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
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Castellina in Chianti vacation rentals

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$2,925
NT$3,365 total
includes taxes & fees
Jul 28 - Jul 29
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$4,052
NT$4,678 total
includes taxes & fees
Aug 21 - Aug 22
Casa Vacanze Squarcialupi
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$4,133
NT$4,694 total
includes taxes & fees
Jul 27 - Jul 28
Residenzia del Sogno
Aerial view

Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (36 reviews)
"Great place to stay in Tuscany! Very nice breakfast also!"
United States
Janet
The price is NT$7,891
NT$8,754 total
includes taxes & fees
Aug 7 - Aug 8
Riserva di Fizzano Residence
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, (674 reviews)
"Good clean rooms and very close to the city center as well as the train station"
United Kingdom
VISHAL
The price is NT$2,655
NT$3,362 total
includes taxes & fees
Jul 30 - Jul 31
Sette Angeli Rooms
Deluxe Room, City View | Premium bedding, down comforters, in-room safe, blackout drapes

Maison Ginori Guelfa

Maison Ginori Guelfa
Historic Centre of Florence
10.0 out of 10, Exceptional, (36 reviews)
"This was an incredible stay. The host was a phenomenal communicator and the property is as beautiful as pictured. If you want to be downtown in the heart of Florence, this is the perfect place to be and it is also far enough from the standard noise. I had peaceful nights and peaceful days, if I chose a late morning. It was literally near everything and I walked to every place I wanted to see. It was safe and easy to get to. I would absolutely stay at this property again and couldn’t have asked...
United States
Joyce
The price is NT$5,286
NT$6,256 total
includes taxes & fees
Jul 31 - Aug 1
Maison Ginori Guelfa
Deluxe Double Room, City View | Room amenity

San Giuliano Inn - Adults Only

San Giuliano Inn - Adults Only
Historic Centre of Florence
9.8 out of 10, Exceptional, (444 reviews)
"Clean, friendly staff. Great location. "
United States
Jeannette
The price is NT$5,419
NT$6,402 total
includes taxes & fees
Jul 27 - Jul 28
San Giuliano Inn - Adults Only
Free daily buffet breakfast

Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (79 reviews)
"We had a wonderful experience! The staff was kind and very helpful. Our room was stunning and very spacious for a family of 5! The breakfast was amazing, and all of the activities on site were very fun - we especially enjoyed the cooking class! I would absolutely love to return here. I recommend looking into and booking on-site activities in advance so you can get the most out of your experience!"
United States
Julia
The price is NT$10,030
NT$11,180 total
includes taxes & fees
Aug 2 - Aug 3
Terre di Baccio
Property grounds

Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (96 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$2,175
NT$2,540 total
includes taxes & fees
Aug 2 - Aug 3
Domus il Palio B&B
Exterior

Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (24 reviews)
"A very peaceful and relaxing B&B that I highly recommend, spacious rooms , clean and well maintained! Host were very pleasing and helpful… definitely recommend!!"
Canada
Sabatino
The price is NT$14,052
NT$15,752 total
includes taxes & fees
Jul 29 - Jul 30
Borgo Argenina
Breakfast meal

B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (203 reviews)
"Excellent location, rooms, staff."
United States
Mario Humberto
The price is NT$3,726
NT$4,246 total
includes taxes & fees
Jul 28 - Jul 29
B&B Il Corso
Room amenity

Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (466 reviews)
"It’s very close to the historical center but feels quiet and like you are separate from it. I loved our stay"
United States
David
The price is NT$3,843
NT$4,374 total
includes taxes & fees
Jul 30 - Jul 31
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, (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$3,892
NT$4,429 total
includes taxes & fees
Aug 26 - Aug 27
La Terrazza Sul Campo Rooming House
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 Lavagnini

The Social Hub Florence Lavagnini

10/10 Excellent
"We stayed here for six nights. The room was small but comfortable and clean. The hotel itself is packed with amenities including a well equipped gym with the most spectacular view of Florence, the free rooftop yoga session was amazing. The bar and pool area also boasts the same view. The hotel is conveniently located and it is an easy 15min walk to the city centre and main train station. Would stay here again next time we visit Florence."
Damien 7-night trip
Posted 5 hours ago
The Social Hub Florence Lavagnini

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 of 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 Chianti Sculpture Park. While here, Buondonno Winery and City Hall Castellina In Chianti 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.