Castellina in Chianti Vacation Rentals from $69: 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 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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Our top choices for Castellina in Chianti vacation rentals

1. Mariani Bed & Breakfast

Castellina in Chianti

Chie

$83 nightly

Sep 1 - Sep 2

Total with taxes and fees

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

2. Residenzia del Sogno

Castellina in Chianti

Katherine

$120 nightly

Sep 20 - Sep 21

Total with taxes and fees

3. Casa Vacanze Squarcialupi

Castellina in Chianti

Jeffrey

$133 nightly

Aug 25 - Aug 26

Total with taxes and fees

4. Riserva di Fizzano Residence

Castellina in Chianti

Janet

$203 nightly

Aug 26 - Aug 27

Total with taxes and fees

5. Villa with large garden in the Chianti hills

Siena

Julie H.

$161 nightly

Sep 1 - Sep 2

Total with taxes and fees

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

Castellina in Chianti

$161 nightly

Sep 13 - Sep 14

Total with taxes and fees

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

Guillermo A.

9. Casa Marisa in Castellina in Chianti

Castellina in Chianti

$311 nightly

Aug 24 - Aug 25

Total with taxes and fees

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

$377 nightly

Sep 1 - Sep 2

Total with taxes and fees

13. La Misura, cottage with garden and swimming pool on the hills of Chianti

Castellina in Chianti

Jami B.

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

Castellina in Chianti

$458 nightly

Sep 22 - Sep 23

Total with taxes and fees

15. The San Leonino House

Castellina in Chianti

$1,267 nightly

Aug 24 - Aug 25

Total with taxes and fees

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

Toscana

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

Castellina in Chianti

18. 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

$283 nightly

Aug 24 - Aug 25

Total with taxes and fees

19. Borgo Argenina

Gaiole in Chianti

Sabatino

$155 nightly

Aug 23 - Aug 24

Total with taxes and fees

20. B&B Il Corso

Siena City Centre

Katherine

$118 nightly

Aug 30 - Aug 31

Total with taxes and fees

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Top Castellina in Chianti Hotel Reviews

The Social Hub Florence Lavagnini

10/10 Excellent

"Great location, pool & pool bar were amazing with great views of the city"

Starhotels Tuscany

10/10 Excellent

"We LOVED our stay. OMG the breakfast was truly out of this world and better than any I ever had at the Ritz Carlton! The tram was just a 2 min walk away making it super easy and convenient to see Florence. I highly recommend the staff at the hotel who always said YES to requests for help. The ambience was perfect with top amenities. We can highly recommend this hotel and plan to stay there again in the future! BRAVO!!!!!"

c-hotels Ambasciatori

8/10 Good

"We had a very good stay in Florence. The location was excellent, the room was comfortable, and overall we were very happy with our experience. There are a few areas that could use a little more attention. Some parts of the hotel looked a bit worn, with noticeable marks and damage on some of the walls, and the elevator was occasionally problematic. These were relatively minor issues, though, and didn’t significantly affect our stay. Overall, we had a great experience and really enjoyed our time here. A very good option for a stay in Florence, and we would happily recommend it!"

Bernini Palace

10/10 Excellent

"The entire stay was perfect, from start to finish. This hotel is to the image of Florence: beautiful and steeped in history. All staff were professional, competent and very pleasant. Our room was comfortable and the all-linen sheets? Dreamy. The breakfast was delicious and suited all tastes. We could not have asked for a better location to explore all that Florence has to offer."

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 $69 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 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.

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Check prices for these dates

Our top choices for Castellina in Chianti vacation rentals

1. Mariani Bed & Breakfast

2. Residenzia del Sogno

3. Casa Vacanze Squarcialupi

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. La Misura, cottage with garden and swimming pool on the hills of Chianti

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

15. The San Leonino House

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

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

18. Terre di Baccio

19. Borgo Argenina

20. B&B Il Corso

Find vacation rentals that suit your style

Top Castellina in Chianti Hotel Reviews

The Social Hub Florence Lavagnini

Maxim Axial

IQ Hotel Firenze

Starhotels Tuscany

Plus Florence - Hostel

Radisson Blu Hotel, Florence

c-hotels Ambasciatori

Albergo Firenze

Bernini Palace

Find out more about Castellina in Chianti

Frequently asked questions

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