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Radda in Chianti holiday lettings

We found 3,040 holiday rentals — enter your dates for availability

Discover a selection of 6 homes and other holiday rentals in Radda in Chianti that are perfect for your trip. Holiday homes offer the best amenities for you and your friends, family or even pets, such as Wi-Fi and a fireplace. At the end of the day, you'll be sure to find a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts - Radda in Chianti

Showing deals for:26 Jun - 3 Jul

Image gallery for Lovely country house in the Chianti region, for 4 persons, near Siena

Property grounds
9.0 out of 10, Wonderful, (10 reviews)
Wonderful
(10 reviews)

Lovely country house in the Chianti region, for 4 persons, near Siena

Castellina in Chianti

13% off
Price is £1,034
for 7 nights, 1 room
£148 per night
includes taxes & fees
Lovely country house in the Chianti region, for 4 persons, near Siena

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Why visit Radda in Chianti

  • Scenic Landscapes: Enjoy breathtaking views of the Chianti hills, perfect for leisurely walks and photography.
  • Cultural Heritage: Discover historic churches, castles, and palaces that reflect the rich history of Tuscany.
  • Wine Tasting: Visit local wineries like Castello di Radda to indulge in exquisite Chianti wines.
  • Charming Streets: Stroll through picturesque streets, soaking in the quaint atmosphere and local charm.
  • Gastronomic Delights: Savor traditional Italian cuisine at delightful eateries throughout the region.

Popular types of accommodation in Radda in Chianti

Vrbo offers a delightful selection of accommodation in Radda in Chianti, catering to various preferences and needs. Whether you're seeking the charm of a villa, the convenience of an apartment, or the comfort of a private vacation home, we've got you covered. Our guests often explore options like Radda in Chianti hotels and Chianti accommodation to find their perfect getaway. Discover the ideal base for your adventure in this picturesque region.

  • Apartments: The most sought-after accommodation in Radda in Chianti, offering a blend of comfort and convenience for solo travellers or couples.
  • Villas: These spacious and luxurious retreats are the second favourite choice, perfect for families or larger groups seeking a touch of elegance.
  • Houses: Ideal for those wanting a home-away-from-home experience, providing ample space and privacy.
  • Caravan Parks: A unique option for adventurous souls, combining outdoor living with community vibes.
  • Cottages: Quaint and cosy, these are perfect for a romantic getaway or a peaceful retreat.**

Top attractions in and around Radda in Chianti

Radda in Chianti offers a picturesque setting for romantic outdoor getaways and cultural exploration. Visitors can immerse themselves in the area's charm by visiting historic churches, castles, and palaces. Notable attractions include the local wineries, such as Castello di Radda, and the stunning Chianti hills, perfect for enjoying the beautiful landscapes. With a blend of culture and romance, Radda is an ideal destination for those seeking a delightful Italian experience.

  • Castello di Albola: Nestled in the picturesque hills of Radda in Chianti, this charming castle exudes romance and history. Explore its lush vineyards and enjoy wine tastings that reflect the rich culture of the region.
  • Siena Cathedral: Located approximately 7.5km away, this stunning Gothic cathedral is a masterpiece of art and architecture. Marvel at its intricate façade and vibrant frescoes that narrate the city's rich cultural heritage.
  • Piazza del Campo: Also situated 7.5km away, this iconic square is renowned for its unique shell shape. It's a vibrant hub of culture, hosting events and surrounded by historic buildings, perfect for enjoying local cuisine and people-watching.

Things to do recommended for couples

For a romantic getaway in Radda in Chianti, indulge in wine tasting at Il Molino di Grace or Badia a Coltibuono, both offering enchanting atmospheres just 2.5km away. For a touch of luxury, visit the Villa a Sesta Polo Club, located 7.5km away, perfect for couples seeking elegance.

Things to do recommended for families

Families visiting Radda in Chianti can explore the wonders of the Chianti Observatory, just 4.3km away, enjoy thrilling karting at the Siena Circuit, 8.1km away, and experience the sports atmosphere at Stadio Artemio Franchi, located 7.5km from town.

Things to do recommended for groups

In Radda in Chianti, groups can indulge in high-end shopping at The Mall Luxury Outlet, embark on an adventurous hike along the Sentierelsa Trail, and savour exquisite wines at Enoteca Italiana. Each experience offers a unique glimpse into the charm of Tuscany.

What do I need to keep in mind when booking a vacation in 'Radda in Chianti

If you're travelling with a group, family, pets, or planning an extended stay, it's essential to filter your search according to your specific needs. Here are some helpful booking tips for Vrbo.

  • Traveling to Radda in Chianti with a group: Think about how many bedrooms you'll require, as well as features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Radda in Chianti with young kids: Travelling with young children can present its own set of challenges. It's important to prioritise their comfort and safety, along with ensuring access to suitable amenities, like a private swimming pool. Additionally, it's wise to think about how close you are to attractions that are family-friendly.
  • Taking your pets with you to Radda in Chianti: For many, a family holiday just wouldn't be the same without their four-legged companion. If that resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels completely at home.
  • Planning for a long term stay visiting Radda in Chianti: If you're in search of holiday rentals with discounts for stays of a month or longer, you've come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to consider including amenities such as a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay in and around Radda in Chianti

Radda in Chianti is a delightful destination perfect for a romantic getaway or outdoor adventure. Surrounded by breathtaking scenery, you can explore charming streets, indulge in local wines, and immerse yourself in the rich history of Tuscany. Nearby towns such as Gaiole and Castellina offer a friendly atmosphere and secluded spots to unwind. Whether you're strolling through vineyards or enjoying traditional Italian cuisine, Radda in Chianti promises an unforgettable experience steeped in beauty and culture.

  • Chianti Region: Nestled merely 1.9km from Radda in Chianti, the Chianti Region is famed for its enchanting landscapes and romantic ambience. This area offers a wealth of outdoor experiences, from scenic walks through vineyards to relaxing afternoons at luxurious spas. Visitors can indulge in body treatments or explore local shops that showcase the best of Tuscan craftsmanship. The rich history of the region is evident in its historic sites and precincts, making it a perfect destination for those seeking both entertainment and cultural immersion.
  • Villa: A charming village situated in the vicinity of Radda in Chianti, Villa is an ideal spot for a romantic getaway. The village is known for its vibrant market and public market, where you can find fresh local produce and artisanal goods. Visitors can partake in guided tours that unveil the beauty and history of the region. With attractions such as captivating castles and serene beaches nearby, Villa promises an outdoor experience that combines relaxation with exploration, ensuring a delightful visit.
  • Volpaia: The picturesque village of Volpaia, also located near Radda in Chianti, is a treasure for those in search of a romantic and entertaining experience. This quaint village offers access to rejuvenating spas, perfect for unwinding after a day of exploration. Nearby, you can discover historic landmarks, impressive monuments, and majestic castles that narrate tales of the past. Volpaia’s charm lies in its ability to provide both relaxation and adventure amidst its stunning Tuscan backdrop.

Best time to go to Radda in Chianti

If you're planning a trip to Radda in Chianti, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April, July and September, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January40.8°F (4.9°C)Light RainMostly SunnySlightly LowSlightly Low
February42.8°F (6.0°C)Light RainMostly SunnyAverageSlightly Low
March47.5°F (8.6°C)Light RainMostly SunnyAverageAverage
April54.0°F (12.2°C)Light RainMostly SunnySlightly HighAverage
May60.4°F (15.8°C)Light RainMostly SunnyAverageAverage
June69.8°F (21.0°C)Light RainSunnyAverageSlightly High
July75.9°F (24.4°C)No Rain (Dry)SunnySlightly HighSlightly High
August75.6°F (24.2°C)No Rain (Dry)SunnyAverageSlightly High
September67.1°F (19.5°C)Light RainMostly SunnySlightly HighAverage
October58.5°F (14.7°C)Light RainMostly SunnyAverageAverage
November50.0°F (10.0°C)Light RainMostly SunnySlightly LowSlightly Low
December43.3°F (6.3°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is a breeze

Are you hoping to save on your next getaway? It might be worth considering some flexibility with your travel dates, as prices can vary. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that suits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board offers a handy platform for you to plan new adventures, resume your previous arrangements, or review and organise your travel itineraries. You’ll discover your saved or booked properties neatly sorted into Potential, Upcoming, or Current Trips. To get started with Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Why people love visiting cosy Radda in Chianti

The area's wineries and churches are just some of the reasons to come on holiday to Radda in Chianti. This scenic and romantic city is well known for its local tours, coffee shops and spas. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in Radda in Chianti

Are you searching for attractions to visit during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Radda in Chianti a one-of-a-kind holiday spot. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Castello di Radda Winery (0.7 mi / 1.2 km)
  • Borgo di Vescine - Tenute di Castelvecchi (2.2 mi / 3.5 km)
  • Castello di Albola (2.8 mi / 4.5 km)
  • Badia a Coltibuono (4 mi / 6.4 km)
  • Il Molino di Grace Winery (4.1 mi / 6.7 km)
  • Cantalici Winery (5.3 mi / 8.5 km)

Exploring the natural landscape of Radda in Chianti

Whether you're looking for fun outdoor activities or just want to take in the scenery, Radda in Chianti is a great place to get outside. These are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • Sentierelsa Trail (12.8 mi / 20.6 km)
  • Terme Antica Querciolaia (17.8 mi / 28.7 km)
  • Arno River (20.1 mi / 32.4 km)
  • Val di Merse (22.6 mi / 36.4 km)
  • Chianti Sculpture Park (6.5 mi / 10.4 km)
  • Gianfranco Carla Fineschi Botanical Rose Garden (7.3 mi / 11.8 km)

How to get to and around Radda in Chianti

The nearest airport is in Peretola Airport (FLR), located 23.4 mi (37.7 km) from the city centre.

Frequently asked questions

What is the best area to stay in Radda In Chianti when booking a holiday rental?
When considering a holiday rental in Radda In Chianti, the historic centre is an excellent choice for its charming atmosphere and accessibility to local attractions. This area is characterised by its picturesque medieval architecture and offers a variety of properties, from cosy apartments to elegant villas. Staying here allows you to immerse yourself in the local culture, with easy access to delightful shops and traditional restaurants serving regional delicacies.

One of the top attractions nearby is the stunning Church of San Niccolò, which is a beautiful example of Romanesque architecture. Additionally, the surrounding vineyards offer opportunities for wine tours, allowing you to sample the renowned Chianti wines. The central square is a lovely spot for a leisurely coffee or gelato, providing a superb backdrop for relaxation after a day of exploring.
How much does it cost to rent a holiday home in Radda In Chianti?
Prices for holiday rentals in Radda In Chianti vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Radda In Chianti to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Radda In Chianti holiday house rentals?
You can find great discounts on house rentals in Radda In Chianti on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of holiday rental accomodation in Radda In Chianti?
In Radda In Chianti, villas are the most popular type of holiday rental, with around 268 available in the picturesque countryside. These villas typically offer spacious interiors, multiple bedrooms, fully equipped kitchens, and private gardens with views of the stunning Tuscan landscape. Many also feature amenities such as swimming pools, outdoor dining areas, and BBQ facilities, great for enjoying the warm Italian evenings.

Holiday houses follow closely behind, with about 64 options that provide a homely atmosphere for families or groups. These properties usually come with comfortable living spaces and outdoor areas to relax after a day of exploring the charming village and surrounding vineyards.

Additionally, there are around 52 apartments available, often situated in the heart of Radda, allowing easy access to local shops, restaurants, and cultural sites. These apartments typically include essential amenities like kitchens and living areas, suiting visitors who prefer a more urban feel while still enjoying the beauty of Tuscany.
Are there any family house rentals in Radda In Chianti?
In Radda in Chianti, Tuscany, there are numerous family-friendly homes available, with around 46 options scattered throughout the area. This picturesque town, located in the heart of the Chianti wine region, is an ideal base for families looking to explore the beautiful Tuscan countryside. Many properties offer spacious living areas, well-equipped kitchens for preparing family meals, and outdoor spaces where children can enjoy the fresh air and stunning views.

Visitors can expect amenities such as private pools, which provide a wonderful spot for relaxation after a day of adventure, and ample gardens superb for outdoor activities. The charming village centre is within easy reach, where families can experience local shops and delightful eateries serving traditional Tuscan cuisine.

Additionally, the surrounding area is rich in history and natural beauty, with opportunities for vineyard tours, hiking trails, and visits to nearby attractions such as castles and historical sites.
Can I rent a holiday home with a pool or hot tub in Radda In Chianti?
In Radda In Chianti, there are plenty of holiday homes available for rent that come equipped with pools and hot tubs, with approximately 82 options to choose from. This picturesque village in Tuscany offers a stunning backdrop of rolling hills and vineyards, making it an ideal destination for relaxation and indulgence.

Travellers can expect a range of amenities in these properties, including private swimming pools, some of which are set within beautifully landscaped gardens, great for soaking up the sun. Many rentals also feature hot tubs, providing a luxurious way to unwind after a day of exploring the charming local wineries and historic sites. Inside, guests will typically find well-appointed kitchens, spacious living areas, and comfortable bedrooms, ensuring a homely atmosphere during their stay.

The surrounding area is rich in culture and natural beauty, with opportunities for hiking, wine tasting, and enjoying authentic Tuscan cuisine in nearby quaint restaurants.
Can I find long-stay holiday rentals in Radda In Chianti?
A long-stay holiday rental in Radda In Chianti is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Radda In Chianti?
In Radda In Chianti, there are numerous pet-friendly house rentals available, providing a delightful experience for both travellers and their furry companions. The area is renowned for its stunning landscapes, rolling hills, and picturesque vineyards, making it an ideal setting for a relaxing getaway. Many of the holiday rentals come equipped with essential amenities such as fully equipped kitchens, outdoor spaces, and sometimes even private pools, allowing guests to enjoy the beauty of the Tuscan countryside in comfort.

The charming village itself offers a variety of local shops, restaurants, and markets, great for exploring the regional cuisine and wines. Additionally, the surrounding countryside features numerous walking trails and opportunities for outdoor activities, including hiking and wine tasting, which are enjoyable with pets.
Are there any remote work holiday rentals in Radda In Chianti?
In Radda In Chianti, Tuscany, there are numerous remote work holiday rentals available, with around 364 options for travellers to choose from. This picturesque town, known for its stunning vineyards and rich history, provides an excellent backdrop for those looking to blend work and leisure. Many properties come equipped with essential amenities for remote work, including free Wi-Fi, dedicated desks, and comfortable desk chairs, ensuring a productive environment.

In addition to a conducive work atmosphere, guests can enjoy the charm of Tuscan living, with nearby attractions such as the medieval architecture of the town centre and the beautiful landscapes of Chianti. Many rentals also offer features like fully equipped kitchens, outdoor terraces with views of the vineyards, and access to communal gardens, enhancing the overall experience. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Radda In Chianti holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Radda In Chianti with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
When is the best time to visit Radda In Chianti for a holiday rental?
The best time to visit Radda In Chianti for a holiday rental is during the peak season from July to September, when the stunning Tuscan countryside is in full bloom. This period draws many travellers eager to indulge in the region's renowned wines and exquisite culinary experiences. The warm summer temperatures, typically ranging from 20 to 30 degrees Celsius, create a friendly space for outdoor activities such as vineyard tours and leisurely strolls through charming, sun-soaked streets.

July stands out as the most popular month, offering numerous events and festivals that showcase local culture, including wine tastings and traditional feasts. It's a vibrant time to soak in the essence of Tuscany, surrounded by fellow visitors who share your passion for exploration and enjoyment.

For those keen on a quieter experience, consider planning your visit in November. This month offers an opportunity to enjoy the tranquillity of Radda In Chianti, with fewer tourists around and a chance to witness the beautiful autumnal scenery. The cooler temperatures, averaging around 10 to 15 degrees Celsius, can be quite refreshing, making it ideal for peaceful explorations of the surrounding vineyards and olive groves.
How early should I book a Radda In Chianti holiday rental?
Book your Radda In Chianti holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Radda In Chianti?
In Radda in Chianti, visitors can immerse themselves in the picturesque landscapes and historical charm of Tuscany. The town itself is known for its stunning medieval architecture, with highlights including the impressive Church of San Niccolò and the quaint streets lined with local shops and wine cellars.

Nearby, the Chianti Classico wine region offers numerous vineyards and wineries where travellers can partake in wine tastings and tours, celebrating the area's rich viticultural heritage. The scenic countryside surrounding Radda provides ample opportunities for hiking and cycling, with trails that lead to breathtaking views of rolling hills and olive groves.

For those interested in cultural experiences, the nearby Castello di Radda is worth a visit, showcasing the region's history and offering a glimpse into the life of a Tuscan castle.
Can I change or cancel my Radda In Chianti home rental booking on Vrbo?
To find Radda In Chianti holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo 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, Vrbo 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 Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Radda In Chianti holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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 Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo 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 Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

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