A vineyard with rows of grapevines, a house surrounded by trees, and a road with vehicles.

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Check availability on Chianti Region Romantic Hotels

This weekend
Oct 30 - Nov 1
Next weekend
Nov 6 - Nov 8

Our top choices for Chianti Region romantic hotels

An aerial view of a historic building complex with a central courtyard, surrounded by vineyards and greenery.

1. La Certosa di Pontignano - Place of Charme

La Certosa di Pontignano - Place of Charme
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (579 reviews)
"Great location amazing place"
United States
Rodolfo
The price is ₩125,436
₩149,829 total
includes taxes & fees
Nov 16 - Nov 17
La Certosa di Pontignano - Place of Charme
A modern bathroom with a glass shower enclosure, a white sink, and a large mirror.

2. Palazzo Leopoldo Dimora Storica & Spa

Palazzo Leopoldo Dimora Storica & Spa
4.0 star property
Radda in Chianti
9.2 out of 10, Wonderful, (305 reviews)
"Very helpful and friendly staff, beautiful and spacious room, and wonderful location in the most lovely town in Tuscany. We loved our stay!"
Canada
Elizabeth
The price is ₩137,215
₩159,825 total
includes taxes & fees
Nov 23 - Nov 24
Palazzo Leopoldo Dimora Storica & Spa
A stone building with ivy-covered walls, a stone pathway, and a garden with flowers.

3. Belvedere di San Leonino

Belvedere di San Leonino
4.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (211 reviews)
"Brautiful scenery, convenient location. Parking was great."
Canada
Kevork
The price is ₩135,855
₩158,304 total
includes taxes & fees
Oct 29 - Oct 30
Belvedere di San Leonino
A cozy living room with a sofa, a coffee table, and a view of greenery through large windows.

4. Dievole Wine Resort

Dievole Wine Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (218 reviews)
"This stay was absolutely perfect. The staff is amazing and we had a great time! The food is also great!"
Norway
Magdalena
The price is ₩359,946
₩407,791 total
includes taxes & fees
Nov 16 - Nov 17
Dievole Wine Resort
A spacious living area with a large window, a sofa, a green armchair, and a patterned armchair.

5. Salvadonica - Borgo del Chianti

Salvadonica - Borgo del Chianti
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (318 reviews)
"Staff was super helpful and attentive. Beautiful stay"
United States
Elsa
The price is ₩84,924
₩99,327 total
includes taxes & fees
Nov 9 - Nov 10
Salvadonica - Borgo del Chianti
A pool with a view of a lush valley and distant buildings.

6. Castello Vicchiomaggio

Castello Vicchiomaggio
Greve in Chianti
9.4 out of 10, Exceptional, (443 reviews)
"Stunning property with beautiful views and extremely friendly and helpful hosts."
United States
Mary Margaret
The price is ₩246,341
₩270,975 total
includes taxes & fees
Nov 2 - Nov 3
Castello Vicchiomaggio
A stone pillar with carvings, a glass door leading outside, and a person sitting on a lounge chair.

7. Hotel Villa Campomaggio

Hotel Villa Campomaggio
4.0 star property
Radda in Chianti
9.4 out of 10, Exceptional, (195 reviews)
"Great hotel"
United States
Dario
The price is ₩196,568
₩225,088 total
includes taxes & fees
Oct 29 - Oct 30
Hotel Villa Campomaggio
A wicker chair, a lantern, and a vase of flowers on a balcony with a mountain view.

8. Borgo Del Cabreo

Borgo Del Cabreo
Greve in Chianti
10.0 out of 10, Exceptional, (288 reviews)
"Idyllic Tuscan hotel in the middle of the vineyards. Friendly staff. Great food. Easy location for seeing Chianti region."
United States
Brian
The price is ₩241,724
₩271,805 total
includes taxes & fees
Oct 31 - Nov 1
Borgo Del Cabreo
An outdoor dining area with a pool, potted plants, and umbrellas.

9. Relais Vignale & Spa

Relais Vignale & Spa
4.0 star property
Radda in Chianti
9.2 out of 10, Wonderful, (323 reviews)
"Stunning views"
United States
Ron
The price is ₩227,742
₩295,866 total
includes taxes & fees
Oct 30 - Oct 31
Relais Vignale & Spa
A stone building with a tiled pathway leading to a large planter.

10. La pietra del cabreo

La pietra del cabreo
Greve in Chianti
10.0 out of 10, Exceptional, (145 reviews)
"Breathtaking views, clean room and kind and friendly staff"
United States
Morvarid
The price is ₩241,724
₩271,806 total
includes taxes & fees
Oct 31 - Nov 1
La pietra del cabreo
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 - Place of Charme

Hotel Borgo di Cortefreda Relais - Place of Charme

8/10 Good
"It was a beautiful place. Location was perfect to travel around. It was very clean. Restaurant is decent and food was good. Breakfast was ok."
Rahul 1-night trip
Posted 14 hours ago
Hotel Borgo di Cortefreda Relais - Place of Charme