Naxos and Lesser Cyclades Luxury Vacations

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Flight and Luxury hotel deals in Naxos and Lesser Cyclades

Price found within the past 48 hours. Click for updated prices.
Art Maisons Aspaki Exclusive Suites

Art Maisons Aspaki Exclusive Suites

CA $2,322
per person
Oct 25 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Thira (JTR)
9.8/10 Exceptional! (145 reviews)
Fanari Villas Santorini

Fanari Villas Santorini

Save 100% on your flight
CA $3,085
per person
Nov 8 - Nov 15
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Thira (JTR)
9.4/10 Exceptional! (327 reviews)
Art Maisons Oia Castle

Art Maisons Oia Castle

Save 100% on your flight
CA $3,940
per person
Nov 1 - Nov 7
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Thira (JTR)
9.6/10 Exceptional! (124 reviews)
We stayed 5 nights at Art Maisons Oia Castle and 1 night at Aspaki the sister property and both are absolutely amazing! From conscience of airport transportation to meeting the bell boy who carried our bags to the room everything was seamless. Oia castle sits right above Ammoudi Bay with the best sunsets I have ever seen right from your porch. Chris was very helpful and handled everything we needed from scheduling catamaran tours, to renting ATVs for us. He truly is one of a kind! The last night Chris arranged for us to end our trip by upgrading us to Aspaki. This was the best dinner experience at EOS. Breathtaking sunset views on the rooftop terrace and amazing dishes and wine. All in all I have 0 complaints and will be a returning customer for sure!

Reviewed on Sep 22, 2026

Aria Suites

Aria Suites

CA $2,631
per person
Oct 26 - Oct 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Thira (JTR)
10/10 Exceptional! (324 reviews)
Phōs The Boutique Luxury Hotel & Villas

Phōs The Boutique Luxury Hotel & Villas

CA $2,938
per person
Oct 27 - Oct 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Thira (JTR)
9.6/10 Exceptional! (40 reviews)
The food was amazing. The views were amazing. It was just a little bit windy, but that’s out of the hotels control but when we got there, they offered us a glass of wine and showed us a map of the whole island and gave recommendations and it was amazing.

Reviewed on Sep 20, 2026

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5* Luxury holidays in Naxos and Lesser Cyclades

Price found within the past 48 hours. Click for updated prices.
Art Maisons Aspaki Exclusive Suites

Art Maisons Aspaki Exclusive Suites

Save 100% on your flight
CA $2,717
per person
Nov 27 - Dec 1
found 18 hours ago
Roundtrip flight included
Toronto (YTO) to Thira (JTR)
9.8/10 Exceptional! (145 reviews)
Art Maisons Oia Castle

Art Maisons Oia Castle

Save 100% on your flight
CA $3,940
per person
Nov 1 - Nov 7
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Thira (JTR)
9.6/10 Exceptional! (124 reviews)
We stayed 5 nights at Art Maisons Oia Castle and 1 night at Aspaki the sister property and both are absolutely amazing! From conscience of airport transportation to meeting the bell boy who carried our bags to the room everything was seamless. Oia castle sits right above Ammoudi Bay with the best sunsets I have ever seen right from your porch. Chris was very helpful and handled everything we needed from scheduling catamaran tours, to renting ATVs for us. He truly is one of a kind! The last night Chris arranged for us to end our trip by upgrading us to Aspaki. This was the best dinner experience at EOS. Breathtaking sunset views on the rooftop terrace and amazing dishes and wine. All in all I have 0 complaints and will be a returning customer for sure!

Reviewed on Sep 22, 2026

Phōs The Boutique Luxury Hotel & Villas

Phōs The Boutique Luxury Hotel & Villas

CA $2,938
per person
Oct 27 - Oct 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Thira (JTR)
9.6/10 Exceptional! (40 reviews)
The food was amazing. The views were amazing. It was just a little bit windy, but that’s out of the hotels control but when we got there, they offered us a glass of wine and showed us a map of the whole island and gave recommendations and it was amazing.

Reviewed on Sep 20, 2026

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3 Night Luxury holidays in Naxos and Lesser Cyclades

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

Delion View Hotel

CA $1,697
per person
Oct 27 - Oct 30
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Thira (JTR)
9.4/10 Exceptional! (307 reviews)
Good

Reviewed on Sep 23, 2026

Art Maisons Aspaki Exclusive Suites

Art Maisons Aspaki Exclusive Suites

CA $2,322
per person
Oct 25 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Thira (JTR)
9.8/10 Exceptional! (145 reviews)
Aria Suites

Aria Suites

CA $1,900
per person
Oct 27 - Oct 30
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Thira (JTR)
10/10 Exceptional! (324 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Naxos and Lesser Cyclades
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4 Night Luxury holidays in Naxos and Lesser Cyclades

Price found within the past 48 hours. Click for updated prices.
Aelia Luxury Suites Thalassa

Aelia Luxury Suites Thalassa

CA $2,057
per person
Nov 6 - Nov 10
found 3 hours ago
Roundtrip flight included
Montreal (YUL) to Thira (JTR)
10/10 Exceptional! (1 review)
Phōs The Boutique Luxury Hotel & Villas

Phōs The Boutique Luxury Hotel & Villas

CA $2,938
per person
Oct 27 - Oct 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Thira (JTR)
9.6/10 Exceptional! (40 reviews)
The food was amazing. The views were amazing. It was just a little bit windy, but that’s out of the hotels control but when we got there, they offered us a glass of wine and showed us a map of the whole island and gave recommendations and it was amazing.

Reviewed on Sep 20, 2026

Aria Suites

Aria Suites

CA $2,225
per person
Oct 27 - Oct 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Thira (JTR)
10/10 Exceptional! (324 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Naxos and Lesser Cyclades
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Plan the perfect luxury Naxos and Lesser Cyclades vacation with Expedia

What are some benefits when booking luxury Naxos and Lesser Cyclades vacations?

When you book a luxury Naxos and Lesser Cyclades vacation, you get to enjoy some of the best amenities and special features available. Luxury vacation options often feature spa facilities right in your accommodation, along with room service and an on-site restaurant. The quality of the bedding and even the water pressure tends to be better, so it's the perfect solution for travellers looking to put their feet up and relax.

How can I find all-inclusive luxury vacations in Naxos and Lesser Cyclades?

If you're looking for something luxurious in Naxos and Lesser Cyclades, all you have to do is take advantage of our search filters. You can implement a filter to only show 5-star accommodations as well as some amenities you may be interested in, like spa facilities and hot tubs. When you opt for an all-inclusive package, you can enjoy luxury alongside a potential discount for booking your accommodation and flight together.

Can I book a cheap luxury vacation?

While luxury vacations tend to be on the more costly end of the spectrum, ranging from CA $1,697, there are a few methods you can try to lower the price as much as possible. When booking a flight and accommodation together, you can enjoy savings of up to 27. After implementing filters for luxury features, you can also sort by price to list the cheapest luxury packages first.

Are there luxury spa vacations?

Yes, luxury spa vacations are available and quite popular in Naxos and Lesser Cyclades. When you book one of these experiences, it's easier than ever to relax, unwind and recharge in between excursions. Either way, you can easily find spa vacations by implementing the spa filter in your search.

What should I look for in a luxury family vacation in Naxos and Lesser Cyclades?

When booking something for the whole family, it's important to consider exactly what kind of experience your family will want.Luxury packages make it easy to keep everyone happy with creature comforts. Kids especially enjoy features like pools, a delicious breakfast and plenty of space. Suites tend to offer your family members a bit more privacy and comfort compared to simple rooms throughout Naxos and Lesser Cyclades.

Can I book last-minute luxury vacations?

Yes, last-minute bookings are often available in Naxos and Lesser Cyclades. All you have to do is enter your travel dates to see what's available. Sometimes, you'll even find additional discounts for booking last-minute, as accommodations are desperate to fill their last remaining spaces.

What can help me find the best luxury vacation deals in Naxos and Lesser Cyclades?

You can use a few strategies to find the best deals on luxury vacation packages. Consider travelling during the off-season to take advantage of the typically lower overall prices. Additionally, staying in the less popular parts of Naxos and Lesser Cyclades or travelling to more obscure destinations altogether can often lead to lower prices.

Can I book a luxury vacation that is fully refundable?

Yes, fully refundable reservations are sometimes available on luxury vacation packages in Naxos and Lesser Cyclades. You can implement a filter for it specifically or check out the policy section on any one of your search results. It should clearly state what's necessary to qualify for a fully refundable booking.

Why should I book my luxury vacation with Expedia?

When you book with Expedia, you can enjoy a one-stop shop for all your travel planning needs. We offer accommodations as well as flights, and you may even be able to enjoy discounts by booking them together. Of course, Expedia Rewards members will find even more discounts and earn points that can be put toward discounts on future bookings.

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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.