Holiday rentals near Castello di Radda Winery

We found 5,165 holiday rentals — enter your dates for availability

If you'd like to stay close to Castello di Radda Winery, scroll through and discover holiday rentals to choose your home away from home. Whether you’re staying in a holiday home with friends, family or even just your pets, you'll find the best amenities for hanging out with the people that matter most, which might include parking and a washer and dryer. At the end of the day, you'll find a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Castello di Radda Winery

Showing deals for:3 July - 10 July

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

What are the best holiday rentals near Castello Di Radda Winery?
The best holiday rentals near Castello Di Radda Winery are predominantly found right in the heart of Radda in Chianti and the surrounding Tuscan countryside. You will find a great selection of properties, mainly consisting of elegant villas with expansive grounds and charming private holiday houses. If you are willing to drive a bit further, renting in nearby areas can be an affordable option for finding larger properties. These best holiday rentals near Castello Di Radda Winery offer a truly authentic experience of the region.

Many top-rated rentals feature amenities so you can have a comfortable stay, including private pools great for cooling off on warm days, and fireplaces for cosy evenings. These homes are ideal for family holidays or groups looking to explore the renowned Chianti region.
Are there any cheap holiday rentals near Castello Di Radda Winery?
There are several affordable holiday rentals near Castello Di Radda Winery, especially if you are flexible with location and travel dates. Budget-friendly stays typically start around AU$345 per night in areas like Radda in Chianti. You might find great deals in March and May during the off-season. These rentals often include free amenities such as WiFi, toiletries, and self-parking, so you can have a comfortable stay.

To get the best value, consider staying slightly outside major hubs. If you're willing to drive a bit further, renting around nearby areas can be an affordable option. Many properties are cosy villas or private homes, offering great value for guests seeking an efficient and comfortable base for their stay.

*Pricing data are based on past 12 months data.
What are the best pet-friendly holiday rentals near Castello Di Radda Winery?
There are over 50 pet-friendly holiday rentals near Castello Di Radda Winery, offering a fantastic base for guests bringing their furry companions. These properties, primarily villas and apartments, are often found in and around Radda in Chianti. Many provide amenities such as private gardens, easy outdoor access, fully equipped kitchens, and comfortable living areas, ensuring a relaxing stay for both guests and their pets.

When searching for the best pet-friendly holiday rentals near Castello Di Radda Winery, it is always wise to confirm specific house rules, potential size restrictions, and any additional fees directly with the property owner before finalising your stay. Castello Di Radda Winery itself welcomes pets in its outdoor areas, allowing them to enjoy the beautiful Tuscan surroundings.
What are the top holiday rentals with pools near Castello Di Radda Winery?
There are approximately 92 holiday rentals near Castello Di Radda Winery that feature swimming pools. Guests can choose from a variety of options, including private outdoor pools, shared community pools, and some with heating. Properties are concentrated in the scenic areas surrounding Radda in Chianti, often taking the form of villas or private homes. These rentals typically come with amenities such as fully equipped kitchens, Wi-Fi, and outdoor spaces with sun loungers, making them ideal for families or groups seeking a comfortable stay amidst the Tuscan landscape.

When selecting your rental, consider whether a private pool offers the seclusion you desire or if a shared pool, often part of a larger estate, provides access to additional facilities. For stays during cooler months, it is advisable to look for properties with heated pools to ensure a pleasant experience. Checking availability well in advance, especially for peak summer dates, is recommended.
What are the best family holiday rentals near Castello Di Radda Winery?
There are over 45 family-friendly holiday homes, including villas and private homes, in the region surrounding Castello Di Radda Winery, offering ample space and comfort for groups. These homes often boast multiple bedrooms and bathrooms, full kitchens, and generous living areas, all designed with families in mind. Many offer outdoor play areas, gardens, patios, and yards where children can play, alongside indoor entertainment like books and games. You can also find properties equipped with travel cribs, highchairs, and even babysitting services.

When selecting a home for your family, look for properties that provide separate spaces for adults and children to unwind, and practical utilities like well-equipped kitchens to prepare meals. Staying nearby means less travel time to Castello Di Radda Winery, allowing more time to enjoy your surroundings.
Are there any luxury holiday rentals near Castello Di Radda Winery?
Near Castello Di Radda Winery, guests can find several luxury holiday rentals, often villas and private homes, that combine the scenic Tuscan landscape with modern comfort. These properties frequently offer upscale amenities such as private pools, heated pools, air conditioning, and fireplaces. Many also boast private chefs, on-site tennis courts, or mountain views, providing an exquisite stay.

These homes are ideal for families or larger groups, providing space and features like room service. Many of these top-tier stays are managed by highly rated Stayz hosts, ensuring a professional and premium experience.
How much is a holiday rental near Castello Di Radda Winery?
Holiday rentals near Castello Di Radda Winery offer a wide range of options to suit different budgets, making it easy for guests to enjoy a memorable stay. Budget-friendly properties typically start around AU$345 per night, providing an affordable option. Mid-range rentals, including private homes, are generally around AU$435 per night, offering more comfort and privacy. Upscale options can cost AU$675 or more per night, especially during peak season.

Enter your destination, travel dates, and number of guests on search to see the best options. You can use filters to set a minimum and maximum nightly price range along with other preferences. Rates may vary based on the season and specific amenities, but with a little planning, guests can find a rental that perfectly balances convenience and value.

*Pricing data are based on past 12 months data.
Where should I stay when visiting Castello Di Radda Winery?
When visiting Castello Di Radda Winery, several nearby areas offer delightful holiday rental options. Many guests choose to stay directly within Radda in Chianti itself. This charming hill-top village provides a wonderful selection of properties, from rustic farmhouses to elegant villas, all within easy reach of Castello Di Radda Winery and local eateries.

Another excellent option is the area around Gaiole in Chianti. This region is renowned for its picturesque vineyards and olive groves, offering a tranquil setting for a holiday rental. Properties here provide a peaceful retreat with convenient access to Castello Di Radda Winery and other wineries in the Chianti Classico region.

For those seeking a slightly more secluded experience, properties located in the countryside between Radda in Chianti and Castellina in Chianti are highly recommended. These homes often boast stunning views of the Tuscan landscape and provide a great base for exploring the wider area.
What is the cheapest month to stay near Castello Di Radda Winery?
The cheapest time to find holiday rentals near Castello Di Radda Winery is typically during the late Winter to early Spring (March) and late Spring (May), excluding any major local festivals. March is frequently the single cheapest month, often providing the best deals on homes and properties, with rates potentially lower compared to the peak summer season. Guests can often find various savings and better deals on holiday rentals during these periods, along with increased availability.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Stayz customer service and Stayz™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare customer service is available 24/7 to support you every step of the way.

Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.