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.
Heritage Hill

Heritage Hill

CA $1,518
per person
Nov 22 - Nov 27
found 1 hour ago
Roundtrip flight included
Toronto (YTO) to Athens (ATH)
9.2/10 Wonderful! (233 reviews)
Art Maisons Aspaki Exclusive Suites

Art Maisons Aspaki Exclusive Suites

Save 100% on your flight
CA $3,266
per person
Nov 22 - Nov 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Thira (JTR)
9.8/10 Exceptional! (152 reviews)
Aether Athens

Aether Athens

CA $1,538
per person
Nov 24 - Nov 30
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Athens (ATH)
10/10 Exceptional! (21 reviews)
Very nice people.. easy walk to the subway.

Reviewed on Oct 14, 2026

Santorini Dreams Villas

Santorini Dreams Villas

CA $2,495
per person
Jan 5 - Jan 11
found 24 hours ago
Roundtrip flight included
Montreal (YUL) to Thira (JTR)
8.4/10 Very good! (15 reviews)
You cannot get to this hotel by vehicle which I didn’t know ahead of time. They “contacted us” on WhatsApp which I don’t have. Our driver once realizing you cannot reach by vehicle dropped us off at the bottom of the hill and said it’s up there. The phone number doesn’t reach anybody so after wandering around up the hills and down the hills for over an hour we finally found some nice person that could help us. He directed us to the hotel. it takes 20 minutes when you know where you’re going to get to the hotel up and down steep steps. We finally got the hotel and the room was not ready. We waited for 2 1/2 hours. Once we were told the room was ready, We went to have a look. When we tried to use the hot tub it was dirty with somebody else’s rose petals. There are no roses in the vicinity. There is no toilet paper. The air conditioning didn’t work, the TV was wasn’t working, safe wasn’t working, the coffee maker wasn’t working. Nothing was as it was advertised. The staff was not able to help with anything. We were never able to get anybody on the phone or speak to a manager. I would not recommend this to anyone.

Reviewed on Aug 17, 2024

Regal Hotel Mitropoleos

Regal Hotel Mitropoleos

Athens City Centre
CA $1,532
per person
Dec 15 - Dec 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Athens (ATH)
9.4/10 Exceptional! (229 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 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 town with white buildings, a dock, and a boat.

Adamas

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 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.

Find hotels in Apollonia
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 village with white buildings, a rocky shoreline, and boats docked in a sheltered cove.

Mandrakia

While visiting Mandrakia, you might make a stop by sights like Geraniá and Tourkothálassa.

Find hotels in Mandrakia

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Cyclades Islands Hotel Deals

Poseidon Hotel & Suites

Poseidon Hotel & Suites

Mykonos Town Mykonos Mykonos Island
CA $237
CA $286 total
Oct 15 - Oct 16
includes taxes & fees
Poseidon Hotel & Suites
El Greco Resort

El Greco Resort

Fira Santorini Santorini Island
Fully refundableReserve now, pay when you stay
CA $107
CA $138 total
Oct 31 - Nov 1
includes taxes & fees
9.2/10 Wonderful! (603 reviews)
"Excellent breakfast and dinner buffet! Nice rooms, with Netflix! Beautiful pools and lounging areas! Close walk to all the shops and restaurants!! Very helpful and friendly staff!"

Reviewed on Oct 13, 2026

El Greco Resort
Mykonos Adonis Hotel

Mykonos Adonis Hotel

Chora Mykonos Mykonos Island
Fully refundableReserve now, pay when you stay
CA $142
CA $167 total
Nov 14 - Nov 15
includes taxes & fees
9.4/10 Exceptional! (640 reviews)
"Great location near bus station taxis & airport all walking distance hotel near ocean beautiful view easy access for walking to city center lots of good places to eat liquar lots of shops"

Reviewed on Oct 14, 2026

Mykonos Adonis Hotel
See all 14,851 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 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.
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A coastal town with a marina filled with boats, a road along the coast, and hills in the background.

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 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 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 beach, and boats in the water.

Ornos Beach

9.0/10 (1,946 reviews)
If a restful vacation is part of your travel plans, Ornos Beach might be the perfect place to seek out during your trip to Ornos. While in this romantic area, you can savor the top-notch restaurants.
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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 village with white buildings and blue domes, a rocky coastline, and the sea.

Oia Blue Dome Church Viewpoint

9.6/10 (1,629 reviews)
Find out about the history of Oia when you spend time at Oia Blue Dome Church Viewpoint. Wander the seaside and beautiful beaches in this romantic 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 $1,518. 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.