Photo by Galyna V

Asciano 5 Stars Hotels

Start date: Check-in selected.
To Date
End date: Check-out

  • 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 Asciano 5 Star Hotels

Tonight
Dec 22 - Dec 23
Tomorrow
Dec 23 - Dec 24
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Asciano 5-star hotels

Ballroom
Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione
5.0 star property
Siena City Centre
9.2 out of 10, Wonderful, (575)
"Great hotel / room, city center, friendly staff. "
United States
Nebojsa
The price is NT$9,071
NT$10,200 total
includes taxes & fees
Dec 23 - Dec 24
Grand Hotel Continental Siena – Starhotels Collezione
Rooftop terrace
Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa
5.0 star property
Cortona Old Town
10.0 out of 10, Exceptional, (255)
"Excellent hotel Staff very knowledgeable and friendly Loved everything about our stay and will return. "
Canada
Florence and Robert
The price is NT$9,525
NT$10,625 total
includes taxes & fees
Jan 4 - 2026/1/5
Monastero di Cortona Hotel & Spa
Villa (Agresto) | Living area | LCD TV, pay movies
Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel
5.0 star property
Montalcino
10.0 out of 10, Exceptional, (70)
"Wonderful stay "
United States
Talib
The price is NT$42,424
NT$47,036 total
includes taxes & fees
Jan 4 - 2026/1/5
Castiglion del Bosco, A Rosewood Hotel
Outdoor pool, pool umbrellas, sun loungers
Castello di Casole, A Belmond Hotel, Tuscany

Castello di Casole, A Belmond Hotel, Tuscany

Castello di Casole, A Belmond Hotel, Tuscany
5.0 star property
Casole d'Elsa
9.6 out of 10, Exceptional, (79)
"Top-notch hotel. Everything, from the grounds, to the breakfast, to the pool, to the spa + gym, is perfect."
United States
Michael
Castello di Casole, A Belmond Hotel, Tuscany
Garden
Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais
5.0 star property
Castelnuovo Berardenga
9.2 out of 10, Wonderful, (192)
"Best in the world!"
United States
ALFREDO
Borgo Scopeto Wine & Country Relais
Indoor pool, outdoor pool, sun loungers
Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World
5.0 star property
Gaiole in Chianti
9.6 out of 10, Exceptional, (261)
"The breakfast was fresh with lots of options and a outdoor setting on the property. The property is beautiful, pool area and spa so peaceful. Excellent service in all areas of hotel! "
Canada
Catherine
Castello di Spaltenna- Small Luxury Hotels of the World
View from property
Castello di Velona Resort Thermal SPA & Winery

Castello di Velona Resort Thermal SPA & Winery

Castello di Velona Resort Thermal SPA & Winery
5.0 star property
Montalcino
9.0 out of 10, Wonderful, (340)
"The property was exquisite. The view spectacular and the staff top notch. The indoor and outdoor thermal pools and sauna made our stay very relaxing. The buffet breakfast was amazing."
United States
Jose
Castello di Velona Resort Thermal SPA & Winery
Garden
Pieve Aldina - Fontenille Collection

Pieve Aldina - Fontenille Collection

Pieve Aldina - Fontenille Collection
5.0 star property
Radda in Chianti
10.0 out of 10, Exceptional, (32)
"Gorgeous design, high quality, delicious food and wine, friendly and helpful staff. "
United States
Lara
Pieve Aldina - Fontenille Collection
Hiking
Borgo Sant'Ambrogio Resort

Borgo Sant'Ambrogio Resort

Borgo Sant'Ambrogio Resort
5.0 star property
Trequanda
9.8 out of 10, Exceptional, (97)
"It was very clean, excellent service and communication with every staff member was great, location was incredible, and overall a very pleasant stay. If you have the opportunity, the stay is great!"
United States
Juan Carlos
The price is NT$5,688
NT$6,367 total
includes taxes & fees
Jan 5 - 2026/1/6
Borgo Sant'Ambrogio Resort
Outdoor pool, sun loungers
Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World
5.0 star property
Cortona
9.8 out of 10, Exceptional, (228)
"Room was wonderful, bathroom spacious and well appointed. Staff amazing and so friendly "
United States
Melodee
Villa di Piazzano - Small Luxury Hotel of the World
2 restaurants, breakfast served
Borgo Vescine

Borgo Vescine

Borgo Vescine
5.0 star property
Radda in Chianti
9.4 out of 10, Exceptional, (244)
"This was a beautiful location. The room was spacious and loved the patio for coffee in the mornings. It was very private. We enjoyed the pool and restaurants were great. Breakfast was amazing. We did the picnic and dinner in the Olive Garden and loved getting to know others at our table. The chefs food choices were so wonderful. We would definitely stay again. "
United States
Sherie
Borgo Vescine
Yoga
The Club House

The Club House

The Club House
5.0 star property
Castelnuovo Berardenga
10.0 out of 10, Exceptional, (8)
"Unbelievable stay. All amenities are included. The staff is very welcoming. Having traveled extensively, this luxury resort is among the most impressive run hotels. The grounds, food, and staff all A+"
United States
Robert
The Club House
Exterior
Hotel Le Fontanelle

Hotel Le Fontanelle

Hotel Le Fontanelle
5.0 star property
Castelnuovo Berardenga
9.8 out of 10, Exceptional, (95)
"We had a perfect stay at this hotel! 100% recommend. "
Netherlands
Andreea
Hotel Le Fontanelle
Exterior
Borgo San Felice Resort

Borgo San Felice Resort

Borgo San Felice Resort
5.0 star property
Castelnuovo Berardenga
9.8 out of 10, Exceptional, (79)
"One of our favorite places we’ve ever stayed at. 100% recommend. Hopefully we can visit again. "
United States
Maria D
Borgo San Felice Resort
Exterior
Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala
5.0 star property
Montepulciano
9.4 out of 10, Exceptional, (123)
"Loved everything about this property! The spa is a lovely experience. Next time will stay longer "
United States
Ann Marie
Precise Tale Poggio Alla Sala
Indoor pool, seasonal outdoor pool
Mercure Petriolo Siena Terme Spa Hotel

Mercure Petriolo Siena Terme Spa Hotel

Mercure Petriolo Siena Terme Spa Hotel
5.0 star property
Civitella Paganico
8.8 out of 10, Excellent, (235)
"We had a great time. I would recommend this hotel when in Tuscany. "
United States
Mike
The price is NT$2,587
NT$2,846 total
includes taxes & fees
Jan 9 - 2026/1/10
Mercure Petriolo Siena Terme Spa Hotel
Junior Suite | View from room
Castello Banfi - Il Borgo - Relais et Chateaux

Castello Banfi - Il Borgo - Relais et Chateaux

Castello Banfi - Il Borgo - Relais et Chateaux
5.0 star property
Montalcino
10.0 out of 10, Exceptional, (126)
"The setting, scenery and hotel were 5 star plus!"
United States
Diana
Castello Banfi - Il Borgo - Relais et Chateaux
2 indoor pools, seasonal outdoor pool
Castel Monastero - The Leading Hotels of the World

Castel Monastero - The Leading Hotels of the World

Castel Monastero - The Leading Hotels of the World
5.0 star property
Castelnuovo Berardenga
8.8 out of 10, Excellent, (144)
"Had two wonderful nights at the Castel Monastero (wish we had more). Will definitely go back"
Canada
John
The price is NT$19,944
NT$22,308 total
includes taxes & fees
Dec 23 - Dec 24
Castel Monastero - The Leading Hotels of the World
Lunch and dinner served, local cuisine
La Posta Hotel & Thermal Spa

La Posta Hotel & Thermal Spa

La Posta Hotel & Thermal Spa
5.0 star property
San Quirico d'Orcia
9.6 out of 10, Exceptional, (70)
"Enjoyed our stay to the fullest!"
United States
Anna
The price is NT$17,296
NT$19,211 total
includes taxes & fees
Dec 23 - Dec 24
La Posta Hotel & Thermal Spa
Outdoor pool, free cabanas, pool umbrellas
Borgo Santo Pietro

Borgo Santo Pietro

Borgo Santo Pietro
5.0 star property
Chiusdino
9.6 out of 10, Exceptional, (57)
"Always wonderful stay here "
United States
Andrew
Borgo Santo Pietro
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Explore similar 4-star hotels

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

Hotel Athena

P Mascagni 55 Siena SI
The price is NT$2,775 per night from Jan 15 to Jan 16
NT$2,775
NT$3,164 total
Jan 15 - 2026/1/16
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
Still don't see what you're looking for?
See all properties in Asciano.
You can also use these popular filters to refine your search.
PoolSpaHot tubBreakfast includedWaterpark
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 Asciano

Terracotta-hued buildings line the medieval streets where you'll find the impressive Basilica of Sant'Agata and Museo Palazzo Corboli. Rent bikes to explore the surrounding Val d'Orcia's cypress-dotted hills, or join cooking classes to master traditional Tuscan pasta recipes.

See all hotels in Asciano
Picturesque surroundings south of Siena. #TakeAHike
Photo by Galyna V
Open Photo by Galyna V

Top Asciano Hotel Reviews

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

10/10 Excellent
"Everything was perfect! Would like to give this Property a 6 Star rating. The staff made you feel like royalty!!"
Sabrina 4-night trip
Posted 4 days ago
Monastero di Cortona Hotel & Spa

Frequently asked questions

What are the best 5-star hotels in Asciano?
If you're looking for a 5-star experience, Castel Monastero offers one of the best of them based on Expedia traveler reviews. Book a room at this Asciano getaway and get ready for first-rate service, upscale furnishings and world-class amenities.
How much does it cost to stay in a 5-star hotel in Asciano?
You'll find a range of pricing options for a 5-star hotel in Asciano on Expedia. How much you'll pay will depend on your vacation dates, length of your trip and other factors. Compare all of the available properties for your desired dates and make use of our pricing and other filters to land the perfect luxury stay.

  • Search for the lowest price per night from NT$1,763

What makes a hotel 5 stars in Asciano?
Flawless guest service is at the heart of every 5-star hotel in Asciano. From the minute you arrive, staff attend to your every need, whether answering room service calls 24/7 or providing in-room massages. Additionally, hotels must offer top-rate conveniences to meet the standard for a 5-star rating. These can include deluxe baths, an on-site spa, swimming pools, fine dining kitchens and knowledgeable concierge.