Simon Vacations from $510
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The Latest Simon Vacation Packages
- Capsis Bristol Boutique Hotel
Aug 24 - Aug 28Capsis Bristol Boutique Hotel + Flight
Thessaloniki City Centre5 nights5.0 star property9.0/10 - Wonderful (147 reviews)"Very nice room. Very freindly and helpful staff. Excellent breakfast and evening meal menu."Reviewed June 19, 2026Roundtrip • Belgrade (BEG) - Thessaloniki (SKG)BEG - SKG • Nonstop SKG - BEG • 1 stop$619$510found 22 hours agoper traveler - Bahar Boutique Hotel
Aug 24 - Aug 28Bahar Boutique Hotel + Flight
Thessaloniki City Centre5 nights4.0 star property9.4/10 - Exceptional (91 reviews)"Great room very modern elegant decor, the staff goes above and beyond to help.AMAZING BREAKFAST WITH YOUR CHOISE FROM THE MENU COOKED TO ORDER AMAZING!!!"Reviewed February 4, 2026Roundtrip • Belgrade (BEG) - Thessaloniki (SKG)BEG - SKG • Nonstop SKG - BEG • 1 stop$706$534found 22 hours agoper traveler - The Modernist Thessaloniki
Aug 24 - Aug 28The Modernist Thessaloniki + Flight
Thessaloniki City Centre5 nights4.0 star property9.8/10 - Exceptional (627 reviews)"The friendly staff and location, wonderful breakfast with amazing view on the terrace Restaurant, hence I always stay at the Modernist when in the City."Reviewed July 19, 2026Roundtrip • Belgrade (BEG) - Thessaloniki (SKG)BEG - SKG • Nonstop SKG - BEG • 1 stop$723$549found 22 hours agoper traveler - Hipsters Hotel
Aug 24 - Aug 28Hipsters Hotel + Flight
Thessaloniki City Centre5 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 • Belgrade (BEG) - Thessaloniki (SKG)BEG - SKG • Nonstop SKG - BEG • 1 stop$641$511found 22 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 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 $510 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.