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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Our top choices for Chianti Region cottages

Property grounds

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

La Quercia, apartment with garden for 6/8 people in the heart of Chianti
Montespertoli
10.0 out of 10, Exceptional, (2 reviews)
"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."
United States
Mark S.
La Quercia, apartment with garden for 6/8 people in the heart of Chianti
Exterior

CASA DEGLI ULIVI - COTTAGE WITH SWIMMING POOL

CASA DEGLI ULIVI - COTTAGE WITH SWIMMING POOL
Castellina in Chianti
10.0 out of 10, Exceptional, (1 review)
"Lovely visit. The views are amazing. "
United States
lyndon s.
CASA DEGLI ULIVI - COTTAGE WITH SWIMMING POOL
Outdoor dining

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

La Misura, cottage with garden and swimming pool on the hills of Chianti
Castellina in Chianti
10.0 out of 10, Exceptional, (2 reviews)
"What a beautiful stay in the enchanting Tuscan countryside! Every detail was attended to and we could not have felt more at home. We can only dream of returning sometime!"
United States
Jami B.
La Misura, cottage with garden and swimming pool on the hills of Chianti
Studio, Patio, Ground Floor | Terrace/patio

Fullino Nero

Fullino Nero
Siena
9.6 out of 10, Exceptional, (52 reviews)
"Great stay! Clean rooms with air conditioning. Beautiful grounds "
United States
Christian
The price is AED 367
AED 420 total
includes taxes & fees
24 Jun - 25 Jun
Fullino Nero
Exterior

Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti

Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti
Monteaperti
10.0 out of 10, Exceptional, (2 reviews)
"We loved this place. Modern cabin set in a rustic Tuscan setting. Beautiful property, very comfortable stay, and very attentive staff. Family owned and operated. Amazing restaurant just steps away. A perfect place for respite"
United States
Ian F.
The price is AED 672
AED 785 total
includes taxes & fees
27 Jun - 28 Jun
Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti
Exterior

Charming double bedroom in cottage in enchanting Monteaperti with WiFi, AC

Charming double bedroom in cottage in enchanting Monteaperti with WiFi, AC
Monteaperti
10.0 out of 10, Exceptional, (1 review)
"This place was fantastic! What a gem. The bed was comfy, the AC was cold, the bathroom was perfect. We shared the cottage with another couple we were traveling with. The bedroom doors open up to a shared living area, the front entrance is through the main indoor dining area.We had breakfast outside each morning. It was perfect. The staff here is just so nice and considerate, a true family affair. A flight of stairs leads down to a lovely restaurant with plentiful outside dining that shouldn't be...
United States
Cary W.
The price is AED 672
AED 785 total
includes taxes & fees
28 Jun - 29 Jun
Charming double bedroom in cottage in enchanting Monteaperti with WiFi, AC
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.
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Top Chianti Region Hotel Reviews

Castello Vicchiomaggio

Castello Vicchiomaggio

10/10 Excellent
"I would absolutely recommend Castello Vicchiomaggio! Our room was magnificent and much larger than anticipated— very clean, had all the extras we needed (hair dryer/iron/etc), and the air conditioning worked great! The property is gorgeous and the view is unbeatable. In addition to visiting the tasting room on the property, we also visited several wineries in the area throughout our stay (Antinori and Castello Verrazzano) and it was a great home base. We enjoyed dinner at the restaurant one night (delicious!) and the included breakfast was a great perk. The pool area is also very nice and they provided a pool bag and extra towels in our room to use there. We were also very charmed by the sweet cat that lives on the grounds and the birds (house martins) that were in the area during the time of our stay! The staff was always helpful and kind— I have nothing but great things to say. One warning: our room was on the third floor of the building and there are no elevators. Luckily my husband was with me and able to haul our luggage up the tight stairs. If you have mobility issues, I would recommend asking for a room on a lower floor."
Taylor 2-night trip
Posted 19 hours ago
Castello Vicchiomaggio