Castellina in Chianti Vacation Rentals from ￥12,613: Search Short-Term Rentals

Q: What are some of the best vacation home rentals in Castellina in Chianti?

Villa La Stella - Casa per Ferie : This vacation home rental outside of 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 .

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In two weeks

In two months

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Our top choices for Castellina in Chianti vacation rentals

1. Mariani Bed & Breakfast

Castellina in Chianti

Chie

￥17,509 total

includes taxes & fees

Aug 13 - Aug 14

2. Casa Vacanze Squarcialupi

Castellina in Chianti

Jeffrey

￥24,531 total

includes taxes & fees

Aug 25 - Aug 26

Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, sun loungers

3. Residenzia del Sogno

Castellina in Chianti

Katherine

￥22,245 total

includes taxes & fees

Aug 30 - Aug 31

4. Riserva di Fizzano Residence

Castellina in Chianti

Janet

￥35,811 total

includes taxes & fees

Sep 8 - Sep 9

5. Villa with large garden in the Chianti hills

Siena

Julie H.

￥25,371 total

includes taxes & fees

Sep 1 - Sep 2

6. Apartment 'Poggio Della Capannina Di Castellina in Chianti' with Private Garden and Wi-Fi

Castellina in Chianti

￥24,391 total

includes taxes & fees

Sep 10 - Sep 11

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

Toscana

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

Castellina in Chianti

Jon M.

9. Casa Marisa in Castellina in Chianti

Castellina in Chianti

￥49,969 total

includes taxes & fees

Aug 19 - Aug 20

10. CASA DEGLI ULIVI - COTTAGE WITH SWIMMING POOL

Castellina in Chianti

lyndon s.

11. Casa Antico Roseto - cottage with swimming pool

Castellina in Chianti

"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...

Lisa S.

12. The Arch Among the Hills of Castellina

Topina

￥61,277 total

includes taxes & fees

Sep 10 - Sep 11

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

Castellina in Chianti

￥96,337 total

includes taxes & fees

Aug 31 - Sep 1

14. The San Leonino House

Castellina in Chianti

￥243,320 total

includes taxes & fees

Aug 24 - Aug 25

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

Toscana

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

Castellina in Chianti

17. Terre di Baccio

Greve in Chianti

"We had a wonderful experience! The staff was kind and very helpful. Our room was stunning and very spacious for a family of 5! The breakfast was amazing, and all of the activities on site were very fun - we especially enjoyed the cooking class! I would absolutely love to return here. I recommend looking into and booking on-site activities in advance so you can get the most out of your experience!"

Julia

￥54,181 total

includes taxes & fees

Aug 15 - Aug 16

18. Borgo Argenina

Gaiole in Chianti

Sabatino

￥47,232 total

includes taxes & fees

Aug 23 - Aug 24

19. B&B Il Corso

Siena City Centre

Katherine

￥21,206 total

includes taxes & fees

Aug 21 - Aug 22

Suite | Premium bedding, Select Comfort beds, minibar, in-room safe

20. La Terrazza Sul Campo Rooming House

Siena City Centre

Margaret

￥21,875 total

includes taxes & fees

Aug 26 - Aug 27

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Top Castellina in Chianti Hotel Reviews

Palazzo Montebello

10/10 Excellent

"Beautiful hotel and walking distance from the centre"

Bernini Palace

10/10 Excellent

"Hotel Bernini Palace is truly a hidden gem in the heart of Florence’s historic city centre. The staff feel like family — anticipating your needs even before you ask. Breakfast was excellent, room service was great, and every visit has been memorable. The secret to their hospitality is simple: everyone, from the door assistant to the concierge, breakfast team, and cleaning staff, greets you with a genuine smile and real care. I’ve stayed here every time I’ve visited Florence, and I wouldn’t choose anywhere else. Truly outstanding hospitality, time and time again.”"

The Social Hub Florence Lavagnini

10/10 Excellent

"I booked this place specifically for the pool & it was such a good idea! It is a short walk into the main attractions, and there is a tram stop right out front which will take you in or to the airport. As someone who finds public transport stressful I found it so easy. The walk is also nice for seeing different things along the way or stopping for an spritz ;) I booked a standard room as a solo traveller & it was one of the biggest rooms I had in Italy. Would be fine for 2 people."

Find out more about Castellina in Chianti

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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 of 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 27 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, Buondonno Winery and City Hall Castellina In Chianti 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.

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Check prices for these dates

Our top choices for Castellina in Chianti vacation rentals

1. Mariani Bed & Breakfast

2. Casa Vacanze Squarcialupi

3. Residenzia del Sogno

4. Riserva di Fizzano Residence

5. Villa with large garden in the Chianti hills

6. Apartment 'Poggio Della Capannina Di Castellina in Chianti' with Private Garden and Wi-Fi

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

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

9. Casa Marisa in Castellina in Chianti

10. CASA DEGLI ULIVI - COTTAGE WITH SWIMMING POOL

11. Casa Antico Roseto - cottage with swimming pool

12. The Arch Among the Hills of Castellina

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

14. The San Leonino House

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

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

17. Terre di Baccio

18. Borgo Argenina

19. B&B Il Corso

20. La Terrazza Sul Campo Rooming House

Find vacation rentals that suit your style

Top Castellina in Chianti Hotel Reviews

Palazzo Montebello

Hotel Calimala Florence

Starhotels Tuscany

Bernini Palace

c-hotels Ambasciatori

The Social Hub Florence Lavagnini

Plus Florence - Hostel

IQ Hotel Firenze

Maxim Axial

Find out more about Castellina in Chianti

Frequently asked questions

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