Villa Strada dei Castelli

Starting from: $ 89 per person per night

Gaiole in Chianti, Toscana

Gaiole in Chianti, , Toscana

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Entire home |

Entire home

Villa|

Villa

14 Guests

|7 Bedrooms|

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Listing Description

“Villa Strada dei Castelli” is a wonderful stone farmhouse, built in 1700 and recently renovated.

The property, a hamlet of the nearby Borgo di Montegrossi, was once the closest farm (total extension of 46 hectares with vineyards, olive groves and pastures), where bread was prepared for the entire village in the ancient wood-fired oven located in the courtyard adjacent to the Villa, the structures of which are still visible. The castle of Montegrossi, also known as Montegrossoli, was the sentinel and last bastion of the medieval feudal system established in Chianti. Built at about 700 meters above sea level on the crest of the last relief of the small mountain range that forms the border between the territories of Chianti and Valdarno Superiore, always the object of disputes between Florence and its enemies, it dominates the pass and the road that connects the two areas, as well as a large part of the valley on both sides.

The villa, of 500 square meters in total (of which 300 square meters are available to our guests) is structured on 2 floors and offers large internal spaces where you can spend your holidays and moments of relaxation.

The materials are traditional, such as terracotta floors, pietra serena, chestnut wood beams and terracotta ceilings give the entire interior a typical Tuscan flavor.

The villa is arranged as follows: on the ground floor there are 2 double bedrooms with 2 bathrooms, separated by an entrance from the large living area with a large kitchen equipped with all the necessary appliances and utensils. A large dining room dominates the living area, with entrance to the external garden through a patio, a porch attached to the house through which you can directly access the front garden. On the first floor of the villa there are a further 5 double bedrooms with 4 bathrooms, and a large living room furnished in typical Tuscan style with an imposing antique fireplace in the center of the room. From the windows of the living room there is a view of the garden and the swimming pool. All bathrooms have large windows and shower.
The rooms are all very spacious, bright and also have large windows overlooking the external courtyard.

Our guests will have exclusive use of the large outdoor spaces, all fenced in their perimeter, to ensure the safety of adults, children and 4-legged friends.

Come and discover Chianti Classico with its traditions, its food, its scents and its wine. You will be amazed!

Price Info

Price per night: Starting from: $ 89 per person

Minimum no of nights: 7

Booking starts only on: Saturday

Security deposit: $ 200

Booking starts/ends only on: Saturday

Extra options:

Truffle hounting: $ 0 Per Guest

Private Chef: $ 0 Per Guest

Food & Wine Tour: $ 0 Per Guest

Cooking Class: $ 0 Per Guest

Mountain Bike: $ 0 Per Guest

Massages: $ 0 Per Guest

Private Transfers: $ 0 Per Guest

Address

Address: Gaiole in Chianti (Ar)

City: Gaiole in Chianti

Area: Toscana

County: Toscana

Zip: 53013

Country: Italia

Details

Property Status: verified

Property ID: 41450

Property Size: 300 m²

Rooms: 7

Bedrooms: 7

Bathrooms: 6

Check-in Hour: From 4:00 p.m.

Check-Out Hour: Before 10.00 am

Late Check-in: From 9:00 p.m.

Optional Services: On request

Features

Amenities

Air Conditioner

Fax

Heating

Internet

Kitchen

Phone (booth/lines)

Satellite channels

Smoke Detectors

Washer

Wireless Internet

Bed and bath

Essentials

Hair dryer

Hangers

Facilities

Breakfast

Elevator in Building

Family/Kid Friendly

Free Parking on Premises

Gym

Hot Tub

Non Smoking

Paddle Board

Pets Allowed

Pool

Smoke Detector

Snorkeling

Suitable for Events

Wheelchair Accessible

Yoga Relaxation Room

Other Features

Dishwasher

Garden or backyard

Smoking Allowed

Terms and Conditions

Smoking Allowed

Pets Allowed

Party Allowed

Children Allowed

Cancellation PolicyCheck your contract documentation for cancellation policy

Other RulesIs kindly asked to the costumer to leave the kitchen in the same conditions in which it was found.

Availability

Maggio 2026

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Giugno 2026

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About

OnlyVillasHoliday

Simona P.

My name is Simona, and I am happy to welcome you to Villa Strada dei Castelli, a special place where the authentic beauty of Tuscany meets peace, nature, and tradition.

This beautiful stone farmhouse, originally built in the 1700s and recently renovated with great care, is located along the famous “Via dei Castelli del Chianti,” surrounded by vineyards, woods, and rolling hills in the heart of the Chianti Classico region.

Villa Strada dei Castelli is much more than a holiday home — it is a place where guests can truly experience the charm of Tuscany, enjoying breathtaking views, unforgettable sunsets, and the quiet atmosphere of the countryside. Thanks to its panoramic position, 700 meters above sea level, the villa offers privacy, relaxation, and a unique connection with nature.

I personally take care of the villa with passion and attention to detail to ensure that every guest feels comfortable and welcomed from the very first moment. I will also be delighted to recommend local wineries, traditional restaurants, medieval villages, and authentic experiences to help you discover the true spirit of Tuscany.

My wish is for every guest to leave Villa Strada dei Castelli with beautiful memories, unforgettable moments, and the desire to return again.

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Villa Strada dei Castelli

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Simona P.

L	M	M	G	V	S	D
				1 $ 89	2 $ 89	3 $ 89
4 $ 89	5 $ 89	6 $ 89	7 $ 89	8 $ 89	9 $ 89	10 $ 89
11 $ 89	12 $ 89	13 $ 89	14 $ 89	15 $ 89	16 $ 89	17 $ 89
18 $ 89	19 $ 89	20 $ 89	21 $ 89	22 $ 89	23 $ 89	24 $ 89
25 $ 89	26 $ 89	27 $ 89	28 $ 89	29 $ 89	30 $ 89	31 $ 89

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Villa Strada dei Castelli

Listing Description

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About

Simona P.