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Holiday houses in Radda in Chianti

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Top-rated holiday rentals in Radda in Chianti

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Guest favourite
Home in Poggio San Marco
4.97 out of 5 average rating, 299 reviews

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

Top Guest favourite
An aerial view showcases the expansive grounds of La settecentesca Villa di Geggiano, surrounded by manicured gardens and lush vineyards. The main villa is prominent, with a circular driveway leading to it, while gentle hills extend into the background.
Cottage in Geggiano
4.99 out of 5 average rating, 151 reviews

Villa di Geggiano – Guesthouse

PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI, THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR. The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idyllic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa.

Top Guest favourite
A charming stone building is nestled in a lush garden, featuring terracotta pots filled with colorful flowers. The structure includes a terracotta roof and wooden windows, creating a rustic look. Green grass and various plants surround the property, enhancing the serene outdoor environment.
Guest suite in Greve in Chianti
4.95 out of 5 average rating, 472 reviews

Selvabella in Chianti B&B. Lo Scricciolo Suite

A tower with an independent entrance through a private loggia offering panoramic views. On the first floor, there is a living room and a small pantry area (it is not a full kitchen) to store food and prepare a light meal or coffee. Climbing one flight of stairs leads to the second floor, which features a bedroom with a double bed and a sofa bed. Attached to the bedroom is the shower cabin and bathroom. Note that there are also three flights of stairs from the parking area to the accommodation.

Top Guest favourite
An aerial view captures the agriturismo nestled in lush greenery, with surrounding hills and vineyards stretching into the distance. The historic farmhouse features traditional terracotta roofs, complemented by the expansive natural landscape bathed in warm sunlight.
Farm stay in Radda in Chianti
4.97 out of 5 average rating, 101 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.

Top Guest favourite
A lush green garden is framed by a rustic pergola made of wooden beams. Grassy paths lead deeper into the garden, where vibrant flowers and trees provide a natural backdrop. Rolling hills and a clear blue sky are visible in the distance, creating a serene outdoor setting.
Home in Castellina in Chianti
4.98 out of 5 average rating, 131 reviews

Private Chianti Cottage, Garden & Vineyard Views

Set in a picturesque hamlet, overlooking the Chianti hills, this charming country house is just 10 minutes from Siena and Castellina in Chianti. Recently renovated, it blends authentic Tuscan charm with modern comforts. The house features two bedrooms, two bathrooms, a cozy living area and a fully equipped kitchen with a dishwasher, two fridges, and a washing machine. Outside, enjoy a beautiful garden and relax in the outdoor marble hot tub, soaking in the breathtaking views.

Top Guest favourite
A charming country house is set against a backdrop of expansive blue sky and lush green hills. The exterior features a combination of stone and plaster, with large arched windows and a welcoming entrance. A pebbled path leads to the front, flanked by garden beds.
Home in Il Poggetto
4.92 out of 5 average rating, 145 reviews

The Loggia

Country house located in Radda, the heart of the Chianti, within walking distance from the historical center and other services such as; Coffee shops, Post Office,grocery stores and restaurants. The house is composed of a full equipped kitchen, living room with a sofa bed, bedroom, loggia and bathroom. The property is surrounded by a garden and there is a nice wooden table in the garden to eat in an open space and another lounge spot to enjoy the magnificent landscape.

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.
Apartment in Radda in Chianti
4.98 out of 5 average rating, 54 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

Guest favourite
A spacious outdoor area is surrounded by greenery and stone buildings. The scenic landscape features a neatly maintained lawn, with a rustic path leading to a wooden door framed by flower pots. Rolling hills can be seen in the distance under a clear blue sky.
Apartment in Radda in Chianti
4.85 out of 5 average rating, 117 reviews

💜 "Ilary" Le Fontanelle Farmhouse

Immagina di alloggiare in una tipica casa in pietra della campagna toscana, nel bel mezzo della natura, a solo 1km dal paese di Radda in Chianti e di poterti affacciare ogni giorno su un panorama mozzafiato che saprà regalarti incantevoli tramonti. -70m2 -aia esterna panoramica riservata -TV con Google TV -parcheggio privato coperto -piscina condivisa (1 giugno - 15 settembre) -riscaldamento (1 novembre - 1 aprile) -wifi -cucina

Guest favourite
A charming stone exterior reveals a rustic villa surrounded by greenery. The entrance features a wooden door and terracotta roof tiles. Potted plants add color, while seating areas are positioned on a patio, inviting relaxation in the scenic surroundings under a clear blue sky.
Home in Radda in Chianti
4.92 out of 5 average rating, 169 reviews

Casa Dante – Authentic Chianti Stay | Views & Relaxation

Wake up to breathtaking views over the rolling hills of Chianti and enjoy a glass of wine at sunset from your private terrace. This peaceful home offers the perfect mix of privacy, comfort, and authentic Tuscan charm. Located just minutes from the center of Radda in Chianti, the house is ideally positioned to explore wineries, charming villages, and the surrounding countryside—while still feeling quiet.

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
5 out of 5 average rating, 9 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.

Top Guest favourite
A charming stone cottage is set amidst rolling hills and lush vineyards. The structure features a covered porch that opens to a green lawn, surrounded by olive trees and gently sloping landscapes, creating a peaceful countryside retreat.
Home in Radda in Chianti
4.93 out of 5 average rating, 57 reviews

Valley view in Chianti

The 'Capanna' is located in the middle of the beautiful hills of Chianti, a quiet place close to the art sites of Tuscany. 2 bedrooms, a large living room and a well-equipped kitchen. The view from the terrace and garden is unique. NOTE: Any heating will be calculated separately according to use. Heating to be paid separately. Abrechnung eventueller Heiz-Kosten nach Zählerstand.

Guest favourite
Condo in Radda in Chianti
4.93 out of 5 average rating, 14 reviews

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.

Popular amenities for Radda in Chianti holiday rentals

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  2. Italy
  3. Tuscany
  4. Radda in Chianti