Hotels in San Gusme

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A stone staircase leading to a door, surrounded by stone walls and a potted plant with green leaves and purple flowers.

A stone building with a window and a light fixture.

A rustic interior with a stone fireplace, wooden beams, and a staircase leading to an upper level.

A stone building with a wooden door, outdoor seating, and a pergola with vines.

1. Agriturismo San Sano

Gaiole in Chianti

$74

$86 total

includes taxes & fees

Oct 21 - Oct 22

A rustic stone building with a wooden pergola, outdoor seating, and a garden with various plants.

A stone archway leading to a window with a view of tall trees and a distant landscape.

A stone building with a tower, surrounded by people dining at tables with candles.

An aerial view of a castle with a swimming pool, surrounded by dense forest and vineyards.

2. Castello di Tornano Wine Resort

Gaiole in Chianti

$153

$177 total

includes taxes & fees

Oct 19 - Oct 20

A historic stone building with multiple windows and a courtyard.

A stone building with outdoor seating and a garden with roses.

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.

A pool area with lounge chairs and a service person attending to a guest.

3. Borgo San Felice Resort

Castelnuovo Berardenga

$777

$866 total

includes taxes & fees

Oct 11 - Oct 12

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.

An interior corridor with arches, columns, and a brick wall.

A corridor with a wooden door at the end, a metal railing on one side, and a light fixture above.

A restaurant setting with wooden chairs, a white tablecloth, and a waiter attending to a table.

4. La Certosa di Pontignano

Castelnuovo Berardenga

$100

$120 total

includes taxes & fees

Oct 16 - Oct 17

A table set for dining with a scenic view of rolling hills and distant mountains.

A spacious dining area with round tables and wicker chairs, a patterned rug, and a wooden ceiling.

An aerial view of a property with a swimming pool, surrounded by trees and a view of the countryside.

A courtyard with brick buildings, a column, and potted plants.

5. Castello di Leonina Relais

Asciano

$166

$190 total

includes taxes & fees

Oct 19 - Oct 20

A terrace with multiple sun loungers and a scenic view of green fields and hills.

A modern hotel room with a bed, a small table with a hat, a red chair, a window with curtains, and a bathroom with a glass shower enclosure.

A spa room with a reception desk, a massage chair, and a window with blinds.

An indoor swimming pool with lounge chairs and a view of the countryside.

6. Precise House Montaperti Siena

Asciano

$112

$130 total

includes taxes & fees

Oct 2 - Oct 3

A building with a stone facade, a central arched doorway, and a window with a decorative frame.

A cozy living room with a sofa, a coffee table, and a view of greenery through large windows.

A narrow, tree-lined road leading to a house with a tiled roof and a stone wall on one side.

A room with a glass table, a vase with flowers, a bottle of wine, and a chair.

7. Dievole Wine Resort

Castelnuovo Berardenga

$360

$405 total

includes taxes & fees

Oct 14 - Oct 15

A covered outdoor seating area with white chairs and tables, overlooking a scenic landscape with mountains and trees.

A long table set for a formal event, with clear chairs and white tablecloths, under a large chandelier and surrounded by greenery.

An outdoor dining area with long tables set for a meal, surrounded by greenery and trees.

A poolside area with a swimming pool, lounge chairs, and a grassy lawn.

8. Il Verreno

Ambra

$225

$252 total

includes taxes & fees

Oct 12 - Oct 13

A pathway lined with trees and a large pot in the center.

A white building with a tiled roof, surrounded by lush greenery and a hilly landscape.

A breakfast buffet with pastries and a coffee machine.

A stone pathway leading to a wooden deck with a railing, surrounded by lush greenery and tall trees.

9. Villa Montarioso

Montarioso

$82

$95 total

includes taxes & fees

Oct 20 - Oct 21

A terrace with stone arches, green plants, and a table set for dining with a scenic mountain view.

A stone building with a balcony, potted plants, and a view of distant hills.

A stone-walled room with a sofa, a coat rack, and a window with curtains.

A rectangular swimming pool with a view of mountains in the background.

10. Podere L'Aquila

Gaiole in Chianti

$169

$469 total

includes taxes & fees

Oct 6 - Oct 7

A swimming pool with lounge chairs and a person in a patterned dress.

A person performing a yoga pose in a grassy area with a historic building in the background.

A stone building with a swimming pool, surrounded by a well-maintained garden and a clear sky.

An indoor dining area with tables set for meals, stone walls, and hanging light fixtures.

11. Castel Monastero - The Leading Hotels of the World

Castelnuovo Berardenga

$616

$689 total

includes taxes & fees

Oct 7 - Oct 8

A stone building with multiple windows and a central entrance.

A dining area with a table set for two, white chairs, and a stone-patterned floor.

A hotel room with a bed, a yellow armchair, a stone wall, and a window with a lamp.

A narrow stone pathway leading to a stone archway, surrounded by lush greenery and a stone wall.

12. Fondaco del Moro

Civitella in Val di Chiana

$70

$77 total

includes taxes & fees

Sep 23 - Sep 24

A stone-walled room with a table set for breakfast, featuring pastries, fruits, and a coffee station.

A poolside area with lounge chairs and umbrellas, surrounded by stone flooring and greenery.

A bedroom with a large bed, wooden beams, stone wall, and a stone fireplace.

A cozy seating area with two chairs and a table, a stone wall, and a clock on a pedestal.

13. Ultimo Mulino Wellness Country Hotel

Gaiole in Chianti

$95

$114 total

includes taxes & fees

Oct 22 - Oct 23

A large, historic building with a tiled roof and multiple windows, surrounded by lush gardens and a stone pathway.

A pool area with lounge chairs and umbrellas, a large building in the background, and a view of the countryside.

A table set for breakfast with various dishes, drinks, and a newspaper.

A spacious living room with a high ceiling, exposed wooden beams, and a large arched brick structure. There are multiple seating areas with floral-patterned sofas and armchairs. A fireplace and bookshelves are visible in the background.

14. Hotel Le Fontanelle

Castelnuovo Berardenga

$561

$629 total

includes taxes & fees

Oct 11 - Oct 12

An aerial view of a villa with a swimming pool, surrounded by lush greenery and a hilly landscape.

A bar area with brick arches, wooden barrels, leather seating, and a wine rack.

A building with arched windows, a courtyard with a pond, and a metal fence.

A traditional villa with a tiled roof, surrounded by lush greenery and hills.

15. Hotel Casafrassi

Castellina in Chianti

$62

$75 total

includes taxes & fees

Sep 27 - Sep 28

A modern building with a sign reading "Palace Hotel."

A red building with a reception sign, a bicycle, potted plants, and luggage.

A buffet setup with various food items including yogurt cups, fruits, and a bowl of grapes.

16. Palace Hotel Due Ponti

Due Ponti

$93

$108 total

includes taxes & fees

Sep 27 - Sep 28

A bedroom with a canopy bed, a bedside table, a chair, a potted plant, and a large mirror.

A rustic outdoor setting with a stone building, round tables, and outdoor seating.

An aerial view of a rural village with traditional stone buildings, terraced fields, and a prominent villa with a swimming pool.

A modern living room with a white sofa, armchairs, and a coffee table.

17. Chapter Chianti, a Member of Design Hotels

Cavriglia

$275

$310 total

includes taxes & fees

Oct 6 - Oct 7

A stone-walled dining area with a table set for four, a bench, and a view through an open doorway to the outside.

A stone building with a courtyard, a covered seating area, and a small bell tower.

A dining area with a stone wall, wooden beams, and a table set for four with wine glasses and plates.

A cozy living room with a stone fireplace, striped sofas, and a coffee table.

18. Borgo di Pietrafitta Relais

Castellina in Chianti

$90

$104 total

includes taxes & fees

Oct 14 - Oct 15

A narrow stone pathway leading to a rustic building with a wooden door and a window.

A cozy living room with a striped sofa, a wooden coffee table, and a bookshelf.

A stone building with wooden shutters, a bench, and hanging purple flowers.

A cozy living room with a fireplace, wooden beams, and comfortable seating.

19. Castello di Fonterutoli Wine Resort

Castellina in Chianti

$207

$232 total

includes taxes & fees

Oct 18 - Oct 19

An outdoor dining area with a pool, potted plants, and umbrellas.

A spa area with a brick archway leading to a circular hot tub surrounded by mosaic tiles.

A restaurant with a table set for two, overlooking a scenic landscape.

An outdoor dining area with a table set for two, overlooking a pool and vineyard.

20. Relais Vignale & Spa

Radda in Chianti

$163

$214 total

includes taxes & fees

Oct 18 - Oct 19

View all properties

Go beyond your typical stay in San Gusme

Check out reviews of San Gusme hotels guests love

Agriturismo San Sano

Gaiole in Chianti

10/10 Exceptional

Angela

Borgo San Felice Resort

Castelnuovo Berardenga

10/10 Exceptional

An unforgettable stay in Tuscany!** Our stay at Borgo San Felice was truly incredible from beginning to end. From the moment our private driver picked us up at the train station and brought us through the beautiful Tuscan countryside to the resort, everything felt seamless and special. The property itself is absolutely breathtaking pictures truly don’t do it justice. We enjoyed dinner on the property, a wonderful couples massage, a private wine tour and tasting, and a relaxing pool day. We...

Yael

La Certosa di Pontignano

Castelnuovo Berardenga

10/10 Exceptional

Jeffrey

Castello di Tornano Wine Resort

Gaiole in Chianti

10/10 Exceptional

Arwen

Il Verreno

Ambra

10/10 Exceptional

James

Dievole Wine Resort

Castelnuovo Berardenga

10/10 Exceptional

Gary

Hotel Le Fontanelle

Castelnuovo Berardenga

10/10 Exceptional

Anonymous traveler

A stone house with a tiled roof, large glass doors, and a stone pathway leading to it.

A spacious living area with a high arched ceiling, a sofa set, and a glass coffee table.

An arched stone structure with a view of a landscaped garden and a building with outdoor seating.

An indoor dining area with brick arches, tables set for dining, and a view of the outdoors.

The Club House

Castelnuovo Berardenga

10/10 Exceptional

debbie

A historic stone building with multiple levels, surrounded by lush greenery and yellow flowering plants.

A pool area with lounge chairs and umbrellas, surrounded by lush greenery and hills in the background.

A courtyard with stone buildings, tables with white tablecloths, and chairs arranged for dining.

A bedroom with a wooden ceiling, a bed with white bedding, a bedside table with a tray of items, and a window with curtains.

Castello La Leccia

Castellina in Chianti

10/10 Exceptional

Sarah

Castello di Leonina Relais

Asciano

10/10 Exceptional

Jennifer

Castel Monastero - The Leading Hotels of the World

Castelnuovo Berardenga

10/10 Exceptional

Raina

A swimming pool with a stone deck, surrounded by trees and a castle-like building in the background.

A stone building with a garden, tall trees, and a clear blue sky.

A restaurant with stone walls and a high ceiling, featuring tables set for dining.

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.

Castello di Spaltenna- Small Luxury Hotels of the World

Gaiole in Chianti

10/10 Exceptional

Lucas

A table set for breakfast with a scenic view of hills and a cloudy sky.

An arched entrance with a brick pathway leading to a building, surrounded by lush greenery and purple flowering vines.

An open wooden door leading to a courtyard with potted plants and a view of buildings in the background.

A two-story building with a central entrance, green shutters, and a brick staircase leading up to the door.

Palazzo di Valli

Siena

10/10 Exceptional

We stayed 3 nights at Palazzo di Valli in late April 2022. The property is beautiful and located in a quiet residential area just south of the city's center. It sits on a hill overlooking a valley, and has it's own orchard and flower gardens. Instead of waking up to the sound of motorcycles and delivery trucks under your window, we woke up to chirping birds. Hosts Lorenzo and Giancarlo were wonderful, offering us recommendations, and helping arrange reservations and transportation. It's a bit of...

Joan

A room with a piano, stone walls, a wooden cabinet, and a bench.

A wooden console table with a mirror above it, a vase with flowers, and a basket of fruit.

A dining area with a yellow table, white chairs, and a kitchen in the background.

A narrow stairway with a small window overlooking a courtyard with a brick building and a wooden ceiling.

Antico Granaione

Rapolano Terme

10/10 Exceptional

Irene

A courtyard with a stone building featuring a bell tower, outdoor seating, and greenery.

A hotel room with a large bed, a vanity with a mirror, and a green archway.

A covered outdoor seating area with a pool in the background.

A courtyard with a bell tower, a well-maintained lawn, and outdoor seating.

Hotel Certosa Di Maggiano

Siena

10/10 Exceptional

Anonymous traveler

A spacious lobby with a stone archway, wooden ceiling beams, a bar area with a wine rack, and a reception desk.

A rustic living room with exposed wooden beams, a sofa, a coffee table, and a dining area with chairs.

A rustic interior with a brick archway, wooden beams, a bar area, and potted plants.

A stone building with a wooden bench outside.

Hotel Colle Etrusco Salivolpi

Castellina in Chianti

10/10 Exceptional

Samantha

A terrace with wicker chairs and a table set for breakfast, overlooking a historic town with terracotta buildings and cypress trees.

A brick building with a sign reading "Villa del Sole" and a view of the sea in the background.

A hotel entrance with a view of historic buildings and a clear sky.

A bedroom with a large window, a bed, a nightstand, and a mirror.

Villa del Sole Siena

Siena City Centre

10/10 Exceptional

Linna

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 stone building with ivy-covered walls, a stone pathway, and a garden with flowers.

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.

Belvedere di San Leonino

Castellina in Chianti

10/10 Exceptional

Oh wow, perfect vacation and a real Tuscany atmosphere, the hotel is a magical old yet perfectly renovated property, the room was amazingly clean and equipped with everything we needed, the pool was open until 8pm and it’s never crowded, very peaceful area, almost like a fantasy movie, breakfast was great, especially the cheese , local pastries and coffee , the staff was lovely, very friendly and helpful, but the real deal was DINNER , I cannot say enough about the food and wine they make,...

Lior