Castellina in Chianti holiday lettings

We found 2,535 holiday rentals — enter your dates for availability

Discover a selection of 29 homes, 32 villas and 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.

Holiday rentals with weekly discounts - Castellina in Chianti

Showing deals for:12 Jun - 19 Jun

Image gallery for PRIVATE VILLA IN THE HEART OF CHIANTI with pools and stunning views

Pool
10 out of 10, Exceptional, (41 reviews)
Exceptional
(41 reviews)

PRIVATE VILLA IN THE HEART OF CHIANTI with pools and stunning views

Castelnuovo Berardenga

9% off
Price is £4,835
for 7 nights, 1 villa
£691 per night
includes taxes & fees
PRIVATE VILLA IN THE HEART OF CHIANTI with pools and stunning views

Find spaces that suit your style

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Why visit Castellina in Chianti

  • Charming architecture: Discover picturesque churches, historic castles, and enchanting piazzas that reflect the rich heritage of Castellina in Chianti.
  • Stunning landscapes: Enjoy breathtaking views of the Chianti hills, ideal for romantic strolls and outdoor adventures.
  • Local wine experiences: Indulge in delightful wine tastings and savour the renowned Chianti wines.
  • Tranquil atmosphere: Experience the serene environment, perfect for relaxation and rejuvenation.
  • Variety of accommodations: Choose from charming apartments to luxurious villas for a memorable stay in this picturesque region.

Popular types of accommodation in Castellina in Chianti

Your journey to Castellina in Chianti begins with selecting the perfect accommodation. From charming apartments to luxurious villas and private holiday homes, the options are plentiful. Discover a range of Castellina in Chianti holiday rentals that promise comfort and convenience, ensuring a memorable stay in this picturesque region. Explore our selection of Chianti accommodation and make your getaway truly special.

  • Apartments: The top choice for visitors in Castellina in Chianti, offering a blend of comfort and convenience in the heart of the town.
  • Villas: A luxurious option for those seeking spacious accommodations with stunning views and elegant surroundings.
  • Houses: Ideal for families or groups, these homes provide a homely atmosphere and privacy during your stay.
  • Caravan Parks: A unique experience for adventurous travellers, featuring various amenities and a close-knit community vibe.
  • Cottages: These quaint, rustic retreats are perfect for a cosy getaway in the picturesque Tuscan landscape.**

Top attractions near Castellina in Chianti

Castellina in Chianti is perfect for a romantic outdoor getaway, offering a delightful mix of culture and entertainment. Explore charming churches, picturesque piazzas, and historic castles, all set against the stunning backdrop of the Chianti hills. This enchanting destination caters to those seeking a unique blend of city and romance, ensuring a memorable experience for every traveller.

  • Monteriggioni Castle: A beautifully preserved medieval fortress, Monteriggioni Castle offers a glimpse into Italy's rich history. Stroll along its ancient walls, enjoy panoramic views of the Tuscany countryside, and immerse yourself in the captivating culture of this charming village.
  • Siena Cathedral: This stunning Gothic cathedral boasts intricate architecture and breathtaking artworks, including works by Michelangelo. Its striking façade and magnificent interior provide a unique cultural experience that reflects Siena's artistic heritage.
  • Piazza del Campo: Renowned for its distinctive shell shape, this vibrant piazza is the heart of Siena. Surrounded by historic buildings, it hosts the famous Palio horse race and offers a lively atmosphere, perfect for soaking up local culture.

Things to do recommended for couples

If you’re seeking a romantic getaway in Castellina in Chianti, visit the enchanting Il Molino di Grace Winery, Isole e Olena Winery, or Casa Sola - Chianti Winery. Each offers a delightful atmosphere perfect for couples looking to enjoy fine wine and each other’s company.

Things to do recommended for families

Families visiting Castellina in Chianti can enjoy a fascinating experience at the Chianti Observatory, just 2.5km away, where they can explore the stars. For some adventure, head to the Siena Circuit, 9.3km away, for thrilling karting fun.

Things to do recommended for groups

Groups visiting Castellina in Chianti can hike the scenic Sentierelsa Trail, experience luxury shopping at The Mall Luxury Outlet, or browse local treasures at Ra-Ma snc, all while soaking in the picturesque Tuscan countryside and vibrant local culture.

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

If you're travelling with a group, family, pets, or planning an extended stay, it's essential to prioritise your search filters accordingly. Here are some helpful booking tips for using Vrbo.

  • Traveling to Castellina in Chianti with a group: Think about how many bedrooms you require, as well as features like a fully equipped kitchen or outdoor areas for group gatherings. Luckily, you can easily apply filters for all these options and more on Vrbo.
  • Traveling to Castellina 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 that suitable amenities, like a private swimming pool, are available. Additionally, it’s wise to think about how close you are to attractions that cater to families.
  • Taking your pets with you to Castellina in Chianti: For many, a family holiday wouldn’t be the same without their furry companion. If this resonates with you, consider exploring Vrbo properties that are pet-friendly. Most of these accommodations come equipped with feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Castellina in Chianti: If you're seeking holiday rentals with discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you'll be able to effortlessly discover and save on monthly rentals. Don't forget to include amenities like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in and around Castellina in Chianti

Castellina in Chianti is a delightful base for a romantic getaway or outdoor adventure in the heart of Tuscany. With its tranquil atmosphere and stunning scenery, visitors can explore charming nearby villages, indulge in local wine tastings, and savour the rich history of the region. From relaxing strolls through vineyards to enjoying the friendly local culture, your holiday in Tuscany promises to be an unforgettable experience filled with luxury and serenity.

  • Lilliano: Nestled in the heart of Castellina in Chianti, Lilliano is a charming village that invites visitors to immerse themselves in its rich culture and history. The area is known for its historic buildings and museums, making it an ideal destination for those seeking a cultural and romantic experience. Lilliano also features a conference venue for events, adding an element of modern convenience amidst its ancient charm. Strolling through the village, you’ll discover quaint streets and local eateries, providing a delightful combination of entertainment and tradition.
  • Fonterutoli: Fonterutoli, another picturesque village in Castellina in Chianti, is famed for its romantic allure and outdoor activities. Visitors can indulge in guided tours that showcase the area’s stunning landscapes and historic buildings. With a rich heritage, Fonterutoli offers notable landmarks and historic places, along with a conference venue for those looking to blend leisure with business. The village is perfect for couples and families alike, providing a vibrant atmosphere that enhances the outdoor experience.
  • Colle Petroso: Located a mere 1.2km from Castellina in Chianti, Colle Petroso offers a unique blend of culture and relaxation. Known for its romantic charm, this village boasts historic sites, including a castle, and even features a beach for those seeking a serene escape. The scenic surroundings make it perfect for leisurely strolls and explorations. Whether you’re interested in history or simply wish to unwind by the water, Colle Petroso provides a delightful retreat with a touch of Tuscan elegance.

Best time to go to Castellina in Chianti

If you're planning a trip to Castellina 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 and July to August, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January40.8°F (4.9°C)Light RainMostly SunnyAverageSlightly 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)SunnySlightly HighSlightly High
September67.1°F (19.5°C)Light RainMostly SunnyAverageAverage
October58.5°F (14.7°C)Light RainMostly SunnySlightly LowAverage
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 simple

Are you keen to save money on your next getaway? It might be worth being flexible with your travel dates, as prices can vary quite a bit. 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 made easy

Vrbo’s Trip Board offers a helpful platform for you to plan your journeys, easily continue from where you last stopped, or manage and view your itineraries. You can effortlessly find your saved or booked properties sorted into categories such as Potential, Upcoming, or Current Trips. To begin exploring the benefits of Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

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)
  • Casa Emma (3.6 mi / 5.7 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)

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:

  • Chianti Sculpture Park (7.3 mi / 11.7 km)
  • Sentierelsa Trail (8.4 mi / 13.6 km)
  • Boboli Gardens (20.2 mi / 32.5 km)
  • Arno River (20.4 mi / 32.8 km)
  • Val di Merse (20.6 mi / 33.2 km)
  • Alta Val d'Elsa River Park (9.5 mi / 15.3 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 rental?
When considering a holiday rental in Castellina In Chianti, the best area to stay is the charming village itself, which serves as a gateway to the beautiful Tuscan countryside. Castellina In Chianti is known for its rich history and stunning landscapes, making it an ideal base for exploring the region.

The village is home to a delightful array of properties, ranging from traditional stone villas to modern apartments, offering a comfortable stay amidst picturesque surroundings. You'll find numerous options that cater to various tastes and budgets, ensuring that there is something for everyone.

One of the top attractions in the area is the stunning Chianti Classico Wine Region, where visitors can partake in wine tastings and vineyard tours, immersing themselves in the local culture. Additionally, the nearby Castello di Brolio, a historic castle with breathtaking views and beautiful gardens, is a must-visit for history enthusiasts and those looking to soak in the stunning scenery.
How much does it cost to rent a holiday home in Castellina In Chianti?
Prices for holiday rentals in Castellina 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 Castellina 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 Castellina In Chianti holiday house rentals?
You can find great discounts on house rentals in Castellina 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 Castellina In Chianti?
In Castellina In Chianti, villas are the most popular type of holiday rental, with about 308 available throughout the picturesque Tuscan countryside. These villas typically feature spacious layouts, multiple bedrooms, fully equipped kitchens, and private outdoor areas, making them superb for families or groups looking to enjoy the stunning landscapes. Many come with amenities such as swimming pools, barbecue facilities, and stunning views of the vineyards and rolling hills.

Holiday houses also see significant interest, with around 224 options that provide a similar charm but may vary in size and amenities. These homes often include comfortable living spaces and outdoor terraces for enjoying the serene surroundings. Additionally, there are approximately 188 apartments available, which are more suited for couples or smaller groups wanting a more compact, yet still comfortable stay. Many of these apartments come with kitchen facilities and easy access to local attractions, such as the nearby Chianti wine region.
Are there any family house rentals in Castellina In Chianti?
In Castellina In Chianti, Tuscany, there are numerous family-friendly holiday rentals available—around 119 in total. This picturesque area is renowned for its stunning landscapes, vineyards, and historical charm, making it an ideal spot for families. Many of these homes feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor terraces or gardens where children can play while parents relax.

Visitors can enjoy amenities such as Wi-Fi, air conditioning, and sometimes even private pools, offering a comfortable base for exploring the region. The locale is conveniently located near various points of interest, including the enchanting town of Radda in Chianti and the beautiful vineyards that dot the landscape, superb for family outings and wine tasting experiences.
Can I rent a holiday home with a pool or hot tub in Castellina In Chianti?
In Castellina In Chianti, there are a remarkable 153 holiday homes available for rent that feature pools and hot tubs, making it an excellent choice for travellers seeking relaxation amid the stunning Tuscan landscape. This charming area is renowned for its picturesque vineyards and rolling hills, with many rentals situated in idyllic settings that offer breathtaking views.

Visitors can expect a range of amenities in these properties, including private swimming pools ideal for cooling off during warm afternoons, and hot tubs superb for unwinding under the stars. Many of these homes also come equipped with fully stocked kitchens, spacious living areas, and outdoor dining spaces, making them ideal for families or groups looking to enjoy a serene holiday experience.

The surrounding region is rich in cultural heritage, with local wineries, historic villages, and beautiful hiking trails just a short drive away. Find your rental in Castellina In Chianti with a pool or a hot tub.
Can I find long-stay holiday rentals in Castellina In Chianti?
A long-stay holiday rental in Castellina 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 Castellina In Chianti?
In Castellina In Chianti, there are numerous pet-friendly house rentals available, offering a range of amenities that cater to both travellers and their furry companions. Many of these properties feature spacious gardens, terraces, and outdoor dining areas, allowing pets to enjoy the beautiful Tuscan countryside alongside their owners. Inside, these rentals typically include fully equipped kitchens, comfortable living spaces, and multiple bedrooms, making them ideal for families or groups.

The area itself is renowned for its stunning landscapes, vineyards, and historic charm, with plenty of opportunities for outdoor activities. Nearby, you'll find pet-friendly wineries and restaurants that welcome dogs, enabling visitors to savour the local cuisine and wines while spending quality time with their pets.
Are there any remote work holiday rentals in Castellina In Chianti?
In Castellina In Chianti, Tuscany, there are numerous remote work holiday rentals available, with around 696 options to choose from. This picturesque area is renowned for its stunning landscapes, vineyards, and charming medieval towns, making it an ideal location for those combining work with leisure. Many properties come equipped with high-speed internet and Wi-Fi, ensuring a smooth remote working experience.

Travellers can expect a variety of amenities such as comfortable workspaces, spacious living areas, and fully equipped kitchens for home-cooked meals. Some rentals also feature outdoor terraces or gardens, providing a pleasant environment for breaks or after-work relaxation. With the enchanting scenery of the Chianti hills surrounding you, it's easy to find inspiration during your workdays. The local area also offers opportunities to explore nearby wineries, indulge in authentic Tuscan cuisine, and enjoy leisurely strolls through the quaint streets of Castellina In Chianti. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Castellina In Chianti holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Castellina 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.
What are popular rental amenities in Castellina In Chianti?
In Castellina In Chianti, popular rental amenities include kitchens, which allow guests to prepare their own meals using local ingredients. Many properties also feature inviting fireplaces, superb for cosy evenings after a day of exploring the beautiful Tuscan countryside. Onsite parking is another common amenity, making it convenient for those travelling by car. Additionally, some rentals permit pets, ensuring that furry companions can join in on the holiday experience. Service animals are also welcomed, suiting those who may require assistance.
When is the best time to visit Castellina In Chianti for a holiday rental?
The best time to visit Castellina In Chianti for a holiday rental is during the peak season from July to September. This vibrant period attracts travellers eager to immerse themselves in the stunning landscapes and rich cultural heritage of Tuscany. With warm temperatures averaging between 25 to 30 degrees Celsius, it's ideal for outdoor activities such as vineyard tours, wine tastings, and leisurely strolls through the picturesque countryside.

July is particularly popular, as visitors flock to experience local festivals, indulge in exquisite cuisine, and enjoy the lively option of the charming towns. The long, sunlit days provide ample opportunity for sightseeing, with nearby attractions such as the historic cities of Florence and Siena just a short drive away.

For those looking for more affordable options, consider planning your visit in November. This quieter month offers a unique chance to explore Castellina In Chianti without the summer crowds, allowing you to savour the beauty of the autumn harvest and experience the region's tranquil charm. The landscape transforms into a tapestry of warm colours, making it a great time for scenic drives and intimate vineyard visits.

Ultimately, your choice will depend on whether you prefer the lively buzz of high season or the peaceful allure of the shoulder months.
How early should I book a Castellina In Chianti holiday rental?
Book your Castellina 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 Castellina In Chianti?
In Castellina In Chianti, visitors can immerse themselves in the charm of the Tuscan countryside, with a range of attractions to explore. The historic town centre is delightful, featuring narrow streets and quaint shops where local artisans showcase their crafts. The impressive Church of San Salvatore is a highlight, offering stunning views over the surrounding vineyards.

Wine enthusiasts will appreciate the area's renowned wineries, many of which offer tours and tastings, providing an authentic taste of Chianti Classico. The surrounding landscape is dotted with picturesque vineyards and olive groves, great for leisurely walks or cycling.

Nearby, the Chianti Sculpture Park is an intriguing site that combines nature with contemporary art, making it a unique attraction for art lovers.
Can I change or cancel my Castellina In Chianti home rental booking on Vrbo?
To find Castellina 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 Castellina 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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