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

4 out of 5
Price was CA $2,164, price is now CA $1,565 per person
CA $1,565
per person
Jan 10 - Jan 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Athens (ATH)
9.2/10 Wonderful! (233 reviews)
The room was clean, the staff were respectful, and the breakfast was great. The hotel was also about a 20-minute walk from major attractions, which was convenient. Overall happy with the stay!

Reviewed on Oct 18, 2026

Anthology of Athens, a member of The Leading Hotels of the World

Anthology of Athens, a member of The Leading Hotels of the World

5 out of 5
Athens City Centre
Save 100% on your flight
Price was CA $4,560, price is now CA $3,100 per person
CA $3,100
per person
Dec 8 - Dec 14
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Athens (ATH)
9.4/10 Exceptional! (73 reviews)
this place was an absolute dream! we only stayed for 2 nights but i wish it would’ve been more. property staff were super helpful with all your needs, they were also very considerate of the construction next door that they had already planned compensation for us at the time of check in. our room was beautiful and spotless, i will say the view is a little obstructed due to the growth of the trees but overall still a great view of athens and you could even see lycabettus hill from our room. if we ever get the chance to return to athens we will most definitely be choosing this hotel again!

Reviewed on Oct 22, 2026

Santorini Dreams Villas

Santorini Dreams Villas

3 out of 5
Price was CA $3,446, price is now CA $2,409 per person
CA $2,409
per person
Jan 9 - Jan 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) 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

Delion View Hotel

Delion View Hotel

4 out of 5
Price was CA $2,972, price is now CA $2,089 per person
CA $2,089
per person
Jan 9 - Jan 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Thira (JTR)
9.4/10 Exceptional! (334 reviews)

Divino Caldera

Divino Caldera

5 out of 5
Price was CA $2,798, price is now CA $2,019 per person
CA $2,019
per person
Jan 9 - Jan 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Thira (JTR)
9.8/10 Exceptional! (50 reviews)
Great welcome , easy quick check in, stunning pool area , nice room , good size , very comfortable

Reviewed on Oct 12, 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 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

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Cyclades Islands Hotel Deals

Poseidon Hotel & Suites

Poseidon Hotel & Suites

4 out of 5
Mykonos Town Mykonos Mykonos Island
The price is CA $234 per night from Oct 28 to Oct 29
CA $234
CA $282 total
Oct 28 - Oct 29
includes taxes & fees
9.6/10 Exceptional! (1,005 reviews)
"Very cute standard plus room with small balcony, offered great side view of windmills and Aegean Sea. Plentiful toiletries in bathroom. Breakfast buffet with very good variety. Poolside bar and restaurant. Great location to conveniences like ATM."

Reviewed on Oct 26, 2026

Poseidon Hotel & Suites
Mykonos Adonis Hotel

Mykonos Adonis Hotel

4 out of 5
Chora Mykonos Mykonos Island
Fully refundableReserve now, pay when you stay
The price is CA $153 per night from Nov 2 to Nov 3
CA $153
CA $178 total
Nov 2 - Nov 3
includes taxes & fees
9.4/10 Exceptional! (645 reviews)
"Le déjeuner est moyen mais on y trouve notre compte. L’immeuble a besoin un peu d’amour. Les fenêtres seraient à changer. Il manquait des ampoules, le drain de la douche ne suffit pas alors l’eau se rendait sur tout le plancher. L’emplacement est bien un peu en retrait pour le calme mais très près ..."

Reviewed on Oct 26, 2026

Mykonos Adonis Hotel
DIAMOND on the cliff Hotel &Suites

DIAMOND on the cliff Hotel &Suites

imerovigli 1 Santorini Cyclades
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DIAMOND on the cliff Hotel &Suites
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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
Open 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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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 $1,565. 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.