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

Castellina in Chianti Vacation Rentals

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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Castellina in Chianti vacation 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, 18, (18 reviews)
"Very nice and quiet neighbourhood. Close to city centre. The host is very kind."
Japan
Chie
The price is NT$2,853
NT$3,285 total
includes taxes & fees
Oct 7 - Oct 8
Mariani Bed & Breakfast
A pool area with lounge chairs and umbrellas, surrounded by greenery and a stone building.

2. Residenzia del Sogno

Residenzia del Sogno
Castellina in Chianti
9.6 out of 10, 15, (15 reviews)
"Beautiful and authentic place, lovely couple running the place that care about you and your stay. "
Canada
Katherine
The price is NT$4,121
NT$4,680 total
includes taxes & fees
Oct 6 - Oct 7
Residenzia del Sogno
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, 37, (37 reviews)
"Great place to stay in Tuscany! Very nice breakfast also!"
United States
Janet
The price is NT$6,307
NT$7,011 total
includes taxes & fees
Sep 15 - Sep 16
Riserva di Fizzano Residence
A balcony with a table, chairs, and a bottle of wine, overlooking a vineyard and distant hills.

4. Casa Vacanze Squarcialupi

Casa Vacanze Squarcialupi
Castellina in Chianti
9.0 out of 10, 4, (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 NT$5,238
NT$5,982 total
includes taxes & fees
Sep 27 - Sep 28
Casa Vacanze Squarcialupi
A restaurant with hanging baskets of greenery, wicker furniture, and a view of the outdoors.

5. Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, 79, (79 reviews)
"The stay was great, and the staff were wonderful. "
United States
SYDNEY
The price is NT$10,091
NT$11,247 total
includes taxes & fees
Sep 21 - Sep 22
Terre di Baccio
A stone building with a garden in front.

6. Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, 27, (27 reviews)
"What an amazing place. We enjoyed it so much."
United States
Tatevik
The price is NT$5,579
NT$6,431 total
includes taxes & fees
Sep 16 - Sep 17
Borgo Argenina
An outdoor swimming pool with a wooden pergola, lounge chairs, and a stone wall backdrop.

7. Guild Living Siena Senior Resort & Residence

Guild Living Siena Senior Resort & Residence
Scacciapensieri
8.8 out of 10, 49, (49 reviews)
"New facilities, its great, nice, friendly"
United Kingdom
tomaz
The price is NT$4,555
NT$5,157 total
includes taxes & fees
Oct 5 - Oct 6
Guild Living Siena Senior Resort & Residence
A table with two wine glasses, a bottle, and a book.

8. Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, 97, (97 reviews)
"Rooms were clean and spacious ! Happy there was a good blow dryer in the room and a heated towel rack. Staff were very friendly and helpful . Would stay again !"
Canada
Alissia
The price is NT$2,169
NT$2,533 total
includes taxes & fees
Oct 7 - Oct 8
Domus il Palio B&B
A bakery display with pastries and a coffee station.

9. B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, 208, (208 reviews)
"We enjoyed our stay very much. Staff was very friendly and offered great advise on places to eat. The rooms had great charm to them. We were delighted with our selection of where to stay."
United States
Enrique
The price is NT$3,904
NT$4,441 total
includes taxes & fees
Sep 27 - Sep 28
B&B Il Corso
A bathroom with a window view of a historic building and a tiled roof.

10. Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, 478, (478 reviews)
"Fantastic location and very friendly staff, we will definitely be back"
United Kingdom
Luis
The price is NT$3,801
NT$4,328 total
includes taxes & fees
Oct 14 - Oct 15
Siena Vip
A modern lobby with white leather sofas, a glass coffee table, and potted plants.

11. ApartHotel Anghel

ApartHotel Anghel
Siena
8.4 out of 10, 346, (346 reviews)
"Great stay highly recommend!!"
United States
jon
The price is NT$3,389
NT$3,875 total
includes taxes & fees
Sep 21 - Sep 22
ApartHotel Anghel
A spacious hotel room with a large bed, a sitting area with chairs, and a view through an arched doorway to another room.

12. La Terrazza Sul Campo Rooming House

La Terrazza Sul Campo Rooming House
Siena City Centre
9.8 out of 10, 248, (248 reviews)
"The location was amazing. I will never forget the view. Room was huge and access to restaurants and shopping. Also fantastic. We want to go back again already."
United States
Margaret
The price is NT$6,122
NT$6,881 total
includes taxes & fees
Oct 5 - Oct 6
La Terrazza Sul Campo Rooming House
A pool area with a water slide and a stage for performances.

13. Hu Norcenni Girasole Village

Hu Norcenni Girasole Village
4.0 star property
Figline e Incisa Valdarno
8.6 out of 10, 331, (331 reviews)
"Amazing venue , lots of kids entertainment. Lots of facilities- shops restaurants. Splash parks were brilliant. Highly recommended."
United Kingdom
Katie
The price is NT$1,900
NT$2,145 total
includes taxes & fees
Sep 15 - Sep 16
Hu Norcenni Girasole Village
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

The Social Hub Florence Belfiore

The Social Hub Florence Belfiore

10/10 Excellent
"Everything was perfect. Center of town, helpful staff who helped with activities around town and getting taxis. Highly recommended for anyone visiting!"
Cameron Jerard 7-night trip
Posted less than an hour ago
The Social Hub Florence Belfiore

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 28 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 Alta Val d'Elsa River 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.