Chianti Region Vacation Homes from AED 218

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 vacation homes

A stone building with multiple windows and a chimney.

1. Agriturismo La Ferrozzola

Castellina in Chianti

Ruth

AED 535 total

includes taxes & fees

8 Nov - 9 Nov

A stone building with a gated entrance, terracotta pots with flowers, and a staircase leading up to the door.

2. UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK

Ruffoli

"This is truly a unique and special property providing incredible value . One of the most beautiful views in a spectacular setting hidden away in the Tuscan hills above Panzano. A perfect location for day trips to vinyards, restaurants and the Chianti area. Our apartment was extremely well appointed and beautifully decorated. Spacious and varied outdoor sitting areas and patios with a very nice pool area. Our hostess Babette was extremely accomodating and informative which added to our overall...

James

AED 653 total

includes taxes & fees

12 Oct - 13 Oct

A view through a wooden door of a courtyard with stone walls and potted plants.

3. Chianti Craft House Badia a Passignano

Tavarnelle Val di Pesa

Oscar O.

AED 745 total

includes taxes & fees

12 Oct - 13 Oct

An outdoor patio with a table, chairs, a grill, and a large umbrella.

4. Vernaccia Country House - Agriturismo Apartment with Pool, Garden & Wi-Fi

Tavarnelle Val di Pesa

Ramona S.

AED 1,184 total

includes taxes & fees

10 Oct - 11 Oct

A living room with a dining table, two sofas, a coffee table, and a ceiling fan.

5. casagreve - stylish house in Tuscan village - breathtaking view from its terrace

Greve in Chianti

Linda L.

AED 1,485 total

includes taxes & fees

14 Oct - 15 Oct

A brick building with a garden, a metal fence, and a clear sky.

6. Casa Marisa in Castellina in Chianti

Castellina in Chianti

AED 1,111 total

includes taxes & fees

11 Oct - 12 Oct

A brick staircase leading to a black gate, surrounded by lush greenery.

7. Chalet in Chianti with swimming pool and tennis court

Siena

rich63perez U.

AED 445 total

includes taxes & fees

10 Oct - 11 Oct

A room with a large sliding glass door leading to a pool area with a view of rolling hills and a distant village.

8. Your nest in the Tuscany countryside

Certaldo - Firenze

AED 943 total

includes taxes & fees

11 Oct - 12 Oct

A stone building with a courtyard, outdoor seating, and potted plants.

9. Wonderful Tuscan farmhouse with large spaces and panoramic views

impruneta

Christine F.

AED 1,046 total

includes taxes & fees

21 Oct - 22 Oct

A covered patio with a wooden table and chairs, stone walls, and a view of a garden.

10. Villa 'Il Fienile Il Sole Verde' with Shared Pool and Wi-Fi

Bucine

AED 1,633 total

includes taxes & fees

10 Oct - 11 Oct

A stone building with a courtyard, a table with chairs, and a wheelbarrow.

11. House with views of the Chianti

impruneta

Chase B.

AED 925 total

includes taxes & fees

14 Oct - 15 Oct

An open doorway leading to an outdoor patio with a wooden table and chairs, a stone floor, and a wooden barrel with bottles.

12. Tuscan Farmhouse with Private Pool & Chianti Vineyard Views - 3 Bedr + AC

Montespertoli

"We found sanctuary at this lovely farmhouse during the July heat wave--refreshing dip in the pool, relaxing dinner in the courtyard, restful sleep in the air-conditioned home. Got up to watch the sunrise over the vineyards, absolutely stunning scenery, and watched three hot air balloons also taking in the sights. Matteo was very welcoming, and we bridged the language barrier with a little help from Google translate. Wished we could have stayed longer!"

Susan A.

AED 1,757 total

includes taxes & fees

14 Oct - 15 Oct

A swimming pool with lounge chairs and umbrellas, surrounded by greenery and hills.

13. Villa Il Frantoio with Shared Pool, Private Terrace & Wi-Fi

Montespertoli

AED 1,149 total

includes taxes & fees

10 Oct - 11 Oct

A stone building with a gravel path, outdoor seating, and greenery.

14. The Arch Among the Hills of Castellina

Topina

AED 1,148 total

includes taxes & fees

2 Nov - 3 Nov

A garden pathway leading to a stone building with a brick wall, a pergola, and a small brick structure in the background.

15. Villa 'La Tinaia Il Sole Verde' with Shared Pool and Wi-Fi

Bucine

"Upon arrival Guido had everything prepared for us. A bottle of his amazing wine that he makes along with 2 wine glasses we’re waiting on the farmhouse table. The home had 2 very comfortable bedrooms and a bathroom along with a living room and kitchen. Front porch overlooks the stunning Tuscany fields. The swimming pool was refreshing and everything was beyond perfect. This location was everything and more. The hosts were so helpful. I will come back her again..make sure to take time for the...

Marianne H.

AED 1,586 total

includes taxes & fees

10 Oct - 11 Oct

A modern kitchen with a tiled backsplash, a dining area with a table and chairs, and a staircase with a plant shelf.

16. Little cozy house

Loro Ciuffenna

AED 362 total

includes taxes & fees

13 Oct - 14 Oct

A swimming pool with lounge chairs, a tiled deck, and surrounding trees.

17. Villa 'La Stalla Il Sole Verde' with Shared Pool, Wi-Fi, Pets Allowed

Bucine

AED 1,512 total

includes taxes & fees

10 Oct - 11 Oct

A stone building with a tiled roof, a small window, and a door.

18. Mhateria Relais

Rignano Sull' Arno

Thomas K.

AED 1,263 total

includes taxes & fees

1 Nov - 2 Nov

A rectangular swimming pool with a wooden deck and metal railing, surrounded by a grassy area with trees and a clear sky.

19. Holiday Home "Limonaia" with Shared Pool, Communal Garden and Wi-Fi

Castelnuovo Berardenga

Anonymous traveler

AED 1,537 total

includes taxes & fees

11 Oct - 12 Oct

A dining area with a brick archway, wooden dining table, chairs, and a chandelier.

20. Holiday Home 'Poggio Loccano' with Private Garden and Balcony

Montevarchi

AED 1,481 total

includes taxes & fees

1 Nov - 2 Nov

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Top Chianti Region Hotel Reviews

Castello Vicchiomaggio

10/10 Excellent

"A unique stay with a picturesque view. Breakfast, lunch, and dinner were fantastic. The property was great for relaxing at but also a good launching spot for exploring some of the nearby towns and sites."

Villa I Barronci Resort & Spa

8/10 Good

"Beautiful views, good location, nice restaurants nearby, friendly staff, lovely breakfast. The heated pool is a nice touch but was always busy, even now, out of season. Sadly, the place felt a little bit run down in the outdoor areas, broken / rotten outdoor furniture and a lot of rubbish dumped around the car park. Beware the huge ants if you plan to stay in the ‘treehouse’; which we felt would benefit from a little renovation, redecoration and sealing better against insects."

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent

"This was a beautiful hotel! Everything from the room to the amenities to the staff. Most of the amenities are complimentary (sauna, steam room, pool, gym, etc). The staff were very helpful as well. We would absolutely stay here again."

Hu Norcenni Girasole Village

10/10 Excellent

"My family and I had such a great time. Such a kid friendly place and at check in they even had a little playground while you waiting and gave the kids bubbles. So great to be in nature and all of the amenities were lovely. The waterparks that were padded on the ground were genius and we did a family wine tasting which was such a lovely memory. Our stay was so nice with the deck and the grocery store is so affordable for dinners in. Love love love! My toddler played all day and there were so many times we got to relax because they had everything that we wanted or needed right on property."

Room 1

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Treat yourself

Be picky

Check prices for these dates

Our top choices for Chianti Region vacation homes

1. Agriturismo La Ferrozzola

2. UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK

3. Chianti Craft House Badia a Passignano

4. Vernaccia Country House - Agriturismo Apartment with Pool, Garden & Wi-Fi

5. casagreve - stylish house in Tuscan village - breathtaking view from its terrace

6. Casa Marisa in Castellina in Chianti

7. Chalet in Chianti with swimming pool and tennis court

8. Your nest in the Tuscany countryside

9. Wonderful Tuscan farmhouse with large spaces and panoramic views

10. Villa 'Il Fienile Il Sole Verde' with Shared Pool and Wi-Fi

11. House with views of the Chianti

12. Tuscan Farmhouse with Private Pool & Chianti Vineyard Views - 3 Bedr + AC

13. Villa Il Frantoio with Shared Pool, Private Terrace & Wi-Fi

14. The Arch Among the Hills of Castellina

15. Villa 'La Tinaia Il Sole Verde' with Shared Pool and Wi-Fi

16. Little cozy house

17. Villa 'La Stalla Il Sole Verde' with Shared Pool, Wi-Fi, Pets Allowed

18. Mhateria Relais

19. Holiday Home "Limonaia" with Shared Pool, Communal Garden and Wi-Fi

20. Holiday Home 'Poggio Loccano' with Private Garden and Balcony

Find vacation rentals that suit your style

Top Chianti Region Hotel Reviews

Castello Vicchiomaggio

Villa I Barronci Resort & Spa

Fattoria di Vegi

Borgo Vescine

Castello di Spaltenna- Small Luxury Hotels of the World

Hotel Toscana Ambassador

Relais Vignale & Spa

Villa Le Barone

Hu Norcenni Girasole Village

Explore a world of travel with Expedia

Search Vacation Homes in Chianti Region

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chianti Region vacation homes

1. Agriturismo La Ferrozzola

2. UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK

3. Chianti Craft House Badia a Passignano

4. Vernaccia Country House - Agriturismo Apartment with Pool, Garden & Wi-Fi

5. casagreve - stylish house in Tuscan village - breathtaking view from its terrace

6. Casa Marisa in Castellina in Chianti

7. Chalet in Chianti with swimming pool and tennis court

8. Your nest in the Tuscany countryside

9. Wonderful Tuscan farmhouse with large spaces and panoramic views

10. Villa 'Il Fienile Il Sole Verde' with Shared Pool and Wi-Fi

11. House with views of the Chianti

12. Tuscan Farmhouse with Private Pool & Chianti Vineyard Views - 3 Bedr + AC

13. Villa Il Frantoio with Shared Pool, Private Terrace & Wi-Fi

14. The Arch Among the Hills of Castellina

15. Villa 'La Tinaia Il Sole Verde' with Shared Pool and Wi-Fi

16. Little cozy house

17. Villa 'La Stalla Il Sole Verde' with Shared Pool, Wi-Fi, Pets Allowed

18. Mhateria Relais

19. Holiday Home "Limonaia" with Shared Pool, Communal Garden and Wi-Fi

20. Holiday Home 'Poggio Loccano' with Private Garden and Balcony

Find vacation rentals that suit your style

Top Chianti Region Hotel Reviews

Castello Vicchiomaggio

Explore a world of travel with Expedia