Castellina in Chianti holiday lettings

We found 2,498 holiday rentals — enter your dates for availability

Discover a selection of 82 homes, 66 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.

Holiday rentals with weekly discounts - Castellina in Chianti

Showing deals for:27 Feb - 6 Mar

Image gallery for Villa with concierge service & heated pool at 20 minute from Florence center

Outdoor dining
10 out of 10, Exceptional, (105 reviews)
Exceptional
(105 reviews)

Villa with concierge service & heated pool at 20 minute from Florence center

Impruneta, Toscana

9% off
Price is £8,504
for 7 nights, 1 villa
£1,215 per night
includes taxes & fees
Villa with concierge service & heated pool at 20 minute from Florence center

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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)
  • 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)
  • 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)
  • Chianti Sculpture Park (7.3 mi / 11.7 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

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 around 80 available throughout the picturesque Tuscan countryside. These villas often feature expansive outdoor spaces, private pools, and stunning views of the vineyards and rolling hills. Many come equipped with fully furnished kitchens, spacious living areas, and several bedrooms, making them ideal for families or groups seeking a tranquil retreat.

Apartments also attract visitors, with approximately 56 scattered across the charming town. These typically offer a more compact living arrangement, featuring essential amenities such as kitchens and comfortable seating areas, great for couples or smaller groups wanting to immerse themselves in local culture.
Are there any family house rentals in Castellina In Chianti?
In Castellina In Chianti, Tuscany, there is a wealth of family-friendly holiday rentals to choose from—about 120 options scattered across this picturesque region. The area is renowned for its stunning landscapes, dotted with vineyards and olive groves, making it an ideal setting for families looking to unwind and explore. Many of these homes provide spacious living areas, fully equipped kitchens great for preparing meals together, and outdoor terraces where children can play while adults relax and enjoy the breathtaking views.
Can I rent a holiday home with a pool or hot tub in Castellina In Chianti?
In Castellina In Chianti, there are plenty of holiday homes available for rent that feature pools and hot tubs, with approximately 172 options to choose from. This picturesque town, located in the heart of Tuscany, offers a tranquil escape surrounded by rolling vineyards and olive groves. Many of the properties boast amenities such as private swimming pools, outdoor terraces, and hot tubs, superb for relaxing after a day of exploring the beautiful countryside. 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, making it an ideal destination for travellers looking to enjoy the beautiful Tuscan countryside with their furry companions. Many of these holiday homes offer charming rustic features, such as exposed beams, terracotta floors, and spacious gardens, great for pets to roam and explore.

Travellers can expect amenities like fully equipped kitchens, outdoor dining areas, and private pools in several properties, allowing for a comfortable and enjoyable stay. The picturesque surroundings provide opportunities for leisurely walks through vineyards and olive groves, with stunning views of the rolling hills that characterise this region.
Are there any remote work holiday rentals in Castellina In Chianti?
In Castellina In Chianti, there are numerous options for remote work holiday rentals, with around 189 available in the area. This picturesque town in Tuscany offers a tranquil backdrop for productivity, featuring properties that often include amenities tailored for remote workers. Many rentals come equipped with reliable Wi-Fi, dedicated desk spaces, and comfortable office setups with ergonomic chairs and monitors, ensuring a conducive environment for work. 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 well-equipped kitchens, which are essential for preparing meals using local ingredients. Many holiday rentals also feature pools, providing a refreshing escape during the warm Tuscan days. Additionally, amenities like refrigerators, cookware, dishware, and utensils are commonly available, ensuring that guests have everything they need for a comfortable stay.
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 period is particularly popular among travellers seeking to immerse themselves in the beautiful Tuscan countryside, with its rolling hills and vineyards ripe for exploration. July stands out as the most sought-after month, offering warm temperatures averaging around 30°C, superb for outdoor activities such as wine tasting tours and leisurely strolls through charming villages.

During these summer months, you'll find a vibrant atmosphere filled with festivals that celebrate local culture, food, and wine, making it an excellent time for those looking to indulge in authentic Italian experiences. The picturesque landscapes offer stunning backdrops for photography and leisurely picnics, ensuring your adventures are both memorable and comfortable.

If you're looking for a more affordable option, consider visiting in November. This quieter month provides a unique opportunity to experience Castellina In Chianti without the summer crowds, allowing you to savour the tranquillity of the countryside and enjoy the beautiful autumn colours. While the temperatures drop to a cooler range of around 15°C, the charm of the region remains, and you may even catch the tail end of the grape harvest.
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 rich culture and stunning landscapes of Tuscany. The town is renowned for its charming medieval architecture, with top attractions including the historic Castello di Castellina, where guests can explore ancient walls and enjoy breathtaking views of the surrounding vineyards.

The local wine, Chianti Classico, is celebrated, and many holiday rentals are situated near vineyards offering tours and tastings, allowing guests to savour the region's renowned wines. Strolling through the quaint streets, visitors will also discover local shops and traditional trattorias, great for sampling authentic Tuscan cuisine.
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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