Chianti Region Vacation Homes from ￥16,182

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 vacation 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

￥29,560 total

includes taxes & fees

Aug 17 - Aug 18

2. Villa with large garden in the Chianti hills

Siena

Julie H.

￥25,377 total

includes taxes & fees

Sep 1 - Sep 2

3. Chianti Craft House Badia a Passignano

Barberino Tavarnelle

Oscar O.

￥33,652 total

includes taxes & fees

Aug 16 - Aug 17

4. House with views of the Chianti

impruneta

Chase B.

￥42,847 total

includes taxes & fees

Aug 31 - Sep 1

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

Greve in Chianti

Linda L.

￥67,120 total

includes taxes & fees

Aug 16 - Aug 17

6. Wonderful Tuscan farmhouse with large spaces and panoramic views

impruneta

Christine F.

￥45,973 total

includes taxes & fees

Sep 8 - Sep 9

7. Casa Marisa in Castellina in Chianti

Castellina in Chianti

￥49,651 total

includes taxes & fees

Sep 13 - Sep 14

8. 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.

￥90,106 total

includes taxes & fees

Sep 8 - Sep 9

View all properties

Find vacation rentals that suit your style

Villas

Aparthotels

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

Top Chianti Region Hotel Reviews

Villa Casagrande Resort & SPA

10/10 Excellent

"What a wonderful 3 night break at Villa Casagrande! My wife and I had a beautiful stay in this historic villa. There’s a little steep walk up to the pool and restaurant next to it which were perfect and where we spent most of our time relaxing and sunbathing with the view of the trees and the Tuscan mountains. The staff were incredible, so kind, quick to help and made our stay even more pleasant. We both had lovely massages and relaxed in the spa area and one evening did the historic tour and wine tasting which was exceptional. The guides and sommeliers were so knowledgeable and so lovely and the organic Chianti wines they produce are an absolute must to taste and buy. The hotel’s main restaurant was the best in Filigne (the local town) and the food was incredible. One of the nights we had a live musician who was fantastic. We had dinner twice there; mushroom tagliatelle, the lamb, the wild boar gnocchi and paccheri carbonara were to die for! It’s only 50 mins on the train to Florence which is one of our favourite cities to explore in one day and we picked this place especially because it’s only a 12 minute walk from the Filigne Valdarno station and avoids the need to hire a car. We went for the comfort room which was spacious and clean and the air con was great and important for us it had a powerful shower. We truly had a wonderful time and absolutely cannot wait to go back next year! Grazie Villa Casagrande!"

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

10/10 Excellent

"Our family of 18 stayed at the Villa this July (2026) and could not have been more pleased with everything associated with our stay. Jacopo and Beatrice truly are first class hosts. They helped us book 3 vehicles that were dropped off and picked up directly at the Villa which was a great time saver. They also provided a grocery shopping service so that we had drinks and snacks at the villa when we arrived.The meal service was truly fantastic! We opted for the Welcome dinner and the Florentine BBQ, both of which were great. We visited a lot of places while in Italy but the family dinners at sunset were among our favorites.The Villa was beautiful and spacious. The grandkids really enjoyed the open spaces and the pool. The views from the back deck of the surrounding Tuscan countryside were also very special. We even got to see hot air balloons on a few occasions. The relative close proximity to Firenze was also clutch for day trips on high-speed trains. There is a good reason why this Villa won the VRBO Vacation Rental of the Year. You simply cannot go wrong here. I am very thankful for the memories that will last a lifetime and role this villa and the hosts played in making that happen!"

Find out more about Chianti Region

Chianti Region Vacation Homes information

Number of reviews	133
Accommodation	417 Vacation Homes
Lowest Price	￥16,182
Highest Price	￥133,137

Explore a world of travel with Expedia

San Gimignano Vacations

Car rental Greve in Chianti

Book Vacation Homes in Chianti Region on Expedia.it

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chianti Region vacation homes

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

2. Villa with large garden in the Chianti hills