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

Castellina in Chianti Vacation Rentals

  • 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

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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, Exceptional, (18 reviews)
"Beautiful view, very clean and everything in great condition. Friendly service. We will definitely stay again."
United States
Frank
The price is ₩117,255
₩135,015 total
includes taxes & fees
Oct 13 - Oct 14
Mariani Bed & Breakfast
A balcony with a table, chairs, and a bottle of wine, overlooking a vineyard and distant hills.

2. Casa Vacanze Squarcialupi

Casa Vacanze Squarcialupi
Castellina in Chianti
9.0 out of 10, Wonderful, (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 ₩157,582
₩182,391 total
includes taxes & fees
Nov 4 - Nov 5
Casa Vacanze Squarcialupi
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, Exceptional, (40 reviews)
"Great place to stay in Tuscany! Very nice breakfast also!"
United States
Janet
The price is ₩244,940
₩272,451 total
includes taxes & fees
Oct 6 - Oct 7
Riserva di Fizzano Residence
A pool area with lounge chairs and umbrellas, surrounded by greenery and a stone building.

4. 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 ₩169,368
₩192,339 total
includes taxes & fees
Oct 6 - Oct 7
Residenzia del Sogno
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, Exceptional, (80 reviews)
"Amazing property and room, only issue is it’s very understaffed so it’s hard to get anything without chasing down workers. They also don’t stay on the property so after like 11pm you’re on your own. Besides that it was a wonderful location and very peaceful."
United States
Gage
The price is ₩365,342
₩407,910 total
includes taxes & fees
Oct 16 - Oct 17
Terre di Baccio
A table with two wine glasses, a bottle, and a book.

6. Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (99 reviews)
"Place was great, beautiful, modern, well maintained and staff was very helpful. I didn’t like that it is far from everything, far from train station, not too many options for food in the vicinity."
United States
Waleska
The price is ₩89,143
₩104,092 total
includes taxes & fees
Oct 20 - Oct 21
Domus il Palio B&B
A stone building with a garden in front.

7. Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (27 reviews)
"What an amazing place. We enjoyed it so much."
United States
Tatevik
The price is ₩268,384
₩307,290 total
includes taxes & fees
Oct 5 - Oct 6
Borgo Argenina
An outdoor swimming pool with a wooden pergola, lounge chairs, and a stone wall backdrop.

8. Guild Living Siena Senior Resort & Residence

Guild Living Siena Senior Resort & Residence
Scacciapensieri
8.8 out of 10, Excellent, (52 reviews)
"Amazing! Thank you!"
United Kingdom
Lucy
The price is ₩156,337
₩178,005 total
includes taxes & fees
Nov 1 - Nov 2
Guild Living Siena Senior Resort & Residence
A villa with a swimming pool, outdoor seating, and a tennis court.

9. Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (80 reviews)
"Beautiful resort in the hills, lovely and charming room, incredibly spacious."
United States
Deanna
The price is ₩171,390
₩194,563 total
includes taxes & fees
Oct 9 - Oct 10
Villa Curina Resort
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, Wonderful, (484 reviews)
"Fantastic location and very friendly staff, we will definitely be back"
United Kingdom
Luis
The price is ₩124,968
₩143,498 total
includes taxes & fees
Nov 2 - Nov 3
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, Very good, (349 reviews)
"Humming noise in the room. Slow internet. Fine bed. Good location."
Netherlands
Lauro
The price is ₩101,218
₩117,374 total
includes taxes & fees
Oct 12 - Oct 13
ApartHotel Anghel
A pool area with two rectangular pools, surrounded by lounge chairs and umbrellas, set against a backdrop of vineyards and tall cypress trees.

12. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (40 reviews)
"Great spot"
Canada
Philippe
The price is ₩225,598
₩248,158 total
includes taxes & fees
Oct 12 - Oct 13
Villa di Sotto
A spacious hotel room with a large bed, a sitting area with chairs, and a view through an arched doorway to another room.

13. La Terrazza Sul Campo Rooming House

La Terrazza Sul Campo Rooming House
Siena City Centre
9.8 out of 10, Exceptional, (251 reviews)
"Great stay. Thanks for the hospitality and kindness."
United Kingdom
Agnieszka
The price is ₩134,965
₩154,496 total
includes taxes & fees
Nov 2 - Nov 3
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.
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

Grand Hotel Baglioni

Grand Hotel Baglioni

10/10 Excellent
"Great hotel within walking distance of the historic centre of Florence. Helpful and knowledgeable staff. Amazing views from the rooftop bar/ restaurant. Thank you"
Emma 4-night trip
Posted 2 hours ago
Grand Hotel Baglioni

Find out more about Castellina in Chianti

Search for Vacation rentals in Castellina in Chianti on Expedia.co.uk! You can easily find your home rentals, villas, Vacation apartments in Castellina in Chianti using one of the methods below:

  • View our selection of featured Vacation rentals in Castellina in Chianti
  • Use the map to find apartments and other Vacation homes in the Castellina in Chianti neighbourhood you prefer
  • Enter your travel dates to view the best deals on Vacation 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?

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 31 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, City Hall Castellina In Chianti and Castellina Fortress 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.