Places to stay near Castiglion del Bosco Winery

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Top-rated vacation rentals near Castiglion del Bosco Winery

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Top guest favorite

Farm stay in Ruscello

4.99 out of 5 average rating, 425 reviews

Farmhouse Fattoria La Parita

Provencal style apartment surrounded by vineyard and olive trees. You will enjoy the tranquility of the countryside 10 km from the city and 4 from the highway. The singing of the acorn and cuckoo will be the soundtrack to the living room while the roe deer burn among the olive trees. An Italian basic breakfast (coffee, tea, milk, cookies, etc.) is included, if you prefer a richer and served breakfast at the table, the cost is €10 per person (€6 from 5 to 15 years, free less than 5 years old). Wallbox EV available.

Top guest favorite

A cozy sitting area features a vintage leather sofa with colorful accents, positioned against a light wall adorned with contemporary wall art. Soft bedding is seen at the back, complemented by warm wooden flooring. Natural light filters through a nearby window, enhancing the inviting space.

Home in Montalcino

5 out of 5 average rating, 125 reviews

Montalcino Townhouse with Private Garden & Spa

A luxury apartment that blends traditional elements with all the modern comforts and some contemporary wall art. The apartment is centrally located in the upper part of town, only around the corner from the main square, in the limited traffic area. You can drive close by to download the luggage. The closest free car park is located at less than 10 minutes walk. Please note that to reach the house you need to walk a fairly steep street: it may not be ideal for those with mobility problems.

Guest favorite

A spacious terrace features natural wooden beams and panoramic views of the surrounding landscape. Comfortable wooden seating arrangements are placed across the area, creating a welcoming environment. Potted plants add a touch of greenery, enhancing the overall ambiance of the outdoor space.

Villa in Montepulciano

4.95 out of 5 average rating, 220 reviews

Amazing Tuscany Villa, FREE parking

Modern villa with panoramic view in Montepulciano, a few steps from San Biagio. The villa is lovingly furnished and equipped with all comforts for a pleasant holiday. Enjoy breathtaking views of the surrounding countryside from the terrace, or relax in the two spacious gardens at your disposal. You will also have at your disposal a large kitchen to dabble in the magnificent art of cooking, something much loved by us Italians!!! Also available: Free Wi-fi Self check-in Reserved car parking

Top guest favorite

A spacious lawn gently slopes up towards a beautifully restored two-level house, featuring warm yellow and red hues. Tall cypress trees line the property, complementing the lush greenery of the surrounding gardens. Soft clouds drift above, enhancing the serene countryside setting.

Home in Gambassi Terme

4.99 out of 5 average rating, 178 reviews

Il Fienile, Luxury Apartment in the Tuscan Hills

‘Il Fienile’ is in an enchanting position immersed in the beauty of the Tuscan hills, with a breathtaking view of the surrounding countryside. It is located in the hamlet of Catignano in Gambassi Terme, just a few kilometres from San Gimignano. The house sits in a protected oasis surrounded by a beautiful private park with olive trees, a pond, pine trees and woods, where you can walk, relax and enjoy the pleasures of unspoilt nature. A unique experience entirely to be enjoyed.

Top guest favorite

The kitchen area features wooden cabinets and modern appliances, including a gas stove and oven. A round table with a colorful design is surrounded by black wire chairs. Large windows provide natural light and views of the surrounding landscape.

Cottage in Castell'Azzara

4.99 out of 5 average rating, 139 reviews

Your Private Tuscan Retreat

This beautiful sheepherder’s stone cottage is equipped with modern comforts and spa facilities free of charge. The large grounds of forest and meadow span a ridge and provide panoramic views of the valley toward Val d’Orcia to the north, the expansive Maremema to the south, and the ancient volcano of Amiata to the west. This is the perfect getaway for those wanting a private retreat from which to explore the rich wine, food, culture, history, and landscape of southern Tuscany.

Guest favorite

An outdoor terrace features a stone basin jacuzzi surrounded by lush greenery. Wooden lounge chairs are positioned nearby, providing a serene spot to relax amidst the trees. The setting offers a tranquil connection to nature.

Apartment in Castelnuovo Berardenga

4.93 out of 5 average rating, 161 reviews

Villa di Geggiano - Perellino Suite

The 700 years old Villa di Geggiano, surrounded by our working vineyard and lovingly maintained gardens, is located in Chianti in Tuscany which is one of the most beautiful regions of Italy. Our guesthouse is located in one of the original garden pavilions of the villa. PLEASE NOTE THAT WE ARE IN THE COUNTRYSIDE WITH VERY FEW PUBLIC TRANSPORT OTHER THAN TAXI SO THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A RENTAL CAR.

Top guest favorite

A cozy sleeping area is presented with natural wood accents and a light-hued headboard. Neatly arranged towels are complemented by a bouquet of dried flowers, creating a serene environment. Subtle wall sconces provide gentle illumination, enhancing the restful atmosphere of the space.

Farm stay in Montepulciano

4.94 out of 5 average rating, 126 reviews

Apartment in the Vineyard with Pool

Immersed in wonderful scenery with vineyards as far as the eye can see, this two-room apartment is part of a finely restored farmhouse with a swimming pool. From your private patio, you can access a fully equipped kitchen (crockery, toaster, kettles, microwave, espresso machine, refrigerator), with a modern extra-comfort sofa bed. You then pass to a large double bedroom with a bathroom equipped with a large shower, soft towels and a complete courtesy line.

Top guest favorite

A view from the entrance features a winding gravel road bordered by tall cypress trees and olive groves. Rolling hills stretch into the distance, creating a gentle and inviting landscape under a partly cloudy sky.

Condo in Asciano

4.97 out of 5 average rating, 290 reviews

Green – The meadows in Tuscany

Apartment consisting of 1 double bedroom, equipped kitchen, large living room, and bathroom TV, BBQ, (we provide the washing machine from 9 a.m. to 8 p.m. in our laundry room to those who request it). We recommend a car as we live in the countryside, both to be independent and to visit the magnificent Tuscany You'll like the outdoor environment because it's magical, day and night Free parking and wifi Convenient location to visit Tuscany and Umbria.

Guest favorite

A rustic villa features natural stone walls and green shutters, set amidst expansive lawns. A paved path leads to a traditional well, surrounded by blooming flowers. In the background, rolling hills and vineyards create a serene countryside backdrop.

Villa in Montepulciano

4.91 out of 5 average rating, 126 reviews

Villa in Montepulciano with a Pool

The Villa "I Girasoli" is part of the holiday farm "Il Serraglio" which covers 17 hectares. The Villa has a total area of 220 square meters that includes two bedrooms, two bathrooms, a large living room with an antique fireplace. Free WiFi. Direct access to the pool (which can be used by our other guests too) * Pool open from March to November. Circular heated pool, up to 32°C (90F) from April to October *

Guest favorite

Villa in Monteroni d'Arbia

4.95 out of 5 average rating, 136 reviews

"Villa Daisy" overlooking Siena

Wonderful villa with independent entrance inside the "Caggiolo" farm, brought to light with careful and thorough renovation that has kept intact the typical features of a Tuscan farm. Beautiful panoramic view of Siena. Located in Ville di Corsano, just 14 km from the city. An ideal place to spend days in total relaxation and enjoy the wonders that this area offers (Chianti, Val d'Orcia, Crete Senesi etc).

Top guest favorite

A bright kitchen features a glass ceiling with arched windows, allowing ample natural light. A wooden dining table is adorned with a bowl of fresh fruit, surrounded by chairs. Shelves display various kitchen items, while the overall space is enhanced by potted plants.

Apartment in Orvieto

5 out of 5 average rating, 103 reviews

Casa Teatro

Casa teatro is an elegant apartment located inside a prestigious building in the heart of Orvieto's historic center, a few steps from Piazza del Popolo and the city's most important tourist sites. The apartment is stylishly furnished, bright, characterized by ceilings and walls with frescoes attributed to the famous 19th-century painter Andrea Galeotti.

Top guest favorite

Home in Torreone

4.97 out of 5 average rating, 102 reviews

Tuscany House | View Breathtaking

Casa Belvedere is 10 minute drive from the center of Cortona. Is located along an old Roman road and enjoys a spectacular view of Cortona. Equipped cooking, 2 double room, 2 bathrooms, sofa bed, large garden with provides all the comforts to relax, sunbathe and have lunch under the pergola, enjoying the view of Cortona and the Val di Chiana.