A coastal walkway with green cushioned benches and thatched umbrellas, leading to a rocky cliffside.

Kalypso Vacations from $2,555

Book a Hotel + Flight or Car together to unlock savings

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.
  • Dec 26 - Jan 1

    Manili Boutique Suites & Villas, an SLH Hotel + Flight

    Archanes-Asterousia
    5 nights
    5.0 star property
    9.6/10 - Exceptional (40 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 October 18, 2026
    Roundtrip • Boston (BOS) - Heraklion (HER)
    BOS - HER • 2 stops HER - BOS • 1 stop
    $2,689
    $2,555
    per traveler
    found 1 day ago
    Manili Boutique Suites & Villas, an SLH Hotel
  • Dec 26 - Jan 1

    Dimargio Luxury Hotel & Spa + Flight

    Heraklion
    5 nights
    5.0 star property
    9.8/10 - Exceptional (61 reviews)
    "Wonderful front desk staff and beautiful place"
    Reviewed October 20, 2026
    Roundtrip • Boston (BOS) - Heraklion (HER)
    BOS - HER • 2 stops HER - BOS • 2 stops
    $3,199
    $2,997
    per traveler
    found 16 hours ago
    Dimargio Luxury Hotel & Spa
  • Dec 27 - Jan 2

    Sekeria Hammam & Suites, Historic Mansion Hotel + Flight

    Heraklion
    5 nights
    3.0 star property
    10/10 - Exceptional (1 review)
    "Great place"
    Reviewed September 27, 2026
    Roundtrip • Boston (BOS) - Heraklion (HER)
    BOS - HER • 2 stops HER - BOS • 1 stop
    $3,214
    $3,045
    per traveler
    found 1 day ago
    Sekeria Hammam & Suites, Historic Mansion Hotel
  • Dec 30 - Jan 2

    Amirandes, A Resort to Live + Flight

    Hersonissos
    2 nights
    5.0 star property
    9.4/10 - Exceptional (242 reviews)
    Roundtrip • Boston (BOS) - Heraklion (HER)
    BOS - HER • 2 stops HER - BOS • 1 stop
    $3,285
    $3,113
    per traveler
    found 1 day ago
    Amirandes, A Resort to Live
  • Dec 26 - Jan 1

    Infinity City Boutique Hotel + Flight

    Heraklion
    5 nights
    4.0 star property
    8.8/10 - Excellent (357 reviews)
    "5 starts for newly renovated stylish hotel beautiful job! Duvet, extra pillows, new comfortable beds. Black out drapes, patio, and 55 inch flat screen TVs with apps for Prime Netflix Disney YouTube watch in your language. Huge bonus! Quiet central friendly staff. Beautiful stylish with mood back lighting. Top notch! Breakfast good. Felt spoiled. Stayed at 2 other hotels in the city looked like prison cells on comparison :)"
    Reviewed November 5, 2026
    Roundtrip • Boston (BOS) - Heraklion (HER)
    BOS - HER • 2 stops HER - BOS • 2 stops
    $3,051
    $2,895
    per traveler
    found 16 hours ago
    Infinity City Boutique Hotel

What to do in Kalypso

Kalypso Hotel Deals

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.

Frequently Asked Questions

How much does a Kalypso vacation package cost?

You can snap up a vacation package to this popular destination from $2,555 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.

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