Castellina in Chianti Holiday Rentals

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Check prices for these dates

Tonight
19 Dec - 20 Dec
Tomorrow
20 Dec - 21 Dec
This weekend
19 Dec - 21 Dec
Next weekend
26 Dec - 28 Dec

Our top choices for Castellina in Chianti holiday rentals

Exterior
Farmhouse in the heart of the real chiantishire

Farmhouse in the heart of the real chiantishire

Farmhouse in the heart of the real chiantishire
Castellina in Chianti
10.0 out of 10, Exceptional, (148)
"Very relaxing farmhouse cottage with pleasant and peaceful views .The only drawback is the ruddy gravel access road which makes for an unpleasant excursion to and from the property."
United States
William H.
Farmhouse in the heart of the real chiantishire
Outdoor dining
Villa with large garden in the Chianti hills

Villa with large garden in the Chianti hills

Villa with large garden in the Chianti hills
Siena
9.6 out of 10, Exceptional, (75)
"Our group enjoyed staying in this location. It was comfortable and a perfect central location for exploring Tuscany."
United States
Jessica P.
Villa with large garden in the Chianti hills
Exterior
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views

ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views

ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
Castellina in Chianti
10.0 out of 10, Exceptional, (64)
"Gorgeous property - we had a wonderful stay "
United Kingdom
Michelle D.
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
Terrace/patio
Palazzo Alfieri Residenza d’epoca

Palazzo Alfieri Residenza d’epoca

Palazzo Alfieri Residenza d’epoca
Historic Centre of Florence
9.2 out of 10, Wonderful, (725)
"This was such a lovely hotel! It was in a great location with an incredible view. The staff was great and the breakfast was absolutely fantastic! I would highly recommend this hotel "
United States
Christine
The price is HK$916
HK$1,135 total
includes taxes & fees
22 Dec - 23 Dec
Palazzo Alfieri Residenza d’epoca
Terrace/patio
Il Rivalta - Place of Charme

Il Rivalta - Place of Charme

Il Rivalta - Place of Charme
4.0 star property
Historic Centre of Florence
9.2 out of 10, Wonderful, (440)
"A really nice place to stay and close to everything you need. Would definitely go back and stay. "
United States
Tejwant
The price is HK$923
HK$1,143 total
includes taxes & fees
21 Dec - 22 Dec
Il Rivalta - Place of Charme
Interior detail
Palazzo Mannaioni Suites

Palazzo Mannaioni Suites

Palazzo Mannaioni Suites
4.0 star property
Historic Centre of Florence
9.2 out of 10, Wonderful, (1072)
"Perfect stay"
United States
Juan P
Palazzo Mannaioni Suites
Exterior
Teatro Luxury Apartments Firenze - Starhotels Collezione

Teatro Luxury Apartments Firenze - Starhotels Collezione

Teatro Luxury Apartments Firenze - Starhotels Collezione
Historic Centre of Florence
9.8 out of 10, Exceptional, (47)
"Great hotel!!"
United States
Roberto
The price is HK$1,327
HK$1,569 total
includes taxes & fees
21 Dec - 22 Dec
Teatro Luxury Apartments Firenze - Starhotels Collezione
Terrace/patio
Numa Palazzo San Niccolò

Numa Palazzo San Niccolò

Numa Palazzo San Niccolò
Historic Centre of Florence
9.4 out of 10, Exceptional, (174)
"Clean, amenities, breakfast! "
United States
Laury
The price is HK$712
HK$892 total
includes taxes & fees
7 Jan - 8 Jan 2026
Numa Palazzo San Niccolò
Indoor pool, open 9:00 AM to 8:00 PM, pool loungers
Forte16 View & Spa

Forte16 View & Spa

Forte16 View & Spa
Santissima Annunziata
9.6 out of 10, Exceptional, (897)
"The room was great, balcony was magnificent and not too far from the major attractions. The front desk was helpful and accommodating. "
United States
Sean
The price is HK$879
HK$1,077 total
includes taxes & fees
7 Jan - 8 Jan 2026
Forte16 View & Spa
Premium bedding, down duvets, in-room safe, desk
La Torre Del Cestello

La Torre Del Cestello

La Torre Del Cestello
Historic Centre of Florence
9.0 out of 10, Wonderful, (229)
"Great location and great rooms"
United States
David
The price is HK$675
HK$870 total
includes taxes & fees
22 Dec - 23 Dec
La Torre Del Cestello
In-room safe, cots/infant beds, bed sheets
Hu Firenze Camping In Town

Hu Firenze Camping In Town

Hu Firenze Camping In Town
Florence
8.8 out of 10, Excellent, (1612)
"It was a grt place to stay"
United States
Sunitha
Hu Firenze Camping In Town
Terrace/patio
Serristori Palace Residence

Serristori Palace Residence

Serristori Palace Residence
Historic Centre of Florence
9.6 out of 10, Exceptional, (168)
"Absolutely fantastic location and wonderful place to stay."
United States
Matt and Katie
Serristori Palace Residence
Seasonal outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas
Fattoria il Milione Agriturismo

Fattoria il Milione Agriturismo

Fattoria il Milione Agriturismo
4.0 star property
Florence
8.2 out of 10, Very good, (226)
"The property is perfect if you’re looking for a place to relax and have the most wonderful views of Tuscany area, the staff, Andrea was really helpful and kind. It’s better if you rent a car to get there, by bus you’ll have to walk a lot. But the place is totally worth it,"
United States
Jorge
The price is HK$470
HK$644 total
includes taxes & fees
9 Jan - 10 Jan 2026
Fattoria il Milione Agriturismo
Premium bedding, down duvets, iron/ironing board, cots/infant beds
Palazzo Branchi

Palazzo Branchi

Palazzo Branchi
Historic Centre of Florence
9.0 out of 10, Wonderful, (287)
"WHAT A GREAT STAY. The location is perfect if you want to stay in the heart of Florence. Easy to reach all of the main attractions. The room was so pretty and spacious. Our host was very helpful, greeted us at the door, and had with great tips! Will stay here again. "
United States
Jeannette
The price is HK$798
HK$988 total
includes taxes & fees
22 Dec - 23 Dec
Palazzo Branchi
Rooftop terrace
Palazzo Graziani

Palazzo Graziani

Palazzo Graziani
Historic Centre of Florence
9.2 out of 10, Wonderful, (623)
"Excellent location, very clean and outstanding staff"
United States
Priyank
The price is HK$1,016
HK$1,246 total
includes taxes & fees
19 Jan - 20 Jan 2026
Palazzo Graziani
Down duvets, Select Comfort beds, in-room safe, desk
Residence Porta al Prato

Residence Porta al Prato

Residence Porta al Prato
4.0 star property
Santa Maria Novella
8.8 out of 10, Excellent, (166)
"We stayed there with family, an old but good property."
Canada
Jeet
Residence Porta al Prato
Exterior
Numa Florence Palazzo Belfiore

Numa Florence Palazzo Belfiore

Numa Florence Palazzo Belfiore
Historic Centre of Florence
9.6 out of 10, Exceptional, (371)
"Great property, plenty of space for my family. The location is great, we were able to walk everywhere including the train station. "
United States
Loren
The price is HK$1,235
HK$1,467 total
includes taxes & fees
11 Jan - 12 Jan 2026
Numa Florence Palazzo Belfiore
Laptop workspace, free WiFi, bed sheets
Bob W Florence Ponte Vecchio

Bob W Florence Ponte Vecchio

Bob W Florence Ponte Vecchio
Historic Centre of Florence
9.2 out of 10, Wonderful, (211)
"Very nice, quiet area of Florence! You cannot ask for a better location within walking distance of so many famous tourist sites! "
United States
Denise
The price is HK$821
HK$1,013 total
includes taxes & fees
16 Jan - 17 Jan 2026
Bob W Florence Ponte Vecchio
Bicycling
PopArtment

PopArtment

PopArtment
San Jacopino
9.0 out of 10, Wonderful, (742)
"Excellent location, very close to tram. Nice spacious room with mini kitchen."
United States
MA ARLENE
The price is HK$825
HK$1,017 total
includes taxes & fees
7 Jan - 8 Jan 2026
PopArtment
Dining room
Palazzo Ottaviani Luxury Apartments

Palazzo Ottaviani Luxury Apartments

Palazzo Ottaviani Luxury Apartments
Historic Centre of Florence
10.0 out of 10, Exceptional, (6)
"The place is absolutely amazing. Rooms were clean and the hotel was walking distance to all major attractions. Very friendly reception. "
United States
Ricardo
The price is HK$4,425
HK$4,996 total
includes taxes & fees
24 Dec - 25 Dec
Palazzo Ottaviani Luxury Apartments
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

10/10 Excellent
"Guest services were so kind! Clean stay with great amenities "
meera 3-night trip
Posted 3 days 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:

  • View our selection of featured holiday rentals in Castellina in Chianti
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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 holiday rentals in Castellina in Chianti?

Yes, there are holiday rentals close to the most popular sights in Castellina in Chianti, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Castellina in Chianti has to offer?

QK Costa58 Home Tower: This holiday 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 holiday rentals will I find in Castellina in Chianti?

With 29 Expedia holiday rentals, you're guaranteed 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 holiday rental in Castellina in Chianti like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Castellina in Chianti. Holiday rentals provide amenities such as hot tubs, fire pits and patios so you'll have everything you want. If you're concerned about a sanitised environment, a holiday rental can offer a sense of seclusion away from shared hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a great choice for families.