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Check prices for these dates

In two weeks
May 29 - May 31
In two months
Jul 10 - Jul 12
In three months
Aug 7 - Aug 9
In four months
Sep 4 - Sep 6

Our top choices for Gaiole in Chianti villas

Property grounds

"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi

"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi
Gaiole in Chianti
10.0 out of 10, Exceptional, (8 reviews)
"Everything about this house is exquisite and very homey. Decors are really tasteful. Outdoors spaces and the views are absolutely beautiful. Kitchen is really well appointed. There is no shortage of dish-wear, silverware and glasses. Location is very central to explore Tuscany. Our host, Lapo is very welcoming and helpful with all recommendations. He is the kind of host that you want to stay in touch and come back to see him. "
United States
Ravin N.
The price is CA $2,302
CA $2,340 total
includes taxes & fees
Jun 13 - Jun 14
"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi
Pool

Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi

Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi
Gaiole in Chianti
The price is CA $1,540
CA $1,819 total
includes taxes & fees
Jun 3 - Jun 4
Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi
Villa, Air conditioning, Courtyard View | Exterior

Villa Montecastello

Villa Montecastello
Monteriggioni
The price is CA $265
CA $296 total
includes taxes & fees
May 18 - May 19
Villa Montecastello
Exterior

Il Poggio dell'Eremita

Il Poggio dell'Eremita
Sinalunga
10.0 out of 10, Exceptional, (62 reviews)
"Fantastic place! Great location. "
Canada
Paul Q.
The price is CA $216
CA $249 total
includes taxes & fees
May 22 - May 23
Il Poggio dell'Eremita
Outdoor dining

VILLA in FLORENTINE HILLS. 220+ EXCELLENT REVIEWS. 100% travelers recommend.

VILLA in FLORENTINE HILLS. 220+ EXCELLENT REVIEWS. 100% travelers recommend.
Florence
10.0 out of 10, Exceptional, (9 reviews)
"We had a lovely stay at this place in the country! It was charming, Paola and family were wonderful and we would stay here again!"
United States
Becky F.
The price is CA $527
CA $808 total
includes taxes & fees
Jun 12 - Jun 13
VILLA in FLORENTINE HILLS. 220+ EXCELLENT REVIEWS. 100% travelers recommend.
Exterior

Villa Il Signorino

Villa Il Signorino
GREVE IN CHIANTI
10.0 out of 10, Exceptional, (2 reviews)
"Nice place 👌 "
United States
Avi A.
The price is CA $504
CA $721 total
includes taxes & fees
May 18 - May 19
Villa Il Signorino
Exterior

Red Heart - relax with those you love in Tuscany.

Red Heart - relax with those you love in Tuscany.
Trequanda
The price is CA $879
CA $1,466 total
includes taxes & fees
May 19 - May 20
Red Heart - relax with those you love in Tuscany.
Exterior

Artisti del Cavallo Tourism

Artisti del Cavallo Tourism
Foiano della Chiana
8.4 out of 10, Very good, (24 reviews)
"Good house for one night. "
Germany
Heiner
The price is CA $111
CA $126 total
includes taxes & fees
May 19 - May 20
Artisti del Cavallo Tourism
Exterior

Luxury Tuscan Villa Collalto with 18 rooms -Perfect for Exclusive Events

Luxury Tuscan Villa Collalto with 18 rooms -Perfect for Exclusive Events
Colle di Val d'Elsa
The price is CA $13,587
CA $15,050 total
includes taxes & fees
May 22 - May 23
Luxury Tuscan Villa Collalto with 18 rooms -Perfect for Exclusive Events
Outdoor dining

Villa Mami: A Tuscan Retreat of Elegance and Charm

Villa Mami: A Tuscan Retreat of Elegance and Charm
Toscana
10.0 out of 10, Exceptional, (1 review)
The price is CA $3,676
CA $4,930 total
includes taxes & fees
Jun 10 - Jun 11
Villa Mami: A Tuscan Retreat of Elegance and Charm
Property grounds

INDEPENDENT VILLA WITH POOL IN THE HEART OF TUSCANY

INDEPENDENT VILLA WITH POOL IN THE HEART OF TUSCANY
San Giovanni d'Asso
9.8 out of 10, Exceptional, (37 reviews)
"Wonderful Graziella and Constantino present a Villa with unique flair. We had the time of our life with cooking and eating too much. Great vacation!! thank You"
Germany
Stephan C.
The price is CA $751
CA $1,140 total
includes taxes & fees
Jun 10 - Jun 11
INDEPENDENT VILLA WITH POOL IN THE HEART OF TUSCANY
Exterior

Villa Marcolina

Villa Marcolina
Castelnuovo Berardenga
The price is CA $1,125
CA $1,250 total
includes taxes & fees
May 25 - May 26
Villa Marcolina
Pool

Bagno a Ripoli, Italy. Entire accommodation: villa

Bagno a Ripoli, Italy. Entire accommodation: villa
Toscana
The price is CA $1,108
CA $1,245 total
includes taxes & fees
May 18 - May 19
Bagno a Ripoli, Italy. Entire accommodation: villa
Hair dryer, bidet, towels, soap

Rooster House, cooking classes and opera

Rooster House, cooking classes and opera
Toscana
The price is CA $158
CA $192 total
includes taxes & fees
May 21 - May 22
Rooster House, cooking classes and opera
Exterior

VILLA IL MATTO with salt pool, with spa and sauna

VILLA IL MATTO with salt pool, with spa and sauna
Toscana
The price is CA $173
CA $606 total
includes taxes & fees
May 18 - May 19
VILLA IL MATTO with salt pool, with spa and sauna
Outdoor dining

Villino Serena Di Lapigio Florence: Mountain View, Private Garden

Villino Serena Di Lapigio Florence: Mountain View, Private Garden
Saltino
The price is CA $742
CA $1,301 total
includes taxes & fees
Jun 1 - Jun 2
Villino Serena Di Lapigio Florence: Mountain View, Private Garden
Exterior

My Exclusive Italy - Classic Suite in a Luxury Wine Estate

My Exclusive Italy - Classic Suite in a Luxury Wine Estate
Rignano sull'Arno
The price is CA $725
CA $797 total
includes taxes & fees
May 18 - May 19
My Exclusive Italy - Classic Suite in a Luxury Wine Estate
Exterior

Villa "Il Fornacino" with Pool, Garden & Wi-Fi

Villa "Il Fornacino" with Pool, Garden & Wi-Fi
Rapolano Terme
9.0 out of 10, Wonderful, (4 reviews)
"Wonderful house. Big, cool even with 36 degrees outside. Very Nice swimming pool with shaddow places if needed. Very friendly and helpfull host."
Netherlands
Toon M.
The price is CA $1,347
CA $1,744 total
includes taxes & fees
May 18 - May 19
Villa "Il Fornacino" with Pool, Garden & Wi-Fi
Exterior

VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
Firenze
The price is CA $22,634
CA $22,634 total
includes taxes & fees
May 19 - May 20
VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
Exterior

Villa 'La Casa Nel Bosco - Antiche Dimore' with Shared Pool, Wi-Fi & Air Conditioning

Villa 'La Casa Nel Bosco - Antiche Dimore' with Shared Pool, Wi-Fi & Air Conditioning
Siena
The price is CA $312
CA $315 total
includes taxes & fees
May 18 - May 19
Villa 'La Casa Nel Bosco - Antiche Dimore' with Shared Pool, Wi-Fi & Air Conditioning
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Gaiole in Chianti Hotel Reviews

Hotel Toscana Ambassador

Hotel Toscana Ambassador

2/10 Terrible
"several disappointing issues during my stay. The air conditioning was poor — I had to go to the front desk just to get it turned on, and even then it barely worked. The beds were very hard and uncomfortable, and the room had a strange smell that made it less pleasant. On top of that, the walls or doors seemed poorly insulated because I could hear everything happening in the hallways. Overall, it did not provide the comfort or rest I expected."
Laura 3-night trip
Posted 2 hours ago
Hotel Toscana Ambassador

Find out more about Gaiole in Chianti

Gaiole in Chianti Villas information

Number of reviews
122
Accommodation
1921 Villas
Lowest Price
CA $126
Highest Price
CA $22,634

Frequently asked questions

How much do villas in Gaiole in Chianti cost?
Prices for villas in Gaiole in Chianti range between CA $126 and CA $22,634 per night. Whatever your budget, you'll find something that fits the bill with Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many villas are there in Gaiole in Chianti?
Gaiole in Chianti has 1921 villas to select from. Find your perfect stay quickly and easily by checking the "Villa" box under the "Property type" tab in our handy filter tool.
Why book your villa in Gaiole in Chianti with Expedia?
We think vacation time shouldn't be complicated, so if you're looking for villas at a nice price, Expedia can help. Save those pennies and opt for an all-inclusive stay, or splurge on a luxury villa to spoil your loved ones. Use our convenient search filters to find an escape in Gaiole in Chianti that suits your needs.
How can I find cheap villas in Gaiole in Chianti?
An excellent way to locate cheap villas in Gaiole in Chianti is with Expedia's filter tool. Narrow your search by star rating, amenities and budget to nab unbeatable rates in only a click or two.
What is there to do near my villa in Gaiole in Chianti?
There are plenty of fantastic things to do in Gaiole in Chianti. Make tracks to leading attractions like Cantalici Winery, Castle of Brolio and Meleto Castle. Badia a Coltibuono, Church of San Sigismondo and PoggioBrandani also appeal to many visitors.