Default HTG hotel image

Compare and book 5 Star hotels in Monti di Sotto, 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 di Sotto 5 Star Hotels

Tonight
2 Sep - 3 Sep
Tomorrow
3 Sep - 4 Sep
This weekend
4 Sep - 6 Sep
Next weekend
11 Sep - 13 Sep

Our top choices for Monti di Sotto 5-star hotels

An interior with a grand arched ceiling, a large clock, and a central round table with chairs.
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.
An outdoor dining setup with a table set for two, surrounded by candles and greenery, with a historic building in the background.

1. Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione
Siena City Centre
United States
Lisa
16.242.910 ₫
18.170.035 ₫ total
includes taxes & fees
15 Sept - 16 Sept
Grand Hotel Continental Siena – Starhotels Collezione
A large building with multiple rooms, surrounded by a field of lavender.
An arched brick corridor leading to a dining area with tables set for a meal.
An outdoor dining area with tables set for a meal, a sign indicating a wine list, and a view of the landscape.
A swimming pool with lounge chairs and umbrellas, surrounded by stone buildings and trees.

2. Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais
Castelnuovo Berardenga
United States
Hannah
16.142.164 ₫
18.059.214 ₫ total
includes taxes & fees
7 Sept - 8 Sept
Borgo Scopeto Wine & Country Relais
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.
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.

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

Castello di Spaltenna- Small Luxury Hotels of the World
Gaiole in Chianti
United States
Rama
10.406.474 ₫
11.749.955 ₫ total
includes taxes & fees
6 Sept - 7 Sept
Castello di Spaltenna- Small Luxury Hotels of the World
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 pool area with lounge chairs and a service person attending to a guest.

4. Borgo San Felice Resort

Borgo San Felice Resort
Castelnuovo Berardenga
Canada
Cynthia
27.862.932 ₫
30.951.486 ₫ total
includes taxes & fees
6 Sept - 7 Sept
Borgo San Felice Resort
A large, historic building with a tiled roof and multiple windows, surrounded by lush gardens and a stone pathway.
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.
A pool area with lounge chairs and umbrellas, a large building in the background, and a view of the countryside.
A restaurant with stone pillars, wooden beams, and white tablecloths. Tables are arranged for dining.

5. Hotel Le Fontanelle

Hotel Le Fontanelle
Castelnuovo Berardenga
Canada
Briana
16.288.824 ₫
18.219.968 ₫ total
includes taxes & fees
21 Sept - 22 Sept
Hotel Le Fontanelle
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.
An outdoor dining area with a long table set for a meal, surrounded by chairs, and string lights overhead.
A garden with tall cypress trees, a variety of shrubs, and a stone pathway.
A resort with a swimming pool, terraced gardens, and a view of rolling hills.

6. COMO Castello Del Nero

COMO Castello Del Nero
Tavarnelle Val di Pesa
United States
Vicente
26.535.733 ₫
29.431.115 ₫ total
includes taxes & fees
1 Oct - 2 Oct
COMO Castello Del Nero
A bedroom with a canopy bed, a bedside table, a chair, a potted plant, and a large mirror.
A modern living room with a white sofa, armchairs, and a coffee table.
An aerial view of a rural village with traditional stone buildings, terraced fields, and a prominent villa with a swimming pool.
An aerial view of a rural village with traditional buildings, a swimming pool, and terraced fields.

7. Chapter Chianti, a Member of Design Hotels

Chapter Chianti, a Member of Design Hotels
Cavriglia
United Kingdom
Samay
10.276.861 ₫
11.485.903 ₫ total
includes taxes & fees
8 Sept - 9 Sept
Chapter Chianti, a Member of Design Hotels
A restaurant with a glass ceiling, wicker hanging decorations, and a tiled floor.
A rural property with terracotta-roofed buildings, a paved driveway, and lush greenery.
A bedroom with a bed, a wooden chair, a desk with a lamp, and a wardrobe.
An indoor dining area with wooden tables and chairs, hanging baskets, and large windows offering a view of the outdoors.

8. Borgo Vescine

Borgo Vescine
Radda in Chianti
United States
Gabrielle
23.741.197 ₫
26.357.125 ₫ total
includes taxes & fees
7 Sept - 8 Sept
Borgo Vescine
A hotel with a pool, outdoor seating, and a mountainous backdrop.
An aerial view of a large estate with a central building surrounded by manicured gardens, a swimming pool, and a fountain.
An outdoor patio with a stone wall, wooden table, chairs, potted plants, and a stone fireplace.
A bedroom with a stone archway, a bed, a chair, a table, and a window with curtains.

9. Castello di Casole, A Belmond Hotel, Tuscany

Castello di Casole, A Belmond Hotel, Tuscany
Casole d'Elsa
United States
sarah
51.384.303 ₫
56.583.185 ₫ total
includes taxes & fees
27 Sept - 28 Sept
Castello di Casole, A Belmond Hotel, Tuscany
A stone building with arched windows, a grassy courtyard, and outdoor seating.
A bedroom with a wooden ceiling, a stone wall, a bed, a desk, a chair, a sofa, and a window with curtains.
A person relaxing in a clear pool surrounded by natural scenery.
An aerial view of a residential property with multiple buildings, a swimming pool, and landscaped gardens.

10. Pieve Aldina - Relais & Châteaux

Pieve Aldina - Relais & Châteaux
Radda in Chianti
Italy
Matteo
9.694.322 ₫
10.905.562 ₫ total
includes taxes & fees
30 Sept - 1 Oct
Pieve Aldina - Relais & Châteaux
A stone house with a tiled roof, large glass doors, and a stone pathway leading to it.
An arched stone structure with a view of a landscaped garden and a building with outdoor seating.
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.

11. The Club House

The Club House
Castelnuovo Berardenga
United States
Karla
21.236.366 ₫
23.662.837 ₫ total
includes taxes & fees
27 Sept - 28 Sept
The Club House
A bed with white bedding and a decorative headboard with a floral pattern.
A covered outdoor seating area with benches and tables, a pathway, and a view of a garden and pool.
An aerial view of a historic building with a central tower, surrounded by lush greenery and a swimming pool.
A dining area with a wooden table set for four, surrounded by bamboo chairs.

12. Hotel Certosa Di Maggiano

Hotel Certosa Di Maggiano
Siena
United States
Tulsi
13.289.315 ₫
14.921.081 ₫ total
includes taxes & fees
7 Sept - 8 Sept
Hotel Certosa Di Maggiano
A swimming pool with lounge chairs and a person in a patterned dress.
A stone building with a swimming pool, surrounded by a well-maintained garden and a clear sky.
A restaurant with brick walls, wooden tables, and hanging lanterns.
A person performing a yoga pose in a grassy area with a historic building in the background.

13. Castel Monastero - The Leading Hotels of the World

Castel Monastero - The Leading Hotels of the World
Castelnuovo Berardenga
United Kingdom
G
17.449.780 ₫
19.497.018 ₫ total
includes taxes & fees
22 Sept - 23 Sept
Castel Monastero - The Leading Hotels of the World
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 cozy living room with a fireplace, a clock, and a sofa.
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 view of a countryside landscape with rolling hills, a swimming pool, and a building with a tiled roof.
A swimming pool with lounge chairs and umbrellas, surrounded by a stone building with multiple windows.
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 di Sotto.
Hotel Athena

Hotel Athena

P Mascagni 55 Siena SI
7.240.484 ₫
8.115.950 ₫ total
3 Sept - 4 Sept
includes taxes & fees
9.2/10 Wonderful! (1,004 reviews)
Hotel Athena
Hotel Toscana Ambassador

Hotel Toscana Ambassador

Via Salceto, 11 Poggibonsi SI
1.869.620 ₫
2.237.938 ₫ total
6 Sept - 7 Sept
includes taxes & fees
8/10 Very good! (362 reviews)
Hotel Toscana Ambassador
Palazzo Ravizza

Palazzo Ravizza

Pian dei Mantellini 34 Siena SI
6.166.800 ₫
6.934.897 ₫ total
4 Sept - 5 Sept
includes taxes & fees
9.4/10 Exceptional! (852 reviews)
Palazzo Ravizza
Still don't see what you're looking for?
See all properties in Monti di Sotto.
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 di Sotto Hotel Reviews

Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais

10/10 Excellent
"Such a beautiful and quiet property. The staff were so friendly and accommodating. The food and drinks were delicious and we enjoyed the spa as well!"
Hannah 3-night trip
Posted 17 hours ago
Borgo Scopeto Wine & Country Relais
Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent
"Great location, beautiful rooms, wonderful staff!"
Lisa 1-night trip
Posted 5 days ago
Grand Hotel Continental Siena – Starhotels Collezione
Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent
"Just an amazing overall experience, super welcoming and hospitable staff. Vacationing in an estate that is 1100 years old makes it even more memorable. Thank you Spaltena"
Ashley 2-night trip
Posted 1 month ago
Castello di Spaltenna- Small Luxury Hotels of the World

Explore a world of travel with Expedia