Castellina in Chianti Rentals
- From $420 per night (USD)
VRBO
12km North of Siena with a stunning view pool & tenniscourt 3 bedrooms ensuite
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This beautiful property is a part of an old 16th century farm situated on the top of one of hills West of Castellina in ...
From $420 per night (USD)VRBO
- From $351 per night (USD)
Expedia
Detached villa with swimming pool and pizza oven for groups up to fourteen people.
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
Our villa located within walking distance from Tregole in the famous wine region of Chianti Classico, has five spacious ...
From $351 per night (USD)Expedia
- From $428 per night (USD)
VRBO
Luxury converted barn with hilltop views in chianti wine region, Tuscany
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
The Barn at Bagnaie is a luxury 3-bedroom Tuscan villa, which we have modernised and furnished to a high standard. The i ...
From $428 per night (USD)VRBO
- From $414 per night (USD)
Expedia
Beautiful Tuscan farmhouse with stunning views of Chianti countryside
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
The house forms part of the oldest wing of Le Bagnaie, a 300 year old farm on a secluded hilltop, which was converted in ...
From $414 per night (USD)Expedia
- From $897 per night (USD)
VRBO
Belvilla by OYO Villa il Colle
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
This property has been cleaned with chemicals that are effective against Coronavirus. Our staff is following all safety ...
From $897 per night (USD)VRBO
- From $325 per night (USD)
Expedia
Casa il Cipresso, in the heart of Chianti with swimming pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Cipresso house is one of the 4 houses of Borgo Montecastelli, and is located right on the border between the provinc ...
From $325 per night (USD)Expedia
- From $193 per night (USD)
VRBO
Casa Antico Roseto - cottage with swimming pool
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
The Antico Roseto house is a portion of the manor house that stands on the top of Borgo Montecastelli. Next to the entra ...
From $193 per night (USD)VRBO
- From $422 per night (USD)
Expedia
Casa Belvedere cottage with swimming pool in the heart of Chianti
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
The Casa Belvedere is one of the 4 houses of Borgo Montecastelli, and is located right on the border between the provinc ...
From $422 per night (USD)Expedia
- From $461 per night (USD)
VRBO
Fully renovated Chianti country home, 10 min from Siena; stunning views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This beautiful 2-bedroom, 2-bathroom Tuscan country home is composed of a ground floor with a comfortable and welcoming ...
From $461 per night (USD)VRBO
- From $916 per night (USD)
Expedia
Wonderful private villa with private pool, WIFI, TV, patio, panoramic view, parking, close to Siena
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
Vacation rental La Corte Di Campalli is a beautiful property (600 sq m) that includes private pool and WiFi internet. T ...
From $916 per night (USD)Expedia
- From $184 per night (USD)
VRBO
Tuscany. Lovely holiday home with swimming pool.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Magnificent high-rise apartment of 80 m2. 2 large double bedrooms. Lovely bathroom w / shower, toilet and bidet. Living ...
From $184 per night (USD)VRBO
- From $108 per night (USD)
Expedia
Villa with large garden in the Chianti hills
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
An important notice: For covid 19, unfortunately, the swimming pool is not open for summer 2020. For the month of August ...
From $108 per night (USD)Expedia
- From $469 per night (USD)
VRBO
Detached stone vacation home in the heart of Chianti Classico, 5 km from Castellina in Chianti.
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 11
Detached stone vacation home in the heart of Chianti Classico, 5 km from Castellina in Chianti. The vacation home is loc ...
From $469 per night (USD)VRBO
- From $190 per night (USD)
VRBO
Vacation apartment with shared pool in the Chianti area.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Vacation apartment with shared pool in the Chianti area. The apartment is located in a beautiful country house in the mi ...
From $190 per night (USD)VRBO
- From $260 per night (USD)
VRBO
Exclusive Garden Place, View and Atmosphere
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
La Rocca property is immersed in the green Chianti hills, 480 meters above sea level, and is an authentic terrace overlo ...
From $260 per night (USD)VRBO
- From $419 per night (USD)
VRBO
This beautiful property in the heart of Chianti about 4 km from Castellina in Chianti, built in the
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
This beautiful property in the heart of Chianti about 4 km from Castellina in Chianti, built in the 15th century as an a ...
From $419 per night (USD)VRBO
- From $328 per night (USD)
VRBO
Detached stone vacation home in the heart of Chianti Classico, 5 km from Castellina in Chianti.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Detached stone vacation home in the heart of Chianti Classico, 5 km from Castellina in Chianti. The vacation home is loc ...
From $328 per night (USD)VRBO
- From $267 per night (USD)
VRBO
Detached stone vacation home in the heart of Chianti Classico, 5 km from Castellina in Chianti.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
Detached stone vacation home in the heart of Chianti Classico, 5 km from Castellina in Chianti. The vacation home is loc ...
From $267 per night (USD)VRBO
- From $419 per night (USD)
VRBO
Antique farmhouse in dominating position
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 12
Spacious stone vacation home in dominant hill position in the heart of Chianti Classico, 5 km from the town of Castellin ...
From $419 per night (USD)VRBO
- From $156 per night (USD)
VRBO
Vacation apartment with shared pool in the Chianti area.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Vacation apartment with shared pool in the Chianti area. The apartment is located in a beautiful country house in the mi ...
From $156 per night (USD)VRBO
- From $137 per night (USD)
VRBO
Apartment in villa with WIFI, pool, TV, terrace, pets allowed, parking, close to San Gimignano
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This charming vacation rental is an old farmhouse that has been tastefully renovated to offer a comfortable and enjoyabl ...
From $137 per night (USD)VRBO
- From $184 per night (USD)
Expedia
Cosy apartment in villa with pool, WIFI, TV, terrace, pets allowed, parking, close to San Gimignano
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This charming vacation rental is an old farmhouse that has been tastefully renovated to offer a comfortable and enjoyabl ...
From $184 per night (USD)Expedia
- From $148 per night (USD)
VRBO
Apartment in villa with pool, WIFI, TV, terrace, pets allowed, parking, close to San Gimignano
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This charming vacation rental is an old farmhouse that has been tastefully renovated to offer a comfortable and enjoyabl ...
From $148 per night (USD)VRBO
- From $199 per night (USD)
Expedia
BACCO- Authentic house with STUNNING VIEW - S. GIMIGNANO \/ SIENA \/ FIRENZE
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Authentic 15th-century house, situated in the middle of Chianti Classic, in the Sant Agnese Natural Park. Close San Gim ...
From $199 per night (USD)Expedia
- From $204 per night (USD)
VRBO
RAFFAELLO - Firenze \/Siena \/San Gimignano - SWIMMING POOL AND TENNIS COURT
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
AUTHENTIC 15TH CENTURY HOUSE IN CHIANTI CLASSICO / ON THE TOP OF A HILL OF OLIVE TREES, IN THE NATURE RESERVE OF SANT'AG ...
From $204 per night (USD)VRBO
- From $331 per night (USD)
Expedia
Cypress trees 1 - Stone barn with swimming pool and breathtaking view
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
<p>A short distance from ecotours, wildlife walks, and more, this smoke-free vacation home lets you experience it all. W ...
From $331 per night (USD)Expedia
- From $312 per night (USD)
VRBO
Cypress trees 2 - Farmhouse with swimming pool and breathtaking view
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
<p>Close to ecotours, cycling, and more, this smoke-free vacation home brings it all within reach. Jump into your car an ...
From $312 per night (USD)VRBO
- From $91 per night (USD)
Expedia
Casa Bruna - Cipresseta del Chianti
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Located in the Chianti hills, the apartment is immersed in the green oasis of the Bosco di Sant’Agnese Nature Reserve: a ...
From $91 per night (USD)Expedia
- From $418 per night (USD)
VRBO
Private Villa with A\/C, private pool, WIFI, TV, patio, panoramic view, close to Greve In Chianti
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Holiday home in a strategic position in Castellina in Chianti. Casa Fioraie is the ideal place to spend a relaxing and f ...
From $418 per night (USD)VRBO
- From $391 per night (USD)
Expedia
Fioraie villa with pool and breathtaking views for 6 people
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
<p>Located in a rural area, this welcoming villa lets you experience it all in Castellina in Chianti. Jump into your car ...
From $391 per night (USD)Expedia
- From $77 per night (USD)
VRBO
Restored farmhouse in heart of chianti with swimming pool and tennis court.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Granaio is a tiny village composed of four groups of houses and a little church on top of a hill in the heart of Chianti ...
From $77 per night (USD)VRBO
- From $1230 per night (USD)
Expedia
Villa Delle Upupe 8, Emma Villas
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
The Price includes: - Utilities: electricity, water, gas for cooking purposes - weekly linen, initial and final cleaning ...
From $1230 per night (USD)Expedia
- From $2610 per night (USD)
VRBO
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
- Bedrooms:
- 12
- Bathrooms:
- 11
- Sleeps:
- 23
Located in Castellina in Chianti in Tuscany, Italy, 'Isola Serena' is a beautiful private luxury villa on 4 acres of lan ...
From $2610 per night (USD)VRBO
- From $856 per night (USD)
Expedia
Villa in San Leonino with 6 bedrooms sleeps 12
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
This beautiful property with private pool is part of the Campalli estate, a huge farm of 750 acres that produces Chianti ...
From $856 per night (USD)Expedia
- From $685 per night (USD)
VRBO
Villa Arnica B: A graceful cottage surrounded by vineyards and olive groves, with Free WI-FI.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Villa Arnica B is a graceful cottage surrounded by vineyards and olive groves. It sleeps four people. From Villa Arnica ...
From $685 per night (USD)VRBO
- From $126 per night (USD)
Expedia
Lovely apartment in villa with WIFI, pool, A\/C, TV, patio, pets allowed, panoramic view and park...
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Country House "Cignanbianco," a beautiful property surrounded by fields and vineyards. The residence comprise ...
From $126 per night (USD)Expedia
- From $157 per night (USD)
VRBO
Nice apartment in villa with pool, WIFI, TV, patio, pets allowed, panoramic view and parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
If you're looking for a beautiful vacation rental in the Italian countryside, look no further than the "Cellole" country ...
From $157 per night (USD)VRBO
- From $122 per night (USD)
Expedia
Beautiful apartment in villa with pool, WIFI, TV, patio, pets allowed, panoramic view and parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
If you're looking for a beautiful vacation rental in the Italian countryside, look no further than the "Cellole" country ...
From $122 per night (USD)Expedia
- From $186 per night (USD)
VRBO
Cosy apartment in villa with WIFI, A\/C, pool, TV, patio, pets allowed, panoramic view and parking
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 9
Welcome to Country House "Cignanbianco," a beautiful property surrounded by fields and vineyards. The residence comprise ...
From $186 per night (USD)VRBO
- From $91 per night (USD)
Expedia
Nice apartment in villa with pool, WIFI, A\/C, TV, patio, pets allowed, panoramic view and parking
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Welcome to Country House "Cignanbianco," a beautiful property surrounded by fields and vineyards. The residence comprise ...
From $91 per night (USD)Expedia
- From $168 per night (USD)
VRBO
Lovely apartment in villa with WIFI, pool, TV, patio, pets allowed, panoramic view and parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
If you're looking for a beautiful vacation rental in the Italian countryside, look no further than the "Cellole" country ...
From $168 per night (USD)VRBO
- From $148 per night (USD)
Expedia
Nice apartment in villa with WIFI, pool, TV, patio, pets allowed, panoramic view and parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
If you're looking for a beautiful vacation rental in the Italian countryside, look no further than the "Cellole" country ...
From $148 per night (USD)Expedia
- Click For Pricing
VRBO
Villa Capannuccia \/ Locanda La Capannuccia
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 9
Villa Capannuccia (Locanda La Capannuccia) is a construction from the 1600s. Located in the Chianti Classico area in the ...
Click For PricingVRBO
- From $314 per night (USD)
Expedia
Podere Gioia by Interhome
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
Podere Gioia consists of two independent housing units. Our offer includes three apartments, two of which are in the sam ...
From $314 per night (USD)Expedia
- From $1079 per night (USD)
VRBO
I Sodi di Bibbiano, Spa and private swimming pool
- Bedrooms:
- 8
- Bathrooms:
- 9
- Sleeps:
- 18
Very large villa in the middle of the vineyard of the Bibbiano Chianti Classico estate. This unit has nine double bedroo ...
From $1079 per night (USD)VRBO
- From $434 per night (USD)
Expedia
Bibbiano - La Limonaia detatched lovely villa with private swimming pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This detatched villa has 2 double bedrooms and 2 bathrooms, a large living area and kitchen. The use of the swimming poo ...
From $434 per night (USD)Expedia
- From $242 per night (USD)
VRBO
Bibbiano - Il Pero typical apartment in a wine estate
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The Apartment Il Pero it is a 2 bedroom flat with 2 bathrooms in the same building of the show room and operations of Bi ...
From $242 per night (USD)VRBO
- From $302 per night (USD)
Expedia
Bibbiano - Il Fico typical apartment in a wine estate
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The Apartment Il Fico it is a 2 bedroom flat with 2 bathrooms in the same building of the show room and operations of Bi ...
From $302 per night (USD)Expedia
- From $682 per night (USD)
VRBO
Casale Cipressi, Castellina in Chianti, Siena and Chianti
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 9
This is a great option for multi-generational families or friends who want to be spoilt. The beautifully kept Casale Cip ...
From $682 per night (USD)VRBO
- From $310 per night (USD)
Expedia
Venus, Podere di Casalta, Castellina in Chianti, Siena and Chianti
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Sitting on the hillside between Castellina in Chianti (8.5Km distance) and Panzano in Chianti (6.5Km distance) down an a ...
From $310 per night (USD)Expedia
- From $398 per night (USD)
VRBO
Bellosguardo, Castellina in Chianti, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Fancy immersing yourself in Chianti Classico country? Then look no further than Bellosguardo, the ideal choice for a fam ...
From $398 per night (USD)VRBO
- From $298 per night (USD)
Expedia
Borea, Podere di Casalta, Castellina in Chianti, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Sitting on the hillside between Castellina in Chianti (8.5Km distance) and Panzano in Chianti (6.5Km distance) down an a ...
From $298 per night (USD)Expedia
- From $372 per night (USD)
VRBO
Athena-Urania, Podere di Casalta, Castellina in Chianti, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Sitting on the hillside between Castellina in Chianti (8.5Km distance) and Panzano in Chianti (6.5Km distance) down an a ...
From $372 per night (USD)VRBO
- From $560 per night (USD)
Expedia
Capanna Leopoldina 10, Rocca di Castellina, Castellina in Chianti, Siena and Chianti
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
The country resort of La Rocca Castellina could not feel more Tuscan. It's an authentic working vineyard with a warm, ho ...
From $560 per night (USD)Expedia
- From $255 per night (USD)
VRBO
Antico Cipresso, Navico, Castellina in Chianti, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Sitting hillside between Castellina in Chianti 9 Km and Panzano in Chianti 7 Km, Navico is an impossibly pretty collecti ...
From $255 per night (USD)VRBO
- From $669 per night (USD)
Expedia
Macia Viva, Castellina in Chianti, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Set above a valley in the heart of Chianti, Macia Viva’s views make this private, stone-built villa very special. The ma ...
From $669 per night (USD)Expedia
- From $411 per night (USD)
VRBO
Ginestra, Castellina in Chianti, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
Set in the foothills of Chianti, this delightful villa for two people has near-360° views of undulating Tuscan countrysi ...
From $411 per night (USD)VRBO
- From $303 per night (USD)
Expedia
Pandora, Podere di Casalta, Castellina in Chianti, Siena and Chianti
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Sitting on the hillside between Castellina in Chianti (8.5Km distance) and Panzano in Chianti (6.5Km distance) down an a ...
From $303 per night (USD)Expedia
- From $199 per night (USD)
VRBO
Athena, Podere di Casalta, Castellina in Chianti, Siena and Chianti
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Sitting on the hillside between Castellina in Chianti (8.5Km distance) and Panzano in Chianti (6.5Km distance) down an a ...
From $199 per night (USD)VRBO
- From $460 per night (USD)
Expedia
Casanovina, Castellina in Chianti, Siena and Chianti
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Set on an open ridge, to the rear of an old farm house this well-appointed villa scores top marks for its dreamy private ...
From $460 per night (USD)Expedia
- From $797 per night (USD)
VRBO
Casale la Canonica, Castellina in Chianti, Siena and Chianti
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
Formerly a priest’s house, Casale la Canonica clusters behind the church that greets you at the top of the drive. Set in ...
From $797 per night (USD)VRBO
- From $161 per night (USD)
Expedia
La Querce, Rocca di Castellina, Castellina in Chianti, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 3
The country resort of La Rocca Castellina could not feel more Tuscan. It's an authentic working vineyard with a warm, ho ...
From $161 per night (USD)Expedia
- From $250 per night (USD)
VRBO
Il Nocino, Rocca di Castellina, Castellina in Chianti, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The country resort of La Rocca Castellina could not feel more Tuscan. It's an authentic working vineyard with a warm, ho ...
From $250 per night (USD)VRBO
- From $287 per night (USD)
Expedia
Casetta Erika, Castellina in Chianti, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
What could be quainter than a little pink cottage in a wood, surrounded by vineyards and olive groves? Casetta Erika is ...
From $287 per night (USD)Expedia
- From $126 per night (USD)
VRBO
Cignanbianco - Tramonto by Interhome
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
<p>Close to hiking trails, winery tours, and more, this pet-friendly vacation home brings it all within reach. Jump into ...
From $126 per night (USD)VRBO
- From $530 per night (USD)
Expedia
Villa Beba, Castellina in Chianti, Siena and Chianti
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
If you've got a larger group of family or friends that you'd like to share the best of Tuscany with - and you dream of e ...
From $530 per night (USD)Expedia
- From $175 per night (USD)
VRBO
Urania, Podere di Casalta, Castellina in Chianti, Siena and Chianti
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Sitting on the hillside between Castellina in Chianti (8.5Km distance) and Panzano in Chianti (6.5Km distance) down an a ...
From $175 per night (USD)VRBO
- From $98 per night (USD)
Expedia
Farmhouse in the Chianti \"La Foresta 1\" with swimming pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Two-room apartment, renovated for 2-3 people with typical Tuscan furnishings Agriturismo La Foresta is a restored farmh ...
From $98 per night (USD)Expedia
- From $1436 per night (USD)
VRBO
Large Chianti Estate, Tuscany weddings, retreats, celebrations, workshops
- Bedrooms:
- 15
- Bathrooms:
- 15
- Sleeps:
- 33
Podere Patrignone is a large estate surrounded by vines, olives and lush forest, and sits on top of a hill with 360-degr ...
From $1436 per night (USD)VRBO
- From $439 per night (USD)
Expedia
Villa \"San Bartolomeo\" with Pool and Wi-Fi - Pets allowed
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Villa San Bartolomeo is located in Castellina in Chianti, 20 km from Siena, and boasts beautiful views of the hills. The ...
From $439 per night (USD)Expedia
- From $115 per night (USD)
VRBO
House in a typical village in the heart of Chianti
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Located in a pretty and peaceful village on the top of a hill in the Chianti area which overlooks a landscape of olive t ...
From $115 per night (USD)VRBO
- From $119 per night (USD)
Expedia
House in a typical village in the heart of Chianti
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Apartment located in a pretty and peaceful village on the top of a hill in the Chianti area which overlooks a landscape ...
From $119 per night (USD)Expedia
- From $168 per night (USD)
VRBO
Cellole - Valluccia by Interhome
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
<p>A short distance from hiking trails, winery tours, and more, this pet-friendly vacation home lets you experience it a ...
From $168 per night (USD)VRBO
- From $170 per night (USD)
Expedia
La Tinaia by Interhome
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
<p>Close to hiking trails, winery tours, and more, this pet-friendly apartment brings it all within reach. With convenie ...
From $170 per night (USD)Expedia
- From $157 per night (USD)
VRBO
Cellole - Cellole 1 (CTC150) by Interhome
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Beautiful on a vinyard country house "Cellole", detached, surrounded by trees and vineyards. 6 apartments in the residen ...
From $157 per night (USD)VRBO
- From $148 per night (USD)
Expedia
Capanna di Sopra by Interhome
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
<p>Close to hiking trails, winery tours, and more, this pet-friendly vacation home brings it all within reach. With conv ...
From $148 per night (USD)Expedia
- From $123 per night (USD)
VRBO
Capanna di Sotto by Interhome
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
<p>Close to hiking trails, winery tours, and more, this pet-friendly vacation home brings it all within reach. With conv ...
From $123 per night (USD)VRBO
- From $126 per night (USD)
Expedia
Cellole - Cellole 2 (CTC151) by Interhome
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
<p>A short distance from hiking trails, winery tours, and more, this pet-friendly apartment lets you experience it all. ...
From $126 per night (USD)Expedia
- From $726 per night (USD)
VRBO
Casale Il Poggino by Interhome
- Bedrooms:
- 6
- Bathrooms:
- 7
- Sleeps:
- 16
<p>A short distance from hiking trails, winery tours, and more, this pet-friendly vacation home lets you experience it a ...
From $726 per night (USD)VRBO
- From $102 per night (USD)
Expedia
Cellole - La Stalla by Interhome
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Beautiful on a vinyard country house "Cellole", detached, surrounded by trees and vineyards. 6 apartments in the residen ...
From $102 per night (USD)Expedia
- From $148 per night (USD)
VRBO
Cellole - Torretta (CTC153) by Interhome
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Beautiful on a vinyard country house "Cellole", detached, surrounded by trees and vineyards. 6 apartments in the residen ...
From $148 per night (USD)VRBO
- From $91 per night (USD)
Expedia
Cignanbianco - Alba by Interhome
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Country house "Cignanbianco", surrounded by fields and vineyards. 3 houses in the residence. 7 apartments in the residen ...
From $91 per night (USD)Expedia
- From $186 per night (USD)
VRBO
Cignanbianco - Alba e Tramonto by Interhome
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 9
Country house "Cignanbianco", surrounded by fields and vineyards. 3 houses in the residence. 7 apartments in the residen ...
From $186 per night (USD)VRBO
- From $1792 per night (USD)
Expedia
Villa in Castellina w. Pool, Garden & Winery
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
The Villa di Castellina is a villa in the heart of the Tuscan hills, located 3 km from the center of Castellina in Chian ...
From $1792 per night (USD)Expedia
- From $141 per night (USD)
VRBO
Farmhouse in the heart of the real chiantishire
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Farmhouse in the heart of Chiantishire at 3 kms minutes distance from the historical township of Castellina in Chianti. ...
From $141 per night (USD)VRBO
- From $405 per night (USD)
Expedia
Casa Fioraie - Holiday Home in Castellina in Chianti, Tuscany
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Holiday home in a strategic position in Castellina in Chianti. Casa Fioraie is the ideal place to spend a relaxing and f ...
From $405 per night (USD)Expedia
- From $501 per night (USD)
VRBO
La Misura, cottage with garden and swimming pool on the hills of Chianti
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
La Misura house is part of Borgo Montecastelli, a beautiful rural complex located right on the border between the provi ...
From $501 per night (USD)VRBO
- From $123 per night (USD)
Expedia
detached villa with private pool and garden
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
<p>Located in a rural area, this welcoming vacation home lets you experience it all in Castellina in Chianti. There's co ...
From $123 per night (USD)Expedia
- Click For Pricing
VRBO
Villa with pool in Chianti countryside
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
<p>A short distance from ecotours, cycling, and more, this smoke-free villa lets you experience it all. With convenient ...
Click For PricingVRBO
- From $367 per night (USD)
Expedia
Beautiful house on Chianti hilltop with exceptional views.
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Spacious (260 sq metres), very well equipped house on two floors forming part of renovated historic farm hamlet. The est ...
From $367 per night (USD)Expedia
- From $375 per night (USD)
VRBO
Beautiful villa for 12 guests with WIFI, private pool, TV, terrace, pets allowed and parking
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
Podere Gioia is a beautiful country house consisting of two independent housing units. The offer includes three apartmen ...
From $375 per night (USD)VRBO
- Click For Pricing
Expedia
Two-room apartment with garden
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
<p>Nestled in Castellina in Chianti, this 2-bedroom, 1-bathroom vacation home brings it all within your reach. Fans of n ...
Click For PricingExpedia
- From $1327 per night (USD)
VRBO
Tregole, Castellina in Chianti, Siena and Chianti
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 14
The vine-clad hills of Chianti are the classic image of Tuscany and the beautiful backdrop for Villa Tregole. Here in th ...
From $1327 per night (USD)VRBO
- From $263 per night (USD)
Expedia
Private Villa with A\/C, private pool, WIFI, TV, patio, pets allowed, panoramic view, parking
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The newly renovated Country house "Olivo" is a charming and detached vacation rental located just 500m from the center o ...
From $263 per night (USD)Expedia
- From $283 per night (USD)
VRBO
CASA DEGLI ULIVI - COTTAGE WITH SWIMMING POOL
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The Casa degli Ulivi is one of the 4 houses of Borgo Montecastelli, and is located right on the border between the provi ...
From $283 per night (USD)VRBO
- From $95 per night (USD)
VRBO
SUSINO - Apartment in a typical Chianti village in the heart of Tuscany
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 3
Apartment obtained from the conversion of a barn that is part of a typical Chianti village in the heart of Tuscany. The ...
From $95 per night (USD)VRBO
- From $263 per night (USD)
VRBO
Olivo by Interhome
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
<p>Close to hiking trails, winery tours, and more, this pet-friendly vacation home brings it all within reach. There's c ...
From $263 per night (USD)VRBO
- From $381 per night (USD)
Expedia
Lovely apartment for 4 people with WIFI, A\/C and TV, close to Siena
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Vacation rental Il Nespolo Charming Apartment Fonterutoli - Siena, is a beautiful stone building (110 sq m) that includ ...
From $381 per night (USD)Expedia
- From $389 per night (USD)
VRBO
Casa Chianti Classico, Panoramic View, Castellina in Chianti, Italy
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
A unique opportunity for an authentic Tuscan experience, in this charming house in the heart of Castellina in Chianti. T ...
From $389 per night (USD)VRBO
- From $1201 per night (USD)
VRBO
FABULOUS 6BD - 6BA VILLA WITH STUNNING POOL & VIEWS IN TOP CHIANTI LOCATION!
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 13
Set in the heart of the magical Chianti Classico region, this wonderful 6 BD – 6 BA Villa dates back to the 15th century ...
From $1201 per night (USD)VRBO