Simon Vacations from $1,074
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The Latest Simon Vacation Packages
- Porto Carras Meliton
Sep 23 - Sep 27Porto Carras Meliton + Flight
Sithonia3 nights5.0 star property8.4/10 - Very Good (119 reviews)Roundtrip • Chicago (CHI) - Thessaloniki (SKG)ORD - SKG • 1 stop SKG - ORD • 1 stop$1,227$1,074found 19 hours agoper traveler - Domes Noruz Kassandra - Adults Only, Halkidiki
Sep 23 - Sep 27Domes Noruz Kassandra - Adults Only, Halkidiki + Flight
Kassandra3 nights5.0 star property9.4/10 - Exceptional (144 reviews)"This was our second stay at the Kassandra, we really enjoyed it , lovely room,plenty of storage, very clean. Beach gorgeous and stylish pool. Breakfast and dinner very good. Service from all staff is excellent"Reviewed July 12, 2026Roundtrip • Chicago (CHI) - Thessaloniki (SKG)ORD - SKG • 1 stop SKG - ORD • 1 stop$1,615$1,331found 19 hours agoper traveler - Pomegranate Wellness Spa Hotel
Sep 23 - Sep 27Pomegranate Wellness Spa Hotel + Flight
Nea Propontida3 nights5.0 star property9.4/10 - Exceptional (86 reviews)"Ok stay, but some details did not match a 5-star luxury suite experience Overall, our stay was okay, and there were some very positive aspects. The service at the outdoor restaurant was great, and the spa service was exceptional. That said, considering this is a 5-star hotel and the Pomegranate Suite is presented as a luxury/high-end room, there were several details that could be improved. We had just spent a week at Sani Dunes, and the contrast was noticeable. A small touch such as fresh..."Reviewed May 1, 2026Roundtrip • Chicago (CHI) - Thessaloniki (SKG)ORD - SKG • 1 stop SKG - ORD • 1 stop$1,642$1,354found 19 hours agoper traveler - ON Residence
Sep 24 - Sep 29ON Residence + Flight
Thessaloniki City Centre4 nights5.0 star property9.8/10 - Exceptional (202 reviews)"The Bad: The hotel failed to reply to multiple Expedia messages regarding a ferry terminal pickup. Communication is paramount. Because of this silence, my wife and I had to walk half a mile at 9:40 PM from the furthest pier, tired and carrying heavy luggage in an unfamiliar city. The Good: The hotel's recovery was outstanding. The next day, Magda the manager was genuinely concerned and went above and beyond to fix the reception lapse. She provided several complimentary drinks and paid for our..."Reviewed July 1, 2026Roundtrip • New York (NYC) - Thessaloniki (SKG)JFK - SKG • 1 stop SKG - EWR • 1 stop$1,675$1,423found 1 hour agoper traveler - Zeus Eleva Ajul
Sep 23 - Sep 27Zeus Eleva Ajul + Flight
Kassandra3 nights5.0 star property8.0/10 - Very Good (8 reviews)"Very nice property. Staff was very friendly. Food was amazing "Reviewed October 11, 2024Roundtrip • Chicago (CHI) - Thessaloniki (SKG)ORD - SKG • 1 stop SKG - ORD • 1 stop$2,125$1,838found 19 hours agoper traveler
Simon Hotel Deals
Frequently Asked Questions
How much does a Simon vacation package cost?
You can pick up a vacation package to this popular destination from $1,074 on Expedia. However, how much your vacation to Simon costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Simon?
If you're hoping to snag a cheap Simon vacation package, consider planning a trip in November, December and January. You're likely to find lower prices on hotels and flights during these months — perfect for travelers wishing to save money.
How many days is enough for Simon?
Usually, a handful of days is enough to visit the top sights during your Simon vacation. But if you want to have some time to relax or take day tours, think about extending your itinerary.
How to find the best Simon package deals?
Finding a cheap Simon package deal is a cinch with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your maximum budget, apply some filters and browse what's available. You can tweak your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most wallet-friendly Simon package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are usually lower.
Is it cheaper to book a Simon vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging hotels and flights separately. Better still, you can personalize your Simon trip to match your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Simon?
Land incredible discounts by booking your flights ahead of time with Expedia. If spontaneity is more your style, snap up one of our last-minute deals for a spur-of-the-moment Simon break.
Does Expedia offer Book Now, Pay Later Simon vacation packages?
Your Simon break is meant to be an escape from your daily routine, not a source of money worries. So to give you that extra flexibility, we've partnered with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there are no hidden costs or late payment fees to worry about.