Gaiole in Chianti Rentals
- From $103 per night (USD)
VRBO
Tuscan apt. magnificent panorama, pure nature, relaxation, private pool, WiFi
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The 4-room apartment is ideal for families and small groups. The entrance is at ground level, two bedrooms and a bathroo ...
From $103 per night (USD)VRBO
- From $127 per night (USD)
Expedia
Chianti Holiday House, private jacuzzi up to 6 pax
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Recently renovated, is located in a scenic hillside location in a picturesque village nestled in the heart of Chianti, s ...
From $127 per night (USD)Expedia
- From $129 per night (USD)
VRBO
STAY IN THE CELLAR AMONG THE CHIANTI HILLS
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Farm stay in Gaiole in Chianti with outdoor pool This farm stay features an outdoor pool. Bathrooms include showers. R ...
From $129 per night (USD)VRBO
- From $1041 per night (USD)
Expedia
Private Villa with WIFI, private pool, A\/C, TV, veranda, panoramic view, parking, close to Siena
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
Villa Agresto is a beautiful property (288 sq m) with air conditioning, private pool and WiFi internet. The property ca ...
From $1041 per night (USD)Expedia
- From $188 per night (USD)
VRBO
Casa del Mastro, San Sano, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
An authentic Chianti village, San Sano allows you to immerse yourself in the charm and character of Tuscan life. Origina ...
From $188 per night (USD)VRBO
- From $10653 per night (USD)
Expedia
Traditional Stone House in the Heart of Chianti
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Perfect for those who want to enjoy a relaxing holiday in the Chianti countryside among vineyards and woods. The place i ...
From $10653 per night (USD)Expedia
- From $347 per night (USD)
VRBO
Montelodoli Capanna, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
With an atmosphere of a private country cottage grandeur, with climbing vines trailing across the exterior walls, this s ...
From $347 per night (USD)VRBO
- From $418 per night (USD)
Expedia
Gittori, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Located just a short stroll from the historical center of Gaiole in Chianti, Gittori is a luxury villa in the heart of t ...
From $418 per night (USD)Expedia
- From $1875 per night (USD)
VRBO
Podere Campi, Gaiole in Chianti, Siena and Chianti
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 10
Podere Campi is one of the most unique villas in Tuscany that we offer. A medieval priests house and originally a strate ...
From $1875 per night (USD)VRBO
- From $87 per night (USD)
Expedia
Tuscan apartment in an idyllic location, grandiose panorama, pool, WiFi
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The 3-room apartment guarantees an enchanting view of the rolling green hills as far as Siena from the bed. It is on the ...
From $87 per night (USD)Expedia
- From $87 per night (USD)
VRBO
Apartment in Tuscan stone house, surrounded by nature with private pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The 3-room apartment offers comfort for families or a small group. It is located at ground level, the terrace is located ...
From $87 per night (USD)VRBO
- From $144 per night (USD)
Expedia
Farmhouse apartment in Chianti with garden and pool for 2 people
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Stone farmhouse. The apartment is carefully furnished and well-stocked. Satellite TV, Wifi, kitchen, fridge, freezer, wa ...
From $144 per night (USD)Expedia
- From $107 per night (USD)
VRBO
Tuscan apartment grandiose panorama, private pool, WiFi, pure nature, relaxation
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
<p>A short distance from birdwatching, wildlife walks, and more, this family-friendly apartment lets you experience it a ...
From $107 per night (USD)VRBO
- From $565 per night (USD)
VRBO
Sestuccia is a beautiful Tuscan villa just a short distance from Gaiole in Chianti
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Sestuccia is a beautiful Tuscan villa, located a short distance from Gaiole in Chianti and also within easy reach of Rad ...
From $565 per night (USD)VRBO
- From $368 per night (USD)
VRBO
Wonderful private villa with A\/C, private pool, WIFI, TV, patio, panoramic view and parking
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Independent house with private pool in the Chianti Classico, in an old hamlet of houses surrounded by vineyards, olive g ...
From $368 per night (USD)VRBO
- From $373 per night (USD)
Expedia
San Sano - Holiday Country Villa with swimming pool in Chianti, Tuscany
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Independent house with private pool in the Chianti Classico, in an old hamlet of houses surrounded by vineyards, olive g ...
From $373 per night (USD)Expedia
- Click For Pricing
VRBO
Villa Gaiole, Borgo di Gaiole
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
ABOUT VILLA GAIOLE This beautifully, spacious 3-bedroom semi-detached villa, sits over 3 floors. It has been thoughtfull ...
Click For PricingVRBO
- From $266 per night (USD)
Expedia
Farmhouse in Chianti
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
The "Crocino in Chianti" offers the opportunity to immerse yourself in the Italian Middle Ages. Here the border disputed ...
From $266 per night (USD)Expedia
- From $188 per night (USD)
VRBO
Casa BD in Gaiole - 150 m² apartment with a view & travel guide - sleeps 8
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
<p>Close to cycling, hiking trails, and more, this family-friendly apartment brings it all within reach. Gaiole in Chian ...
From $188 per night (USD)VRBO
- From $1004 per night (USD)
Expedia
Belvilla by OYO Villa Petra
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
This property has been cleaned with chemicals that are effective against Coronavirus. Our staff is following all safety ...
From $1004 per night (USD)Expedia
- Click For Pricing
VRBO
In Gaiole in Chianti, this independent vacation home with private pool awaits you amidst the nature
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
In Gaiole in Chianti, this independent vacation home with private pool awaits you amidst the nature of the Chianti Class ...
Click For PricingVRBO
- From $528 per night (USD)
VRBO
In the heart of the Chianti area, between Radda in Chianti, Gaiole and Panzano, there is an enchante
- Bedrooms:
- 7
- Bathrooms:
- 8
- Sleeps:
- 18
In the heart of the Chianti area, between Radda in Chianti, Gaiole and Panzano, there is an enchanted hamlet where you c ...
From $528 per night (USD)VRBO
- From $588 per night (USD)
VRBO
CASA VISTA - Four Bedroom Villa, Sleeps 8
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Located in a small village in the very heart of Chianti classico, you find this restored ancient house next to the churc ...
From $588 per night (USD)VRBO
- From $215 per night (USD)
Expedia
Beautiful apartment with shared pool in a typical historic village in Chianti.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Beautiful apartment with shared pool in a typical historic village in Chianti. Galenda is located between the towns of ...
From $215 per night (USD)Expedia
- From $256 per night (USD)
VRBO
Sestuccina
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Villa La Grotta is a romantic cottage with a double bedroom, kitchen, living room and bathroom. The villa is located a f ...
From $256 per night (USD)VRBO
- From $521 per night (USD)
Expedia
Villa Fauno A: A welcoming apartment located in a small hamlet at the foot of a castle, with Free WI-FI.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Villa Fauno A is a welcoming apartment located in a small hamlet at the foot of a castle. It sleeps four people. From Vi ...
From $521 per night (USD)Expedia
- From $435 per night (USD)
VRBO
Villa Fauno D: A welcoming apartment located in a small hamlet at the foot of a castle, with Free WI-FI.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Villa Fauno D is a welcoming apartment located in a small hamlet at the foot of a castle. It sleeps four people. From Vi ...
From $435 per night (USD)VRBO
- From $160 per night (USD)
Expedia
Detached house, in the heart of Chianti Classico, pool, quiet panoramic position, WiFi
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
The house is located on the outskirts of the historic hamlet Starda (12th century). Century). The pool is private, for ...
From $160 per night (USD)Expedia
- From $625 per night (USD)
VRBO
Secluded villa in the Chianti hills. Last Minute deal: 27April to 18May 10% off
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Ciao from Petra & Alexa! We warmly welcome you in our unbeatable location, halfway between Siena and Florence! First of ...
From $625 per night (USD)VRBO
- From $422 per night (USD)
Expedia
Beautiful detached stone vacation home with private pool, whose origins date back to 1500, on the hi
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful detached stone vacation home with private pool, whose origins date back to 1500, on the hills of Chianti Class ...
From $422 per night (USD)Expedia
- From $1232 per night (USD)
VRBO
Villa in Gaiole In Chianti with 4 bedrooms sleeps 8
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This stone built property is located in a very secluded and panoramic location in the heart of Chianti Classico, 5 km fr ...
From $1232 per night (USD)VRBO
- Click For Pricing
Expedia
Apartment in the castle, with restaurant and swimming pool, pink
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
This stunning large apartment of 80 sqm for 5 people is located in the medieval castle, near the restaurant and the rece ...
Click For PricingExpedia
- From $306 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 $306 per night (USD)VRBO
- From $158 per night (USD)
Expedia
Casa della Nonna C, 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 $158 per night (USD)Expedia
- From $215 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 $215 per night (USD)VRBO
- From $304 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 $304 per night (USD)Expedia
- From $180 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 $180 per night (USD)VRBO
- From $202 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 $202 per night (USD)Expedia
- From $307 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 $307 per night (USD)VRBO
- From $178 per night (USD)
Expedia
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 $178 per night (USD)Expedia
- From $200 per night (USD)
VRBO
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 $200 per night (USD)VRBO
- From $533 per night (USD)
Expedia
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 $533 per night (USD)Expedia
- From $1224 per night (USD)
VRBO
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 $1224 per night (USD)VRBO
- From $319 per night (USD)
Expedia
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 $319 per night (USD)Expedia
- From $333 per night (USD)
VRBO
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 $333 per night (USD)VRBO
- From $715 per night (USD)
Expedia
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 $715 per night (USD)Expedia
- From $196 per night (USD)
VRBO
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 $196 per night (USD)VRBO
- From $174 per night (USD)
Expedia
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 $174 per night (USD)Expedia
- From $165 per night (USD)
VRBO
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 $165 per night (USD)VRBO
- From $315 per night (USD)
Expedia
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 $315 per night (USD)Expedia
- From $267 per night (USD)
VRBO
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 $267 per night (USD)VRBO
- From $294 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 $294 per night (USD)Expedia
- From $211 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 $211 per night (USD)VRBO
- From $162 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 $162 per night (USD)Expedia
- From $569 per night (USD)
VRBO
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 $569 per night (USD)VRBO
- From $579 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 $579 per night (USD)Expedia
- From $343 per night (USD)
VRBO
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 $343 per night (USD)VRBO
- From $424 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 $424 per night (USD)Expedia
- From $141 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 $141 per night (USD)VRBO
- From $169 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 $169 per night (USD)Expedia
- From $172 per night (USD)
VRBO
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 $172 per night (USD)VRBO
- From $160 per night (USD)
Expedia
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 $160 per night (USD)Expedia
- From $245 per night (USD)
VRBO
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 $245 per night (USD)VRBO
- From $202 per night (USD)
Expedia
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 $202 per night (USD)Expedia
- From $469 per night (USD)
VRBO
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 $469 per night (USD)VRBO
- From $245 per night (USD)
Expedia
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 $245 per night (USD)Expedia
- From $135 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 $135 per night (USD)VRBO
- From $229 per night (USD)
Expedia
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 $229 per night (USD)Expedia
- From $143 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 $143 per night (USD)VRBO
- From $569 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 $569 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 $177 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 $177 per night (USD)Expedia
- From $152 per night (USD)
VRBO
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 $152 per night (USD)VRBO
- From $202 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 $202 per night (USD)Expedia
- From $201 per night (USD)
VRBO
Casa della Nonna A, 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 $201 per night (USD)VRBO
- From $199 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 $199 per night (USD)Expedia
- From $552 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 $552 per night (USD)VRBO
- From $208 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 $208 per night (USD)Expedia
- From $353 per night (USD)
VRBO
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 $353 per night (USD)VRBO
- From $143 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 $143 per night (USD)Expedia
- From $328 per night (USD)
VRBO
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 $328 per night (USD)VRBO
- From $216 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 $216 per night (USD)Expedia
- From $249 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 $249 per night (USD)VRBO
- From $785 per night (USD)
Expedia
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 $785 per night (USD)Expedia
- From $675 per night (USD)
VRBO
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 $675 per night (USD)VRBO
- From $560 per night (USD)
Expedia
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 $560 per night (USD)Expedia
- From $246 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 $246 per night (USD)VRBO
- From $146 per night (USD)
Expedia
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 $146 per night (USD)Expedia
- From $185 per night (USD)
VRBO
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 $185 per night (USD)VRBO
- From $368 per night (USD)
Expedia
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 $368 per night (USD)Expedia
- From $211 per night (USD)
VRBO
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 ...
From $211 per night (USD)VRBO
- From $176 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 $176 per night (USD)Expedia
- From $202 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 $202 per night (USD)VRBO
- From $210 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 $210 per night (USD)Expedia
- From $373 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 $373 per night (USD)VRBO
- From $212 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 $212 per night (USD)Expedia
- From $239 per night (USD)
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 ...
From $239 per night (USD)VRBO
- From $307 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 $307 per night (USD)Expedia
- From $248 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 $248 per night (USD)VRBO
- From $153 per night (USD)
Expedia
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 $153 per night (USD)Expedia