Chianti Region Vacation Homes

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

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 Chianti Region holiday homes

1. 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

HK$1,435 total

includes taxes & fees

4 Aug - 5 Aug

2. Chianti Craft House Badia a Passignano

Barberino Tavarnelle

Oscar O.

HK$1,654 total

includes taxes & fees

10 Aug - 11 Aug

3. Villa with large garden in the Chianti hills

Siena

Julie H.

HK$1,248 total

includes taxes & fees

1 Sept - 2 Sept

4. Casa Marisa in Castellina in Chianti

Castellina in Chianti

HK$2,441 total

includes taxes & fees

1 Sept - 2 Sept

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

Greve in Chianti

Linda L.

HK$3,263 total

includes taxes & fees

31 Aug - 1 Sept

6. House with views of the Chianti

impruneta

Chase B.

HK$2,278 total

includes taxes & fees

30 Aug - 31 Aug

7. Wonderful Tuscan farmhouse with large spaces and panoramic views

impruneta

Christine F.

HK$2,432 total

includes taxes & fees

26 Aug - 27 Aug

8. Farmhouse in Chianti

gaiole in chianti

"This location provided our blended family an authentic experience in a small village on top of a mountain in Chianti. The house is surrounded by olive groves and wine grapes. The pool was great and the village, literally less than a city block up the road. Folks are incredibly friendly and helpful. Two of the rooms had their own bathrooms and the other two share a bathroom. There is a common kitchen for cooking and eating. We cooked most nights and ate on the outside terrace. Allesandra is a...

Lara W.

HK$4,972 total

includes taxes & fees

1 Sept - 2 Sept

9. Holiday Home 'Il Piccolo Rifugio' with Private Pool, Garden and Wi-Fi

Figline Valdarno

HK$2,350 total

includes taxes & fees

24 Aug - 25 Aug

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

Montevarchi

HK$2,613 total

includes taxes & fees

10 Aug - 11 Aug

11. Historic 'Felciolina' Country House with Private Terrace, 30 Minutes from Florence

Rignano sull'Arno

Anonymous traveller

HK$1,499 total

includes taxes & fees

1 Sept - 2 Sept

12. The Arch Among the Hills of Castellina

Topina

HK$2,956 total

includes taxes & fees

1 Sept - 2 Sept

13. Holiday Home 'Sandra House Certaldo' with Private Garden and Wi-Fi

Certaldo

Anonymous traveller

HK$1,609 total

includes taxes & fees

1 Sept - 2 Sept

14. Country Resort in Impruneta with 2 bedrooms sleeps 6

Impruneta

HK$2,396 total

includes taxes & fees

1 Sept - 2 Sept

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

Montespertoli

HK$1,320 total

includes taxes & fees

1 Sept - 2 Sept

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

Bucine

"Pros: Wunderschönes charmantes, rustikales Ferienhaus in der wunderschönen Toskana. Tolle Lage, sehr freundlicher und charmanter Gastgeber. Senore Guidi und seine Ehefrau sind zauberhafte Gastgeber. Sehr hilfsbereit und zuvorkommend! Die Fotos der Unterkunft stimmen zu 100% überein! Toller Poolbereich. Senor Guidi hat zur Wein- und Olivenöl -Verkostung eingeladen und uns auf Anfrage zu einer persönlichen Begehung seiner Oliven-und-Weinberge mitgenommen. Sehr persönliche und menschliche...

Anonymous traveller

HK$4,366 total

includes taxes & fees

8 Aug - 9 Aug

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

BARBERINO TAVARNELLE

Ramona S.

HK$3,915 total

includes taxes & fees

1 Sept - 2 Sept

18. 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.

HK$4,366 total

includes taxes & fees

9 Aug - 10 Aug

19. Apartment "Bilocale Vermiglio" with Shared Pool & Wi-Fi

Castiglion Fibocchi

"Pros: Il giardino è bellissimo e curato, bella la piscina, abbiamo apprezzato anche il fatto che ci siano tavoli e panche per sedersi, gustarsi il tramonto, il pranzo o la cena nella propria privacy. L'esterno in generale è un luogo davvero rilassante. Ci sono molti spazi per i bambini. I proprietari sono stati gentili, estremamente disponibili ed è stato davvero piacevole scambiare delle chiacchiere. Cons: Il letto è un po' scomodo e il bagno è molto piccolo, privo di bidet con la porta molto...

Anonymous traveller

HK$1,469 total

includes taxes & fees

3 Aug - 4 Aug

20. Villa Latini Agriturismo La Capanna

Montespertoli

View all properties

Find holiday rentals that suit your style

Villas

Residences

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

Top Chianti Region Hotel Reviews

Relais Vignale & Spa

10/10 Excellent

"This place is absolutely amazing. The pictures don't do it justice. The rooms are simple, but the staff, food, pool, and views are wonderful. I would highly recommend this place as a couples getaway. The included breakfast and nice parking situation were huge benefits as well."

Villa I Barronci Resort & Spa

10/10 Excellent

"This was a fabulous stay. The property is beautiful, the grounds were fun to walk and the swimming pool was lovely. Breakfast every morning was delicious. Hotel was very quiet during the week but was noticeably busier starting Friday (I think local people come just for the weekend). Our room was spacious and very clean. Bed was very comfortable. There is a bar near the pool that serves drinks in the afternoon and dinner nightly on the terrace. The nearby town was so cute and had a coop as well as numerous delicious restaurants (I recommend Nonno’s for a rustic, authentic dinner, La Carboneira for pizzas and I Pini for gelato. I would stay here again and highly recommend!"

Salvadonica - Borgo del Chianti

10/10 Excellent

"This is the Tuscan escape you dream about! We absolutely loved our stay at Salvadonica! A peaceful retreat surrounded by vineyards, hills, and incredible sunsets! It’s perfectly situated to explore Chianti and other locations nearby. The restored farmhouse offers wonderful accommodations that are comfortable and private. There’s a refreshing pool, outdoor movies, yoga in the vineyard, and plenty of spaces to escape and relax. The onsite restaurant La Volpenera, was casually elegant and delicious! Try the gelato with the Salvadonica olive oil…you won’t be sorry. The included breakfast buffet featured a variety of options and was perfect start to each day. We signed up for the Wine and Olive Oil Tasting with Sommelier Irene which gave us a personalized tasting of Salvedonica’s products and history. Excellent experience! And we took the Cooking Class with Chef Ivana which was the best meal we had on our entire trip! Cooking with Ivana felt like we were spending the day with family! Everyone working here provided exceptional service! I only wish we had a longer stay! Can’t wait to return to Salvadonica!"

Villa Il Palagio

10/10 Excellent

"Our family of five enjoyed our time at the property very much. The rooms were comfortable and the surrounding area is beautiful. The pool is a huge plus to cool down and have a relaxing time. The Rignano train station nearby makes it easy to get around Italy, by connecting to Florence’s main station. Truly an asset. The A1 highway is also nearby connecting you within easy access to beautiful Tuscany. Restaurants in the area were very good also. I would definitely stay again at Vila Il Palagio."

Hotel Villa Campomaggio

10/10 Excellent

"I was fortunate enough to stay in this beautiful hotel whilst photographing a wedding in Tuscany and I was so pleased that I am hoping to stay again as soon as I can. The staff were lovely, the hotel was beautiful and the surrounding areas were stunning. The spa was clean and calming, with three different rooms to try and a jacuzzi. I was offered a free yoga class one morning and my room was cleaned before 10am every day. On my last day, I checked out at 11am after breakfast and was offered a place to keep my bags so that I could stay out by the pooI until I needed to leave. I would highly recommend this beautiful hotel to anyone travelling through Tuscany!"

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

10/10 Excellent

"Our hosts and the property lived up to all our expectations! Communication with Beatrice and Jacopo was excellent. This was especially important as we planned this trip ourselves. When we arrived, they were so welcoming. They made us feel at home. This was the perfect Tuscan experience for our family. We were 3 generations and the villa was just what we needed. The pool was a welcome respite after our days out. The kitchen was equipped with everything we needed for the days we chose to cook. But, the best meals of our trip were those cooked by Beatrice and Jacopo! We had breakfast and dinner prepared by them. An abundance of food! Don’t miss out on this! And don’t scroll past this property. Book it and you will be in for a treat!"

Find out more about Chianti Region