Chianti Region Cottage: Find The Top Holiday Cottages in Chianti Region

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 cottages

A stone building with a pathway leading to it, surrounded by trees and greenery.

1. Casa il Cipresso, in the heart of Chianti with swimming pool

Castellina in Chianti

Guillermo A.

A rustic outdoor dining area with a stone wall, wooden furniture, and potted plants.

2. La Misura, cottage with garden and swimming pool on the hills of Chianti

Castellina in Chianti

Jami B.

A stone building with a gravel path, potted plants, and a large vase with flowers.

3. Il Melograno, Chianti apartment in farmhouse for 4 people with garden

Montespertoli

An aerial view of a rural estate with a large building, a swimming pool, and surrounding vegetation.

4. Casa Antico Roseto - cottage with swimming pool

Castellina in Chianti

"The borgo was perfect for our family of 6 adults. The views from the pool were spectacular. We had what we needed in kitchen and we grilled one night. The stone structure set on mountainside gave natural coolness for comfort with amazing views- even from the shower! There is AC which we didn’t use but good idea for peak summer. We walked to a great restaurant and also walked to winery for wine tasting. We shared the property but it felt private with our own outdoor dining areas. Maurizio was...

Lisa S.

A stone building with a small entrance, a chimney, and a view of green hills.

5. CASA DEGLI ULIVI - COTTAGE WITH SWIMMING POOL

Castellina in Chianti

lyndon s.

6. La Quercia, apartment with garden for 6/8 people in the heart of Chianti

Montespertoli

Mark S.

A stone building with a view of rolling hills.

7. Casa Belvedere cottage with swimming pool in the heart of Chianti

Castellina in Chianti

A stone building with a rustic entrance, a small patio area with outdoor furniture, and a wooden fence in the foreground.

8. Fullino Nero

Siena

Christian

includes taxes & fees

20 Sept - 21 Sept

View all properties

Find holiday rentals that suit your style

Aparthotels

Villas

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

Top Chianti Region Hotel Reviews

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."