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Holiday rentals in Radda in Chianti

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Top-rated holiday rentals in Radda in Chianti

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Guest favourite
A shaded garden area features a hammock suspended from a tree and a round table with chairs, set against a backdrop of lush greenery and rolling hills. The panoramic view extends under a partly cloudy sky.
Home in Poggio San Marco

Charming converted Hayloft overlooking the Chianti Hills

Inspired by the rustic Tuscan style, this gorgeously refurbished hayloft features ceilings with exposed beams and bricks and thoughtful touches for a stylish and comfortable decor. From the relaxing hammock and the stone made barbecue in a panoramic garden to the cozy fireplace, every space feels open and inviting. Immersed in total peace and tranquillity with a breathtaking view over the Chianti hills, halfway between Florence, Arezzo and Siena, the barn is a perfect homebase to visit Tuscany. The accommodation has 2 floors. The upper floor spaces 2 double bedrooms with wonderful views of the olive trees and a bathroom with window and large masonry shower. On the ground floor a cozy and spacious living area with fireplace and a kitchenette with gas stove a large fridge and oven. The barn has ceilings with exposed beams and bricks. Outside there is a panoramic garden set on its own where, in the shade of a walnut trees, you can relax on a hammock or grill your meal (included an authentic local Fiorentina steak :-) on the stone made barbecue. A garden table is there for romantic dinners 'al fresco'. Immersed in total peace and tranquility halfway between Florence, Arezzo and Siena the barn is a perfect homebase to visit Tuscany. To find the exact location of the house type the following code in GMaps: 8FMHGG25+QV The house is in the countryside. The closest towns are Cavriglia and the small Medioeval villages of Moncioni and Montegonzi. In each town you can find great local restaurants and a small grocery shop. Moncioni is 3 km far away. A big supermarket is located in Montevarchi and you can reach it in 8 minutes by car ( exactly 7 km far away). In Montevarchi you can also find one of the best farmer markets in Tuscany! The station of Montevarchi is 8 km away from the barn. From there you can take train to Florence and Arezzo. Siena can be reached in 30 minutes by car. The easy access to the motorway A1/E35 Milan-Florence-Rome (the Valdarno exit is only at 13 km) allows you to reach numerous interesting spots within a short time, both in Tuscany and Umbria, while few kilometres south of Cavriglia you enter the suggestive territory of the Crete Senesi. Out in the countryside, the home offers an authentic experience of Tuscany. Small towns and villages are a short drive away providing acces to exceptional local restaurants and fantastic farmers markets. A big supermarket is located in Montevarchi (7 km far away). The railway station is 8 km away from the barn. From there you can take train to Florence and Arezzo. Cities of interest like Siena, Montepulciano, Pienza and Monteriggioni can be reached in 40 minutes by car The only way to reach the house is by car. A taxi service is active from Montevarchi You will be provided of blankets and towels. The kitchen is equipped with and kind of pots, pans, bowl, plates and silverware. You are welcome to use them. Free Netflix available

4.97 out of 5 average rating, 308 reviews
Guest favourite
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

Agriturismo Casa Giulia di Sopra

L'appartamento CASA GIULIA DI SOPRA, ristrutturato nel 2022 e situato al primo piano, è una porzione di un'antica colonica situata nel cuore del Chianti Classico. E' circondato dai vigneti di Villa Calcinaia, tenuta di proprietà dei Conti Capponi dal 1524. L'appartamento si trova a 130 mt. di distanza dalla piscina condivisa, aperta da maggio ad ottobre.L'appartamento dispone di un'area esterna dotata di tavolo e sedie dove gli ospiti potranno desinare e godersi un bicchiere di vino al tramonto.

4.95 out of 5 average rating, 107 reviews
Guest favourite
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

Villa Padronale - IlVillinoFarmhouse

Intero piano superiore della Villa Padronale appena ristrutturata in stile tradizionale toscano.Gli alti soffitti con le travi a vista rendono il posto accogliente e perfetto per famiglie o gruppi di amici.Nella casa si trovano due grandi camini(in salotto e cucina)funzionali.Alloggio privato, non condiviso. La casa ha una ampia terrazza coperta,giardino con divani,bbq,firepit,parking privato. La piscina tra gli ulivi e i vigneti e' ideale per il relax ha un accesso privato alla zona condivisa

4.93 out of 5 average rating, 256 reviews
Guest favourite
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.
Flat in Radda in Chianti

La Capannina del Chianti

Appartamento rustico in stile toscano situato nel cuore del Chianti, appena fuori dal centro storico di Radda. L'alloggio, recentemente ristrutturato, è dotato di : · 1 camera con due letti singoli o un letto matrimoniale (a scelta dell'ospite) · 1 camera con letto matrimoniale · 1 culla · 1 bagno · Wi-Fi gratuito (fibra ottica) · Cucina accessoriata e macchina del caffè · Lavasciuga · Soggiorno con Smart TV da 43" · Giardino esterno condiviso con tavolo ed ombrellone ad uso esclusivo

4.96 out of 5 average rating, 67 reviews
Top guest favourite
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

Sestuccia

Villa Sestuccia is a lovely Tuscan villa near the popular towns of Gaiole and Radda in Chianti. In this wonderful villa there are 4 bedrooms with private bathrooms.The exterior of the villa is composed by 4 living areas: the "wisteria living", the "panorama living", the "Mondrian living", the "outdoor patio" and a vegetable garden. There is also a swimming pool, a SPA and an outdoor hot tub for 6 people. Inside the fenced property you can find a chicken coop and a beautiful vineyard. Enjoy!

4.99 out of 5 average rating, 76 reviews
Guest favourite
Home in Barberino Tavarnelle

stupenda villa nel chianti, giardino panoramico

“DIMORA BADIA A PASSIGNANO” Vivrete un soggiorno meraviglioso e ristorativo nel cuore del chianti classico. soggiornerete in un antico fienile totalmente restaurato in pietra con grande giardino recintato e un antico gazebo, adatto a gruppi numerosi e famiglie. le camere sono comode e spaziose per 8 persone. la ristrutturazione è stata eseguita finemente, tenendo conto di ogni minimo particolare estetico per poter farvi respirare l’antica tradizione toscana mixata con la comoda modernità.

4.96 out of 5 average rating, 48 reviews
Top guest favourite
Home in Il Poggetto

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.

4.93 out of 5 average rating, 155 reviews
Top guest favourite
A rustic building is seen under a starry night sky, with a partial roof providing shelter. Soft light glows from the interior, illuminating the entrance. Lush greenery and trees surround the scene, adding depth to the serene nighttime landscape.
Farm stay in Simignano

Casa al Gianni - Capanna

Ciao, siamo Cristina e Carmelo! Vi aspettiamo a "Casa al Gianni", il nostro agriturismo tra i boschi della Montagnola Senese a soli 20 minuti da Siena. Qui la vita rallenta: Solo il profumo della terra, il canto degli uccelli e la simpatia dei nostri animali. È un invito a riscoprire la bellezza delle piccole cose, immersi nel verde della Toscana più vera. Non è solo una vacanza, è un ritorno alle origini. Questo angolo di pace vi resterà nell'anima. Vi aspettiamo!

4.93 out of 5 average rating, 294 reviews
Top guest favourite
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

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.

4.98 out of 5 average rating, 107 reviews
Top guest favourite
A panoramic view reveals rolling hills adorned with vineyards and olive groves, stretching under a dramatic sky. The tan-coloured buildings of the property are nestled among lush greenery, while a serene pool reflects the surrounding landscape.
Flat in Quercegrossa

Tuscany jem: La Casa del Fattore del Chianti

Questo meraviglioso appartamento appena ristrutturato conserva il fascino dei casolari del Chianti e le comodità di un appartamento moderno. La casa è situata all'interno del complesso della Fattoria di Petroio, azienda vitivinicola del Chianti Classico. Potrete godere della bellezza e della tranquillità delle colline del Chianti, mentre vi immergete nella vita dinamica di un'azienda dedita alla produzione di vini di qualità.

4.98 out of 5 average rating, 89 reviews
Guest favourite
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

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.

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

Appartamento Holly House

Intero appartamento, un letto matrimoniale e un comodo divano letto, su richiesta una culla per bebè. • Un ampio parcheggio gratuito • Una cucina accessoriata • Un resede privato, con divano e tavolo da pranzo. •Wi-FI gratuito. • Aria condizionata • Riscaldamento • Bagno con doccia e bidet • Distanza solo 500m dal centro storico di Radda in Chianti.

4.95 out of 5 average rating, 20 reviews

Popular amenities for Radda in Chianti holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great holiday rentals in Radda in Chianti

Guest favourite
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.
Holiday home in Radda in Chianti

Tuscany Country House, Central Chianti, Pano Views

4.98 out of 5 average rating, 46 reviews
Superhost
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

Casa a schiera nel Chianti

4.79 out of 5 average rating, 39 reviews
Guest favourite
Flat in Cavriglia

Apartment Comfort | Quiet Escape in Tuscany

4.93 out of 5 average rating, 60 reviews
Top guest favourite
The villa is depicted with a stone exterior, surrounded by olive trees and rolling vineyards. A circular pool is featured in the foreground, offering a tranquil spot for relaxation. Umbrellas provide shade over lounge chairs nearby, enhancing the serene outdoor space.
Villa in Radda in Chianti

Villa con piscina nel Chianti - Castellare Petroso

5.0 out of 5 average rating, 33 reviews
Superhost
Home in Gaiole in Chianti

Fienile House

4.63 out of 5 average rating, 8 reviews
Top guest favourite
The villa's exterior is showcased with a spacious garden featuring green grass and a few chairs for relaxation. A covered terrace is visible, along with a dining table set for al fresco meals. The house features large windows, and lush greenery surrounds the property.
Home in Castellina in Chianti

CHIANTI CLASSICO, VIEWS, WALK TO RESTAURANT

5.0 out of 5 average rating, 73 reviews
Guest favourite
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.
Flat in Radda in Chianti

Tuscany Chianti Village Experience

5.0 out of 5 average rating, 22 reviews
Guest favourite
A narrow street lined with charming buildings, featuring arched doorways and an inviting sign for a local establishment. Potted plants add greenery to the scene, while a few people are seen walking leisurely. The clear blue sky above enhances the architecture's historical character.
Flat in Radda in Chianti

Heart of Chianti - a warm flat in Radda

4.92 out of 5 average rating, 124 reviews

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.

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