Gaiole in Chianti Villas from CA $211

A stone castle with battlements overlooking a lush valley with vineyards.

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Our top choices for Gaiole in Chianti villas

A terrace with wicker furniture, a stone planter with flowers, and a view of vineyards and hills.

1. Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi

Gaiole in Chianti

Bernard K.

CA $2,358 total

includes taxes & fees

Oct 6 - Oct 7

An outdoor patio with a wooden table and chairs, a hanging lantern, and a view of the surrounding landscape.

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

Gaiole in Chianti

"Pros: La casa è sita in una posizione super tranquilla in mezzo al verde e alla natura. Tutto è curato alla perfezione. Nota di merito per il verde e i fiori e per la gentilezza dei proprietari. Cons: La posizione che è un pregio per qualcuno per altri potrebbe non esserlo. In effetti per arrivare al podere ci sono 2 km di strada bianca molto stretta. Una volta arrivati si è però ripagati ampiamente del piccolo disagio!"

Anonymous traveller

CA $1,846 total

includes taxes & fees

Sep 28 - Sep 29

An outdoor patio with a wooden pergola, a table set for breakfast, and a view of the surrounding garden.

3. Villa Bellavista - Homelike Villas

Montegonzi

A stone building with a swimming pool, wooden deck, and a tall tree.

4. Villa 'La Petrosa' with Private Pool, Private Garden and Balcony

Radda in Chianti

Amber M.

CA $2,896 total

includes taxes & fees

Oct 4 - Oct 5

A stone building with an arched entrance, surrounded by gravel, potted plants, and trees.

5. Villa Montecastello

Monteriggioni

Alvaro

CA $258 total

includes taxes & fees

Sep 28 - Sep 29

A two-story building with a stone staircase leading to a wooden door. There is a small outdoor table and a potted plant on the porch.

6. Villa Il Signorino

GREVE IN CHIANTI

Avi A.

CA $735 total

includes taxes & fees

Sep 28 - Sep 29

A garden with outdoor seating, a shade structure, and a view of the surrounding landscape.

7. Rooster House, cooking classes and opera

Tavarnelle Val di Pesa

CA $211 total

includes taxes & fees

Sep 28 - Sep 29

A covered outdoor patio with a wooden table and chairs, a vase of flowers, and a view of the countryside.

8. Villa Capanna: A Window onto Tuscany

Vico dʼArbia

CA $2,759 total

includes taxes & fees

Oct 17 - Oct 18

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Top Gaiole in Chianti Hotel Reviews

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent

"Concierge staff is fantastic. Bar staff as well. Location can’t be beat. Ground zero for Siena activity."

Hotel Casolare Le Terre Rosse

10/10 Excellent

"Beautiful property close to San Gimignano historic center. Loved having option to have all meals here. Breakfast was way more expensive than other hotels so just had breakfast in town. But other meals were reasonably priced. If they would step up their game a bit (more pillows, seating in rooms, provide wine glasses and opener, cozy it up a bit with amenities), they could easily be a 4 star because the property itself is certainly 4 star."

Fattoria di Vegi

10/10 Excellent

"This is a newly renovated and opened property cared for by a wonderful family. Everything has been taken care of down to the last detail. The food is delicious, the rooms are well appointed and till we thoroughly enjoyed exploring the property and every interesting nook! There's lots to do including a ping pong table and a beautiful pool. My only regret was not staying longer"

Villa Pitiana

10/10 Excellent

"Beautiful property with priceless views. The on-site restaurant also offered a nice light lunch. The pool area could have been spruced up a bit with some better furniture, but the room was beautiful. Be careful when using the shower as well as it is easy for the water to spray onto the floor. Make sure you understand where the property is located before booking as it is quite a ways outside of Florence city center. I rented a car and drove through the Tuscan hills to arrive."

Find out more about Gaiole in Chianti

Gaiole in Chianti Villas information

Number of reviews	244
Accommodation	1891 Villas
Lowest Price	CA $211
Highest Price	CA $11,298

Frequently asked questions

How much do villas in Gaiole in Chianti cost?

Prices for villas in Gaiole in Chianti range between CA $211 and CA $11,298 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 1891 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.

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Search Gaiole in Chianti Villa Rentals from CA $211

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Gaiole in Chianti villas

1. Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi

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

3. Villa Bellavista - Homelike Villas

4. Villa 'La Petrosa' with Private Pool, Private Garden and Balcony

5. Villa Montecastello

6. Villa Il Signorino

7. Rooster House, cooking classes and opera

8. Villa Capanna: A Window onto Tuscany

9. Villa Torre Among the Hills of Siena

10. Il Poggio dell'Eremita

11. Luxury Villa in the Florentine hills

12. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32

13. GuestHost - Porta Romana Elegant House with Private Parking!

14. Villa 'Cascina Gretaio' with Mountain View, Private Pool and Wi-Fi

15. Villa with Pool - Two Bedrooms

16. My Exclusive Italy - Classic Suite in a Luxury Wine Estate

17. Isolotto degli Angeli – Villa with Pool, Hot Tub & Garden in Tuscany

18. Villa Sunset, in the heart of Chianti

19. My Exclusive Italy - Exclusive Suite with view in a Luxury Wine Estate

20. Villa Mami: A Tuscan Retreat of Elegance and Charm

Find vacation rentals that suit your style

Top Gaiole in Chianti Hotel Reviews

Grand Hotel Continental Siena – Starhotels Collezione

Find out more about Gaiole in Chianti

Gaiole in Chianti Villas information

Frequently asked questions

Explore a world of travel with Expedia