
Gaiole in Chianti Rentals

- From $775 per night (USD)
VRBO
Canonica di Vertine, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Canonica di Vertine is a unique holiday home located in the picturesque medieval hamlet of Vertine. This historic buildi ...
From $775 per night (USD)VRBO
- From $235 per night (USD)
Expedia
Basilico, Castellare in Chianti, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Castellare in Chianti's cottages and apartments are nestled in the woods in the uplands of Gaiole in Chianti 8 Km from t ...
From $235 per night (USD)Expedia
- From $191 per night (USD)
VRBO
Villa Rosabella, San Regolo in Brolio, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
San Regolo in Brolio is a lovely modern hamlet of villas, located on the edge of the village of San Regolo. It’s within ...
From $191 per night (USD)VRBO
- From $159 per night (USD)
Expedia
Vinaio, Montefiorile, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
A Chianti Classico hillside resort, Montefiorile's cottages are nestled on a south bank with magnificent views across ro ...
From $159 per night (USD)Expedia
- From $187 per night (USD)
VRBO
Capanna di Camporata, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Capanna di Camporata is a charming Chianti holiday home, ideal for a relaxing getaway for two. This single-storey stone ...
From $187 per night (USD)VRBO
- From $287 per night (USD)
Expedia
Nicchio, Agriturismo Vinci, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Surrounded by the rolling Chianti hills covered with vineyards and olive groves, this property is wonderfully positioned ...
From $287 per night (USD)Expedia
- From $180 per night (USD)
VRBO
Bell´Aria, Montebuoni, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Once a wine and olive oil producing estate, Montebuoni's original stone buildings have been restored into cottages and a ...
From $180 per night (USD)VRBO
- From $153 per night (USD)
Expedia
Pesci, Montefiorile, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
A Chianti Classico hillside resort, Montefiorile's cottages are nestled on a south bank with magnificent views across ro ...
From $153 per night (USD)Expedia
- From $836 per night (USD)
VRBO
Tenuta Lo Spugno, Radda in Chianti, Siena and Chianti
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
A delicate balance of rustic farmhouse style and modern comfort, Tenuta Lo Spugno is an extraordinary, and thoroughly pr ...
From $836 per night (USD)VRBO
- From $170 per night (USD)
Expedia
Il Sole, Montefiorile, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
A Chianti Classico hillside resort, Montefiorile's cottages are nestled on a south bank with magnificent views across ro ...
From $170 per night (USD)Expedia
- From $530 per night (USD)
VRBO
Vecchio Frantoio, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Vecchio Frantoio is a beautifully restored holiday home in Chianti with a terraced garden and a large pool. Once a histo ...
From $530 per night (USD)VRBO
- From $635 per night (USD)
Expedia
Valliole, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This sprawling 17th-century villa occupies a dreamy position in the heart of rolling Chianti country with views across o ...
From $635 per night (USD)Expedia
- From $250 per night (USD)
VRBO
Trifoglio, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Trifoglio is a beautifully restored stone cottage set in an authentic 18th-century hamlet in the heart of Chianti Classi ...
From $250 per night (USD)VRBO
- From $171 per night (USD)
Expedia
Santa Lucia, Montebuoni, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Once a wine and olive oil producing estate, Montebuoni's original stone buildings have been restored into cottages and a ...
From $171 per night (USD)Expedia
- From $448 per night (USD)
VRBO
Il Trebbio, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Il Trebbio is a charming holiday home in Chianti, peacefully located on a hill with panoramic views over vineyards and t ...
From $448 per night (USD)VRBO
- From $136 per night (USD)
Expedia
Il Balcone, Borgo Gaiole, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Borgo Gaiole is a large hamlet with 40 villas, all overlooking the Chianti town of Gaiole. It's a short walk into the pr ...
From $136 per night (USD)Expedia
- From $205 per night (USD)
VRBO
Sesamo, Castellare in Chianti, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Castellare in Chianti's cottages and apartments are nestled in the woods in the uplands of Gaiole in Chianti 8 Km from t ...
From $205 per night (USD)VRBO
- From $241 per night (USD)
Expedia
La Torre Vecchia, Vignale, Castelnuovo Berardenga, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Set on a Chianti hillside, Vignale is a beautifully restored collection of original farm buildings, thoughtfully transfo ...
From $241 per night (USD)Expedia
- From $180 per night (USD)
VRBO
La Chiocciola, Montefienali, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
In the upland of the Chianti vineyards and forests on an ancient Roman road, the 13th century Montefienali resort sits o ...
From $180 per night (USD)VRBO
- From $291 per night (USD)
Expedia
Casa Isabella, San Sano, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
An authentic Chianti village, San Sano allows you to immerse yourself in the charm and character of Tuscan life. Origina ...
From $291 per night (USD)Expedia
- From $241 per night (USD)
VRBO
Salvia, Castellare in Chianti, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Castellare in Chianti's cottages and apartments are nestled in the woods in the uplands of Gaiole in Chianti 8 Km from t ...
From $241 per night (USD)VRBO
- From $530 per night (USD)
Expedia
Torretta Barbischio, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Torretta Barbischio is a characterful Chianti holiday home, ideal for a relaxing stay with family or friends. The buildi ...
From $530 per night (USD)Expedia
- From $269 per night (USD)
VRBO
Private villa in heart of the Chianti, pool and wifi
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Aia di Ama is a traditional Chianti country house offering the perfect setting for a relaxing holiday with friends or fa ...
From $269 per night (USD)VRBO
- From $183 per night (USD)
Expedia
Vin Santo, Vignale, Castelnuovo Berardenga, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Set on a Chianti hillside, Vignale is a beautifully restored collection of original farm buildings, thoughtfully transfo ...
From $183 per night (USD)Expedia
- From $167 per night (USD)
VRBO
Origano, Castellare in Chianti, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Castellare in Chianti's cottages and apartments are nestled in the woods in the uplands of Gaiole in Chianti 8 Km from t ...
From $167 per night (USD)VRBO
- From $227 per night (USD)
Expedia
La Torre, Pretaccione, Castelnuovo Berardenga, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Once the home of travelling priests 1000 years ago, Pretaccione has been sympathetically restored into individually owne ...
From $227 per night (USD)Expedia
- From $115 per night (USD)
VRBO
Bella Vista, Montebuoni, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Once a wine and olive oil producing estate, Montebuoni's original stone buildings have been restored into cottages and a ...
From $115 per night (USD)VRBO
- From $206 per night (USD)
Expedia
Pinturicchio, Pretaccione, Castelnuovo Berardenga, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Once the home of travelling priests 1000 years ago, Pretaccione has been sympathetically restored into individually owne ...
From $206 per night (USD)Expedia
- From $297 per night (USD)
VRBO
L'Agrifoglio, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
L’Agrifoglio is a charming holiday home in the heart of the Chianti Classico region, set within a peaceful historic haml ...
From $297 per night (USD)VRBO
- From $264 per night (USD)
Expedia
La Rana, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Perfect for small groups of friends or a family of four who favour both privacy and proximity to local village life, thi ...
From $264 per night (USD)Expedia
- From $173 per night (USD)
VRBO
Due Leoni, Montebuoni, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Once a wine and olive oil producing estate, Montebuoni's original stone buildings have been restored into cottages and a ...
From $173 per night (USD)VRBO
- From $135 per night (USD)
Expedia
Villa Violetto, San Regolo in Brolio, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
San Regolo in Brolio is a lovely modern hamlet of villas, located on the edge of the village of San Regolo. It’s within ...
From $135 per night (USD)Expedia
- From $530 per night (USD)
VRBO
Le Volte, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 5
- Bathrooms:
- 3
- Sleeps:
- 6
Le Volte is a welcoming Chianti holiday home, ideal for a relaxing stay with family or friends. Set in a small hamlet, i ...
From $530 per night (USD)VRBO
- From $220 per night (USD)
Expedia
La Vigna, Montebuoni, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Once a wine and olive oil producing estate, Montebuoni's original stone buildings have been restored into cottages and a ...
From $220 per night (USD)Expedia
- From $151 per night (USD)
VRBO
La Contessina, Montebuoni, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Once a wine and olive oil producing estate, Montebuoni's original stone buildings have been restored into cottages and a ...
From $151 per night (USD)VRBO
- From $194 per night (USD)
Expedia
Mietitore, Montefiorile, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
A Chianti Classico hillside resort, Montefiorile's cottages are nestled on a south bank with magnificent views across ro ...
From $194 per night (USD)Expedia
- From $146 per night (USD)
VRBO
Il Portico, Montefienali, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
In the upland of the Chianti vineyards and forests on an ancient Roman road, the 13th century Montefienali resort sits o ...
From $146 per night (USD)VRBO
- From $241 per night (USD)
Expedia
Vaniglia, Castellare in Chianti, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Castellare in Chianti's cottages and apartments are nestled in the woods in the uplands of Gaiole in Chianti 8 Km from t ...
From $241 per night (USD)Expedia
- From $243 per night (USD)
VRBO
L'Oliveta, Montebuoni, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Once a wine and olive oil producing estate, Montebuoni's original stone buildings have been restored into cottages and a ...
From $243 per night (USD)VRBO
- From $191 per night (USD)
Expedia
Villa Giacinto, San Regolo in Brolio, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
San Regolo in Brolio is a lovely modern hamlet of villas, located on the edge of the village of San Regolo. It’s within ...
From $191 per night (USD)Expedia
- From $424 per night (USD)
VRBO
La Capannina, Pretaccione, Castelnuovo Berardenga, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Once the home of travelling priests 1000 years ago, Pretaccione has been sympathetically restored into individually owne ...
From $424 per night (USD)VRBO
- From $907 per night (USD)
Expedia
Il Molinaccio, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Il Molinaccio is a unique holiday home in the heart of Chianti, with a rich history that stretches back to the Middle Ag ...
From $907 per night (USD)Expedia
- From $846 per night (USD)
VRBO
Villa San Michele, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
Villa San Michele enjoys a wonderfully private location on a Chianti hilltop and was once the residence of wealthy lando ...
From $846 per night (USD)VRBO
- From $134 per night (USD)
Expedia
Taglialegna, Montefiorile, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
A Chianti Classico hillside resort, Montefiorile's cottages are nestled on a south bank with magnificent views across ro ...
From $134 per night (USD)Expedia
- From $300 per night (USD)
VRBO
Sangiovese, Vignale, Castelnuovo Berardenga, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Set on a Chianti hillside, Vignale is a beautifully restored collection of original farm buildings, thoughtfully transfo ...
From $300 per night (USD)VRBO
- From $135 per night (USD)
Expedia
Villa Fiorella, San Regolo in Brolio, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
San Regolo in Brolio is a lovely modern hamlet of villas, located on the edge of the village of San Regolo. It’s within ...
From $135 per night (USD)Expedia
- From $360 per night (USD)
VRBO
Villa Riecine, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
An exquisite combination of modern and rustic styles, set on a wine-producing country estate, Riecine is a thoroughly co ...
From $360 per night (USD)VRBO
- From $242 per night (USD)
Expedia
Casa Dante, San Donato in Perano, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Perched on vines San Donato in Perano dates back to a medieval castle. The resort is restored into six individually owne ...
From $242 per night (USD)Expedia
- From $274 per night (USD)
VRBO
Sassolaia, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Close to two of the Chianti’s most renowned and beautiful towns, and with views across the olive groves and vineyards, a ...
From $274 per night (USD)VRBO
- From $797 per night (USD)
Expedia
Sestuccia, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Sestuccia is a beautifully renovated stone house set in the rolling hills of the Chianti Classico region. This modern vi ...
From $797 per night (USD)Expedia
- From $105 per night (USD)
VRBO
Casa Barbara, Montebuoni, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Once a wine and olive oil producing estate, Montebuoni's original stone buildings have been restored into cottages and a ...
From $105 per night (USD)VRBO
- From $178 per night (USD)
Expedia
La Casanova, Radda in Chianti, Siena and Chianti
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
This charming single-storey stone cottage clings to a south-facing hillside, offering fabulous views of the surrounding ...
From $178 per night (USD)Expedia
- From $142 per night (USD)
VRBO
Casetta con Vista, Montebuoni, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Once a wine and olive oil producing estate, Montebuoni's original stone buildings have been restored into cottages and a ...
From $142 per night (USD)VRBO
- From $257 per night (USD)
Expedia
Sangiovese all'Aia, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Sangiovese all’Aia is a charming holiday home in Chianti, located on the grounds of Agriturismo Trappoline, where wine a ...
From $257 per night (USD)Expedia
- From $312 per night (USD)
VRBO
Il Boschetto, Radda in Chianti, Siena and Chianti
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Il Boschetto is a charming Chianti holiday home with beautiful views over olive groves, vineyards and the rolling Tuscan ...
From $312 per night (USD)VRBO
- From $200 per night (USD)
Expedia
Casa Maria, Villa a Sesta, Castelnuovo Berardenga, Siena and Chianti
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Villa a Sesta is a collection of six Chianti country cottages of traditional Tuscan stone with terracotta tiles and expo ...
From $200 per night (USD)Expedia
- From $181 per night (USD)
VRBO
Ciacchieri, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Ciacchieri is a charming Chianti holiday accommodation with a private pool, ideal for couples or small families. The apa ...
From $181 per night (USD)VRBO
- From $183 per night (USD)
Expedia
Raffaello, Montefienali, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
In the upland of the Chianti vineyards and forests on an ancient Roman road, the 13th century Montefienali resort sits o ...
From $183 per night (USD)Expedia
- From $425 per night (USD)
VRBO
Le Cerreta, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Le Cerreta is a traditional Tuscan stone villa in a secluded setting, offering breathtaking panoramic views, an elegant ...
From $425 per night (USD)VRBO
- From $159 per night (USD)
Expedia
Scorpione, Montefiorile, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
A Chianti Classico hillside resort, Montefiorile's cottages are nestled on a south bank with magnificent views across ro ...
From $159 per night (USD)Expedia
- From $241 per night (USD)
VRBO
Maggiorana, Castellare in Chianti, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Castellare in Chianti's cottages and apartments are nestled in the woods in the uplands of Gaiole in Chianti 8 Km from t ...
From $241 per night (USD)VRBO
- From $207 per night (USD)
Expedia
Casa Minuccia, Villa a Sesta, Castelnuovo Berardenga, Siena and Chianti
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Villa a Sesta is a collection of six Chianti country cottages of traditional Tuscan stone with terracotta tiles and expo ...
From $207 per night (USD)Expedia
- From $191 per night (USD)
VRBO
Villa Girasole , San Regolo in Brolio, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
San Regolo in Brolio is a lovely modern hamlet of villas, located on the edge of the village of San Regolo. It’s within ...
From $191 per night (USD)VRBO
- From $411 per night (USD)
Expedia
Casa Virginia, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Casa Virginia is a welcoming Chianti holiday home, ideal for a relaxing break with family or a small group of friends. S ...
From $411 per night (USD)Expedia
- From $178 per night (USD)
VRBO
La Taverna, Montebuoni, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Once a wine and olive oil producing estate, Montebuoni's original stone buildings have been restored into cottages and a ...
From $178 per night (USD)VRBO
- From $193 per night (USD)
Expedia
Malvasia, Vignale, Castelnuovo Berardenga, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Set on a Chianti hillside, Vignale is a beautifully restored collection of original farm buildings, thoughtfully transfo ...
From $193 per night (USD)Expedia
- From $187 per night (USD)
VRBO
Timo, Castellare in Chianti, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Castellare in Chianti's cottages and apartments are nestled in the woods in the uplands of Gaiole in Chianti 8 Km from t ...
From $187 per night (USD)VRBO
- From $391 per night (USD)
Expedia
Casa Zaccardi, Pretaccione, Castelnuovo Berardenga, Siena and Chianti
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Once the home of travelling priests 1000 years ago, Pretaccione has been sympathetically restored into individually owne ...
From $391 per night (USD)Expedia
- From $308 per night (USD)
VRBO
Angolino, Radda in Chianti, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Tucked away at the end of a quiet road, yet barely a mile from Radda, one of Chianti’s main market towns, Angolino is a ...
From $308 per night (USD)VRBO
- From $158 per night (USD)
Expedia
Bacco, Montefiorile, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
A Chianti Classico hillside resort, Montefiorile's cottages are nestled on a south bank with magnificent views across ro ...
From $158 per night (USD)Expedia
- From $228 per night (USD)
VRBO
Pergola, Montebuoni, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Once a wine and olive oil producing estate, Montebuoni's original stone buildings have been restored into cottages and a ...
From $228 per night (USD)VRBO
- From $364 per night (USD)
Expedia
Poggio della Villa, Radda in Chianti, Siena and Chianti
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Poggio della Villa is a beautiful Chianti holiday home just two kilometres from the centre of Radda, offering everything ...
From $364 per night (USD)Expedia
- From $248 per night (USD)
VRBO
Mastro 3, San Sano, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
An authentic Chianti village, San Sano allows you to immerse yourself in the charm and character of Tuscan life. Origina ...
From $248 per night (USD)VRBO
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Expedia
BOSSI CASTLE App. Geranium
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Castle of Bossi is located in the southern part of the Chianti Classico in the municipality of Castelnuovo Berardeng ...
Click For PricingExpedia
- Click For Pricing
VRBO
CASTLE OF BOSSI Ginestra Apartment
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Castello di Bossi is located in the southern part of the Chianti Classico in the municipality of Castelnuovo Berarde ...
Click For PricingVRBO
- From $222 per night (USD)
VRBO
Apartment \"Pieve\" - Chianti as you've always dreamed of it
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The 70 m² apartment with private garden, for pleasant outdoor breakfasts or relaxing al fresco dinners on summer evening ...
From $222 per night (USD)VRBO
- From $151 per night (USD)
VRBO
BELLAVISTA (Castle of Bossi) Colombaia
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Bellavista is a beautiful tuscan house, divided into 8 apartments, located in the domaine of Castello di Bossi, in the ...
From $151 per night (USD)VRBO
- From $279 per night (USD)
Expedia
BELLAVISTA (Castle of Bossi) San Polo
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Bellavista is a beautiful tuscan house, divided into 8 apartments, located in the domaine of Castello di Bossi, in the s ...
From $279 per night (USD)Expedia
- From $234 per night (USD)
VRBO
BELLAVISTA (Castle of Bossi) San Giusto
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Bellavista is a beautiful tuscan house, divided into 8 apartments, located in the domaine of Castello di Bossi, in the s ...
From $234 per night (USD)VRBO
- From $234 per night (USD)
Expedia
BELLAVISTA (Castello di Bossi) SAN PAOLO apartment
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Bellavista is a beautiful tuscan house, divided into 8 apartments, located in the domaine of Castello di Bossi, in the s ...
From $234 per night (USD)Expedia
- From $126 per night (USD)
VRBO
Antico Borgo di Montefienali - Apartment il Portico
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Borgo di Montefienali is a medieval hamlet , dating back to the 13th Century , was once a resting place along the ancien ...
From $126 per night (USD)VRBO
- Click For Pricing
Expedia
Antico Borgo Montefienali - Apartment La Chiocciola
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Borgo di Montefienali is a medieval hamlet , dating back to the 13th Century , was once a resting place along the ancien ...
Click For PricingExpedia
- From $222 per night (USD)
VRBO
Podere Lucignano Secondo - La Mangiatoia
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
In the very heart of the charming Tuscan countryside, among the smooth hills of Sienese Chianti and the fragrance of its ...
From $222 per night (USD)VRBO
- From $1657 per night (USD)
Expedia
Gated Private Estate🏡 San Felice Adjacent 🌈Classic Views, 🍇Vineyards
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Private residence of an American owner, made available to guests certain periods from May through October. A gated and p ...
From $1657 per night (USD)Expedia
- From $150 per night (USD)
VRBO
La Farfalla n°5 by Interhome
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Carefully renovated "Podere La Massa" consists of a detached house and 8 apartments. It is surrounded by olive groves, f ...
From $150 per night (USD)VRBO
- From $1109 per night (USD)
Expedia
VILLA GAIA - Five Bedroom Villa, Sleeps 10
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
A typical Chianti Villa in Tuscany, once a a 15th century mill, located in the countryside, just 15 minutes from Siena, ...
From $1109 per night (USD)Expedia
- From $1237 per night (USD)
VRBO
Villa Agresto, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
Agresto sits on its own private hilltop, decorated with vineyards manicured by the Ricasoli estate. With 360-degree surr ...
From $1237 per night (USD)VRBO
- From $528 per night (USD)
Expedia
Podere Lucignano Secondo - La Villa
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
In the very heart of the charming Tuscan countryside, among the smooth hills of Sienese Chianti and the fragrance of its ...
From $528 per night (USD)Expedia
- From $222 per night (USD)
VRBO
Podere Lucignano Secondo - Le Logge
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
In the very heart of the charming Tuscan countryside, among the smooth hills of Sienese Chianti and the fragrance of its ...
From $222 per night (USD)VRBO
- From $577 per night (USD)
Expedia
Mulinaccio di Badia, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 8
Could there be a more apt setting for a Chianti wine region villa than on the sloping vines of a famous wine estate? Mul ...
From $577 per night (USD)Expedia
- From $110 per night (USD)
VRBO
Tribolina by Interhome
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Manor house "Tribolina", 550 m a.s.l.. 2 houses in the residence. 3 km from the centre of Cavriglia, 12 km from the cent ...
From $110 per night (USD)VRBO
- From $146 per night (USD)
Expedia
La Colomba n°4 by Interhome
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Carefully renovated "Podere La Massa" consists of a detached house and 8 apartments. It is surrounded by olive groves, f ...
From $146 per night (USD)Expedia
- From $303 per night (USD)
VRBO
Lo Scoiattolo n° 10 by Interhome
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Carefully renovated "Podere La Massa" consists of a detached house and 8 apartments. It is surrounded by olive groves, f ...
From $303 per night (USD)VRBO
- From $150 per night (USD)
Expedia
Il Ghiro n°8 by Interhome
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Carefully renovated "Podere La Massa" consists of a detached house and 8 apartments. It is surrounded by olive groves, f ...
From $150 per night (USD)Expedia
- From $113 per night (USD)
VRBO
Special offer Newly renovated fine detached villa with fireplace.
- Bedrooms:
- 0
- Bathrooms:
- 2
- Sleeps:
- 4
Independent house in an ancient village of the '900, located 10 km from the center of Siena (15 minutes by car). Just r ...
From $113 per night (USD)VRBO
- From $482 per night (USD)
Expedia
Il Gufo n°1 by Interhome
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 16
Carefully renovated "Podere La Massa" consists of a detached house and 8 apartments. It is surrounded by olive groves, f ...
From $482 per night (USD)Expedia
- From $87 per night (USD)
VRBO
Cerbiatto n°5A by Interhome
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Carefully renovated "Podere La Massa" consists of a detached house and 8 apartments. It is surrounded by olive groves, f ...
From $87 per night (USD)VRBO
- From $115 per night (USD)
Expedia
Pulcino n°3 by Interhome
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Carefully renovated "Podere La Massa" consists of a detached house and 8 apartments. It is surrounded by olive groves, f ...
From $115 per night (USD)Expedia
- From $147 per night (USD)
VRBO
Il Pettirosso n°7 by Interhome
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Carefully renovated "Podere La Massa" consists of a detached house and 8 apartments. It is surrounded by olive groves, f ...
From $147 per night (USD)VRBO
- From $356 per night (USD)
Expedia
Private Villa with A/C, private pool, WIFI, TV, patio, pets allowed, panoramic view, parking
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Property Summary Villa del Poggio is a rustic single-family house located in the peaceful countryside just 2 km from the ...
From $356 per night (USD)Expedia