Papaflessas Vacations from $1,219

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The Latest Papaflessas Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Jan 10 - Jan 16

    Kyparissia Beach Hotel + Flight

    Trifylia
    5 nights
    3.0 star property
    8.6/10 - Excellent (68 reviews)
    Roundtrip • Boston (BOS) - Kalamata (KLX)
    BOS - ATH • 1 stop ATH - BOS • 1 stop
    $1,261
    $1,219
    per traveler
    found 1 day ago
    Kyparissia Beach Hotel
  • Jan 10 - Jan 16

    Karalis City Hotel + Flight

    Pylos-Nestoras
    5 nights
    3.0 star property
    8.6/10 - Excellent (143 reviews)
    Roundtrip • Boston (BOS) - Kalamata (KLX)
    BOS - ATH • 1 stop ATH - BOS • 1 stop
    $1,274
    $1,223
    per traveler
    found 1 day ago
    Karalis City Hotel
  • Jan 10 - Jan 16

    Artina Hotel + Flight

    Trifylia
    5 nights
    3.0 star property
    9.6/10 - Exceptional (80 reviews)
    "Nice side view of the sea and modern room. Friendly host and very helpful. Lovely quiet location walking distance to the town and restaurants.Highly recommend"
    Reviewed September 6, 2026
    Roundtrip • Boston (BOS) - Kalamata (KLX)
    BOS - ATH • 1 stop ATH - BOS • 1 stop
    $1,258
    $1,219
    per traveler
    found 1 day ago
    Artina Hotel
  • Jan 10 - Jan 16

    Kleopatra Hotel + Flight

    Messini
    5 nights
    3.0 star property
    8.6/10 - Excellent (97 reviews)
    "Great stay very near Kalamata airport. Huge lovely room, good breakfast. Also located near local taverna for late evening meal on arrival. Recommended."
    Reviewed September 8, 2026
    Roundtrip • Boston (BOS) - Kalamata (KLX)
    BOS - ATH • 1 stop ATH - BOS • 1 stop
    $1,277
    $1,248
    per traveler
    found 1 day ago
    Kleopatra Hotel
  • Jan 10 - Jan 16

    Elegant Beach Hotel + Flight

    Trifylia
    5 nights
    3.0 star property
    8.0/10 - Very good (12 reviews)
    Roundtrip • Boston (BOS) - Kalamata (KLX)
    BOS - ATH • 1 stop ATH - BOS • 1 stop
    $1,286
    $1,259
    per traveler
    found 1 day ago
    Elegant Beach Hotel

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