Cyclades Islands Vacation Packages

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Your Cyclades Islands Vacation

Make organizing your next great adventure easy with a Cyclades Islands vacation package. If it's culture, gift and craft shops and views you're searching for, you won't be disappointed. Start your trip to Cyclades Islands with some time in Oia visiting popular sights like Kamari Beach and Santorini Caldera. Platis Gialos is another top city that lures crowds from near and far. Ornos Beach and Paradise Beach are two of the top places to see in this destination. Start packing your suitcase, because your Cyclades Islands vacation is just clicks away with Expedia.

Top Cyclades Islands Vacation Deals

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

Elite City Resort

CA $1,675
per person
Nov 15 - Nov 22
found 6 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Athens (ATH)
8.6/10 Excellent! (230 reviews)
From the outset, this place couldn't do enough to be welcoming and accommodating. We thoroughly enjoyed our stay and the beach is close and was a lovely way to start our vacation!

Reviewed on Sep 8, 2026

Lotus Center Inn

Lotus Center Inn

Athens City Centre
CA $1,770
per person
Oct 28 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Athens (ATH)
9/10 Wonderful! (259 reviews)
Art Maisons Oia Castle

Art Maisons Oia Castle

Save 100% on your flight
CA $3,940
per person
Nov 1 - Nov 7
found 19 hours 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

Aelia Luxury Suites Thalassa

Aelia Luxury Suites Thalassa

CA $2,115
per person
Nov 9 - Nov 15
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Thira (JTR)
10/10 Exceptional! (1 review)
Iliovasilema Suites

Iliovasilema Suites

CA $3,524
per person
Oct 24 - Oct 31
found 3 hours ago
Roundtrip flight included
Vancouver (YVR) to Thira (JTR)
9.4/10 Exceptional! (341 reviews)

Where to stay in Cyclades Islands

Find the best Cyclades Islands areas and neighborhoods for the activities you enjoy most. Learn more about Cyclades Islands
A coastal town with white buildings, a dock, and a boat.

Adamas

1 out of top 10 points of interest in this area

Adamas is known for its waterfront views, and you can plan a trip to Papikinou Beach and Adamas Port while you're in town.

Find hotels in Adamas
A densely packed white village with terraced buildings on a hillside.

Old Town Naxos

1 out of top 10 points of interest in this area

The pristine beaches and captivating waterfront views are top of the list for many visitors to Old Town Naxos. A stop by Port of Naxos or Naxos Archaeological Museum might round out your trip.

Find hotels in Old Town Naxos
A coastal village with white buildings, a prominent mountain, and a clear blue sky.

Plaka

The beaches and restaurants are a few reasons travelers visit Plaka. Though there aren't many top sights in the neighborhood, you can visit Catacombs of Milos and Plathiena Beach, a few notable attractions nearby.

Find hotels in Plaka
A coastal landscape with white cliffs and the ocean.

Apollonia

Unique features of Apollonia include the beaches and restaurants. Make a stop by Pollonia Beach or Pollonia Dock while you're exploring the area.

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A coastal town with white buildings, a prominent church, and a hilltop landmark.

Tripití

Tripití is popular for its waterfront views, and you can check out Milos Folk and History Museum, a top attraction in the neighborhood.

Find hotels in Tripití

Ready to book your vacation to Cyclades Islands?

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Cyclades Islands Hotel Deals

CAVO TAGOO MYKONOS

CAVO TAGOO MYKONOS

TAGOO MYKONOS Mykonos
CA $848
CA $989 total
Oct 4 - Oct 5
includes taxes & fees
CAVO TAGOO MYKONOS
Volcano View Hotel Santorini

Volcano View Hotel Santorini

Fira Santorini Santorini Island
CA $312
CA $379 total
Oct 21 - Oct 22
includes taxes & fees
9.4/10 Exceptional! (1,000 reviews)
"The property has beautiful views and the staff is amazing. The hotel is old and the rooms need to be updated. There was an odor in our room. The pool has cracked tile and no pool service except for a very small bar. 20 minute walk to downtown Fira."

Reviewed on Sep 21, 2026

Volcano View Hotel Santorini
Myconian Deos - The Set

Myconian Deos - The Set

Agios Vasilios, Chora Mykonou Mykonos Mykonos Island
Fully refundableReserve now, pay when you stay
CA $489
CA $580 total
Oct 22 - Oct 23
includes taxes & fees
9.8/10 Exceptional! (60 reviews)
"Beautiful property!!! ⭐️⭐️⭐️⭐️⭐️"

Reviewed on Sep 14, 2026

Myconian Deos - The Set
See all 14,907 properties in Cyclades Islands
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.
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Stay near popular Cyclades Islands attractions

A coastal road with a steep drop-off, a clear blue sea, and rocky cliffs.

Athinios Port

8.4/10 (4,035 reviews)
Explore the waterfront of Athinios Port and enjoy activities such as boating in Órmos Athiniós. Stroll along the seaside or discover the area's volcano viewpoints.
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A coastal view with waves crashing onto the shore and a distant shoreline with buildings.
Photo by Lillian Phua

Port of Naxos

9.0/10 (1,141 reviews)
Explore the waterfront in Naxos Town with a trip to Port of Naxos. Wander the beautiful beaches and waterfront in this quaint area.
See properties
A marina with numerous yachts docked, a large cruise ship, and a coastal town with white buildings.

Mykonos New Port

8.8/10 (3,440 reviews)
Explore the waterfront in Tourlos with a trip to Mykonos New Port. Wander the beautiful beaches and seaside in the area.
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A coastal town with white buildings, a harbor with boats, and a stone wall.

Port of Parikia

9.0/10 (825 reviews)
Explore the waterfront in Parikia with a trip to Port of Parikia. Wander the beautiful beaches and waterfront in this quaint area.
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A pebbled beach with sun loungers and thatched umbrellas.

Kamari Beach

9.0/10 (3,927 reviews)
If a restful vacation is part of your travel plans, Kamari Beach might be the perfect place to seek out during your trip to Santorini. Wander the seaside or discover the area's beautiful sunsets.
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A coastal town with white buildings, a beach, and boats in the water.

Ornos Beach

9.0/10 (1,946 reviews)
Nothing says vacation like spending a lazy day at Ornos Beach, a popular beach in Ornos. While in this romantic area, you can savor the top-notch restaurants.
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A coastal town with a beach, clear blue waters, and pink flowers.

Paradise Beach

8.8/10 (2,477 reviews)
If a restful vacation is part of your travel plans, Paradise Beach might be the perfect place to seek out during your trip to Paradise. You can enjoy the bars while in the area.
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Frequently asked questions

How much does a Cyclades Islands vacation package cost?
Chart your own course with our Cyclades Islands vacation packages, which start from only CA $1,675. Pick the flights and hotels that suit your style. Then, add on a few sightseeing tours for an amazing adventure.
How do I get a cheap travel package to Cyclades Islands?
Combine your flights and hotels, add extras such as tours, and save with a Cyclades Islands vacation package. You won't just enjoy big discounts on your escape — you'll have loads of choice within your reach too. When you book through Expedia, you'll have your pick of over 550 airlines and 1,000,000 hotels across the globe. Your dream vacation begins right here, right now!
Where should I stay in Cyclades Islands?
Fira is a terrific city to include in your itinerary. This is where you'll find popular sights such as Museum of Prehistoric Thira and Archaeological Museum of Thera. Mykonos Town also lures many globetrotters eager to explore some of the best attractions in Cyclades Islands. They include Windmills of Mykonos and Church of Panagia Paraportiani.
What are the top hotels in Cyclades Islands?
Have a look at Palladium Hotel and Grand Beach Mykonos. They're top picks for many travelers to Mykonos Town. If Oia is next stop on your itinerary, De Sol Spa Hotel and Caldera Premium Villas - Adults Only are a couple of welcoming options.
How far in advance should I book my Cyclades Islands vacation?
It's difficult to pick the ideal time for airfares, but we generally say the earlier, the better. Most international journeys on Expedia become available up to 12 months in advance. If you can't book ahead, don't stress. Budget prices appear from time to time within a few weeks of departure dates.
What does an Expedia Cyclades Islands travel package include?
Expedia has all you need to lock in Cyclades Islands escape, but what your package looks like is your call. Select from a combination of rental cars, hotels and flights. After some activities or tours to fill in your time? Once you've made your booking, you can add them on too. Whatever your budget or style, there's a deal to meet your needs.
What should I know before booking a Cyclades Islands travel package?
Whether it's relaxation or adventure you're chasing, a Cyclades Islands vacation package lets you plan your escape your way. Plus, you'll get access to great discounts just for combining your hotel with your rental car and flights. The more you bundle, the more you'll save!
Can I choose my airline with a Cyclades Islands Expedia vacation package?
Yes — that's one of the best things about an Expedia package. You can pick and choose your flights, hotels and more. We have more than 550 partner airlines globally, so you have lots of choice when creating your Cyclades Islands getaway.
If I'm not able to travel, can I cancel my Cyclades Islands vacation package?
You can cancel your Cyclades Islands booking if your plans have been upended. Whether you'll incur a fee or not depends on your airline, hotel or car rental company. It may be possible to change or cancel your booking free of charge if you booked in the last 24 hours. Head to our Customer Service Portal for more information.

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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.