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

Holiday Rentals in Castellina in Chianti

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Castellina in Chianti holiday rentals

1. 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 €97
includes taxes & fees
7 Aug - 8 Aug
Mariani Bed & Breakfast

2. Casa Vacanze Squarcialupi

Casa Vacanze Squarcialupi
Castellina in Chianti
8.8 out of 10, Excellent, (3 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 €130
includes taxes & fees
21 Aug - 22 Aug
Casa Vacanze Squarcialupi

3. 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 €121
includes taxes & fees
30 Aug - 31 Aug
Residenzia del Sogno

4. 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 €204
includes taxes & fees
24 Aug - 25 Aug
Riserva di Fizzano Residence

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

6. 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 €142
includes taxes & fees
1 Sept - 2 Sept
Villa with large garden in the Chianti hills

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. Casa Marisa in Castellina in Chianti

Casa Marisa in Castellina in Chianti
Castellina in Chianti
The price is €286
includes taxes & fees
9 Aug - 10 Aug
Casa Marisa in Castellina in Chianti

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, (1 review)
"Beautiful setting with a rustic and friendly vibe. The place was clean and well-kept. We enjoyed every minute! A bonus was that the nights were cool (did t need the AC), and we slept with the windows open, despite the heat during the day."
Canada
Jon M.
Casa il Cipresso, in the heart of Chianti with swimming pool

10. 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

11. 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

12. The Arch Among the Hills of Castellina

The Arch Among the Hills of Castellina
Topina
The price is €373
includes taxes & fees
4 Sept - 5 Sept
The Arch Among the Hills of Castellina

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

Apartment 'La Casa Della Gina' with Wi-Fi
Castellina in Chianti
Apartment 'La Casa Della Gina' with Wi-Fi

14. The San Leonino House

The San Leonino House
Castellina in Chianti
The price is €1,323
includes taxes & fees
23 Aug - 24 Aug
The San Leonino House

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. Sette Angeli Rooms

Sette Angeli Rooms
Historic Centre of Florence
8.8 out of 10, Excellent, (677 reviews)
"Good clean rooms and very close to the city center as well as the train station"
United Kingdom
VISHAL
The price is €88
includes taxes & fees
9 Aug - 10 Aug
Sette Angeli Rooms

17. Maison Ginori Guelfa

Maison Ginori Guelfa
Historic Centre of Florence
10.0 out of 10, Exceptional, (36 reviews)
"This was an incredible stay. The host was a phenomenal communicator and the property is as beautiful as pictured. If you want to be downtown in the heart of Florence, this is the perfect place to be and it is also far enough from the standard noise. I had peaceful nights and peaceful days, if I chose a late morning. It was literally near everything and I walked to every place I wanted to see. It was safe and easy to get to. I would absolutely stay at this property again and couldn’t have asked...
United States
Joyce
The price is €146
includes taxes & fees
9 Aug - 10 Aug
Maison Ginori Guelfa

18. Soggiorno Pezzati Daniela

Soggiorno Pezzati Daniela
Historic Centre of Florence
8.8 out of 10, Excellent, (93 reviews)
"Excellent location in walking distance to everything you need. The bed is very comfortable and the ensuite is a good size. "
Australia
Kitty
The price is €83
includes taxes & fees
9 Aug - 10 Aug
Soggiorno Pezzati Daniela

19. Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (79 reviews)
"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!"
United States
Julia
The price is €304
includes taxes & fees
19 Aug - 20 Aug
Terre di Baccio

20. Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (24 reviews)
"A very peaceful and relaxing B&B that I highly recommend, spacious rooms , clean and well maintained! Host were very pleasing and helpful… definitely recommend!!"
Canada
Sabatino
The price is €269
includes taxes & fees
9 Aug - 10 Aug
Borgo Argenina
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Castellina in Chianti Hotel Reviews

Find out more about Castellina in Chianti

Everything you need to know about Castellina in Chianti holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Castellina in Chianti holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Castellina in Chianti holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Castellina in Chianti holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Castellina in Chianti holiday rentals we have selected for you start as low as €74 per night. Entering your travel dates in the search wizard 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 holiday 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 holiday.

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. 

Explore a world of travel with Expedia

Frequently asked questions

Are there holiday rentals in Castellina in Chianti?

Yes, there are holiday rentals close to the most popular sights in Castellina in Chianti, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Castellina in Chianti has to offer?

Villa La Stella - Casa per Ferie: This holiday 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 holiday 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 Beautiful house on Chianti hilltop with exceptional views. .

How many holiday rentals will I find in Castellina in Chianti?

With 30 Expedia holiday rentals, you're guaranteed 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 holiday rental in Castellina in Chianti like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Castellina in Chianti. Holiday rentals provide amenities such as hot tubs, fire pits and patios so you'll have everything you want. If you're concerned about a sanitised environment, a holiday rental can offer a sense of seclusion away from shared hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a great choice for families.