Default HTG hotel image

Compare and book 5 Star hotels in Monti, Gaiole in Chianti

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Monti 5 Star Hotels

Tonight
17 Oct - 18 Oct
Tomorrow
18 Oct - 19 Oct
Next weekend
23 Oct - 25 Oct
In two weeks
30 Oct - 1 Nov

Our top choices for Monti 5-star hotels

An interior with a grand arched ceiling, a large clock, and a central round table with chairs.
A grand entrance with a revolving door, potted plants, and a classic stone facade.
A grand hallway with high ceilings, ornate columns, and a central chandelier. There are seating areas with tables and chairs, and a large potted plant in the middle.
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.

1. Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione
Siena City Centre
Canada
Steven
8.439.887 ₫
9.457.949 ₫ total
includes taxes & fees
15 Nov - 16 Nov
Grand Hotel Continental Siena – Starhotels Collezione
A historic stone building with multiple windows and a courtyard.
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 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.

2. Borgo San Felice Resort

Borgo San Felice Resort
Castelnuovo Berardenga
Canada
Cynthia
19.856.998 ₫
22.132.005 ₫ total
includes taxes & fees
25 Oct - 26 Oct
Borgo San Felice Resort
A spacious interior with high arched ceilings, stone walls, and a central round mirror reflecting the room. Tables and chairs are arranged for dining or socializing.
A resort with a swimming pool, terraced gardens, and a view of rolling hills.
A garden with tall cypress trees, a variety of shrubs, and a stone pathway.
An outdoor dining area with a long table set for a meal, surrounded by chairs, and string lights overhead.

3. COMO Castello Del Nero

COMO Castello Del Nero
Tavarnelle Val di Pesa
United States
Lauren
18.752.373 ₫
20.859.707 ₫ total
includes taxes & fees
8 Nov - 9 Nov
COMO Castello Del Nero
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.
A modern kitchen with a large window, wooden ceiling, and a view of a forested area.
A modern living room with a white sofa, armchairs, and a coffee table.

4. Chapter Chianti, a Member of Design Hotels

Chapter Chianti, a Member of Design Hotels
Cavriglia
Canada
Michael
6.943.374 ₫
7.811.296 ₫ total
includes taxes & fees
19 Oct - 20 Oct
Chapter Chianti, a Member of Design Hotels
A swimming pool with a stone deck, surrounded by trees and a castle-like building in the background.
A restaurant with stone walls and a high ceiling, featuring tables set for dining.
An outdoor dining area with stone buildings and a tower, illuminated by ambient lighting.
A stone building with a garden, tall trees, and a clear blue sky.

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

Castello di Spaltenna- Small Luxury Hotels of the World
Gaiole in Chianti
United States
Michelle
8.545.227 ₫
9.689.755 ₫ total
includes taxes & fees
30 Oct - 31 Oct
Castello di Spaltenna- Small Luxury Hotels of the World
A large building with multiple rooms, surrounded by a field of lavender.
A historic estate with a central courtyard, surrounded by lush gardens and vineyards.
An arched brick corridor leading to a dining area with tables set for a meal.
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
Scott
9.509.428 ₫
10.750.492 ₫ total
includes taxes & fees
5 Nov - 6 Nov
Borgo Scopeto Wine & Country Relais
A hotel room with a large bed, a vanity with a mirror, and a green archway.
A dining area with round tables, chairs, chandeliers, and large windows with curtains.
A courtyard with a stone building featuring a bell tower, outdoor seating, and greenery.
A covered outdoor seating area with a pool in the background.

7. Hotel Certosa Di Maggiano

Hotel Certosa Di Maggiano
Siena
United States
Tulsi
6.973.139 ₫
7.844.526 ₫ total
includes taxes & fees
12 Nov - 13 Nov
Hotel Certosa Di Maggiano
A hotel with a pool, outdoor seating, and a mountainous backdrop.
A bedroom with a stone archway, a bed, a chair, a table, and a window with curtains.
An outdoor patio with a stone wall, wooden table, chairs, potted plants, and a stone fireplace.
A cozy living room with a stone wall, wooden beams, a sofa, a coffee table, and a view through open doors.

8. Castello di Casole, A Belmond Hotel, Tuscany

Castello di Casole, A Belmond Hotel, Tuscany
Casole d'Elsa
United States
sarah
24.660.294 ₫
27.184.347 ₫ total
includes taxes & fees
12 Nov - 13 Nov
Castello di Casole, A Belmond Hotel, Tuscany
A stone building with arched windows, a grassy courtyard, and outdoor seating.
An aerial view of a residential property with multiple buildings, a swimming pool, and landscaped gardens.
A bedroom with a wooden ceiling, a stone wall, a bed, a desk, a chair, a sofa, and a window with curtains.
A cozy living room with a sofa, a dining table with chairs, a hanging lamp, and a mirror on the wall.

9. Pieve Aldina - Relais & Châteaux

Pieve Aldina - Relais & Châteaux
Radda in Chianti
United States
Paul
9.001.587 ₫
10.133.930 ₫ total
includes taxes & fees
28 Oct - 29 Oct
Pieve Aldina - Relais & Châteaux
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 staircase with candles and a sign reading "CANTINA".
An indoor dining area with tables set for meals, stone walls, and hanging light fixtures.

10. Castel Monastero - The Leading Hotels of the World

Castel Monastero - The Leading Hotels of the World
Castelnuovo Berardenga
United Kingdom
G
14.581.086 ₫
16.328.501 ₫ total
includes taxes & fees
1 Nov - 2 Nov
Castel Monastero - The Leading Hotels of the World
A restaurant with a glass ceiling, wicker hanging decorations, and a tiled floor.
An aerial view of a villa surrounded by vineyards, with a swimming pool and outdoor seating area.
A rural property with terracotta-roofed buildings, a paved driveway, and lush greenery.
An indoor dining area with wooden tables and chairs, hanging baskets, and large windows offering a view of the outdoors.

11. Borgo Vescine

Borgo Vescine
Radda in Chianti
United States
Natalie
11.963.434 ₫
13.391.990 ₫ total
includes taxes & fees
27 Oct - 28 Oct
Borgo Vescine
A large, historic building with a tiled roof and multiple windows, surrounded by lush gardens and a stone pathway.
A table set for breakfast with various dishes, drinks, and a newspaper.
A restaurant with stone pillars, wooden beams, and white tablecloths. Tables are arranged for dining.
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.

12. Hotel Le Fontanelle

Hotel Le Fontanelle
Castelnuovo Berardenga
United States
Cristina
14.164.484 ₫
15.870.240 ₫ total
includes taxes & fees
25 Oct - 26 Oct
Hotel Le Fontanelle
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.
A large indoor swimming pool with clear water, surrounded by modern architecture and a glass railing.
An arched stone structure with a view of a landscaped garden and a building with outdoor seating.

13. The Club House

The Club House
Castelnuovo Berardenga
United States
Natalyn
9.247.742 ₫
10.462.637 ₫ total
includes taxes & fees
1 Nov - 2 Nov
The Club House
A stone villa with a swimming pool, outdoor seating, and a scenic sunset view.
An arched stone corridor leading to a room with a billiards table, a lamp, and a view of the outdoors.
A large, historic building with multiple wings and a courtyard.
An open doorway leading to a living room with a sofa, a coffee table, and a lamp.

14. Podere Cavalbianco

Podere Cavalbianco
Monte San Savino
United States
Edith
Podere Cavalbianco
A dining area with a long table set for breakfast, featuring bread, pastries, and fruit.
A swimming pool with lounge chairs and umbrellas, surrounded by a stone building with multiple windows.
A cozy living area with wicker sofas, a coffee table, and a brick wall.
A restaurant with brick arches, wooden tables, and a piano.

15. Agriturismo San Fabiano

Agriturismo San Fabiano
Monteroni d'Arbia
United States
James
Agriturismo San Fabiano
Save an average of 15% on thousands of hotels when you're signed in

Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Monti.
Hotel Executive

Hotel Executive

Via Nazareno Orlandi 32 Siena SI
2.342.069 ₫
2.663.312 ₫ total
1 Nov - 2 Nov
includes taxes & fees
8.4/10 Very good! (555 reviews)
Hotel Executive
NH Siena

NH Siena

Piazza La Lizza 1 Siena SI
2.690.214 ₫
3.046.271 ₫ total
2 Nov - 3 Nov
includes taxes & fees
NH Siena
Hotel Athena

Hotel Athena

P Mascagni 55 Siena SI
3.077.177 ₫
3.471.687 ₫ total
13 Nov - 14 Nov
includes taxes & fees
Hotel Athena
Still don't see what you're looking for?
See all properties in Monti.
You can also use these popular filters to refine your search.
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.

Top Monti Hotel Reviews

Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent
"Beautiful quaint 1000 year old monastery turned into a hotel! The staff was extremely accommodating and we really enjoyed our stay. Very easy to get around all of Tuscany from this hotel."
Michelle 3-night trip
Posted 5 days ago
Castello di Spaltenna- Small Luxury Hotels of the World
Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais

10/10 Excellent
"Beautiful Borgo with views over Sienna and wonderful Tuscan countryside. In peak summer there is a family pool and adults only pool. The family pool was quiet and nice area to relax. About 20-30 mins to Siena we explored lots of lovely hill top places for dinner each night. Pool side dining was ok, club sandwiches that type of thing not extensive choice but adequate. Stunning views, good location to explore surrounding area. Would definitely recommend. I stayed with my family two boys age 9 and 13 and they loved it. Accommodation was very comfortable and spacious."
Louise 4-night trip
Posted 10 days ago
Borgo Scopeto Wine & Country Relais
Borgo Vescine

Borgo Vescine

10/10 Excellent
"The staff was amazing and incredibly kind."
Natalie 2-night trip
Posted 2 weeks ago
Borgo Vescine

Explore a world of travel with Expedia