Luxury Vacations in Naxos and Lesser Cyclades 2026

Photo by William Keller

Plan, book, travel with confidence
Better together
Save up to CA $4,200 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place

Flight and Luxury hotel deals in Naxos and Lesser Cyclades

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

Delion View Hotel

CA $1,328

per person

Nov 28 - Dec 4

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Thira (JTR)

9.4/10 Exceptional! (307 reviews)

Great location and superb view on Caldera. Shared balcony to watch the sunset if you don’t feel standing with a crowd. Challenging to find for the first time, so contact George to help you get in. Lots of stairs🙂 I wouldn’t recommend breakfast though, convenient but not too great 😌 Overall recommended!

Reviewed on Sep 15, 2026

Grand Ambassador Santorini Hotel

CA $2,427

per person

Oct 18 - Oct 21

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Thira (JTR)

9.4/10 Exceptional! (261 reviews)

We had a beautiful view and a private pool. The rooms were clean and had everything we needed. Everyone was so friendly and incredibly helpful. Our check out was 11am but our flight wasn't until 11:50pm that night so the staff offered us a couple of options to help us pass the time and let us come back to freshen up before our flight, which was so helpful and greatly appreciated. Food was really good too! I am so glad we stayed here.

Reviewed on Sep 15, 2026

Art Maisons Aspaki Exclusive Suites

CA $3,138

per person

Nov 3 - Nov 8

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Thira (JTR)

9.8/10 Exceptional! (145 reviews)

Aspaki is a must sta

Reviewed on Sep 10, 2026

Aria Suites

CA $2,045

per person

Oct 27 - Nov 1

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Thira (JTR)

10/10 Exceptional! (324 reviews)

Excellent, Staff was on point and accommodation to our needs were perfect like our view ever morning. They also recommended place to go near by.

Reviewed on Sep 6, 2026

Art Maisons Oia Castle

CA $3,292

per person

Oct 26 - Oct 30

found 9 hours ago

Roundtrip flight included

Montreal (YUL) to Thira (JTR)

9.6/10 Exceptional! (124 reviews)

Everything was amazing!

Reviewed on Jul 27, 2026

Don't see what you're looking for?

See all available trips from Columbus to Naxos and Lesser Cyclades

View all trips

5* Luxury holidays in Naxos and Lesser Cyclades

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

Grand Ambassador Santorini Hotel

CA $2,427

per person

Oct 18 - Oct 21

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Thira (JTR)

9.4/10 Exceptional! (261 reviews)

Reviewed on Sep 15, 2026

Art Maisons Aspaki Exclusive Suites

CA $3,138

per person

Nov 3 - Nov 8

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Thira (JTR)

9.8/10 Exceptional! (145 reviews)

Aspaki is a must sta

Reviewed on Sep 10, 2026

Art Maisons Oia Castle

CA $3,292

per person

Oct 26 - Oct 30

found 9 hours ago

Roundtrip flight included

Montreal (YUL) to Thira (JTR)

9.6/10 Exceptional! (124 reviews)

Everything was amazing!

Reviewed on Jul 27, 2026

Don't see what you're looking for?

See all available trips from Columbus to Naxos and Lesser Cyclades

View all trips

3 Night Luxury holidays in Naxos and Lesser Cyclades

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

Aelia Luxury Suites Thalassa

CA $1,565

per person

Nov 14 - Nov 16

found 1 day ago

Roundtrip flight included

Vancouver (YVR) to Thira (JTR)

10/10 Exceptional! (1 review)

Grand Ambassador Santorini Hotel

CA $2,161

per person

Oct 19 - Oct 21

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Thira (JTR)

9.4/10 Exceptional! (261 reviews)

Reviewed on Sep 15, 2026

Art Maisons Aspaki Exclusive Suites

CA $2,524

per person

Oct 19 - Oct 21

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Thira (JTR)

9.8/10 Exceptional! (145 reviews)

Aspaki is a must sta

Reviewed on Sep 10, 2026

Don't see what you're looking for?

See all available trips from Columbus to Naxos and Lesser Cyclades

View all trips

4 Night Luxury holidays in Naxos and Lesser Cyclades

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

Esperas Santorini

CA $1,616

per person

Oct 26 - Oct 29

found 10 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to Thira (JTR)

9.6/10 Exceptional! (356 reviews)

Grand Ambassador Santorini Hotel

CA $2,427

per person

Oct 18 - Oct 21

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Thira (JTR)

9.4/10 Exceptional! (261 reviews)

Reviewed on Sep 15, 2026

Aria Suites

CA $1,643

per person

Oct 26 - Oct 29

found 10 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to Thira (JTR)

10/10 Exceptional! (324 reviews)

Excellent, Staff was on point and accommodation to our needs were perfect like our view ever morning. They also recommended place to go near by.

Reviewed on Sep 6, 2026

Don't see what you're looking for?

See all available trips from Columbus to Naxos and Lesser Cyclades

View all trips

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 $1,328, 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 33. 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.