Castellina in Chianti holiday homes

We found 2,320 holiday rentals — enter your dates for availability

Discover a selection of 83 homes, 60 apartments and other holiday rentals in Castellina in Chianti that are perfect for your trip. Whether you're staying in a holiday rental with family or friends, you'll find the best amenities for hanging out with the people that matter most, which might include cable TV and a washer and dryer. You're sure to find a property to rent that has what everyone needs, including places that are non-smoking or accessible.

Find spaces that suit your style

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  • More quality time

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  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Rustic Castellina in Chianti will entice you

Enjoy the wineries and other features of Castellina in Chianti. This relaxing city attracts visitors thanks to its forests and bird watching. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Sightseeing in and around Castellina in Chianti

Do you want to discover things to do while you're in the area? Venture out of your holiday home and check out everything that makes Castellina in Chianti a fun spot to go on holiday. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Isole e Olena Winery (3.5 mi / 5.6 km)
  • Il Molino di Grace Winery (3.7 mi / 6 km)
  • Buondonno Winery (3.9 mi / 6.3 km)
  • Castello di Radda Winery (4.5 mi / 7.3 km)
  • Borgo di Vescine - Tenute di Castelvecchi (4.6 mi / 7.4 km)
  • Casa Sola - Chianti Winery (4.7 mi / 7.5 km)

Exploring the natural landscape of Castellina in Chianti

Whether you're an active traveller or just want to appreciate the scenery, Castellina in Chianti is a great spot to appreciate mother nature. Here are some of the area’s most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • Sentierelsa Trail (8.4 mi / 13.6 km)
  • Alta Val d'Elsa River Park (9.5 mi / 15.3 km)
  • Boboli Gardens (20.2 mi / 32.5 km)
  • Arno River (20.4 mi / 32.8 km)
  • Chianti Sculpture Park (7.2 mi / 11.6 km)
  • Le Caldane Thermal Baths (9.4 mi / 15.1 km)

Travelling to and around Castellina in Chianti

Fly into Peretola Airport (FLR), the closest airport, located 23.2 mi (37.4 km) from the city centre.

Frequently asked questions

What is the best area to stay in Castellina in Chianti when booking a holiday home?
If you're considering a Castellina in Chianti getaway, Lilliano is one of the most desirable places to stay. Whether you go for a condo, cottage or another property style, you'll always have the whole place to yourself.
What is the most popular type of holiday home accommodation in Castellina in Chianti?
The most popular types of holiday homes in Castellina in Chianti are apartments. Ready for more choices? Bookabach has numerous options to match our guests' unique needs, so you'll see holiday properties in loads of shapes and sizes. The ideal home away from home is waiting for you — get hold of yours today.
How much does it cost to rent a holiday home in Castellina in Chianti?
The average price for a holiday home in Castellina in Chianti depends on several factors, like length of stay, property type and season. Whether you're searching for a sprawling villa with space for extended family or a quaint cabin ideal for just you and the kids, just add your travel dates to find stays with amazing value.
How much does it cost to rent a beach house in Castellina in Chianti?
The average price for a holiday home near the beach in Castellina in Chianti depends on when you're visiting the area and the style and size of property you're looking for. You can quickly and easily find prices on Bookabach by entering your dates of travel. Then use the filters to select the number of bedrooms and amenities that you prefer, such as WiFi, air conditioning and a hot tub.
Are there pet-friendly holiday homes in Castellina in Chianti?
Yes. You'll have your pick of 217 holiday homes that cater to pets in Castellina in Chianti. Many of our pet-friendly holiday homes have an outdoor space for your furry friend to play in, complimentary treats, special dog beds and proximity to parks and green space. Apply the "Pets allowed" filter to find your pawfect place on Bookabach.
Can I rent a house with a pool in Castellina in Chianti?
Add an extra element of fun to your adventure by staying in one of the 187 houses with a private pool in Castellina in Chianti. Use our search filter to find the kind of property you want on Bookabach, and then spend carefree days splashing and playing in a swimming pool that's for your use only.
What are popular home amenities in Castellina in Chianti?
The most popular home amenities people are searching for in Castellina in Chianti are nearby museums, an electric car charging station and a chef. Whether you're on the road with family, friends or even pets, Bookabach holiday properties come with the best amenities for beginning new traditions with the people who matter most.
Are there large group holiday homes in Castellina in Chianti?
There are 29 holiday homes in Castellina in Chianti that can host a group of 10 or more guests. Whether you're organising a trip with the family or an event like a party, there's enough room to get your favourite people together under the same roof.
Are there holiday homes in Castellina in Chianti that welcome kids?
Bring the entire group together for a fun-filled adventure in Castellina in Chianti at one of our 217 family-friendly holiday homes. Lots of these stays offer amenities that are suitable for trips with the little ones, such as dining rooms, living rooms and entertainment units. Simply click on the "Properties good for families" filter and book your favourite.
What are the top attractions for families in Castellina in Chianti?
Keeping the kids entertained during your stay in Castellina in Chianti is a snap with these cool family-friendly attractions:

  • Monteriggioni Castle
  • Meleto Castle
  • Castello di Radda Winery

Are there one-bedroom holiday homes in Castellina in Chianti?
Castellina in Chianti has 41 one-bedroom homes on offer. Often positioned in desirable areas due to their compact size, a one-bedroom holiday home is ideal if you're travelling with your partner or a buddy. And with home comforts like laundry facilities and more privacy than a standard hotel, you'll be able to kick back and relax while discovering this exciting destination.
Can I find two-bedroom holiday homes in Castellina in Chianti?
Pick from 95 two-bedroom holiday properties in Castellina in Chianti. Give your little ones the second room or fill it with a couple of your best buddies. There's a spot for whoever's fortunate enough to come along for the ride.
Are there holiday homes with WiFi in Castellina in Chianti?
Whether you'd like to keep up with the headlines, send some emails or surf social media, there are 68 holiday homes with WiFi in Castellina in Chianti. Check the "WiFi" box when searching on Bookabach and stay connected on your holiday.
How can I find holiday homes with air conditioning in Castellina in Chianti?
Castellina in Chianti has 63 holiday homes where you'll be able to kick back in air-conditioned comfort. To find a property on Bookabach offering this perk, enter your preferred travel dates and use the handy filter tool to select the "air conditioning" box.
How old do you have to be to rent a holiday home in Castellina in Chianti?
The minimum age can differ across properties on Bookabach, so be sure to look at the rules of the holiday home in Castellina in Chianti you're considering. But usually, it's 16, 18 or 21.
How long can I rent a holiday home in Castellina in Chianti for?
It's up to the Castellina in Chianti property. To look over a list of options offering extended stays, simply type your travel dates and guest number into the Bookabach search page. Enjoy having the entire place to yourself, along with home comforts such as a fully-equipped kitchen and outdoor spaces to play in. Keep your eyes open for long-term stays that offer weekly or monthly discounts.

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