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Dec 26 - Dec 28
In two weeks
Jan 2 - Jan 4
In one month
Jan 16 - Jan 18
In two months
Feb 13 - Feb 15

Our top choices for Chianti Region cottages

Outdoor dining
OLIVE TREES HOUSE WITH POOL

Cottage in Castellina in Chianti

OLIVE TREES HOUSE WITH POOL
OLIVE TREES HOUSE WITH POOL
Outdoor dining
Casa La Misura, garden and pool in the heart of Chianti

Cottage in Castellina in Chianti

Casa La Misura, garden and pool in the heart of Chianti
10.0 out of 10, Exceptional, (2)
"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.
Casa La Misura, garden and pool in the heart of Chianti
Garden
Fullino Nero

Cottage in Siena

Fullino Nero
9.6 out of 10, Exceptional, (49)
"Great stay! Clean rooms with air conditioning. Beautiful grounds "
United States
Christian
$103 nightly
The price is $119
Dec 22 - Dec 23
Total with taxes and fees
Fullino Nero
Exterior
Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti

Cottage in Monteaperti

Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti
10.0 out of 10, Exceptional, (2)
"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.
$190 nightly
The price is $196
Dec 22 - Dec 23
Total with taxes and fees
Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti
Pool
La Fonte, our quaint little west facing cottage for two people.

Cottage in Cortona

La Fonte, our quaint little west facing cottage for two people.
$208 nightly
The price is $214
Dec 22 - Dec 23
Total with taxes and fees
La Fonte, our quaint little west facing cottage for two people.
Property grounds
The Garden of Olives

Cottage in Castiglion Fiorentino

The Garden of Olives
$231 nightly
The price is $231
Dec 22 - Dec 23
Total with taxes and fees
The Garden of Olives
Pool
A stylish Tuscan cottage for four people with stunning views over the valley and Cortona

Cottage in Cortona

A stylish Tuscan cottage for four people with stunning views over the valley and Cortona
$328 nightly
The price is $334
Dec 22 - Dec 23
Total with taxes and fees
A stylish Tuscan cottage for four people with stunning views over the valley and Cortona
Exterior
Charming double bedroom in cottage in enchanting Monteaperti with WiFi, AC

Cottage in Monteaperti

Charming double bedroom in cottage in enchanting Monteaperti with WiFi, AC
10.0 out of 10, Exceptional, (1)
"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.
$190 nightly
The price is $196
Dec 22 - Dec 23
Total with taxes and fees
Charming double bedroom in cottage in enchanting Monteaperti with WiFi, AC
Exterior
Casa Palmira - Country House

Cottage in Mulinaccio

Casa Palmira - Country House
$937 nightly
The price is $940
Jan 10 - Jan 11, 2026
Total with taxes and fees
Casa Palmira - Country House
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

Hotel Borgo di Cortefreda Relais

Hotel Borgo di Cortefreda Relais

10/10 Excellent
"The hotel and services exceeded my expectations."
Vili 2-night trip
Posted 3 weeks ago
Hotel Borgo di Cortefreda Relais

Find out more about Chianti Region

Chianti Region Cottages information

Number of reviews
51
Accommodation
29 Cottages
Lowest Price
$119
Highest Price
$940

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