Search Cottages in Chianti Region

Most properties are fully refundable. Because flexibility matters.

Save an average of 15% on thousands of hotels with Expedia Rewards

Search over 2.9 million properties and 550 airlines worldwide

Find properties with these dates

Featured Cottages in Chianti Region and around

Exceptionally pretty cottage with pool, views, in walking distance from Panzano
10.0 out of 10, Exceptional, (41)
"For our 20th anniversary since getting together, my husband and I decided to splash out on a holiday with our two daughters. The cottage was ideally located close to Panzano, where it was easy to park to go shopping at the market on Sunday and to eat out in the evening. The beds were comfortable, excellent showers, esp. the one by the downstairs bedroom. Well-stocked kitchen with a good range of cutlery and various items from olive oil to washing up liquid. The living room was a lovely place to...
Exceptionally pretty cottage with pool, views, in walking distance from Panzano
Cottage "Podere in Volpaia" with Garden & Wi-Fi
10.0 out of 10, Exceptional, (2)
"Nous avons séjourné 10 jours dans cette charmante maison en Août 2023. Cristina nous a bien accueillie, la maison est très fonctionnelle, Il y a une belle terrasse couverte et un petit coin de verdure privé. La maison est entourée de vignes et d'oliviers, nous avons pu déguster l'huile et le chianti produits sur place. Cristina, la propriétaire, nous a organisé un repas et nous a fait déguster les vins de sa production. Le petit village de Radda est à 10 min en voiture, on y trouve tout ce...
Cottage "Podere in Volpaia" with Garden & Wi-Fi
La Misura, cottage with garden and swimming pool on the hills of Chianti
10.0 out of 10, Exceptional, (2)
"We had a wonderful couple days at La Misura. Niccolò was super nice and helped us get settled. The view was like a painting of Tuscany. It was everything we could have wanted. This is a beautiful location. We will go back soon. Thank you!"
La Misura, cottage with garden and swimming pool on the hills of Chianti
Save an average of 15% on thousands of hotels when you're signed in
La Quercia, apartment with garden for 6/8 people in the heart of Chianti
10.0 out of 10, Exceptional, (2)
"We had a wonderful 7 day stay. The location is perfect. It is an easy drive to all the towns in Tuscany. The property is beautiful and quiet. The views are amazing. Patrizia was a great host and very helpful with restaurant and winery recommendations."
La Quercia, apartment with garden for 6/8 people in the heart of Chianti
Il Girasole, apartment in farmhouse with garden in the heart of Chianti
10.0 out of 10, Exceptional, (1)
"Hôtes adorables, disponibles et attentionnés. Appartement impeccable et frais dans un vallon du Chianti magnifique. Problèmes de réseau et de chemin cahoteux largement compensés par la qualité de l'endroit et la position stratégique au regard des balades et visites à faire dans cette splendide région."
Il Girasole, apartment in farmhouse with garden in the heart of Chianti
Apartment/ flat - Barberino val d'ElsaHouse with character
9.8 out of 10, Exceptional, (39)
"We had a lovely 12 day stay in this charming little villa near Tuscany. Loretta was a wonderful host and the location was perfect for us. We enjoyed exploring Sienna, Florence and nearby Poggibonsi, but days in the pool at the villa were hard to beat (especially with the 40 degree heat)."
Apartment/ flat - Barberino val d'ElsaHouse with character
Typical country house with garden near Florence Siena Pisa San Gimignano
9.8 out of 10, Exceptional, (47)
"Distant views of olive groves and vineyards. Misty cool mornings, listening to church bells and birdsong. THIS was our home base in Tuscany that we were lucky enough to have discovered. All of the photos and descriptions do not do justice to this beautiful villa 30 minutes outside of Florence! Close to the tram, which brought us into Florence 4 times during our incredible 2 week stay we also took advantage of our rented car to drive the beautiful scenic roads to nearby medieval villages and...
Typical country house with garden near Florence Siena Pisa San Gimignano
Cottage. DEPENDANCE IL BORRACCIO con vista giardino sulla campagna del Chianti.
8.8 out of 10, Excellent, (16)
"We loved the area, outside space, pool and the host of this property. A slightly better equipped kitchen would have made property perfect, especially as we stayed in August and were not allowed to have a bbq due to fire risk. Overall we had a lovely holiday and would recommend the villa to others."
Cottage. DEPENDANCE IL BORRACCIO con vista giardino sulla campagna del Chianti.
Belvilla by OYO Cottage in Tavarnelle with Garden
8.0 out of 10, Very good, (1)
Belvilla by OYO Cottage in Tavarnelle with Garden
Casa Antico Roseto - cottage with swimming pool
8.0 out of 10, Very good, (1)
"The villa is lovely. The property is amazing. Check-in and out were easy and the owners are very kind. The only complaint we really had with our stay was that it is probably not the best place to stay during the summer months when it is 95+ outside. The villa has no air conditioning and even the fans they provided us did not prepare us for the heat inside even late at night. When we opened the windows we had a lot of mosquitoes and other bugs enter the house so we were forced to close up most of...
Casa Antico Roseto - cottage with swimming pool
Charming 4-Bed Cottage 15 minutes from Florence
Charming 4-Bed Cottage 15 minutes from Florence
Podere le Fonti
Podere le Fonti
Casa Belvedere cottage with swimming pool in the heart of Chianti
Casa Belvedere cottage with swimming pool in the heart of Chianti
Beautiful 1-bedroom cottage with garden and views over olive groves, pool
Beautiful 1-bedroom cottage with garden and views over olive groves, pool
Belvilla by OYO Cottage in Tavarnelle With Garden
Belvilla by OYO Cottage in Tavarnelle With Garden
Charming 4-bed Cottage 15 Minutes From Florence
Charming 4-bed Cottage 15 Minutes From Florence
CASA DEGLI ULIVI - COTTAGE WITH SWIMMING POOL
CASA DEGLI ULIVI - COTTAGE WITH SWIMMING POOL
Casa il Cipresso, in the heart of Chianti with swimming pool
Casa il Cipresso, in the heart of Chianti with swimming pool
Villa Gaia
Villa Gaia
Cottage nel Chianti con Piscina. Vista Sulle Colline e sui Vigneti Toscani
Cottage nel Chianti con Piscina. Vista Sulle Colline e sui Vigneti Toscani
Don't see what you're looking for?
See all available properties in Chianti Region
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other property types in Chianti Region

ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
10.0 out of 10, Exceptional, (49)
"We cannot recommend this villa highly enough!! There are no words to fully describe the beauty of Isola Serena. The main villa & new guesthouses, along with the outdoor spaces, were so thoughtfully and beautifully restored - the property was both luxurious and authentic to Tuscan style. It was easily the most beautiful place we have ever had the opportunity to stay, with views that almost seemed like they couldn't be real! The hosts, Serena and Peter, were so kind and communicative before &...
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
Villa Il Palagio
8.6 out of 10, Excellent, (23)
"A great suite. Reception can help with taxis to and from the local train station. Fast trains to Firenze / Florence. Restaurant only open for breakfast during the low season, so dinner is a bit of a mission: Reception helped with ordering pizza 🍕"
The price is €149
per night
16 May - 17 May
Villa Il Palagio
Hu Norcenni Girasole Village
4.0 star property
8.4 out of 10, Very good, (236)
"The location is really beautiful. There are constant shuttles to transport from one location to other within the property. Nice food options and music on specific days Clean Cabins If you have not booked shuttle from the Figline station to this place- you may have a hard time getting a taxi from the station. I recommend to plan ahead for the commute from the train station to this property."
The price is €41
per night
13 May - 14 May
Hu Norcenni Girasole Village
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.