Simon Vacations from $1,034
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Simon Vacation Packages
- Hipsters Hotel
Oct 7 - Oct 11Hipsters Hotel + Flight
Thessaloniki City Centre4 nights3.0 star property10/10 - Exceptional (4 reviews)"We absolutely loved staying at the Hipsters! It was my first time in Greece and I will certainly come back! The cleaning, the staff, the breakfast, the location, everything was perfect. Thank you so much for having us! "Reviewed April 28, 2026Roundtrip • New York (EWR) - Thessaloniki (SKG)EWR - SKG • 1 stop SKG - EWR • 1 stop$1,187$1,034found 1 day agoper traveler - Domes Noruz Kassandra - Adults Only, Halkidiki
Sep 16 - Sep 20Domes 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 • New York (EWR) - Thessaloniki (SKG)EWR - ATH • 1 stop ATH - EWR • 1 stop$1,877$1,508found 1 day agoper traveler - The Excelsior Small Luxury Hotels of the World
Sep 24 - Sep 29The Excelsior Small Luxury Hotels of the World + Flight
Thessaloniki City Centre4 nights5.0 star property9.6/10 - Exceptional (432 reviews)"This was a great place to stay. I was here for five nights which gave me 4 days in Thessaloniki, two of which I used for out-of-town excursions. The neighbourhood was safe and walkable. The staff was friendly and helpful. There was a really nice breakfast buffet. My room was spacious and had two small balconies where you could get some fresh air and look out upon the neighbourhood. I am happy to recommend this hotel."Reviewed July 19, 2026Roundtrip • New York (NYC) - Thessaloniki (SKG)JFK - SKG • 1 stop SKG - JFK • 1 stop$1,964$1,674found 4 hours agoper traveler - ON Residence
Oct 7 - Oct 11ON 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 (EWR) - Thessaloniki (SKG)EWR - SKG • 1 stop SKG - EWR • 1 stop$1,418$1,223found 1 day agoper traveler - The Met Hotel, a member of Design Hotels
Oct 7 - Oct 11The Met Hotel, a member of Design Hotels + Flight
Thessaloniki4 nights5.0 star property9.2/10 - Wonderful (897 reviews)"Great concierge welcome. Quick check in. Spacious lobby, well stocked bar and an amazing clean and updated rooms. Great stay over all."Reviewed July 10, 2026Roundtrip • New York (EWR) - Thessaloniki (SKG)EWR - SKG • 1 stop SKG - EWR • 1 stop$1,223$1,075found 1 day 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 $1,034 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.