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

Castellina in Chianti Vacation Rentals

Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Castellina in Chianti vacation rentals

A balcony with a table, chairs, and a bottle of wine, overlooking a vineyard and distant hills.

1. 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
$114 nightly
The price is $128
Nov 4 - Nov 5
Total with taxes and fees
Casa Vacanze Squarcialupi
A kitchen with wooden cabinets, a glass display case, and a dining area with a table and chairs.

2. 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
$79 nightly
The price is $91
Oct 15 - Oct 16
Total with taxes and fees
Mariani Bed & Breakfast
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, (42 reviews)
"Great place to stay in Tuscany! Very nice breakfast also!"
United States
Janet
$195 nightly
The price is $217
Oct 19 - Oct 20
Total with taxes and fees
Riserva di Fizzano Residence
A stone building with multiple windows and a chimney.

4. Agriturismo La Ferrozzola

Agriturismo La Ferrozzola
Castellina in Chianti
9.4 out of 10, Exceptional, (9 reviews)
"Very nice agriturismo. "
United States
Ruth
$128 nightly
The price is $145
Nov 8 - Nov 9
Total with taxes and fees
Agriturismo La Ferrozzola
A pool area with lounge chairs and umbrellas, surrounded by greenery and a stone building.

5. 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
$132 nightly
The price is $150
Oct 9 - Oct 10
Total with taxes and fees
Residenzia del Sogno
A stone-paved entrance with a grill, potted plants, and a door leading to an interior space.

6. 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
$138 nightly
The price is $142
Oct 15 - Oct 16
Total with taxes and fees
Apartment 'Poggio Della Capannina Di Castellina in Chianti' with Private Garden and Wi-Fi
A bedroom with a bed, nightstands, a chair, and a door.

7. Apartment 'La Casa Della Gina' with Wi-Fi

Apartment 'La Casa Della Gina' with Wi-Fi
Castellina in Chianti
$540 nightly
The price is $544
Oct 25 - Oct 26
Total with taxes and fees
Apartment 'La Casa Della Gina' with Wi-Fi
A brick building with a garden, a metal fence, and a clear sky.

8. Casa Marisa in Castellina in Chianti

Casa Marisa in Castellina in Chianti
Castellina in Chianti
$298 nightly
The price is $302
Oct 12 - Oct 13
Total with taxes and fees
Casa Marisa in Castellina in Chianti
A stone gate with two animal statues, a lamp post, and a dirt path leading through a wooded area.

9. Casa il Cipresso, in the heart of Chianti with swimming pool

Casa il Cipresso, in the heart of Chianti with swimming pool
Castellina in Chianti
10.0 out of 10, Exceptional, (2 reviews)
"Maurizio was an excellent host, he was very helpful in explaining the house and amenities during the check in process, and also sent us a lot of references for food shopping, restaurants, wineries and things to do while in Tuscany.I highly recommend this property."
United States
Guillermo A.
Casa il Cipresso, in the heart of Chianti with swimming pool
A stone staircase leading up to a historic building with a tower, surrounded by lavender fields.

10. Rondine cosy apartment in the Chianti garden pool tennis wifi

Rondine cosy apartment in the Chianti garden pool tennis wifi
Toscana
Rondine cosy apartment in the Chianti garden pool tennis wifi
A rustic outdoor dining area with a stone wall, wooden furniture, and potted plants.

11. 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 reviews)
"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
A stone building with a gravel path, outdoor seating, and greenery.

12. The Arch Among the Hills of Castellina

The Arch Among the Hills of Castellina
Topina
$308 nightly
The price is $313
Nov 2 - Nov 3
Total with taxes and fees
The Arch Among the Hills of Castellina
A stone staircase leading up to a historic building with a tower, surrounded by lavender fields.

13. Istrice cosy apartment in the Chianti garden swimming pool, tennis and wifi

Istrice cosy apartment in the Chianti garden swimming pool, tennis and wifi
Toscana
Istrice cosy apartment in the Chianti garden swimming pool, tennis and wifi
A restaurant with hanging baskets of greenery, wicker furniture, and a view of the outdoors.

14. 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
$302 nightly
The price is $336
Nov 8 - Nov 9
Total with taxes and fees
Terre di Baccio
A stone building with a garden in front.

15. Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (28 reviews)
"What an amazing place. We enjoyed it so much."
United States
Tatevik
$171 nightly
The price is $197
Oct 15 - Oct 16
Total with taxes and fees
Borgo Argenina
A spacious hotel room with a large bed, a sitting area with chairs, and a view through an arched doorway to another room.

16. 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
$96 nightly
The price is $110
Nov 3 - Nov 4
Total with taxes and fees
La Terrazza Sul Campo Rooming House
A hotel room with a bed, a bedside table with a lamp, a potted plant, and a view of the outside through the window.

17. PALAZZO DEL PAPA

PALAZZO DEL PAPA
Siena City Centre
9.6 out of 10, Exceptional, (116 reviews)
"Hamza is so helpful!! Finding the property is a little tricky, but he helped every step of the way! He also provided excellent dining suggestions and a great cooking class!"
United States
Charles
$181 nightly
The price is $203
Nov 3 - Nov 4
Total with taxes and fees
PALAZZO DEL PAPA
An outdoor swimming pool with a wooden pergola, lounge chairs, and a stone wall backdrop.

18. Guild Living Siena Senior Resort & Residence

Guild Living Siena Senior Resort & Residence
Scacciapensieri
8.8 out of 10, Excellent, (55 reviews)
"Amazing! Thank you!"
United Kingdom
Lucy
$104 nightly
The price is $119
Nov 1 - Nov 2
Total with taxes and fees
Guild Living Siena Senior Resort & Residence
A bathroom with a window view of a historic building and a tiled roof.

19. Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (486 reviews)
"Great location right in the heart of everything and next to an escalator that takes you to the main plaza. Very comfortable bed, friendly staff. Convenient parking option very close by."
United States
Heather
$93 nightly
The price is $107
Nov 2 - Nov 3
Total with taxes and fees
Siena Vip
A villa with a swimming pool, outdoor seating, and a tennis court.

20. 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
$107 nightly
The price is $123
Oct 25 - Oct 26
Total with taxes and fees
Villa Curina Resort
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

Hotel La Fortezza

Hotel La Fortezza

10/10 Excellent
"We only stayed here one night before traveling to a wedding about an hour away, but the stay was wonderful. The room with clean and well kept and the staff was friendly, knowledgeable, and extremely helpful! It is a bit of a walk from some of the city’s attractions, but there is a tram stop just a 2 minute walk away and the area is lovely and very walkable. Have already recommended to friends who need a place to stay on their return travel home."
Colleen 1-night trip
Posted 9 hours ago
Hotel La Fortezza

Find out more about Castellina in Chianti

Everything you need to know about Castellina in Chianti vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Castellina in Chianti vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Castellina in Chianti vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Castellina in Chianti vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Castellina in Chianti. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Castellina in Chianti in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $49 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Castellina in Chianti rentals

At Expedia, we put the best Castellina in Chianti vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Castellina in Chianti rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Castellina in Chianti vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Castellina in Chianti. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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

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.