Simon Vacations from $575
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
Aug 27 - Aug 30Hipsters Hotel + Flight
Thessaloniki City Centre3 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 • Tel Aviv (TLV) - Thessaloniki (SKG)TLV - SKG • Nonstop SKG - TLV • 1 stop$680$575found 14 hours agoper traveler - Domes Noruz Kassandra - Adults Only, Halkidiki
Aug 27 - Aug 30Domes Noruz Kassandra - Adults Only, Halkidiki + Flight
Kassandra3 nights5.0 star property9.4/10 - Exceptional (145 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 • Tel Aviv (TLV) - Thessaloniki (SKG)TLV - SKG • Nonstop SKG - TLV • 1 stop$1,480$1,129found 14 hours agoper traveler - Porto Carras Meliton
Aug 27 - Aug 30Porto Carras Meliton + Flight
Sithonia3 nights5.0 star property8.4/10 - Very Good (121 reviews)Roundtrip • Tel Aviv (TLV) - Thessaloniki (SKG)TLV - SKG • Nonstop SKG - TLV • 1 stop$1,191$932found 14 hours agoper traveler - ON Residence
Oct 11 - Oct 17ON Residence + Flight
Thessaloniki City Centre5 nights5.0 star property9.8/10 - Exceptional (204 reviews)"Beautiful hotel, prime location,"Reviewed July 24, 2026Roundtrip • Los Angeles (LAX) - Thessaloniki (SKG)LAX - SKG • 1 stop SKG - LAX • 1 stop$1,624$1,377found 16 hours agoper traveler - Sani Beach
Sep 12 - Sep 18Sani Beach + Flight
Kassandra5 nights5.0 star property9.8/10 - Exceptional (95 reviews)"Beautiful resort, with amazing facilities and friendly and helpful staff. Chris at Bousoulas beach was a stand out staff memeber. Excellent service and took care of our every needs. Christina, the front office manager went above and beyond to make sure our second visit was perfect. We will be returning next year indefinitely."Reviewed June 9, 2026Roundtrip • Houston (IAH) - Thessaloniki (SKG)IAH - ATH • 1 stop ATH - IAH • 1 stop$2,650$2,275found 1 day agoper traveler
Frequently Asked Questions
How much does a Simon vacation package cost?
You can pick up a vacation package to this popular destination from $575 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.