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
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

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)
"Very nice and quiet neighbourhood. Close to city centre. The host is very kind."
Japan
Chie
$90 nightly
The price is $104
Oct 7 - Oct 8
Total with taxes and fees
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, Exceptional, (15 reviews)
"Beautiful and authentic place, lovely couple running the place that care about you and your stay. "
Canada
Katherine
$119 nightly
The price is $135
Sep 16 - Sep 17
Total with taxes and fees
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, Exceptional, (37 reviews)
"Great place to stay in Tuscany! Very nice breakfast also!"
United States
Janet
$211 nightly
The price is $235
Sep 14 - Sep 15
Total with taxes and fees
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, 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
$142 nightly
The price is $159
Sep 20 - Sep 21
Total with taxes and fees
Casa Vacanze Squarcialupi
A stone-paved entrance with a grill, potted plants, and a door leading to an interior space.

5. 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
$149 nightly
The price is $154
Sep 15 - Sep 16
Total with taxes and fees
Apartment 'Poggio Della Capannina Di Castellina in Chianti' with Private Garden and Wi-Fi
A stone staircase leading up to a historic building with a tower, surrounded by lavender fields.

6. 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 brick building with a garden, a metal fence, and a clear sky.

7. Casa Marisa in Castellina in Chianti

Casa Marisa in Castellina in Chianti
Castellina in Chianti
$309 nightly
The price is $313
Sep 15 - Sep 16
Total with taxes and fees
Casa Marisa in Castellina in Chianti
A kitchen with white cabinets, a blue refrigerator, and a dining area with white chairs.

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

Apartment 'La Casa Della Gina' with Wi-Fi
Castellina in Chianti
$737 nightly
The price is $741
Oct 12 - Oct 13
Total with taxes and fees
Apartment 'La Casa Della Gina' with Wi-Fi
A stone building with a gravel path, outdoor seating, and greenery.

9. The Arch Among the Hills of Castellina

The Arch Among the Hills of Castellina
Topina
$342 nightly
The price is $347
Oct 2 - Oct 3
Total with taxes and fees
The Arch Among the Hills of Castellina
A pool area with lounge chairs and a stone building in the background.

10. The San Leonino House

The San Leonino House
Castellina in Chianti
The San Leonino House
A stone staircase leading up to a historic building with a tower, surrounded by lavender fields.

11. 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.

12. Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (79 reviews)
"The stay was great, and the staff were wonderful. "
United States
SYDNEY
$332 nightly
The price is $369
Sep 28 - Sep 29
Total with taxes and fees
Terre di Baccio
A stone building with a garden in front.

13. 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
$176 nightly
The price is $203
Sep 16 - Sep 17
Total with taxes and fees
Borgo Argenina
An outdoor swimming pool with a wooden pergola, lounge chairs, and a stone wall backdrop.

14. Guild Living Siena Senior Resort & Residence

Guild Living Siena Senior Resort & Residence
Scacciapensieri
8.8 out of 10, Excellent, (49 reviews)
"New facilities, its great, nice, friendly"
United Kingdom
tomaz
$138 nightly
The price is $157
Oct 5 - Oct 6
Total with taxes and fees
Guild Living Siena Senior Resort & Residence
A table with two wine glasses, a bottle, and a book.

15. Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (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
$62 nightly
The price is $73
Oct 14 - Oct 15
Total with taxes and fees
Domus il Palio B&B
A bakery display with pastries and a coffee station.

16. B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (207 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
$123 nightly
The price is $140
Sep 27 - Sep 28
Total with taxes and fees
B&B Il Corso
A bathroom with a window view of a historic building and a tiled roof.

17. Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (478 reviews)
"Fantastic location and very friendly staff, we will definitely be back"
United Kingdom
Luis
$120 nightly
The price is $137
Oct 14 - Oct 15
Total with taxes and fees
Siena Vip
A modern lobby with white leather sofas, a glass coffee table, and potted plants.

18. ApartHotel Anghel

ApartHotel Anghel
Siena
8.4 out of 10, Very Good, (346 reviews)
"Great stay highly recommend!!"
United States
jon
$112 nightly
The price is $128
Oct 6 - Oct 7
Total with taxes and fees
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.

19. 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
$166 nightly
The price is $188
Oct 13 - Oct 14
Total with taxes and fees
La Terrazza Sul Campo Rooming House
A pool area with a water slide and a stage for performances.

20. Hu Norcenni Girasole Village

Hu Norcenni Girasole Village
4.0 star property
Figline e Incisa Valdarno
8.6 out of 10, Excellent, (331 reviews)
"Amazing venue , lots of kids entertainment. Lots of facilities- shops restaurants. Splash parks were brilliant. Highly recommended."
United Kingdom
Katie
$55 nightly
The price is $62
Sep 14 - Sep 15
Total with taxes and fees
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

Hotel Horto Convento

Hotel Horto Convento

10/10 Excellent
"Loved the hotel but wished that they would have a small restaurant as the grounds are lovely"
Afsaneh 1-night trip
Posted 4 hours ago
Hotel Horto Convento

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 $51 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 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.