Best Villas in Chianti Region 2026

A vineyard with rows of grapevines, a house surrounded by trees, and a road with vehicles.

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Our top choices for Chianti Region villas

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

1. Rooster House, cooking classes and opera

Tavarnelle Val di Pesa

includes taxes & fees

24 Sept - 25 Sept

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.

2. Villa Il Signorino

GREVE IN CHIANTI

Avi A.

includes taxes & fees

23 Sept - 24 Sept

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

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

Radda in Chianti

Amber M.

additional charges may apply

4 Oct - 5 Oct

An outdoor dining area with tables and chairs, surrounded by greenery and a view of trees and hills.

4. Villa with Pool - Two Bedrooms

Rignano sull'Arno (Florence)

includes taxes & fees

11 Oct - 12 Oct

An open wooden door leading to a balcony with a round table and two chairs, overlooking a garden with trees and flowers.

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

Impruneta

Maria H.

includes taxes & fees

25 Sept - 26 Sept

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

6. Villa Bellavista - Homelike Villas

Montegonzi

A pool area with a stone archway, lounge chairs, and a stone wall with greenery behind.

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

Rignano sull'Arno

includes taxes & fees

23 Sept - 24 Sept

A spacious room with a high ceiling, wooden beams, a glass table, green chairs, and a fireplace.

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

Rignano sull'Arno

includes taxes & fees

16 Oct - 17 Oct

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Top Chianti Region Hotel Reviews

Hu Norcenni Girasole Village

10/10 Excellent

"Perfect can’t fault it. Maybe a bigger train/bus at peak times would help. Lovely restaurant, bars, ice cream. Clean swimming pools. Good, kind, friendly staff. Safe place. Clean accommodation. Peaceful environment. Must take mosquito treatment as they’re bad out here. Lovely bonus is the pump at the pools to pump donuts up. Can’t fault it. Will 100000% return."

Castello Vicchiomaggio

10/10 Excellent

"very nice historic hotel with great views of the country side and great atmphere. Room size and ammenities were wonderful. The breakfeast was great. Restaurant was nice with historic dishes. Only down side was the gluten and nut free options were limited...mainly for gluten sufferers, since the only gluten free pasta is Penne, which is not great for all dishes and frustratingsince Italy produces a very large variety of great gluten free pasta shapes. Also, my travel partner and I did the same pasta, one gluten free (penne) and one not gluten free. The non-gluten-free pasta came beautifully presented, while the gluten-free pasta came like it was thrown together last minute… like as if you were sitting at your own kitchen table. Impression given with the dinner is that people with allergies, are more a bit of a bother, and the typical mission in Italy, to give visitors an excellent culinary experience, is more less abandoned for people with allergies. that said, accommodating allergies is very difficult these days and at least the menu was clear about which foods contain which allergens."

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."

Find out more about Chianti Region

Chianti Region Villas information

Number of reviews	3
Accommodation	529 Villas
Lowest Price	£68
Highest Price	£897

Frequently asked questions

How much do villas in Chianti Region cost?

Villas in Chianti Region cost between £68 and £897 per night. These escapes offer the privacy of your own space at a price that doesn't break the bank. 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 Chianti Region?

Chianti Region has 529 villas to choose from. Enter your destination and dates and lock in your perfect trip today.

Why book your villa in Chianti Region with Expedia?

We think arranging a holiday should be a breeze, so if you're looking for villas at a great price, Expedia delivers. Keep costs down and choose an all-inclusive stay, or splurge on a plush villa to spoil the ones you love most. Our handy filters make it easy to find a property in Chianti Region that matches your needs.

How can I find cheap villas in Chianti Region?

With Expedia's user-friendly filter tool, scoring cheap villas in Chianti Region has never been easier. To find stays that won't break the bank, fine-tune your search by star rating, budget and amenities.

What is there to do near my villa in Chianti Region?

Whether you love food, shopping, history or sightseeing, Chianti Region offers something for everyone! The major city of San Gimignano boasts lots of things to do, including Archaeological Museum - Spezieria Santa Fina - Raffaele De Grada Modern and Contemporary Art Gallery, Historical Torture Museum and Ornithological Museum. If you're headed to Radda in Chianti, Castello di Albola, Castello di Radda Winery and Borgo di Vescine - Tenute di Castelvecchi shouldn't be missed.

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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 Chianti Region villas

1. Rooster House, cooking classes and opera

2. Villa Il Signorino

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

4. Villa with Pool - Two Bedrooms

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

6. Villa Bellavista - Homelike Villas

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

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

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

10. Villa Sunset, in the heart of Chianti

11. Molino In Chianti - Villa with Private Pool

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

13. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

14. Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests

15. "Villa Bellavista" with Private Pool, Private Whirlpool & Wi-Fi

16. Villa with Pool - 3 Bedrooms with independent bathroom

17. Apartments Florence - Villa Fonte Morgana with pool

18. Villa Milani with Shared Pool, Private Terrace & Wi-Fi

19. Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites

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

Find holiday rentals that suit your style

Top Chianti Region Hotel Reviews

Hu Norcenni Girasole Village

Find out more about Chianti Region

Chianti Region Villas information

Frequently asked questions

Explore a world of travel with Expedia