Best Villas in Gaiole in Chianti 2026

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

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Our top choices for Gaiole in Chianti villas

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

Gaiole in Chianti

Bernard K.

additional charges may apply

19 Oct - 20 Oct

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

includes taxes & fees

12 Oct - 13 Oct

3. Villa Bellavista - Homelike Villas

Montegonzi

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

Radda in Chianti

Amber M.

additional charges may apply

24 Sept - 25 Sept

Villa, Air conditioning, Courtyard View | Exterior

5. Villa Montecastello

Monteriggioni

Alvaro

includes taxes & fees

25 Sept - 26 Sept

6. Villa Il Signorino

GREVE IN CHIANTI

Avi A.

includes taxes & fees

23 Sept - 24 Sept

7. Rooster House, cooking classes and opera

Tavarnelle Val di Pesa

includes taxes & fees

23 Sept - 24 Sept

8. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32

Siena

includes taxes & fees

22 Sept - 23 Sept

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Top Gaiole in Chianti Hotel Reviews

Poderi Arcangelo

10/10 Excellent

"Location is beautiful. We were in the separate house."

Villa Pitiana

10/10 Excellent

"The property is unique, rustic and isolated yet close to Chianti, and Florence. Morning on the terrace watching the valley illuminate as the sun rises from the east; makes the morning coffee and the view worth enduring the crisp morning air. For those that travel with a car it is the perfect place from which to explore the region. Just go!"

Fattoria di Vegi

10/10 Excellent

"What an amazing hotel. The attention to detail on the refurb of the property is phenomenal. Once the tennis court, spa etc are completed this will easily be high hundreds per night. We visited all the other properties in the surrounding area and nothing came close to this hotel. The food and drinks were also brilliant - best meal we had in Tuscany was in the hotel. My only suggestions would be to rotate the staff more - they seemed slightly over worked. Easily one of the best hotels I have stayed in."

Grand Hotel Continental Siena – Starhotels Collezione

8/10 Good

"Our stay was just ok. Very noisy streets. And the bread at the breakfast buffet was extremely stale for both mornings. We could not eat it. If you are allergic to dust be warned that their curtains and bed headers are very dusty."

Find out more about Gaiole in Chianti

Gaiole in Chianti Villas information

Number of reviews	239
Accommodation	1835 Villas
Lowest Price	£68
Highest Price	£6,014

Frequently asked questions

How much do villas in Gaiole in Chianti cost?

Prices for villas in Gaiole in Chianti range between £68 and £6,014 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 1835 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.

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Chianti Region Holiday Rentals

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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. Villa Il Signorino

7. Rooster House, cooking classes and opera

8. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32

9. Villa Capanna: A Window onto Tuscany

10. Villa Torre Among the Hills of Siena

11. Luxury Villa in the Florentine hills

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

13. Il Poggio dell'Eremita

14. Villa with Pool - Two Bedrooms

15. Villa Sunset, in the heart of Chianti

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

17. Artisti del Cavallo Tourism

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

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

20. Villa with Florence Pool / Breakfast, Quitedian housekeeping, AirCon whirlpool

Find holiday rentals that suit your style

Top Gaiole in Chianti Hotel Reviews

Poderi Arcangelo

Find out more about Gaiole in Chianti

Gaiole in Chianti Villas information

Frequently asked questions

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