Gaiole in Chianti Villas - Best Villa Gaiole in Chianti 2026

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

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

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.

includes taxes & fees

3 Nov - 4 Nov

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

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

Radda in Chianti

Amber M.

includes taxes & fees

1 Nov - 2 Nov

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

3. Villa Montecastello

Monteriggioni

Alvaro

includes taxes & fees

26 Oct - 27 Oct

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.

4. Villa Il Signorino

GREVE IN CHIANTI

Avi A.

includes taxes & fees

18 Oct - 19 Oct

A landscaped garden with a central fountain, a pool, and a small building with a tiled roof.

5. VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31

Siena

Ron M.

includes taxes & fees

16 Oct - 17 Oct

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

6. Rooster House, cooking classes and opera

Tavarnelle Val di Pesa

includes taxes & fees

16 Oct - 17 Oct

A stone building with a tower, surrounded by trees and a garden.

7. Villa Capannina with Private Pool, Wi-Fi and Air Conditioning

Vico dʼArbia

Marina O.

includes taxes & fees

17 Oct - 18 Oct

A rustic stone building with a tower, covered walkways, and a grassy courtyard.

8. Villa Torre Among the Hills of Siena

Vico dʼArbia

includes taxes & fees

17 Oct - 18 Oct

View all properties

Find holiday rentals that suit your style

Apartments

Aparthotels

Save an average of 15% on thousands of hotels when you're signed in

Top Gaiole in Chianti Hotel Reviews

Castello di Tornano Wine Resort

10/10 Excellent

"We liked it all! Very well maintained castle with it's unique character. Beautiful mideval style rooms. Good breakfast and decent restaurant. Would definitely stay there again."

Hu Firenze Camping In Town

10/10 Excellent

"It was a really nice experience staying at Hu Firenze. It was away from the hustle and bustle of the city and the main tourist areas, while a bus stop right across the street made it easy to get to the city centre. We also got to enjoy a bit of the Tuscan countryside experience. The only issue was that there is another Hu campsite called Hu Certosa, so you need to be careful not to book the wrong one, especially when travelling in a group and everyone is booking separately. This happened to us, but fortunately, the staff allowed my brother to stay with us since our accommodation had an extra bed. However, we had already paid for a tent at Hu Certosa. My recommendation would be to start breakfast earlier than 7:30 a.m. This would allow guests to leave at different times and help avoid long queues at the bus stop."

Hotel Casolare Le Terre Rosse

10/10 Excellent

"Great Family run hotel with friendly staff. Perfectly located to explore Tuscany.. we visited Sienna, Certaldo, Volterra, Sam Gimignano and Livorno on the coast. There is a walkable (5mins) winery called Il Colombaio which I would highly recommended. The breakfast buffet was fabulous."

Hotel Mulino di Firenze, WorldHotels Crafted

10/10 Excellent

"From the moment we arrived to the moment we left the staff were fantastic. Lapo, at the front desk, was extremely helpful in making last minute arrangements for anything we needed. The entire staff from the porters, bar tenders, cleaning staff and managers were friendly and accommodating. The property was picturesque and absolutely stunning. We wish we would have stayed more days just to enjoy the property itself. If you're having an afternoon drink on the patio bar or enjoying a scrumptious evening meal in the restaurant you will not be disappointed."

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	359
Accommodation	1804 Villas
Lowest Price	€84
Highest Price	€7,014

Frequently asked questions

How much do villas in Gaiole in Chianti cost?

Prices for villas in Gaiole in Chianti range between €84 and €7,014 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 1804 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 holiday 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.

Room 1

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