Nicest hotel that we stayed at in Italy. Exceptional service and they strive to be upscale and deliver. Impeccable views, grounds, rooms, and restaurant. Almost felt too nice to be true-- blend of older style with new updates. A bit Disney-fied in feel that it seems to cater to mostly Americans and few locals. However, this means no hassles, broken fixtures, etc. (but it is a very different feel like a California spa vs. an old Italy village hotel). Only minor note is that it is a bit removed...
Nicest hotel that we stayed at in Italy. Exceptional service and they strive to be upscale and deliver. Impeccable views, grounds, rooms, and restaurant. Almost felt too nice to be true-- blend of older style with new updates. A bit Disney-fied in feel that it seems to cater to mostly Americans and few locals. However, this means no hassles, broken fixtures, etc. (but it is a very different feel like a California spa vs. an old Italy village hotel). Only minor note is that it is a bit removed...
The most beautiful hotel in the heart of Chianti. The service was above and beyond. Everything about this charming hotel was amazing. We cannot wait to go back.
The most beautiful hotel in the heart of Chianti. The service was above and beyond. Everything about this charming hotel was amazing. We cannot wait to go back.
Lauren
Reviewed September 11, 2026Reviewed September 11, 2026
This was an excellent experience. Not only is the infrastructure fabulous but its location is great.
Staff is friendly with an excellent service attitude. Restaurant in the hotel is amazing too!
This was an excellent experience. Not only is the infrastructure fabulous but its location is great.
Staff is friendly with an excellent service attitude. Restaurant in the hotel is amazing too!
Ariel O
Reviewed October 29, 2026Reviewed October 29, 2026
The accomodations were awesome! I would highly recommend this hotel. She does not take credit cards and it is difficult to find. However, she will send you an e-mail prior to arrival with all these details as well as how to find the hotel. You can park out front while checking in and then you drive about 100 meters to a free parking lot .... very convenient. The City is wodnerful are easily walkable!
The accomodations were awesome! I would highly recommend this hotel. She does not take credit cards and it is difficult to find. However, she will send you an e-mail prior to arrival with all these details as well as how to find the hotel. You can park out front while checking in and then you drive about 100 meters to a free parking lot .... very convenient. The City is wodnerful are easily walkable!
A beautiful, relaxing property with incredibly kind and professional staff. Villa Lena has a character of its own that feels truly personal. We loved the design of the rooms and the touches of art throughout. The food was delicious and you could tell care was taken with its making. And again all of the staff was incredibly friendly and it was easy to get help when needed. We traveled here with two children and greatly appreciated all the support from the staff. Highly recommend Villa Lena.
A beautiful, relaxing property with incredibly kind and professional staff. Villa Lena has a character of its own that feels truly personal. We loved the design of the rooms and the touches of art throughout. The food was delicious and you could tell care was taken with its making. And again all of the staff was incredibly friendly and it was easy to get help when needed. We traveled here with two children and greatly appreciated all the support from the staff. Highly recommend Villa Lena.
Amazing! This was our favorite stop of our honeymoon. The staff was very friendly and even upgraded our room. Very quaint location and love the animals and farm dogs! The breakfast included every morning was great.
Amazing! This was our favorite stop of our honeymoon. The staff was very friendly and even upgraded our room. Very quaint location and love the animals and farm dogs! The breakfast included every morning was great.
Hotel is in fantastic location right in the middle of the action. Our room overlooked a small square across the street that had a holiday concert that we were able to watch from the room. Hotel bar is pricey, as expected by a 5* lobby bar, but staff is friendly and prompt. Only complaint is the flatness of the pillows and that's stretching. Breakfast is great (buffet plus small menu), staff is quick to recommend dinner places and cafes, and Siena is one of the best towns in Italy. Very...
Hotel is in fantastic location right in the middle of the action. Our room overlooked a small square across the street that had a holiday concert that we were able to watch from the room. Hotel bar is pricey, as expected by a 5* lobby bar, but staff is friendly and prompt. Only complaint is the flatness of the pillows and that's stretching. Breakfast is great (buffet plus small menu), staff is quick to recommend dinner places and cafes, and Siena is one of the best towns in Italy. Very...
Matt
Reviewed December 9, 2016Reviewed December 9, 2016
Seriously the most unique and beautiful hotel!! The views are breathtaking. Do the wine tasting!! Enjoy the views! We rented a car- we were able to venture out to get snacks at a grocery store and try some local dining.
Seriously the most unique and beautiful hotel!! The views are breathtaking. Do the wine tasting!! Enjoy the views! We rented a car- we were able to venture out to get snacks at a grocery store and try some local dining.
We booked this by chance on the last day of the season and it did not disappoint. The level of warmth and responsiveness made our stay very enjoyable. From recommending and booking our restaurant reservations, to a wonderful breakfast and spa experience, this turned out to be a stay we wouldn’t forget.
We booked this by chance on the last day of the season and it did not disappoint. The level of warmth and responsiveness made our stay very enjoyable. From recommending and booking our restaurant reservations, to a wonderful breakfast and spa experience, this turned out to be a stay we wouldn’t forget.
Candice
Reviewed November 2, 2026Reviewed November 2, 2026
It was a quiet, and enjoyable stay. The gentlemen at the reception were always pleasant. My room was clean with plenty of space. The bed was very comfortable. The check in was easy.
The location was central to the things that I wanted to do. Although I had planned on walking from the train station, I ended up taking a taxi for €11.90. It was worth it as the streets are very hilly and not easy to navigate with luggage.
When checking out, they called a taxi for me and even offered to carry my...
It was a quiet, and enjoyable stay. The gentlemen at the reception were always pleasant. My room was clean with plenty of space. The bed was very comfortable. The check in was easy.
The location was central to the things that I wanted to do. Although I had planned on walking from the train station, I ended up taking a taxi for €11.90. It was worth it as the streets are very hilly and not easy to navigate with luggage.
When checking out, they called a taxi for me and even offered to carry my...
Shelley
Reviewed September 26, 2026Reviewed September 26, 2026
We loved everything about our stay. The location was ideal between Siena and Florence. The grounds were so verdant and lovely. The villa was beautiful with no detail overlooked. And the owners treated us like family. When booking from California I always wonder if the pictures online are an oversell. Not here! Our stay was magical. Thank you!
We loved everything about our stay. The location was ideal between Siena and Florence. The grounds were so verdant and lovely. The villa was beautiful with no detail overlooked. And the owners treated us like family. When booking from California I always wonder if the pictures online are an oversell. Not here! Our stay was magical. Thank you!
What are the best 5-star hotels in Castel San Gimignano?
If you're looking for a 5-star experience, Castello di Casole, A Belmond Hotel, Tuscany offers one of the best of them based on reviews by our customers. Book this Castel San Gimignano escape and you can look forward to the highest standard of service, luxurious guest rooms and top-notch facilities.
How much does it cost to stay in a 5-star hotel in Castel San Gimignano?
There are many different pricing options for 5-star hotels in Castel San Gimignano on Expedia. How much you'll pay will depend on when you plan to travel, length of your trip and other factors. Compare available accommodations for your preferred dates and make use of our pricing and other filters to find the ideal high-end stay.
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What makes a hotel 5 stars in Castel San Gimignano?
From high-end dining venues and all-day gyms to pools and dreamy bedding, the 5-star experience in Castel San Gimignano is all about luxury and comfort. But it takes more than just upscale conveniences to receive a 5-star rating. Accommodations also have to deliver extraordinary guest-focused services like beauty treatments, laundry and dry cleaning and concierge services.
Are there any 5-star all-inclusive resorts in Castel San Gimignano?
Find a luxury getaway that includes your room, meals, activities and entertainment in Castel San Gimignano with the help of Expedia's filter tool. Search for properties with a 5-star rating and select the "All inclusive" filter. Be sure to check what's included in the upfront price. That way, you'll be ready to maximize all the premium perks as soon as you arrive.
What are the top 5-star spa hotels in Castel San Gimignano?
Castello di Casole, A Belmond Hotel, Tuscany combines upmarket accommodations with indulgent wellness therapies and experiences. Select from a menu of massages, facials and more at this well-known 5-star spa getaway in Castel San Gimignano.
Are there any 5-star vacation rentals in Castel San Gimignano?
You won't find any 5-star vacation rentals in Castel San Gimignano on our site, but there are some other top-rated properties worth looking into. Scan through our vacation rentals in Castel San Gimignano to book the ideal place for your stay.