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 $1,276
per person
Nov 22 - Nov 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) 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

Art Maisons Oia Castle

Art Maisons Oia Castle

CA $2,990
per person
Nov 11 - Nov 16
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Thira (JTR)
9.6/10 Exceptional! (124 reviews)
Everything was amazing!

Reviewed on Jul 27, 2026

Lotus Center Inn

Lotus Center Inn

Athens City Centre
CA $2,200
per person
Oct 13 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Athens (ATH)
9/10 Wonderful! (259 reviews)
Art Maisons Aspaki Exclusive Suites

Art Maisons Aspaki Exclusive Suites

CA $2,642
per person
Nov 13 - Nov 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Thira (JTR)
9.8/10 Exceptional! (145 reviews)
Excellent place and great staff. The ladies at front desk are excellent, the bar guys are the best! Definitely recommend it for anyone looking for comfort and location is next to the blue dome. Ahmed the guy who helped us with our luggage he is the best ! Thank you all and also the house keeping people.

Reviewed on Sep 5, 2026

West East Suites

West East Suites

CA $3,270
per person
Oct 11 - Oct 17
found 13 hours ago
Roundtrip flight included
Montreal (YUL) to Thira (JTR)
9.8/10 Exceptional! (215 reviews)
We had an amazing stay and overall had a wonderful experience. The property is absolutely beautiful, the views are breathtaking, and everything from the room to the service and overall atmosphere was exceptional. It was truly a memorable stay. The only area that could have been handled better was our arrival and check-in experience. We arrived around 11:00 AM after a long journey and were understandably quite jet-lagged and tired. We knew that official check-in was at 3:00 PM, so we completely understood that our room might not be ready right away. Thankfully, the room was ready around 1:00 PM, which we really appreciated. However, when we followed up a couple of times during those two hours, the receptionist at the front desk appeared irritated by our questions, which made us feel a little uncomfortable, particularly given how exhausted we were after travelling. That said, this was a relatively minor issue in what was otherwise an exceptional stay. Once we were settled in, everything was fantastic, and we truly enjoyed our time here. We would absolutely recommend the property and would happily return in the future.

Reviewed on Sep 8, 2026

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.

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.

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.

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.

Colorful seaside houses with balconies, a rocky shoreline, and a clear blue sky.

Klima

Though Klima might not have many top sights, you can venture to the surrounding area to see attractions like Catacombs of Milos and Plathiena Beach.

Ready to book your vacation to Cyclades Islands?

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Cyclades Islands Hotel Deals

Poseidon Hotel & Suites

Poseidon Hotel & Suites

Mykonos Town Mykonos Mykonos Island
CA $211
CA $256 total
Oct 1 - Oct 2
includes taxes & fees
9.6/10 Exceptional! (1,001 reviews)
"The staff were all friendly and accommodating. Room was clean and comfortable positioned right along the water view which created great atmosphere for photos."

Reviewed on Sep 9, 2026

Poseidon Hotel & Suites
CAVO TAGOO MYKONOS

CAVO TAGOO MYKONOS

TAGOO MYKONOS Mykonos
CA $921
CA $1,072 total
Oct 6 - Oct 7
includes taxes & fees
CAVO TAGOO MYKONOS
DIAMOND on the cliff Hotel &Suites

DIAMOND on the cliff Hotel &Suites

imerovigli 1 Santorini Cyclades
8.2/10 Very good! (28 reviews)
"Great room, great place, location is perfect and the price is amazing !! Thanks you looking for next year return:)"

Reviewed on Sep 6, 2026

Get rates
DIAMOND on the cliff Hotel &Suites
See all 14,999 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.

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 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 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 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 pebbled beach with sun loungers and thatched umbrellas.

Kamari Beach

9.0/10 (3,927 reviews)
Nothing says vacation like spending a lazy day at Kamari Beach, a popular beach in Santorini. Wander the seaside or discover the area's beautiful sunsets.
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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 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 $1,276. 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.