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Castellina in Chianti Vacation Rentals

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Our top choices for Castellina in Chianti vacation rentals

1. 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 CA $279
CA $310 total
includes taxes & fees
Sep 8 - Sep 9
Riserva di Fizzano Residence

2. 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 CA $126
CA $145 total
includes taxes & fees
Aug 21 - Aug 22
Mariani Bed & Breakfast

3. 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 CA $179
CA $207 total
includes taxes & fees
Aug 31 - Sep 1
Casa Vacanze Squarcialupi

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 CA $164
CA $187 total
includes taxes & fees
Sep 1 - Sep 2
Residenzia del Sogno

5. Villa with large garden in the Chianti hills

Villa with large garden in the Chianti hills
Siena
9.6 out of 10, Exceptional, (81 reviews)
"It was a little tricky finding the villa but worth it. Better instructions would be helpful. The home was lovely. The gardens wonderful. A great respite fromThe city."
United States
Julie H.
The price is CA $193
CA $222 total
includes taxes & fees
Sep 2 - Sep 3
Villa with large garden in the Chianti hills

6. Casa Marisa in Castellina in Chianti

Casa Marisa in Castellina in Chianti
Castellina in Chianti
The price is CA $347
CA $433 total
includes taxes & fees
Aug 24 - Aug 25
Casa Marisa in Castellina in Chianti

7. 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

8. 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
The price is CA $132
CA $213 total
includes taxes & fees
Sep 15 - Sep 16
Apartment 'Poggio Della Capannina Di Castellina in Chianti' with Private Garden and Wi-Fi

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

10. 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

11. CASA DEGLI ULIVI - COTTAGE WITH SWIMMING POOL

CASA DEGLI ULIVI - COTTAGE WITH SWIMMING POOL
Castellina in Chianti
10.0 out of 10, Exceptional, (1 review)
"Lovely visit. The views are amazing. "
United States
lyndon s.
CASA DEGLI ULIVI - COTTAGE WITH SWIMMING POOL

12. Casa Antico Roseto - cottage with swimming pool

Casa Antico Roseto - cottage with swimming pool
Castellina in Chianti
8.8 out of 10, Excellent, (3 reviews)
"The borgo was perfect for our family of 6 adults. The views from the pool were spectacular. We had what we needed in kitchen and we grilled one night. The stone structure set on mountainside gave natural coolness for comfort with amazing views- even from the shower! There is AC which we didn’t use but good idea for peak summer. We walked to a great restaurant and also walked to winery for wine tasting. We shared the property but it felt private with our own outdoor dining areas. Maurizio was...
United States
Lisa S.
Casa Antico Roseto - cottage with swimming pool

13. The Arch Among the Hills of Castellina

The Arch Among the Hills of Castellina
Topina
The price is CA $462
CA $525 total
includes taxes & fees
Sep 14 - Sep 15
The Arch Among the Hills of Castellina

14. 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

15. Casa Belvedere cottage with swimming pool in the heart of Chianti

Casa Belvedere cottage with swimming pool in the heart of Chianti
Castellina in Chianti
Casa Belvedere cottage with swimming pool in the heart of Chianti

16. The San Leonino House

The San Leonino House
Castellina in Chianti
The price is CA $1,084
CA $2,125 total
includes taxes & fees
Aug 23 - Aug 24
The San Leonino House

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

Apartment 'La Casa Della Gina' with Wi-Fi
Castellina in Chianti
The price is CA $963
CA $1,034 total
includes taxes & fees
Aug 31 - Sep 1
Apartment 'La Casa Della Gina' with Wi-Fi

18. Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (474 reviews)
"Fantastic location and very friendly staff, we will definitely be back"
United Kingdom
Luis
The price is CA $171
CA $194 total
includes taxes & fees
Aug 30 - Aug 31
Siena Vip

19. B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (205 reviews)
"Lovely B&B right in the heart of Siena. Pierre was incredibly helpful and kept me up to date prior to my arrival with suggestions for dining out, shopping and bars. Would highly recommend"
United Kingdom
Katherine
The price is CA $163
CA $185 total
includes taxes & fees
Aug 21 - Aug 22
B&B Il Corso

20. ApartHotel Anghel

ApartHotel Anghel
Siena
8.4 out of 10, Very good, (344 reviews)
"Great stay highly recommend!!"
United States
jon
The price is CA $127
CA $146 total
includes taxes & fees
Aug 30 - Aug 31
ApartHotel Anghel
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

Find out more about Castellina in Chianti

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Castellina in Chianti. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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 26 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 Sentierelsa Trail. 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.