A city with historic towers and a vineyard.

Compare and book 5 Star hotels in Castel San Gimignano, San Gimignano

  • 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 Castel San Gimignano 5 Star Hotels

Tonight
9 Oct - 10 Oct
Tomorrow
10 Oct - 11 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 Oct

Our top choices for Castel San Gimignano 5-star hotels

A person performing a yoga pose on a wooden deck with a view of a landscape.
A person in a pool with water jets, surrounded by a natural landscape and mountains in the background.
A modern hotel lobby with a reflective floor, arched seating areas, and a central column.
A spacious interior with arched brick ceilings, a central dining area, and a cozy seating arrangement.

1. Castelfalfi

Castelfalfi
Montaione
United States
Evelin
£671
includes taxes & fees
9 Nov - 10 Nov
Castelfalfi
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.

2. Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione
Siena City Centre
United States
Lisa
£285
includes taxes & fees
9 Nov - 10 Nov
Grand Hotel Continental Siena – Starhotels Collezione
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 garden with tall cypress trees, a variety of shrubs, and a stone pathway.
An outdoor dining area with tables and chairs, a chef preparing food, and a scenic view in the background.
A resort with a swimming pool, terraced gardens, and a view of rolling hills.

3. COMO Castello Del Nero

COMO Castello Del Nero
Tavarnelle Val di Pesa
United States
Lauren
£643
includes taxes & fees
29 Oct - 30 Oct
COMO Castello Del Nero
A large building with multiple rooms, surrounded by a field of lavender.
A swimming pool with lounge chairs and umbrellas, surrounded by stone buildings and trees.
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.

4. Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais
Castelnuovo Berardenga
United States
Scott
£314
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.
An arched hallway with a marble reception desk, potted plants, and a staircase in the background.
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.

5. Hotel Certosa Di Maggiano

Hotel Certosa Di Maggiano
Siena
United States
Tulsi
£222
includes taxes & fees
9 Nov - 10 Nov
Hotel Certosa Di Maggiano
A hotel with a pool, outdoor seating, and a mountainous backdrop.
A cozy living room with a stone wall, wooden beams, a sofa, a coffee table, and a view through open doors.
A bedroom with a stone archway, a bed, a chair, a table, and a window with curtains.
An aerial view of a large estate with a central building surrounded by manicured gardens, a swimming pool, and a fountain.

6. Castello di Casole, A Belmond Hotel, Tuscany

Castello di Casole, A Belmond Hotel, Tuscany
Casole d'Elsa
United States
sarah
£822
includes taxes & fees
6 Nov - 7 Nov
Castello di Casole, A Belmond Hotel, Tuscany
A covered outdoor dining area with a table set for four, overlooking a scenic landscape with hills and a body of water.
A round bar area with a central light fixture and a variety of bottles and glasses.
A stone-walled room with a bench and a small shelf.
A stone building with a tiled roof, a gravel path leading to a wooden archway, and a sign reading "LA FONTE".

7. Borgo Pignano Volterra Tuscany

Borgo Pignano Volterra Tuscany
Volterra
£415
includes taxes & fees
7 Nov - 8 Nov
Borgo Pignano Volterra Tuscany
A serene infinity pool with lounge chairs and umbrellas, surrounded by natural scenery and a clear view of distant mountains.
A bathroom with a bathtub, a chandelier, and a view of the outdoors.
A rustic dining area with brick walls, hanging plants, and candle-lit tables.
A cozy living room with a fireplace, elegant furniture, and a chandelier.

8. Borgo Santo Pietro

Borgo Santo Pietro
Chiusdino
United States
Rachel
£941
includes taxes & fees
31 Oct - 1 Nov
Borgo Santo Pietro
A stone building with arched windows, a grassy courtyard, and outdoor seating.
A cozy living room with a sofa, a dining table with chairs, a hanging lamp, and a mirror on the wall.
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.

9. Pieve Aldina - Relais & Châteaux

Pieve Aldina - Relais & Châteaux
Radda in Chianti
United States
Paul
£296
includes taxes & fees
22 Oct - 23 Oct
Pieve Aldina - Relais & Châteaux
A large building with a swimming pool, surrounded by greenery and outdoor lighting.
A courtyard with a stone bridge over a small water feature, surrounded by greenery and a building with arched windows.
A dining area with tables and chairs, a kitchen in the background, and a patterned wall.
A large, multi-story building with a symmetrical facade, multiple windows, and a central entrance.

10. LHP Certaldo Resort

LHP Certaldo Resort
Certaldo
Canada
Arash
£123
includes taxes & fees
18 Oct - 19 Oct
LHP Certaldo Resort
A restaurant with a glass ceiling, wicker hanging decorations, and a tiled floor.
An indoor dining area with wooden tables and chairs, hanging baskets, and large windows offering a view of the outdoors.
A bedroom with a bed, a wooden chair, a desk with a lamp, and a wardrobe.
A rural property with terracotta-roofed buildings, a paved driveway, and lush greenery.

11. Borgo Vescine

Borgo Vescine
Radda in Chianti
United States
Natalie
£365
includes taxes & fees
7 Nov - 8 Nov
Borgo Vescine
An outdoor dining area with wicker chairs and tables, white tablecloths, and umbrellas, overlooking a scenic landscape.
A spacious living room with a large window offering a view of the countryside. There are two armchairs, a sofa, and a coffee table with a vase of flowers.
A poolside area with lounge chairs and umbrellas, overlooking a scenic landscape.
A dining area with stone walls, wooden beams, and round tables set for a meal.

12. Villa Le Calvane

Villa Le Calvane
Montespertoli
United States
Ilya
£457
includes taxes & fees
20 Oct - 21 Oct
Villa Le Calvane
A stone house with a tiled roof, large glass doors, and a stone pathway leading to it.
An indoor dining area with brick arches, tables set for dining, and a view of the outdoors.
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.

13. The Club House

The Club House
Castelnuovo Berardenga
United States
Natalyn
£285
includes taxes & fees
2 Nov - 3 Nov
The Club House
A swimming pool surrounded by lush greenery and a wooden deck.
A large estate with multiple buildings, including a central tower-like structure and several smaller buildings.
A backyard with a swimming pool, wooden deck, hanging light fixture, and a wooden fence.
An open doorway to a patio with a table set for two, surrounded by gravel and trees.

14. Agriturismo Il Cerreto

Agriturismo Il Cerreto
Pomarance
Canada
Andreas
£106
includes taxes & fees
13 Oct - 14 Oct
Agriturismo Il Cerreto
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 Castel San Gimignano.
Hotel Executive

Hotel Executive

Via Nazareno Orlandi 32 Siena SI
£57
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
£87
5 Nov - 6 Nov
includes taxes & fees
NH Siena
Hotel Athena

Hotel Athena

P Mascagni 55 Siena SI
£98
9 Nov - 10 Nov
includes taxes & fees
9.2/10 Wonderful! (1,008 reviews)
Hotel Athena
Still don't see what you're looking for?
See all properties in Castel San Gimignano.
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.

Learn more about Castel San Gimignano

Medieval towers rise dramatically from this hilltop town, where you can climb Torre Grossa for panoramic Tuscan countryside views. Sample award-winning Vernaccia wine at local enotecas and explore the impressive art collection inside the Civic Museum's ancient walls.

See all hotels in Castel San Gimignano
A city with historic towers and a vineyard.

Top Castel San Gimignano Hotel Reviews

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 2 days ago
Borgo Scopeto Wine & Country Relais
Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent
"Beautiful hotel and very helpful staff. Excellent location in the heart of Siena. Disappointed with our hotel room. Not up to our expectations."
JOHN 3-night trip
Posted 3 days ago
Grand Hotel Continental Siena – Starhotels Collezione

Find out more about Castel San Gimignano

Frequently asked questions

What are the best 5-star hotels in Castel San Gimignano?
If you're seeking a 5-star experience, Castello di Casole, A Belmond Hotel, Tuscany offers one of the best of them according to reviews by our travellers. Check in to this Castel San Gimignano getaway and you'll get first-rate service, well-appointed guest rooms and superior facilities.
How much does it cost to stay in a 5-star hotel in Castel San Gimignano?
The amount you pay for a 5-star hotel in Castel San Gimignano depends on factors like when you plan to go and the length of your stay. A top tip for bagging the best deal? Use our pricing filters to compare all of the available hotels for your preferred dates.
  • Search for the lowest price per night from £57
What makes a hotel 5 stars in Castel San Gimignano?
Impeccable guest service is the hallmark of every 5-star hotel in Castel San Gimignano. From the moment you arrive, staff attend to your every whim, whether recommending activities and tours or providing a nightly turn-down service. Also, hotels have to feature superior conveniences to be entitled to a 5-star rating. These can include luxury toiletries, saunas or spas, pools, gourmet kitchens and knowledgeable concierge.

Explore a world of travel with Expedia