Chianti Region Luxury Holidays

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Top flight + Luxury hotel deals in Chianti Region

Price found within the past 48 hours. Click for updated prices.
LHP Certaldo Resort

LHP Certaldo Resort

£479
per person
22 Oct - 26 Oct
found 1 hour ago
Return direct flight included
London (LON) to Florence (FLR)
9.2/10 Wonderful! (543 reviews)
For our Tuscany tour, we decided to stay at LHP Certaldo Resort as it was very near to railway station. I turned out to be best location as train station is 7-9 min walk and area is very safe even at late evening. It is quiet location away from all noises and very easy to go to Pisa, Florence, San Gimignano, Siena, Cirque Terre without having to worry about driving. Check Train time tables to make the most of your time. The resort is an excellent property with all amenities and even a swimming pool ! They have included breakfast that is so nice with so many varieties to enjoy with plenty of choices for vegetarians. The staff is superb, lady at the front desk is so courteous and helpful in case if you have questions. Other staffs are equally nice and servers you with smile.

Reviewed on 14 Sept 2026

Palazzo Leopoldo Dimora Storica & Spa

Palazzo Leopoldo Dimora Storica & Spa

£528
per person
25 Oct - 30 Oct
found 1 day ago
Return direct flight included
Manchester (MAN) to Florence (FLR)
9.2/10 Wonderful! (297 reviews)
We had room 16 at the very top floor with beautiful views of the valley. The room has a separate sitting area with a pullout bed perfect for families. Also very conveniently located in the heart of Radda. Breakfast was lovely and the staff is so nice, even remembered our coffee preferences each morning. Only word of caution is there are no elevators to the rooms so if you have mobility concerns, this might not work. We did get our exercise to counteract all the lovely food!

Reviewed on 13 Sept 2026

Villa Le Calvane

Villa Le Calvane

Save 100% on your flight
£1,151
per person
22 Oct - 26 Oct
found 1 hour ago
Return direct flight included
London (LON) to Florence (FLR)
9.8/10 Exceptional! (89 reviews)
Great staff! Beautiful property. The food is amazing. The pool is beautiful. The view is unreal. We live it. We will be back. Thanks

Reviewed on 3 Aug 2026

Villa Scacciapensieri Boutique Hotel

Villa Scacciapensieri Boutique Hotel

Scacciapensieri
£718
per person
24 Oct - 31 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
9.2/10 Wonderful! (457 reviews)
The villa is amazing and the perfect little world in itself. Its closeness to Siena makes it easier to visit the city. The patio is the perfect place to view Siena at sunset. The staff was very courteous and ready to help. This hotel is a gem.

Reviewed on 16 Sept 2026

Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

Siena City Centre
£1,773
per person
24 Oct - 31 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
9.2/10 Wonderful! (625 reviews)
Our stay was just ok. Very noisy streets. And the bread at the breakfast buffet was extremely stale for both mornings. We could not eat it. If you are allergic to dust be warned that their curtains and bed headers are very dusty.

Reviewed on 16 Sept 2026

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5* Luxury holidays in Chianti Region

Price found within the past 48 hours. Click for updated prices.
LHP Certaldo Resort

LHP Certaldo Resort

£479
per person
22 Oct - 26 Oct
found 1 hour ago
Return direct flight included
London (LON) to Florence (FLR)
9.2/10 Wonderful! (543 reviews)
For our Tuscany tour, we decided to stay at LHP Certaldo Resort as it was very near to railway station. I turned out to be best location as train station is 7-9 min walk and area is very safe even at late evening. It is quiet location away from all noises and very easy to go to Pisa, Florence, San Gimignano, Siena, Cirque Terre without having to worry about driving. Check Train time tables to make the most of your time. The resort is an excellent property with all amenities and even a swimming pool ! They have included breakfast that is so nice with so many varieties to enjoy with plenty of choices for vegetarians. The staff is superb, lady at the front desk is so courteous and helpful in case if you have questions. Other staffs are equally nice and servers you with smile.

Reviewed on 14 Sept 2026

Villa Le Calvane

Villa Le Calvane

Save 100% on your flight
£1,151
per person
22 Oct - 26 Oct
found 1 hour ago
Return direct flight included
London (LON) to Florence (FLR)
9.8/10 Exceptional! (89 reviews)
Great staff! Beautiful property. The food is amazing. The pool is beautiful. The view is unreal. We live it. We will be back. Thanks

Reviewed on 3 Aug 2026

Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

Siena City Centre
£1,773
per person
24 Oct - 31 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
9.2/10 Wonderful! (625 reviews)
Our stay was just ok. Very noisy streets. And the bread at the breakfast buffet was extremely stale for both mornings. We could not eat it. If you are allergic to dust be warned that their curtains and bed headers are very dusty.

Reviewed on 16 Sept 2026

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3 Night Luxury holidays in Chianti Region

Price found within the past 48 hours. Click for updated prices.
Hotel Palazzo San niccolò & Spa

Hotel Palazzo San niccolò & Spa

£351
per person
3 Dec - 6 Dec
found 1 hour ago
Return direct flight included
Manchester (MAN) to Florence (FLR)
9.2/10 Wonderful! (195 reviews)
Great stay!

Reviewed on 4 Sept 2026

LHP Certaldo Resort

LHP Certaldo Resort

£370
per person
28 Oct - 31 Oct
found 19 hours ago
Return flight included
London (LGW) to Florence (FLR)
9.2/10 Wonderful! (543 reviews)
For our Tuscany tour, we decided to stay at LHP Certaldo Resort as it was very near to railway station. I turned out to be best location as train station is 7-9 min walk and area is very safe even at late evening. It is quiet location away from all noises and very easy to go to Pisa, Florence, San Gimignano, Siena, Cirque Terre without having to worry about driving. Check Train time tables to make the most of your time. The resort is an excellent property with all amenities and even a swimming pool ! They have included breakfast that is so nice with so many varieties to enjoy with plenty of choices for vegetarians. The staff is superb, lady at the front desk is so courteous and helpful in case if you have questions. Other staffs are equally nice and servers you with smile.

Reviewed on 14 Sept 2026

Palazzo Leopoldo Dimora Storica & Spa

Palazzo Leopoldo Dimora Storica & Spa

£355
per person
3 Dec - 6 Dec
found 1 hour ago
Return direct flight included
Manchester (MAN) to Florence (FLR)
9.2/10 Wonderful! (297 reviews)
We had room 16 at the very top floor with beautiful views of the valley. The room has a separate sitting area with a pullout bed perfect for families. Also very conveniently located in the heart of Radda. Breakfast was lovely and the staff is so nice, even remembered our coffee preferences each morning. Only word of caution is there are no elevators to the rooms so if you have mobility concerns, this might not work. We did get our exercise to counteract all the lovely food!

Reviewed on 13 Sept 2026

Don't see what you're looking for?
See all available trips from Manchester to Chianti Region
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4 Night Luxury holidays in Chianti Region

Price found within the past 48 hours. Click for updated prices.
Hotel Chiusarelli

Hotel Chiusarelli

Siena City Centre
£209
per person
1 Nov - 5 Nov
found 24 hours ago
Return flight included
Manchester (MAN) to Florence (FLR)
9/10 Wonderful! (1,004 reviews)
This hotel is well maintained and delicious breakfast. Great location to walk to everything in Siena

Reviewed on 22 Sept 2026

LHP Certaldo Resort

LHP Certaldo Resort

£479
per person
22 Oct - 26 Oct
found 1 hour ago
Return direct flight included
London (LON) to Florence (FLR)
9.2/10 Wonderful! (543 reviews)
For our Tuscany tour, we decided to stay at LHP Certaldo Resort as it was very near to railway station. I turned out to be best location as train station is 7-9 min walk and area is very safe even at late evening. It is quiet location away from all noises and very easy to go to Pisa, Florence, San Gimignano, Siena, Cirque Terre without having to worry about driving. Check Train time tables to make the most of your time. The resort is an excellent property with all amenities and even a swimming pool ! They have included breakfast that is so nice with so many varieties to enjoy with plenty of choices for vegetarians. The staff is superb, lady at the front desk is so courteous and helpful in case if you have questions. Other staffs are equally nice and servers you with smile.

Reviewed on 14 Sept 2026

Villa Le Calvane

Villa Le Calvane

Save 100% on your flight
£1,151
per person
22 Oct - 26 Oct
found 1 hour ago
Return direct flight included
London (LON) to Florence (FLR)
9.8/10 Exceptional! (89 reviews)
Great staff! Beautiful property. The food is amazing. The pool is beautiful. The view is unreal. We live it. We will be back. Thanks

Reviewed on 3 Aug 2026

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All you need to know about luxury holidays in Chianti Region

What can I expect from a luxury Chianti Region holiday?

Luxury on holiday is all about relaxing and feeling good. Whether you choose a sumptuous spa, Michelin-starred restaurant or super-king bed is your call. Use our amenities filters to find the things that tick all your boxes.

How can I find all-inclusive luxury holidays in Chianti Region?

Tick the all-inclusive and 5-star filters to find the crème de la crème of Chianti Region holidays. With everything included in the package price, you can drink and dine to your heart’s content, without worrying about that bill at the end.

Can I book a cheap luxury holiday to Chianti Region?

A luxury holiday doesn’t have to break the bank. Travel out of peak season, choose a hotel or resort a little way out or go for a last-minute getaway and you’ll find some cracking deals. Sort by price to find luxury holidays to Chianti Region starting at £209. Prices and availability are subject to change. Additional terms may apply.

Are there luxury spa holidays in Chianti Region?

For sunset massages on the shoreline and view-filled saunas, use our spa filter to find your ideal Chianti Region spa hotel. Book a whole weekend soaking away your stresses, or hop into the spa after the beach, some golf or a local advent-ahhhh.

What should I look for when booking a luxury family holiday in Chianti Region?

Luxury isn’t just for adults. Those little touches designed for little people make a family holiday genuinely stress free … which is the greatest luxury of all. Look for spacious suites, pools toddlers can splash in, and breakfast buffets with waffles, pancakes and Nutella galore.

Can I book luxury last-minute holidays to Chianti Region?

You can wangle a top-notch luxury holiday in Chianti Region for a fraction of the normal price by booking last minute. Just enter your dates and see what’s available – if you’re flexible ... even better!

Can I book a luxury holiday in Chianti Region with free cancellation and/or flexible dates?

If you’re splashing out on a luxury holiday, make sure your money is safe by booking with free cancellation. Just use the fully refundable filter and make sure you read all the terms and conditions.

Why should I book my luxury travel to Chianti Region with Expedia?

Nobody does luxury quite like Expedia. With so many gorgeous properties in Chianti Region to choose from, as well as access to first-class flight deals and hire cars with horsepower, there’s no better place to book.

Top Luxury Chianti Region Hotels

COMO Castello Del Nero

COMO Castello Del Nero

Strada Spicciano 7 Barberino Tavarnelle FI
  • 18 min drive from Tenuta Torciano Winery
Stay at this luxury hotel in Barberino Tavarnelle. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Poggio al Bosco and Castello di Barberino ...
9.6/10 Exceptional! (145 reviews)
"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."

Reviewed on 11 Sept 2026

COMO Castello Del Nero
Castel Monastero - The Leading Hotels of the World

Castel Monastero - The Leading Hotels of the World

Monastero D'Ombrone Castelnuovo Berardenga SI
  • 1 hour drive from Tenuta Torciano Winery
Stay at this luxury hotel in Castelnuovo Berardenga. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Berardenga Riding Centre and Villa ...
9/10 Wonderful! (147 reviews)
"Beautiful hotel, staff amazing, tranquil surroundings, and incredible food. The perfect stay in Tuscany!"

Reviewed on 7 Sept 2026

Castel Monastero - The Leading Hotels of the World
Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

Banchi Di Sopra 85 Siena SI
  • 47 min drive from Tenuta Torciano Winery
Stay at this luxury hotel in Siena. Enjoy free Wi-Fi, 2 bars/lounges and breakfast (surcharge). Our guests praise the helpful staff in their reviews. Popular ...
9.2/10 Wonderful! (631 reviews)
"Our stay was just ok. Very noisy streets. And the bread at the breakfast buffet was extremely stale for both mornings. We could not eat it. If you are allergic to dust be warned that their curtains and bed headers are very dusty."

Reviewed on 16 Sept 2026

Grand Hotel Continental Siena – Starhotels Collezione
See all 4,915 properties in Chianti Region
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.

Things to do

City Sightseeing Florence Hop-on Hop-off

City Sightseeing Florence Hop-on Hop-off Bus Tour

£21
per adult
76% of travellers recommend
City Sightseeing Florence Hop-on Hop-off Bus Tour
Florence: Pasta & Tiramisu Cooking Class with Unlimited Wine

Florence: Pasta & Tiramisu Cooking Class with Unlimited Wine

£18
per adult
94% of travellers recommend
Florence: Pasta & Tiramisu Cooking Class with Unlimited Wine
Florence: Pasta Cooking Class with Unlimited Wine

Florence: Pasta Cooking Class with Unlimited Wine

£14
per adult
94% of travellers recommend
Florence: Pasta Cooking Class with Unlimited Wine
See all activities in Chianti Region

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.