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

Tonight
Sep 23 - Sep 24
Tomorrow
Sep 24 - Sep 25
This weekend
Sep 25 - Sep 27
Next weekend
Oct 2 - Oct 4

Our top choices for Chianti Region romantic hotels

A candle on a tray with corks, a glass with a drink and an orange slice, and a table with chairs in an outdoor setting with arches in the background.
A corridor with a wooden door at the end, a metal railing on one side, and a light fixture above.
An aerial view of a historic building complex with a central courtyard, surrounded by vineyards and greenery.
An interior corridor with arches, columns, and a brick wall.

1. La Certosa di Pontignano

La Certosa di Pontignano
Castelnuovo Berardenga
United States
Roberto
NT$3,182
NT$3,791 total
includes taxes & fees
Oct 16 - Oct 17
La Certosa di Pontignano
A stone pillar with carvings, a glass door leading outside, and a person sitting on a lounge chair.
A landscaped garden with a swimming pool, a vineyard in the background, and a stone pathway.
An aerial view of a property with a swimming pool, a sun terrace, and a vineyard in the background.
A spa area with stone flooring, wooden chairs, a table with amenities, and a view of a garden through a glass door.

2. Hotel Villa Campomaggio

Hotel Villa Campomaggio
Radda in Chianti
United States
Krishna
NT$5,795
NT$6,593 total
includes taxes & fees
Oct 20 - Oct 21
Hotel Villa Campomaggio
An outdoor dining area with a pool, potted plants, and umbrellas.
An outdoor dining area with a table set for two, overlooking a pool and vineyard.
A villa with a swimming pool, outdoor seating, and a garden.
A restaurant with a table set for two, overlooking a scenic landscape.

3. Relais Vignale & Spa

Relais Vignale & Spa
Radda in Chianti
United States
Ali
NT$5,598
NT$7,273 total
includes taxes & fees
Oct 8 - Oct 9
Relais Vignale & Spa
A pool with a view of a lush valley and distant buildings.
A bedroom with a large arched window, a bed, a hanging light fixture, and a view of a green landscape.
A terraced vineyard with stone walls and a stone pathway leading to a seating area with metal chairs and tables.
A courtyard with stone buildings, arched doorways, and potted plants.

4. Castello Vicchiomaggio

Castello Vicchiomaggio
Greve in Chianti
Canada
Maryse
NT$5,125
NT$5,638 total
includes taxes & fees
Sep 27 - Sep 28
Castello Vicchiomaggio
A cobblestone street lined with historic stone buildings, some with ivy, and large terracotta pots with flowers.
A lobby with a marble reception desk, a vase with pampas grass, and a view of the garden through a large window.
An outdoor patio with stone flooring, a table with chairs, and potted plants.

5. Hotel Borgo San Luigi

Hotel Borgo San Luigi
Monteriggioni
Canada
Raman
NT$5,019
NT$5,775 total
includes taxes & fees
Oct 23 - Oct 24
Hotel Borgo San Luigi
A rustic cellar with brick walls, wooden barrels, and a stone ceiling. There is a wooden table with a wine bottle and glasses, and a television mounted on the wall.
A person relaxing in a hot tub with a view of a building and trees in the background.
A rustic stone building with a garden in front.
A stone building with ivy-covered walls, a stone pathway, and a garden with flowers.

6. Belvedere di San Leonino

Belvedere di San Leonino
Castellina in Chianti
Canada
Els
NT$3,947
NT$4,560 total
includes taxes & fees
Oct 15 - Oct 16
Belvedere di San Leonino
A pool with a stone wall and a tree, surrounded by a clear sky and distant mountains.
A room with a wooden door, a white cabinet with a book and candles, and two framed pictures on the wall.
A stone wall, a pink building, and a pool with a garden.
A minimalist room with a wooden desk, two chairs, a mirror, and a vase with flowers.

7. Villa Barberino

Villa Barberino
Meleto
United Kingdom
Claire
NT$5,253
NT$5,778 total
includes taxes & fees
Oct 15 - Oct 16
Villa Barberino
A spacious lobby with a stone archway, wooden ceiling beams, a bar area with a wine rack, and a reception desk.
A rustic interior with a brick archway, wooden beams, a bar area, and potted plants.
A clear blue pool with lounge chairs and a stone building in the background.
A stone building with a wooden bench outside.

8. Hotel Colle Etrusco Salivolpi

Hotel Colle Etrusco Salivolpi
Castellina in Chianti
United States
Monica
NT$3,971
NT$4,477 total
includes taxes & fees
Oct 18 - Oct 19
Hotel Colle Etrusco Salivolpi
A poolside area with outdoor seating and umbrellas, overlooking a scenic landscape.
A bedroom with a large bed, a view of a green landscape through a sliding door, and a potted plant on the windowsill.
A table with breakfast items, a clear view of the countryside, and a white umbrella.
A pathway lined with wooden fences and benches, leading to a covered seating area with tables and chairs.

9. Villa I Barronci Resort & Spa

Villa I Barronci Resort & Spa
San Casciano in Val di Pesa
United States
Juan Antonio
NT$4,335
NT$4,986 total
includes taxes & fees
Oct 23 - Oct 24
Villa I Barronci Resort & Spa
A stone staircase leading to a door, surrounded by stone walls and a potted plant with green leaves and purple flowers.
A pool surrounded by lush greenery and vineyards, with a stone building in the background.
A rustic interior with a stone fireplace, wooden beams, and a staircase leading to an upper level.
A stone building with a window and a light fixture.

10. Agriturismo San Sano

Agriturismo San Sano
Gaiole in Chianti
Australia
Glen
NT$2,357
NT$2,738 total
includes taxes & fees
Oct 18 - Oct 19
Agriturismo San Sano
View all properties

Top Chianti Region Hotel Reviews

Hotel Villa Campomaggio

Hotel Villa Campomaggio

10/10 Excellent
"Great hotel"
Dario 2-night trip
Posted 2 hours ago
Hotel Villa Campomaggio
Castello Vicchiomaggio

Castello Vicchiomaggio

10/10 Excellent
"very nice historic hotel with great views of the country side and great atmphere. Room size and ammenities were wonderful. The breakfeast was great. Restaurant was nice with historic dishes. Only down side was the gluten and nut free options were limited...mainly for gluten sufferers, since the only gluten free pasta is Penne, which is not great for all dishes and frustratingsince Italy produces a very large variety of great gluten free pasta shapes. Also, my travel partner and I did the same pasta, one gluten free (penne) and one not gluten free. The non-gluten-free pasta came beautifully presented, while the gluten-free pasta came like it was thrown together last minute… like as if you were sitting at your own kitchen table. Impression given with the dinner is that people with allergies, are more a bit of a bother, and the typical mission in Italy, to give visitors an excellent culinary experience, is more less abandoned for people with allergies. that said, accommodating allergies is very difficult these days and at least the menu was clear about which foods contain which allergens."
edward 2-night trip
Posted 5 days ago
Castello Vicchiomaggio
Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent
"The experience was exceptional, the dinners in both restaurants on site were spectacular. The staff was amazing, friendly, and made our stay very memorable. We are planning to return soon."
David 3-night trip
Posted 8 days ago
Castello di Spaltenna- Small Luxury Hotels of the World
COMO Castello Del Nero

COMO Castello Del Nero

10/10 Excellent
"The most beautiful hotel in the heart of Chianti. The service was above and beyond. Everything about this charming hotel was amazing. We cannot wait to go back."
Lauren 3-night trip
Posted 12 days ago
COMO Castello Del Nero
Borgo Vescine

Borgo Vescine

10/10 Excellent
"⭐️⭐️⭐️⭐️⭐️ We genuinely did not want to leave Borgo Vescine was everything we hoped a stay in Tuscany would be. The property is absolutely stunning, incredibly peaceful, and so beautifully cared for that once we arrived, we honestly didn’t want to leave. What made the experience even more special was the staff. Everyone we encountered was warm, welcoming and genuinely delightful. The hospitality never felt forced or overly formal. We simply felt very well taken care of throughout our stay. We had dinner at the property and the restaurant was excellent, which made staying in for the evening an easy decision. Breakfast was included with our stay and was such a delicious treat each morning. Being able to wake up somewhere this beautiful, have a wonderful breakfast and then simply enjoy the property was exactly the kind of Tuscan experience we were looking for. The grounds themselves are gorgeous and meticulously maintained, with beautiful views and so many quiet little areas to sit and take everything in. Despite everything the property offers, it still feels serene, intimate and wonderfully quiet. Borgo Vescine is the kind of place that makes you reconsider whatever plans you had for the day because you would rather just stay there. One of our favorite stays in Tuscany and a property I would happily return to. Highly recommend."
Nadege 1-night trip
Posted 13 days ago
Borgo Vescine
Villa Le Barone

Villa Le Barone

10/10 Excellent
"Excellent stay with wonderful , friendly staff!"
Kathleen 3-night trip
Posted 2 weeks ago
Villa Le Barone

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