Gaiole in Chianti Villas ￥24,295

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 Tub, and Wi-Fi

Gaiole in Chianti

Bernard K.

￥357,736 total

includes taxes & fees

Sep 18 - Sep 19

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 traveler

￥212,575 total

includes taxes & fees

Sep 1 - Sep 2

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.

￥178,749 total

includes taxes & fees

Sep 17 - Sep 18

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

5. Villa Montecastello

Monteriggioni

Alvaro

￥32,313 total

includes taxes & fees

Sep 5 - Sep 6

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

6. Rooster House, cooking classes and opera

Toscana

￥24,295 total

includes taxes & fees

Sep 1 - Sep 2

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.

7. Villa Il Signorino

GREVE IN CHIANTI

Avi A.

￥84,385 total

includes taxes & fees

Sep 1 - Sep 2

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

￥359,238 total

includes taxes & fees

Sep 14 - Sep 15

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Top Gaiole in Chianti Hotel Reviews

Villa I Barronci Resort & Spa

10/10 Excellent

"Great place."

"Villa Torre in Chianti" Vrbo Vacation Rental of the Year 2026- 8 bedrooms A/C

10/10 Excellent

"WOW! What a beautiful place and awesome hosts! 15 of us traveled to celebrate several birthdays, to enjoy, to discover the area, eat well and create new experiences. For all of these I used the experience and recommendations of Jacopo and Beatrice. We maintained communication for 3 months, and everything turned out perfect! They are the perfect hosts and this is a perfect house whether you want to rest or use it as a base with a large group. The villa(house) is large, with plenty of to do's, with a nice pool and quiet surroundings. The pictures are accurate and the dinners from Beatrice are amazing. Do not hesitate to stay on this place, to pay for the villa and the experiences, and to work together with Jacopo and Beatrice for the perfect celebration and vacation. Don't skip taking a tour of local wineries and eating in one of the local restaurants. 100% Recommended!!"

Hu Firenze Camping In Town

8/10 Good

"The accommodation is very good value for money. Nice facilities. The food in the restaurant is excellent and at a very reasonable price. Just one small complaint. We arrived in a torrential downpour, but had to wander around the site in the dark looking for our chalet. I thought a little buggy to help travellers would be a good idea."

Borgo Scopeto Wine & Country Relais

10/10 Excellent

"This is a very special Tuscan style hotel in the beautiful countryside surrounded by vineyards and olive groves. The staff were excellent, special mention goes to Elisa ,and the food was amazing. My only feedback, if you pay for a treatment the other spa facilities should be included. Also, the gym is very small but let's I wasn't there to train."

Poderi Arcangelo

8/10 Good

"Lovely place. Rooms are a nice nice. We stayed in a junior suite. Pool was lovely and the view from it was incredible. Ball games etc not allowed in the pool and the pool area bar didn’t open until about 5/6pm. This is not a criticism as it created a quiet and relaxed vibe which was fitting of the view and location, but worth noting. Breakfast was nice, we would have preferred a little more choice, but no complaints, they hosted a pizza night on one of our stays, the pizza was ok, we would have preferred to have the Tuscan dinner another night but didn’t work with our plans, All in all a lovely stay, would happily return."

Find out more about Gaiole in Chianti

Gaiole in Chianti Villas information

Number of reviews	248
Accommodation	1841 Villas
Lowest Price	￥24,295
Highest Price	￥898,077

Frequently asked questions

How much do villas in Gaiole in Chianti cost?

Prices for villas in Gaiole in Chianti range between ￥24,295 and ￥898,077 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 1841 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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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 Tub, 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. Rooster House, cooking classes and opera

7. Villa Il Signorino

8. Villa Capanna: A Window onto Tuscany

9. The San Leonino House

10. Villa Torre Among the Hills of Siena

11. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

12. Luxury Villa in the Florentine hills

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

14. Il Poggio dell'Eremita

15. Villa with Pool - Two Bedrooms

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

17. Villa Sunset, in the heart of Chianti

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

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

20. Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~

Find vacation rentals that suit your style

Top Gaiole in Chianti Hotel Reviews

Villa I Barronci Resort & Spa

Find out more about Gaiole in Chianti

Gaiole in Chianti Villas information

Frequently asked questions

Explore a world of travel with Expedia