taxes & fees
Dec 10 - Dec 11
Numa Palazzo San Niccolò
Exterior detail
Villa il Fedino

Villa il Fedino

San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (97)
"We had a wonderfull welcome, very professional ,friendly and helpful in every aspect. Great villa with Tuscany vibe and breathtaking views.Close enough to Florence.You can't ask for better. We will return again."
Canada
Mario
The price is ￥22,993
￥26,011 total
includes taxes & fees
Dec 15 - Dec 16
Villa il Fedino
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Castellina in Chianti Hotel Reviews

Hotel Pendini

Hotel Pendini

10/10 Excellent
"Amazing!!!"
Christina Louise 6-night trip
Posted 4 hours ago
Hotel Pendini

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
  • Use the map to find apartments and other holiday homes in the Castellina in Chianti neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Castellina in Chianti while they last

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. Some other top choices in Castellina in Chianti are Farmhouse in the heart of the real chiantishire and Villa with large garden in the Chianti hills.

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

With 80 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, Buondonno Winery and Casa Vinicola Luigi Cecchi 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.