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

Search Boutique Hotels in Chianti Region

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check availability on Chianti Region Boutique Hotels

Tonight
9 Sept - 10 Sept
Tomorrow
10 Sept - 11 Sept
This weekend
11 Sept - 13 Sept
Next weekend
18 Sept - 20 Sept

Our top choices for Chianti Region boutique hotels

A historic stone building with multiple windows and a courtyard.
A stone building with outdoor seating and a garden with roses.
An outdoor dining area with tables set for two, covered by large umbrellas, and a brick wall in the background.
A room with a large window overlooking a landscape with trees and hills. There are two upholstered sofas with a patterned rug in the center.

1. Borgo San Felice Resort

Borgo San Felice Resort
Castelnuovo Berardenga
Canada
Cynthia
£599
includes taxes & fees
7 Oct - 8 Oct
Borgo San Felice Resort
An interior with a grand arched ceiling, a large clock, and a central round table with chairs.
A spacious lobby with a high ceiling, ornate columns, and a central chandelier. There are multiple seating areas with chairs and tables, and a large potted plant in the center.
A grand entrance with a revolving door, potted plants, and a classic stone facade.
An outdoor dining setup with a table set for two, surrounded by candles and greenery, with a historic building in the background.

2. Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione
Siena City Centre
United States
Lisa
£515
includes taxes & fees
14 Sept - 15 Sept
Grand Hotel Continental Siena – Starhotels Collezione
A lobby with ornate columns, a reception desk, and a staircase.
A lobby with a reception desk, a large floral arrangement, and a lamp. There are columns and a chandelier.
A balcony with two wicker lounge chairs, each with rolled towels, and potted plants.
A grand lobby with high ceilings, ornate columns, and a grand piano. Tables and chairs are arranged for guests.

3. Bernini Palace

Bernini Palace
Historic Centre of Florence
United States
Glenda
£399
includes taxes & fees
5 Oct - 6 Oct
Bernini Palace
An aerial view of a town with a large lake, surrounded by greenery and hills.
A table set for dining with a view of a lake and hills in the background.
A poolside area with lounge chairs and umbrellas, a stone building, and a large orange house with a tiled roof.
An arched entrance leading to a pool area with a decorative emblem on the wall.

4. Villa La Massa

Villa La Massa
Bagno a Ripoli
United Kingdom
Katie
£666
includes taxes & fees
9 Oct - 10 Oct
Villa La Massa
A restaurant with multiple tables and chairs, a bar area, and large windows allowing natural light.
A hallway with a modern ceiling design, a framed portrait on the wall, and a sign with a number.
A hotel lobby with a floral-patterned carpet, a reception desk, and a large arched doorway leading to the entrance.

5. UNA Hotels Vittoria Firenze

UNA Hotels Vittoria Firenze
Oltrarno
United States
Pablo
£146
includes taxes & fees
14 Sept - 15 Sept
UNA Hotels Vittoria Firenze
A cozy outdoor seating area with wicker furniture, a large potted plant, and lanterns.
An outdoor dining area with tables set for guests, surrounded by lush greenery and a pergola structure.
A cozy lounge area with a sofa, armchairs, a fireplace, and a large mirror.
An outdoor dining area with tables and chairs, overlooking a historic building with a dome and bell tower.

6. Grand Hotel Baglioni

Grand Hotel Baglioni
Historic Centre of Florence
United States
Angela
£248
includes taxes & fees
18 Sept - 19 Sept
Grand Hotel Baglioni
A balcony with two wooden chairs, a table with a teapot and glasses, and a view of a building with a clock tower.
A cozy living room with a high ceiling, two armchairs, a coffee table with magazines, and a window with curtains.
A staircase with a railing, a mirror, and a vase on the landing.
A building facade with stone masonry, arched windows, and a hanging sign.

7. Porcellino Gallery

Porcellino Gallery
Historic Centre of Florence
United States
Denisse
£220
includes taxes & fees
9 Oct - 10 Oct
Porcellino Gallery
A spacious living room with a leather sofa, a coffee table, and a television.
A modern building with a stone facade, large windows, and a covered patio area.
An open dining area with a rustic stone wall, wooden chairs, a table set with white tablecloths, and a variety of flowers.
A hotel room with a large bed, a seating area with a coffee table, and a view of the cityscape through large windows.

8. Riva Lofts Florence

Riva Lofts Florence
Isolotto
United Kingdom
Joyce
£159
includes taxes & fees
5 Oct - 6 Oct
Riva Lofts Florence
A dining area with a table set for two, a window with a view of historic buildings, and a chair with a cushion.
A hallway with a checkered floor, a wooden console table with books, a lamp, and a chair.
A dining area with multiple tables and chairs, large windows with curtains, and a chandelier.
A hotel corridor with a checkered floor, a hanging lantern, and a clear sign for the hotel named 'PENDINI'.

9. Hotel Pendini

Hotel Pendini
Historic Centre of Florence
United States
Monica
£251
includes taxes & fees
10 Sept - 11 Sept
Hotel Pendini
A large, classical building with a symmetrical facade, multiple windows, and a central entrance with a canopy.
A grand room with ornate gold detailing, multiple chandeliers, and a central table with a vase of flowers.
A luxurious living room with a fireplace, two sofas, and a coffee table with books.
A poolside area with lounge chairs and umbrellas, a clear pool, and a building with arched windows in the background.

10. Villa Cora

Villa Cora
Oltrarno
Canada
Xiang
£602
includes taxes & fees
13 Sept - 14 Sept
Villa Cora
View all properties

Top Chianti Region Hotel Reviews

Explore a world of travel with Expedia