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
Nov 6 - Nov 8
Next weekend
Nov 13 - Nov 15

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, (580 reviews)
"Great location amazing place"
United States
Rodolfo
The price is NT$2,351
NT$2,877 total
includes taxes & fees
Nov 4 - Nov 5
La Certosa di Pontignano - Place of Charme
A spa area with a stone ceiling, a pool, and two sun loungers.

2. Hotel Palazzo San niccolò & Spa

Hotel Palazzo San niccolò & Spa
4.0 star property
Radda in Chianti
9.2 out of 10, Wonderful, (198 reviews)
"Great stay!"
United States
Afeefa
The price is NT$2,367
NT$2,822 total
includes taxes & fees
Dec 1 - Dec 2
Hotel Palazzo San niccolò & Spa
A modern hotel room with a bed, a desk, a chair, and a TV.

3. Park Hotel Chianti

Park Hotel Chianti
4.0 star property
Tavarnelle Val di Pesa
9.0 out of 10, Wonderful, (280 reviews)
"The staff are very helpful and kind."
Canada
Manuel
The price is NT$2,072
NT$2,497 total
includes taxes & fees
Nov 22 - Nov 23
Park Hotel Chianti
A spacious room with a high wooden ceiling, a fireplace, and a large arched doorway. There are several pieces of antique furniture, including a sofa and armchairs.

4. Castello Di Montemasso

Castello Di Montemasso
Greve in Chianti
9.8 out of 10, Exceptional, (28 reviews)
"The Castello Di Montemasso is a beautiful place with nice staffs. Their breakfast is awesome."
United States
Quan
The price is NT$3,572
NT$3,965 total
includes taxes & fees
Nov 8 - Nov 9
Castello Di Montemasso
A stone building with ivy-covered walls, a stone pathway, and a garden with flowers.

5. 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 NT$3,485
NT$4,052 total
includes taxes & fees
Nov 11 - Nov 12
Belvedere di San Leonino
A modern interior with a yellow sofa, blue armchair, and a dining area with chairs and a table.

6. Moody smart & comfy Hotel

Moody smart & comfy Hotel
3.0 star property
Terranuova Bracciolini
9.6 out of 10, Exceptional, (13 reviews)
"Alles was perfect!"
Belgium
Rocco
The price is NT$3,163
NT$4,134 total
includes taxes & fees
Nov 5 - Nov 6
Moody smart & comfy Hotel
A spa area with stone walls, a white massage chair, and a potted plant.

7. 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 NT$3,370
NT$3,925 total
includes taxes & fees
Nov 23 - Nov 24
Palazzo Leopoldo Dimora Storica & Spa
An indoor courtyard with stone flooring, arched columns, and tables set up for dining.

8. Villa Casagrande Resort & SPA

Villa Casagrande Resort & SPA
4.0 star property
Figline e Incisa Valdarno
9.2 out of 10, Wonderful, (414 reviews)
"Restaurant was great. Towels have too much use"
United States
Ana
The price is NT$3,507
NT$3,931 total
includes taxes & fees
Nov 8 - Nov 9
Villa Casagrande Resort & SPA
An outdoor dining area with a table and chairs, surrounded by greenery and a view of a building in the background.

9. Chiantirooms Guesthouse

Chiantirooms Guesthouse
Greve in Chianti
9.8 out of 10, Exceptional, (53 reviews)
"Friendly host and great place to stay. "
Canada
Pasquale
The price is NT$3,299
NT$3,774 total
includes taxes & fees
Nov 6 - Nov 7
Chiantirooms Guesthouse
A courtyard with snow-covered plants and a metal railing.

10. Bed & Breakfast Le Terrazze del Chianti

Bed & Breakfast Le Terrazze del Chianti
Tavarnelle Val di Pesa
9.6 out of 10, Exceptional, (45 reviews)
"Unique was the Terrasse… wonderful view on the village and surroundings"
Germany
Janine und Thomas
The price is NT$2,850
NT$3,281 total
includes taxes & fees
Dec 3 - Dec 4
Bed & Breakfast Le Terrazze del Chianti
A covered outdoor seating area with a tiled roof, surrounded by lush greenery and a view of distant hills.

11. Hotel Villa San Giorgio

Hotel Villa San Giorgio
3.0 star property
Poggibonsi
9.0 out of 10, Wonderful, (116 reviews)
"Very buetifull hotel with magnificent view on Tuscany hills. Very kind staff, clean room and Very good breakfast."
United States
Arik
The price is NT$1,951
NT$2,146 total
includes taxes & fees
Nov 22 - Nov 23
Hotel Villa San Giorgio
A hotel with a prominent "HOTEL" sign, a name sign below, and a well-lit entrance.

12. Hotel Il Viandante

Hotel Il Viandante
3.0 star property
Terranuova Bracciolini
9.2 out of 10, Wonderful, (172 reviews)
"I always stay here when in town. The staff are lovely. The hotel is cozy. And the breakfast is the best you will find!"
United States
jessica
The price is NT$2,962
NT$3,986 total
includes taxes & fees
Nov 8 - Nov 9
Hotel Il Viandante
An outdoor patio with stone flooring, tables, chairs, string lights, and potted plants.

13. Agriturismo Montemagni di Sopra

Agriturismo Montemagni di Sopra
Greve in Chianti
9.6 out of 10, Exceptional, (22 reviews)
"Amazing stay. Will be coming back next time I'm in the area."
United States
Abel
The price is NT$4,340
NT$4,919 total
includes taxes & fees
Nov 3 - Nov 4
Agriturismo Montemagni di Sopra
A person sitting by a swimming pool with a stone building in the background.

14. Hotel Borgo di Cortefreda Relais - Place of Charme

Hotel Borgo di Cortefreda Relais - Place of Charme
4.0 star property
Tavarnelle Val di Pesa
9.4 out of 10, Exceptional, (531 reviews)
"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."
United States
Rahul
The price is NT$3,322
NT$3,872 total
includes taxes & fees
Nov 29 - Nov 30
Hotel Borgo di Cortefreda Relais - Place of Charme
A yellow building with stone pillars, multiple windows, and a statue in the garden.

15. Villa San Lucchese

Villa San Lucchese
4.0 star property
Poggibonsi
9.4 out of 10, Exceptional, (360 reviews)
"Very nice"
United Kingdom
James
The price is NT$3,109
NT$3,420 total
includes taxes & fees
Nov 29 - Nov 30
Villa San Lucchese
A stone house with a tiled roof, large glass doors, and a stone pathway leading to it.

16. The Club House

The Club House
5.0 star property
Castelnuovo Berardenga
10.0 out of 10, Exceptional, (23 reviews)
"Beautiful property excellent staff great spa loved everything about it!!"
United States
Natalyn
The price is NT$11,596
NT$13,119 total
includes taxes & fees
Nov 9 - Nov 10
The Club House
A building with a courtyard, arched entrance, and surrounding trees.

17. Villa il Poggiale - Dimora Storica

Villa il Poggiale - Dimora Storica
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (163 reviews)
"Such a magical place to stay! And the restaurant was delicious"
United States
Amber
The price is NT$3,284
NT$3,649 total
includes taxes & fees
Dec 2 - Dec 3
Villa il Poggiale - Dimora Storica
A stone building with a tiled roof, green shutters, and a small staircase leading to a door.

18. Castello di Fonterutoli Wine Resort

Castello di Fonterutoli Wine Resort
Castellina in Chianti
9.4 out of 10, Exceptional, (234 reviews)
"The staff and experience staying at Castello Di Fonterutoli was amazing! Everyone was so kind and welcoming! Cannot wait to go back☺️"
United States
Micaela
The price is NT$5,923
NT$6,661 total
includes taxes & fees
Nov 15 - Nov 16
Castello di Fonterutoli Wine Resort
A poolside area with lounge chairs and a large pool, surrounded by well-manicured lawns and tall cypress trees.

19. One Belvedere Tuscany

One Belvedere Tuscany
Poggibonsi
9.8 out of 10, Exceptional, (9 reviews)
"Beautiful property with the best staff."
Canada
Hyun Min
The price is NT$8,185
NT$9,003 total
includes taxes & fees
Nov 3 - Nov 4
One Belvedere Tuscany
A balcony with a view of a town square, a clock tower, and a street with parked cars.

20. Hotel Bellavista Impruneta

Hotel Bellavista Impruneta
3.0 star property
Impruneta
9.2 out of 10, Wonderful, (134 reviews)
"We had a great stay at this hotel, staff was amazing and very helpful, room was excellent, clean and made us feel safe and comfortable!"
United States
NORMA
The price is NT$1,928
NT$2,266 total
includes taxes & fees
Nov 5 - Nov 6
Hotel Bellavista Impruneta
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

Borgo Vescine

Borgo Vescine

10/10 Excellent
"There are no words to describe our experience at this incredibly beautiful and wonderful charming several century old village resort in Chianti. It was everything you imagined Italy to be in wine country. Probably one of my favorite places I have ever stayed at, and I’ve stayed at hundreds of of places around the world. The staff was wonderful, the accommodations were just super cool. It was once a village dating back over 100+ years. It was truly remarkable that the owner discovered it and restored it, creating a truly wonderful experience and beautiful Tuscany. We definitely will stay here every time we go to Tuscany in the future. This is a must-stay place!"
James 2-night trip
Posted 2 days ago
Borgo Vescine

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