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From $310 per night (USD)
VRBO
Villa Sofia Jacuzzi® Spa
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Villa is on two floors with independent entrance, exclusive Wellness Center with Jacuzzi® for 3 people, sauna and ch ...
From $310 per night (USD)
VRBO
From $2 per night (USD)
Expedia
villa rental chianti - Vacation villa chianti
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
In the heart of the Chianti Classico region, this large hillside working estate offers a tranquil, classic Tuscan experi ...
From $2 per night (USD)
Expedia
From $177 per night (USD)
VRBO
Mantegna, Galenda, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
A Chianti Classico hamlet resort, Galenda's cottages lay on a ridge with magnificent views across rolling hills draped w ...
From $177 per night (USD)
VRBO
From $111 per night (USD)
Expedia
Casa Allegra, 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 $111 per night (USD)
Expedia
From $224 per night (USD)
VRBO
Lavanda, Castellare in Chianti, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
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 $224 per night (USD)
VRBO
From $284 per night (USD)
Expedia
Casa Primula, Gaiole in Chianti, Siena and Chianti
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Here’s a novel proposition, a villa that can be divided into two apartments, with a third set of lodgings just down the ...
From $284 per night (USD)
Expedia
From $126 per night (USD)
VRBO
Villa Mimosa , 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 $126 per night (USD)
VRBO
From $212 per night (USD)
Expedia
Rosmarino, 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 $212 per night (USD)
Expedia
From $332 per night (USD)
VRBO
Sestuccina, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This romantic contemporary hideaway garners top marks from those who’ve discovered it – including, not surprisingly, a h ...
From $332 per night (USD)
VRBO
From $172 per night (USD)
Expedia
Private Chianti villa with private pool, wifi
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This enchanting hideaway for two is a hop and a skip from Radda and Gaiole, two of Chianti’s most popular small towns. T ...
From $172 per night (USD)
Expedia
From $187 per night (USD)
VRBO
Peperoncino, 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 $121 per night (USD)
Expedia
Casa del Vignaiolo, 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 $121 per night (USD)
Expedia
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VRBO
Terrazza Alta, Borgo Gaiole, Gaiole in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
Borgo Gaiole is a large hamlet with 40 villas, all overlooking the Chianti town of Gaiole. It's a short walk into the pr ...
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VRBO
From $388 per night (USD)
Expedia
La Casa di Radda, Radda in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
A sleek and charming bungalow in the town of Radda in Chianti, La Casa di Radda is a lovely getaway for 5 people. It’s a ...
From $388 per night (USD)
Expedia
From $547 per night (USD)
VRBO
Podere Terrena, Gaiole in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Guests of this attractive stone villa in the heart of Chianti, which is made even more beautiful by climbing roses and p ...
From $547 per night (USD)
VRBO
From $978 per night (USD)
Expedia
Borratella, Gaiole in Chianti, Siena and Chianti
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
A luxurious old stone villa set among acres of vines in the heart of Chianti, Borratella is a fabulous holiday home for ...
From $978 per night (USD)
Expedia
From $283 per night (USD)
VRBO
La Fontanella, Gaiole in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Set on a slight rise, with extensive views of undulating vineyards, Fontanella has a relaxed feel inside and out. At the ...
From $283 per night (USD)
VRBO
From $176 per night (USD)
Expedia
I Cipressi, Vignale, Castelnuovo Berardenga, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Ledged on a Chianti hillside, Vignale's original farm stone buildings have been respectfully restored into a small colle ...
From $176 per night (USD)
Expedia
From $317 per night (USD)
VRBO
Villa Solata, Bucine, Arezzo and Cortona
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Villa Solata is a handsome manor house, with ochre-painted walls, green shutters and knock-out views of the surrounding ...
From $317 per night (USD)
VRBO
From $301 per night (USD)
Expedia
Casetta Kiwi, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
The secluded lavender-edged pool of Casetta Kiwi is sun-drenched all day long. At 18 meters in length, this is a serious ...
From $301 per night (USD)
Expedia
From $576 per night (USD)
VRBO
Canonica di Vertine, Gaiole in Chianti, Siena and Chianti
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
One for history lovers. Canonica di Vertine is an extraordinary property with a deep history, as one would expect from i ...
From $576 per night (USD)
VRBO
From $206 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 $206 per night (USD)
Expedia
From $181 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 $181 per night (USD)
VRBO
From $158 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 $158 per night (USD)
Expedia
From $208 per night (USD)
VRBO
Casa Rosa, Gaiole in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
This cute little house is set in a historic hamlet created from the medieval castle of Vertine and makes a great base fo ...
From $208 per night (USD)
VRBO
From $168 per night (USD)
Expedia
Capanna di Camporata, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This typical Chianti cottage is ideal for a couple who are looking for a romantic and peaceful hideaway, yet it is also ...
From $168 per night (USD)
Expedia
From $255 per night (USD)
VRBO
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 $255 per night (USD)
VRBO
From $162 per night (USD)
Expedia
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 $162 per night (USD)
Expedia
From $116 per night (USD)
VRBO
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 $116 per night (USD)
VRBO
From $752 per night (USD)
Expedia
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 $752 per night (USD)
Expedia
From $146 per night (USD)
VRBO
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 $146 per night (USD)
VRBO
From $621 per night (USD)
Expedia
Vecchio Frantoio, Gaiole in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Vecchio Frantoio is a beautifully restored two-storey stone-built villa in the hamlet of Casanuova di Ama, surrounded by ...
From $621 per night (USD)
Expedia
From $584 per night (USD)
VRBO
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 $584 per night (USD)
VRBO
From $253 per night (USD)
Expedia
Trifoglio, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Wish list: a restored stone barn, deep in the heart of Chianti, surrounded by castles and quaint villages. If this chime ...
From $253 per night (USD)
Expedia
From $169 per night (USD)
VRBO
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 $169 per night (USD)
VRBO
From $576 per night (USD)
Expedia
Il Trebbio, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
If your Chianti villa wish-list includes a hill, a view, a private pool and a property oozing with atmosphere, you'll lo ...
From $576 per night (USD)
Expedia
From $122 per night (USD)
VRBO
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 $122 per night (USD)
VRBO
From $179 per night (USD)
Expedia
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 $179 per night (USD)
Expedia
From $233 per night (USD)
VRBO
La Torre Vecchia, Vignale, Castelnuovo Berardenga, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Ledged on a Chianti hillside, Vignale's original farm stone buildings have been respectfully restored into a small colle ...
From $233 per night (USD)
VRBO
From $156 per night (USD)
Expedia
La Chiocciola, Montefienali, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Deep in the upland forests of the Chianti on an ancient Roman road, the 13th century Montefienali resort sits on a ridge ...
From $156 per night (USD)
Expedia
From $117 per night (USD)
VRBO
Casa Girasole, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Couples will be able to immerse themselves in history at Casa Girasole. This former wine cellar is set in a charming med ...
From $117 per night (USD)
VRBO
From $194 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 $194 per night (USD)
Expedia
From $212 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 $212 per night (USD)
VRBO
From $580 per night (USD)
Expedia
Torretta Barbischio, Gaiole in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Set in a tiny hamlet with an excellent local restaurant a short distance from Gaiole, one of Chianti’s most popular hill ...
From $580 per night (USD)
Expedia
From $242 per night (USD)
VRBO
Private villa in heart of the Chianti, pool and wifi
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Set in the heart of Chianti Classico, Aia di Ama provides a tranquil rural retreat amid vineyards and olive groves that ...
From $242 per night (USD)
VRBO
From $159 per night (USD)
Expedia
Vin Santo, Vignale, Castelnuovo Berardenga, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Ledged on a Chianti hillside, Vignale's original farm stone buildings have been respectfully restored into a small colle ...
From $159 per night (USD)
Expedia
From $145 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 $145 per night (USD)
VRBO
From $207 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 $207 per night (USD)
Expedia
From $175 per night (USD)
VRBO
Lippi, Galenda, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
A Chianti Classico hamlet resort, Galenda's cottages lay on a ridge with magnificent views across rolling hills draped w ...
From $175 per night (USD)
VRBO
From $118 per night (USD)
Expedia
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 $118 per night (USD)
Expedia
From $211 per night (USD)
VRBO
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 $211 per night (USD)
VRBO
From $330 per night (USD)
Expedia
L'Agrifoglio, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Something of a Tardis, this renovated cottage in Bricciano, a hamlet of 18th-century farmhouses in the heart of the Chia ...
From $330 per night (USD)
Expedia
From $242 per night (USD)
VRBO
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 $242 per night (USD)
VRBO
From $152 per night (USD)
Expedia
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 $152 per night (USD)
Expedia
From $141 per night (USD)
VRBO
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 $141 per night (USD)
VRBO
From $580 per night (USD)
Expedia
Le Volte, Gaiole in Chianti, Siena and Chianti
Bedrooms:
5
Bathrooms:
3
Sleeps:
6
What a delicious villa! It’s no surprise that Le Volte, set in a hamlet in the heart of Chianti’s hills, gets a very hig ...
From $580 per night (USD)
Expedia
From $174 per night (USD)
VRBO
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 $174 per night (USD)
VRBO
From $134 per night (USD)
Expedia
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 $134 per night (USD)
Expedia
From $158 per night (USD)
VRBO
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 $158 per night (USD)
VRBO
From $127 per night (USD)
Expedia
Il Portico, Montefienali, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Deep in the upland forests of the Chianti on an ancient Roman road, the 13th century Montefienali resort sits on a ridge ...
From $127 per night (USD)
Expedia
From $212 per night (USD)
VRBO
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 $212 per night (USD)
VRBO
From $174 per night (USD)
Expedia
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 $174 per night (USD)
Expedia
From $545 per night (USD)
VRBO
Camporatina, Gaiole in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
5
Sleeps:
6
The ideal holiday home for mixed groups or families, Camporatina is an attractive property – both inside and out – and i ...
From $545 per night (USD)
VRBO
From $180 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 $180 per night (USD)
Expedia
From $397 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 $397 per night (USD)
VRBO
From $847 per night (USD)
Expedia
Il Molinaccio, Gaiole in Chianti, Siena and Chianti
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
With origins dating back to the 10th Century, Il Molinaccio was initially built as a defence watchtower and has since be ...
From $847 per night (USD)
Expedia
From $683 per night (USD)
VRBO
Villa San Michele, Gaiole in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
It’s no surprise to discover that the wealthy landowners who once ruled over much of this area chose this villa as their ...
From $683 per night (USD)
VRBO
From $158 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 $158 per night (USD)
Expedia
From $273 per night (USD)
VRBO
Sangiovese, Vignale, Castelnuovo Berardenga, Siena and Chianti
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Ledged on a Chianti hillside, Vignale's original farm stone buildings have been respectfully restored into a small colle ...
From $273 per night (USD)
VRBO
From $369 per night (USD)
Expedia
Bellini, Galenda, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
A Chianti Classico hamlet resort, Galenda's cottages lay on a ridge with magnificent views across rolling hills draped w ...
From $369 per night (USD)
Expedia
From $126 per night (USD)
VRBO
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 $126 per night (USD)
VRBO
From $324 per night (USD)
Expedia
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 $324 per night (USD)
Expedia
From $146 per night (USD)
VRBO
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 $146 per night (USD)
VRBO
From $257 per night (USD)
Expedia
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 $257 per night (USD)
Expedia
From $776 per night (USD)
VRBO
Sestuccia, Gaiole in Chianti, Siena and Chianti
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Visit in the heat of the summer and you will be living outdoors at Sestuccia – and doing so in great style. The main vil ...
From $776 per night (USD)
VRBO
From $82 per night (USD)
Expedia
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 $82 per night (USD)
Expedia
From $169 per night (USD)
VRBO
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 $169 per night (USD)
VRBO
From $99 per night (USD)
Expedia
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 $99 per night (USD)
Expedia
From $285 per night (USD)
VRBO
Sangiovese all'Aia, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Sangiovese all'Aia is a delightful villa and a fine choice if you are a family of four or a couple seeking just a little ...
From $285 per night (USD)
VRBO
From $325 per night (USD)
Expedia
Il Boschetto, Radda in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Set across the first floor of a large stone farmhouse, this villa in rural Chianti offers comfortable lodgings for six p ...
From $325 per night (USD)
Expedia
From $266 per night (USD)
VRBO
Il Paretaio, Montevarchi, Arezzo and Cortona
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Head for the hills on the edge of the Chianti to stay at this little beauty – a romantic bolthole just for two. You’ll f ...
From $266 per night (USD)
VRBO
From $187 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 $187 per night (USD)
Expedia
From $165 per night (USD)
VRBO
Ciacchieri, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
You will feel a real part of Tuscan life in Ciacchieri, a cheerfully decorated apartment in Gaiole, a small town at the ...
From $165 per night (USD)
VRBO
From $138 per night (USD)
Expedia
Raffaello, Montefienali, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Deep in the upland forests of the Chianti on an ancient Roman road, the 13th century Montefienali resort sits on a ridge ...
From $138 per night (USD)
Expedia
From $387 per night (USD)
VRBO
Le Cerreta, Gaiole in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Set atop a sunlit Chianti hill near the beautiful town of Gaiole, Le Cerreta is an exceptional private hideaway. It’s sh ...
From $387 per night (USD)
VRBO
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Expedia
Il Fienile di Montefienali, Montefienali, Gaiole in Chianti, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Deep in the upland forests of the Chianti on an ancient Roman road, the 13th century Montefienali resort sits on a ridge ...
Click For Pricing
Expedia
From $116 per night (USD)
VRBO
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 $116 per night (USD)
VRBO
From $212 per night (USD)
Expedia
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 $212 per night (USD)
Expedia
From $187 per night (USD)
VRBO
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 $187 per night (USD)
VRBO
From $207 per night (USD)
Expedia
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 $207 per night (USD)
Expedia
From $363 per night (USD)
VRBO
Casa Virginia, Gaiole in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
You will love Casa Virginia’s openness: set on a gentle slope above a vineyard, with a backdrop of olive trees, pines an ...
From $363 per night (USD)
VRBO
From $154 per night (USD)
Expedia
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 $154 per night (USD)
Expedia
Click For Pricing
VRBO
Podere Filazzi, Gaiole in Chianti, Siena and Chianti
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Immersed in a deep green valley with rolling hills and gorgeous views, Podere Filazzi is a country villa with charming d ...
Click For Pricing
VRBO
From $201 per night (USD)
Expedia
Malvasia, Vignale, Castelnuovo Berardenga, Siena and Chianti
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Ledged on a Chianti hillside, Vignale's original farm stone buildings have been respectfully restored into a small colle ...
From $201 per night (USD)
Expedia
From $163 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 $163 per night (USD)
VRBO
From $424 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 $424 per night (USD)
Expedia
From $330 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 $330 per night (USD)
VRBO
From $127 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 $127 per night (USD)
Expedia
From $207 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 $207 per night (USD)
VRBO
From $312 per night (USD)
Expedia
Poggio della Villa, Radda in Chianti, Siena and Chianti
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Arrive at this delightful stone-built villa on the edge of the Chianti town of Radda and you will quickly shake off any ...
From $312 per night (USD)
Expedia

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