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

Search Hotels with Entertainment in Chianti Region

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Check availability on Chianti Region Hotels with Entertainment

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

Our top choices for Chianti Region hotels with entertainment

A swimming pool with a stone deck, surrounded by trees and a castle-like building in the background.
A room with a large window offering a view of a hilly landscape. There is a sofa with patterned upholstery and a lamp on a side table.
An outdoor dining area with stone buildings and a tower, illuminated by ambient lighting.
A restaurant with stone walls and a high ceiling, featuring tables set for dining.

1. Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World
Gaiole in Chianti
United States
Rama
£333
includes taxes & fees
21 Oct - 22 Oct
Castello di Spaltenna- Small Luxury Hotels of the World
A stone building with a garden in front.
A stone building with a bell tower, arched windows, and a gravel driveway.
A view through a window with a metal grid, featuring a stone building, greenery, and a clear sky.
A courtyard with stone walls, potted plants, and a metal fence.

2. Borgo Argenina

Borgo Argenina
Gaiole in Chianti
United States
Tatevik
£150
includes taxes & fees
28 Sept - 29 Sept
Borgo Argenina
A spacious lobby with a reception desk, seating area, and a large vase.
A hotel room with two beds, a desk with a computer, a chair, and a tray of breakfast items.
A modern hotel lobby with a curved reception desk, seating area, and a bar.
A hotel room with a large bed, two armchairs, a small table with a tray of breakfast items, a television, and curtains.

3. Hotel Valdarno

Hotel Valdarno
Montevarchi
United States
Emmanuel
£90
includes taxes & fees
24 Sept - 25 Sept
Hotel Valdarno
A courtyard with stone walls, arched windows, and potted plants.
An outdoor courtyard with stone walls, arched windows, and potted plants.
A covered outdoor area with brick arches, potted plants, and a door leading to a building.
A rustic interior with a stone wall, a wooden staircase, and a view of the outdoors.

4. Castello di Bossi

Castello di Bossi
Castelnuovo Berardenga
Mexico
CESAR JAVIER
£143
includes taxes & fees
20 Oct - 21 Oct
Castello di Bossi
A pool area with lounge chairs and a view of a vineyard.
An aerial view of a castle-like building surrounded by lush greenery and vineyards.
A narrow alleyway with cobblestone path, surrounded by traditional stone buildings with green shutters.
An outdoor dining area with tables arranged in a semi-circle, surrounded by trees and a view of the countryside.

5. Agriturismo Bio Fattoria Bacio

Agriturismo Bio Fattoria Bacio
Certaldo
United States
Ulrike
£78
includes taxes & fees
28 Sept - 29 Sept
Agriturismo Bio Fattoria Bacio
A large building with multiple rooms, surrounded by a field of lavender.
An outdoor dining area with tables set for a meal, a sign indicating a wine list, and a view of the landscape.
A historic estate with a central courtyard, surrounded by lush gardens and vineyards.
A swimming pool with lounge chairs and umbrellas, surrounded by stone buildings and trees.

6. Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais
Castelnuovo Berardenga
United States
Hannah
£478
includes taxes & fees
7 Oct - 8 Oct
Borgo Scopeto Wine & Country Relais
A swimming pool with a clear blue water surface, surrounded by a well-lit deck area with outdoor seating.
A corridor with a vine-covered archway leading to a building entrance.
A breakfast table with bowls of cereal, a glass of orange juice, and a cup.
A corridor with a tiled floor leading to a building with a white exterior and multiple windows.

7. Villa Il Palagio

Villa Il Palagio
Rignano sull'Arno
United States
Amber
£79
includes taxes & fees
28 Sept - 29 Sept
Villa Il Palagio
A clear blue pool with a view of green hills and a distant building.
A billiards table in a room with stone walls, a wooden ceiling, and a cozy seating area.
A balcony with a table and chairs, overlooking a mountainous landscape.
A compact kitchen with a wooden ceiling, a sink, and a small countertop.

8. Casale Rosennano Apartment – Shared Garden, Wi-Fi, Medieval Setting

Casale Rosennano Apartment – Shared Garden, Wi-Fi, Medieval Setting
Rosennano
£328
includes taxes & fees
24 Sept - 25 Sept
Casale Rosennano Apartment – Shared Garden, Wi-Fi, Medieval Setting

9. Villa Sunset, in the heart of Chianti

Villa Sunset, in the heart of Chianti
Greve in Chianti
Italy
elisa b.
Villa Sunset, in the heart of Chianti
A dining room with a large wooden table, chairs, a chandelier, and a painting on the wall.
A building with a large entrance, potted plants, and a statue in the foreground.
A room with a chandelier, a piano, a sofa, and a large painting on the wall.
A room with a fireplace, two sofas, a table, and two lamps.

10. Villa Milani with Shared Pool, Private Terrace & Wi-Fi

Villa Milani with Shared Pool, Private Terrace & Wi-Fi
Montespertoli
United States
Scott M.
£1,700
includes taxes & fees
30 Sept - 1 Oct
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
View all properties

Top Chianti Region Hotel Reviews

Hu Norcenni Girasole Village

Hu Norcenni Girasole Village

10/10 Excellent
"Perfect can’t fault it. Maybe a bigger train/bus at peak times would help. Lovely restaurant, bars, ice cream. Clean swimming pools. Good, kind, friendly staff. Safe place. Clean accommodation. Peaceful environment. Must take mosquito treatment as they’re bad out here. Lovely bonus is the pump at the pools to pump donuts up. Can’t fault it. Will 100000% return."
Sade 3-night trip
Posted 2 days ago
Hu Norcenni Girasole Village
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

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