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Vacation rentals in Radda in Chianti

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Top-rated vacation rentals in Radda in Chianti

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite
A spacious kitchen showcases a large stone fireplace with a wooden mantle as its centerpiece. Light streams through the window, illuminating the wooden beams overhead. A dining table is set for a meal, while traditional utensils adorn the walls, enhancing the inviting ambiance.
Villa in Castellina in Chianti
4.93 out of 5 average rating, 254 reviews

Manor House - IlVillinoFarmhouse

Entire upper floor of the newly renovated Manor House in traditional Tuscan style. High ceilings with exposed beams make the place cozy and perfect for families or groups of friends. In the house, there are two large functional fireplaces (in the living room and kitchen). Private, non-shared accommodation. The house has a large covered terrace, garden with sofas, BBQ, fire pit, private parking. The swimming pool among the olive trees and vineyards is ideal for relaxation and has private access to the shared area

Guest favorite
The historic farmhouse is surrounded by tall, ancient cypress trees and lush greenery. A gravel patio with outdoor seating is visible in the foreground, leading to an inviting garden area. The sky is clear with scattered clouds, creating a bright and welcoming ambiance.
Vacation home in Radda in Chianti
4.98 out of 5 average rating, 46 reviews

Tuscany Country House, Central Chianti, Pano Views

Tour (no spaces) www. escapetochianti. com/experience Perfect central base in Tuscany! The Farmhouse at Vignale has spectacular views overlooking organic vineyards in the heart of Chianti Classico wine country. Our spacious, historic artist-inspired stone house has 3 bedrooms, 1 bath (add 1bd/1ba extra fee) large living room, massive fireplace & great kitchen. Minutes to top restaurants & Chianti hill towns; easy drive to Florence & Siena; an ideal location for day trips to all parts of Tuscany

Top guest favorite
Farm stay in Radda in Chianti
4.97 out of 5 average rating, 103 reviews

1500 Stone House in Chianti Heart private lake B

Welcome to Agriturismo Podere Tegline, your gateway to an unforgettable Tuscan vacation. Immerse yourself in the secrets of Chianti Classico Wine as you reside in a meticulously restored ancient farmhouse from the 1500s. We strive to offer an authentic experience that resonates with the charm of the past, within a breathtaking natural oasis as in a small paradise. 2005-2026 We have been hosting for 21 years,and guests have come from 67 different countries: we have been Superhost for 11 years.

Guest favorite
Apartment in Radda in Chianti
5.0 out of 5 average rating, 10 reviews

Chianti dreaming in Radda

This apartment located on the outskirts of Radda in Chianti is the ideal choice for those looking for an elegant and comfortable retreat in the heart of Tuscany: • 3 Bedrooms: each has a king size bed (160x200 cm), private bathroom, smart TV, wardrobe and desk to ensure maximum privacy and comfort • Very bright living room • 4th guest bathroom • Tuscan charm: recently renovated, enhancing the exposed beams and terracotta floors • Fast internet (fiber optics) • Self check-in

Guest favorite
The kitchen area features wooden cabinetry and modern appliances, including a microwave and coffee maker. A round wooden table with simple chairs is surrounded by natural light from large windows, offering views of the surrounding vineyards.
Home in Greve in Chianti
4.95 out of 5 average rating, 101 reviews

Casa Giulia di Sopra Farmhouse

The CASA GIULIA DI SOPRA apartment, renovated in 2022 and located on the first floor, is a portion of an ancient farmhouse located in the heart of Chianti Classico. It is surrounded by the vineyards of Villa Calcinaia, an estate owned by the Capponi Counts since 1524. The apartment is 130 meters away from the shared swimming pool, open from May to October. The apartment has an outdoor area with a table and chairs where guests can dine and enjoy a glass of wine at sunset.

Top guest favorite
Home in Il Poggetto
4.93 out of 5 average rating, 152 reviews

La Loggia

Immerse yourself in the authentic Tuscan dream. "La Loggia" is a charming home in the heart of Chianti Classico, just 300 meters on foot from the historic center of Radda. It offers the perfect blend of countryside quietness and village convenience, featuring a large private garden with breathtaking panoramic views over vineyards and a beautiful glass-enclosed loggia. The perfect oasis to relax and enjoy the sunset after exploring Siena, Florence, and nearby wineries.

Top guest favorite
A large swimming pool surrounded by a brick patio and manicured lawns is highlighted in this image. Sun loungers are positioned along the pool's edge, with lush greenery and trees creating a serene backdrop. The villa's charming structure is visible in the distance under a partly cloudy sky.
Villa in Barberino Tavarnelle
4.98 out of 5 average rating, 104 reviews

Podere Tignano, 4-bedroom villa in the Chianti!

Nestled among the rolling hills of Chianti between Florence and Siena, Podere Tignano offers breathtaking views over vineyards, olive groves, and golden grain fields. This charming Tuscan stone villa blends authentic rural character with modern comfort and welcomes up to 8 guests in 4 bedrooms. Surrounded by peaceful countryside and featuring a private swimming pool, it is the perfect retreat for those seeking relaxation, nature, and the true spirit of Tuscany.

Guest favorite
A serene bedroom features two single beds that can be combined into a double, complemented by soft pillows and warm bedding. Natural light filters through the window, adorned with patterned curtains. Rustic decor includes wooden accents and artwork on the walls, enhancing the inviting atmosphere.
Apartment in Radda in Chianti
4.97 out of 5 average rating, 63 reviews

The Chianti Cabin

Rustic Tuscan-style apartment located in the heart of Chianti, just outside the historic center of Radda. The recently renovated accommodation is equipped with: · 1 bedroom with two single beds or a double bed (guest's choice) · 1 bedroom with a double bed · 1 crib · 1 bathroom · Free wifi (fiber optics) · Equipped kitchen and coffee machine · Washer-dryer · Living room with 43" Smart TV · Shared outdoor garden with table and umbrella for exclusive use

Top guest favorite
A spacious outdoor area features a swimming pool surrounded by lush green lawns and dotted with comfortable sun loungers. Umbrellas provide shade, and the serene landscape is framed by tall trees and gentle hills in the background.
Farm stay in Greve in Chianti
4.99 out of 5 average rating, 429 reviews

Typical Tuscan country house

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, dominates the Chianti valleys and enjoys a splendid view of the surrounding hills and the city of Florence just 35 minutes by car This apartment is one level, totally independent with private garden. Restored and furnished with great care to make the guest's stay as comfortable and relaxing as possible, in the full respect of the Tuscan rural style.

Top guest favorite
A welcoming living area is featured with an orange sofa complemented by two decorative cushions. A large piece of artwork hangs above the couch, while a stone wall adds texture. A potted plant and a wooden console table enhance the room's natural elements.
Condo in Greve in Chianti
4.98 out of 5 average rating, 195 reviews

The Nest in Chianti

We would like to inform you that for this emergency we are doing everything possible to help and protect our guests by adopting a detailed and strict cleaning, disinfecting and sanitizing of all parts of the house. Cozy apartment, finely renovated in the historic center on the second floor overlooking the beautiful square of Greve in Chianti. You can spend wonderful moments of relaxation on its condominium terrace.

Superhost
A stone bungalow is viewed from the poolside, featuring a private pool surrounded by sun loungers and an umbrella. The terrace, equipped with a dining table and chairs, shows lush greenery and elegant flowers in window boxes.
Villa in Radda in Chianti
5.0 out of 5 average rating, 10 reviews

La Casa di Radda

La Casa di Radda is a welcoming holiday home in the Chianti Classico region, notable for its proximity to the charming village of Radda. Just a short walk separates the house from the delightful restaurants, cafés, and small shops in the town center. It is ideal for a family vacation or a getaway with friends, offering the perfect setting for relaxing days in a rural environment.

Guest favorite
Condo in Radda in Chianti
4.95 out of 5 average rating, 19 reviews

Appartamento Holly House

Entire apartment, a double bed and a comfortable sofa bed, a baby crib on request. • Ample free parking • A fully equipped kitchen • A private courtyard, with a sofa and dining table. • Free Wi-Fi. • Air conditioning • Heating • Bathroom with shower and bidet • Distance only 500m from the historic center of Radda in Chianti.

Popular amenities for Radda in Chianti vacation rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great vacation rentals in Radda in Chianti

Guest favorite
Home in Barberino Tavarnelle
4.96 out of 5 average rating, 46 reviews

Beautiful farmhouse in the Chianti panoramic garden

Superhost
A stone villa is presented with rustic charm, featuring gentle exterior lighting that highlights its natural textures. A serene pool reflects the surroundings, while lounge chairs are arranged for relaxation. Lush greenery and trees provide a peaceful backdrop to this charming countryside retreat.
Home in Galenda
5.0 out of 5 average rating, 14 reviews

Casa Pernice · Chianti villa with private pool

Guest favorite
A pleasant backyard space features a well-maintained lawn and a flowering tree. A stone pathway leads to a seating area with a table and chairs, inviting outdoor dining. The house's exterior is characterized by warm-toned walls and brown window shutters.
Home in Radda in Chianti
4.84 out of 5 average rating, 38 reviews

Townhouse in Chianti

Guest favorite
A window framed by white trim offers a view of rolling green hills, dotted with trees and vines. Overcast skies create a serene atmosphere, while a garden filled with shrubs is visible at the base of the window.
Apartment in Radda in Chianti
5.0 out of 5 average rating, 22 reviews

Tuscany Chianti Village Experience

Guest favorite
Apartment in Cavriglia
4.95 out of 5 average rating, 37 reviews

Apartment Comfort | Quiet Escape in Tuscany

Top guest favorite
A serene outdoor area features a turquoise swimming pool surrounded by chaise lounges. Vibrant pink roses bloom near the edge, while lush greenery provides a natural backdrop. A stone villa with a tiled roof is visible in the distance, highlighting the tranquil setting.
Villa in Gaiole in Chianti
4.99 out of 5 average rating, 74 reviews

Sestuccia

Guest favorite
Castle in Tignano
5.0 out of 5 average rating, 25 reviews

Luxury Medieval Tower • Exclusive Chianti Stay

Top guest favorite
A spacious bedroom features a four-poster bed draped with soft fabric. Two bedside lamps create gentle illumination. An arched bookshelf filled with books is visible in the background, alongside a cozy seating area with upholstered chairs, highlighting a mix of comfort and elegance.
Villa in Panzano in Chianti
4.93 out of 5 average rating, 94 reviews

Luxury Villa on Chianti Wine Estate

Frequently Asked Questions

  • What are the best places to stay in Radda in Chianti?

    Stay in vacation rentals or agriturismo settings across Radda in Chianti, ranging from village apartments to countryside villas. Many accommodations have easy access to local food, walking trails, and cultural sites.

  • What are the best things to do in Radda in Chianti with kids?

    Radda in Chianti has family-friendly walking trails, hands-on workshops at local farms, and gelato tastings in the village. Children often enjoy watching grape harvest activities and exploring castles around the area.

  • What are some of the best things to do in Radda in Chianti?

    Explore historic streets in Radda in Chianti, visit local wineries, and enjoy panoramic views from nearby hilltops. The area has traditional restaurants, artisan shops, and medieval sites for a mix of cultural and culinary experiences.

  • How is the weather in Radda in Chianti?

    Radda in Chianti has cool, wetter winters around 33–49°F (0–9°C), and warm, drier summers near 60–89°F (16–32°C). Spring and autumn bring mild temperatures and lush landscapes, ideal for exploring outdoors.

  • When is the best time to visit Radda in Chianti?

    Late spring is often recommended for bright landscapes and mild afternoons near 74°F (23°C). Early autumn draws visitors with vineyard harvests and lively local festivities, set against cooler days around 68°F (20°C).

  • What are the best places to visit in Radda in Chianti?

    Explore the historic village center, visit traditional wineries, and wander through local artisan markets in Radda in Chianti. Medieval churches and scenic countryside make for enjoyable stops throughout the area.

  • What are some hiking trails in Radda in Chianti?

    Radda in Chianti has scenic trails winding through vineyards, forests, and along historical routes. Many routes feature gentle hills and panoramic views, making them accessible for a range of experience levels.

  • What are some family activities we can do in Radda in Chianti?

    Families can explore walking trails, take part in hands-on cooking classes, or enjoy interactive visits to vineyards and farms in Radda in Chianti. Gelato shops and markets around the village are popular with all ages.

  • What are some of the best day trip ideas from Radda in Chianti?

    Day trips often include exploring medieval villages, visiting renowned wineries, or hiking in surrounding Tuscan hills. Historic sites, local food markets, and artisan workshops around the region are frequently suggested.

  • Are there any pet friendly accommodations available in Radda in Chianti?

    Many accommodations around Radda in Chianti welcome pets, including vacation rentals and rural stays. Green spaces and walking paths make it easier to enjoy the area with your animal companions.

  • What are some local tips for visiting Radda in Chianti?

    Bring comfortable shoes for wandering village streets and vineyard paths, and sample locally made olive oil or wine. Early mornings offer quieter views, and many visitors appreciate learning a few Italian phrases for connecting with residents.

  • What is Radda in Chianti known for?

    Radda in Chianti is known for its locally rooted wine culture, preserved medieval architecture, and scenic countryside dotted with vineyards. The area has traditional festivals and culinary experiences that highlight Tuscan heritage.

  • What are the best hidden gems to explore in Radda in Chianti?

    Radda in Chianti has tucked-away artisan studios, scenic vineyard paths, and lesser-known local trattorias serving regional specialties. Some visitors enjoy discovering quiet chapels and small historical sites nestled within the village.

  • What are the best foods to try in Radda in Chianti?

    Radda in Chianti has locally made wines, pecorino cheese, wild boar pasta, and freshly baked bread. Olive oil tastings and gelato from village shops are frequently suggested by visitors.

  • What should I bring for a trip to Radda in Chianti?

    Pack layers for cooler evenings, comfortable walking shoes, and a reusable water bottle. If you plan to visit vineyards or the countryside, sunscreen and a hat are often recommended during warmer months.

  • What is the nightlife in Radda in Chianti like?

    Nightlife in Radda in Chianti centers on relaxed wine bars, trattorias, and occasional live music in local venues. Evening strolls and small village squares create a laid-back, sociable atmosphere.

  • What are the most popular events or festivals in Radda in Chianti?

    Radda nel Bicchiere is frequently suggested for wine tastings in early summer, and Festa del Perdono brings the community together with music, food, and cultural activities in early autumn. Both events are rooted in local traditions and highlight the region’s wine culture.

  • Are there family friendly vacation rentals in Radda in Chianti?

    Radda in Chianti has many family-friendly vacation rentals, including spacious villas and apartments in the village or countryside. Typically, these stays feature easy access to outdoor spaces and local attractions.

Destinations to explore