Kalypso Vacations from $1,417

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 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

Your Kalypso Vacation

Take away the hard part of planning your next grand adventure with a Kalypso vacation package. Whether you're in town for its history, food or something else, this city offers limitless opportunities for discovery. If a sightseeing tour is part of the program during your trip to Kalypso, visit major attractions like Plakias Beach, Preveli Beach and Monastery of Preveli. Stop daydreaming and start doing. Browse the range of options on Expedia today and finally put your Kalypso vacation plans into gear!

The Latest Kalypso vacation packages

Price found within the past 48 hours. Click for updated prices.
Dimargio Luxury Hotel & Spa

Dimargio Luxury Hotel & Spa

$1,417
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Heraklion (HER)
9.8/10 Exceptional! (61 reviews)
Wonderful front desk staff and beautiful place

Reviewed on Oct 20, 2026

Amirandes, A Resort to Live

Amirandes, A Resort to Live

$3,423
per person
Dec 27 - Jan 2
found 2 hours ago
Roundtrip non-stop flight included
New York (JFK) to Heraklion (HER)
9.4/10 Exceptional! (239 reviews)
I'm actually quite disappointed with this hotel. I wished I complained when we arrived. First of all, the hotel grounds itself is amazinggggg. Food is amazing. The only let down was the room. The room is so basic for what you pay at this hotel. Everything else is so well thought of but then you go into your room and it's so meh. Nothing speculatar about the room itself. Very underwhelming. We got the pool with private garden and there was no access way to the garden. You have to swim to get to the private garden. The pool itself is so small, what's the point. You can't have a proper swim. The pool was dirty too. The room was also dirty although it is daily cleaned on the surface. Under the bed was Dusty! And under the table cabinet was Dusty. I was quite disappointed to be honest for whats advertised. I think they purposely do not show the room and instead use a floor plan. If I saw the room, I would have picked a different hotel. Everything else is perfect though, it's just the room that was underwhelming for me.

Reviewed on Sep 30, 2026

Vespera City Hotel

Vespera City Hotel

$2,590
per person
Dec 27 - Jan 2
found 2 hours ago
Roundtrip non-stop flight included
New York (JFK) to Heraklion (HER)
9.2/10 Wonderful! (43 reviews)
Metropole Urban Hotel

Metropole Urban Hotel

$1,512
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Heraklion (HER)
9.2/10 Wonderful! (317 reviews)
Property was good and breakfast at the restaurant in the morning was plentiful as well (leave a lot of time for it). Area was quiet and nice. The thing that was annoying, however, was tha light in the washroom was turning on at night when you tried using it, waking up both yourself and your family members.

Reviewed on Oct 18, 2026

Manili Boutique Suites & Villas, an SLH Hotel

Manili Boutique Suites & Villas, an SLH Hotel

$2,615
per person
Dec 27 - Jan 2
found 2 hours ago
Roundtrip non-stop flight included
New York (JFK) to Heraklion (HER)
9.6/10 Exceptional! (37 reviews)
Nice hotel and a good location in town and short drive to many wineries (5 minute walk to restaurants). Quiet. Outdoor private hot tub is not heated (so was not really useable in October).

Reviewed on Oct 18, 2026

Don't see what you're looking for?
See all available trips from Columbus to Kalypso
View all trips

What to do in Kalypso

Arkadi, Melidoni, Margarites Half day

Arkadi, Melidoni, Margarites, olive oil factory

$28
per adult
Arkadi, Melidoni, Margarites, olive oil factory
Rethymno: Melidoni Cave and Arkadi Monastery Half-Day Trip

From Rethymno: Arkadi Monastery,Melidoni Cave and Margarites

$28
per adult
From Rethymno: Arkadi Monastery,Melidoni Cave and Margarites
Crete: Elounda Boat Trip with BBQ

Crete: Elounda Boat Trip with BBQ

$28
per adult
Crete: Elounda Boat Trip with BBQ
See all activities in Kalypso

Kalypso Hotel Deals

Kalypso Cretan Village Resort and Spa

Kalypso Cretan Village Resort and Spa

Karavos Beach Plakias Agios Vasileios Crete
$46 nightly
$63 total
Oct 26 - Oct 27
Total with taxes and fees
6.8/10 (170 reviews)
"Loved the room and pools. The lagoon was pretty epic and the hiking trails were well maintained. The resort itself is a bit dated and had the cost been higher than what we paid I probably wouldn't review it as highly. However everything was clean so thats kind of my main expectations with hotels. ..."

Reviewed on Oct 23, 2026

Kalypso Cretan Village Resort and Spa
Nautilux Rethymno by Mage Hotels

Nautilux Rethymno by Mage Hotels

Australon Polemiston 23 Rethymno Crete
Fully refundableReserve now, pay when you stay
$177 nightly
$206 total
Nov 7 - Nov 8
Total with taxes and fees
9.6/10 Exceptional! (425 reviews)
"Beautiful hotel, excellent staff and great food."

Reviewed on Oct 24, 2026

Nautilux Rethymno by Mage Hotels
Aristea Hotel Rethymnon

Aristea Hotel Rethymnon

110 Martyron Sq. Rethymno Crete
Aristea Hotel Rethymnon
See all 4,102 properties in Kalypso
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.

Find the Best Kalypso Vacation Packages

Kalypso Essential Information

Language
Greek
Currency
Euros
Local Welcome
Ya su
Local Goodbye
Yiá sou
Closest Airport
Ioannis Daskalogiannis Airport (CHQ)
Top Sights
Plakias Beach, Ammoudaki Beach and Damnóni Beach

More vacations you might like

Frequently asked questions

How much does a Kalypso vacation package cost?
You can snap up a vacation package to this popular destination from $1,417 on Expedia. However, how much your vacation to Kalypso costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Kalypso?
If you'd like to book a cheap Kalypso vacation package, consider planning a trip in November, December and January. You'll typically find lower rates on hotels and airfares during these quieter months — ideal for budget-conscious travelers.
How many days is enough for Kalypso?
With a well-organized itinerary, you can easily tick off the most popular Kalypso attractions in a handful of days. But if you'd like to discover lesser-known spots or take day trips, think about booking your Kalypso vacation for longer.
How to find the best Kalypso package deals?
Begin your search for a Kalypso package deal by entering your destination and preferred trip dates under our "Packages" tab. Then add some filters, like "Guest rating" and "Property type," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the perfect Kalypso package deal straight away, simply play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Kalypso escape underway.
Is it cheaper to book a Kalypso vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your car rental, hotel and flight into one great-value price and you could save hundreds of dollars. You'll usually score a better deal than booking each component separately. And you'll still enjoy the freedom to create a tailored Kalypso vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Kalypso?
If you're considering a spur-of-the-moment Kalypso getaway, browse our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can score amazing deals on your hotels and flights by booking ahead.
How to plan a trip to Kalypso?
  1. Choose your dates: What you want to do in Kalypso and your favorite season will help you decide when to go.
  2. Calculate your budget: Make sure you have enough money to pay for everything from transportation and meals to activities and flights. Your accommodations will probably be the biggest expense during your trip to Kalypso.
  3. Organize your Kalypso getaway with Expedia's trip planning tool: Look for and book stays and things to do all in one place. You can also collaborate with friends and family to plan an unforgettable trip to Kalypso together.
  4. Decide how many days away: Start by compiling a list of the attractions you'd like to experience in Kalypso. Then, estimate how long you'll need for each, as well as any travel time.
  5. Combine your hotel and flights: Awesome destination, check. Length of stay, check. Now all that's left is to find a Kalypso vacation package that brings all your bookings together.
  6. Book activities and experiences ahead of time: Whether it's a ticket to a major attraction or a walking tour, you won't have to worry about missing out on Kalypso's highlights. Find all the incredible things to do in Kalypso with our dedicated travel guide.
Does Expedia offer Book Now, Pay Later Kalypso vacation packages?
Your Kalypso getaway is meant to be an escape from your busy life, not a reason for money-related stress. So to allow you a little more flexibility, we've partnered with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the total cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.