Surfside Vacations from $802
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Your Surfside Vacation
Experience the best that Surfside has to offer with a customized Surfside vacation package. From its walking and watersports to its coastal beaches and more, prepare to be captivated by this coastal neighborhood. When it's time to see the sights, you'll find a lot of awesome attractions nearby including Old Orchard Beach Pier, Palace Playland and Dunegrass Golf Club. Tick off one, two or all during your trip to Surfside. Whatever your ideal Surfside vacation may look like, you can turn it into reality with Expedia.
The Latest Surfside Vacation Packages
- 84 Main
Dec 18 - Dec 2184 Main + Flight
Kennebunk3 nights4.0 star property9.8/10 - Exceptional (58 reviews)"The property was very spacious, well equipped, and well taken care of. There was lots of natural light and a very large outdoor deck accessible from all bedrooms and the living room."Reviewed July 17, 2026Roundtrip • Atlanta (ATL) - Portland (PWM)ATL - PWM • 1 stop PWM - ATL • 1 stop$939$802found 1 day agoper traveler - Blind Tiger Portland - Danforth Street.
Dec 26 - Jan 1Blind Tiger Portland - Danforth Street. + Flight
West End6 nights3.5 star property9.6/10 - Exceptional (206 reviews)Roundtrip • Atlanta (ATL) - Portland (PWM)ATL - PWM • Nonstop PWM - ATL • Nonstop$2,153$1,703found 1 day agoper traveler - Evalina Hotel
Jan 11 - Jan 14Evalina Hotel + Flight
Downtown Portland3 nights2.5 star property10/10 - Exceptional (19 reviews)Roundtrip • Dallas (DFW) - Portland (PWM)DAL - PWM • 1 stop PWM - DFW • 1 stop$1,048$872found 1 day agoper traveler - The Docent's Collection at 121 Middle Street
Jan 15 - Jan 18The Docent's Collection at 121 Middle Street + Flight
Downtown Portland3 nights3.5 star property9.6/10 - Exceptional (429 reviews)"Pros: Room was nice and spacious. Kitchen had everything we needed. Location was awesome - very close to all the things we wanted to do. Excellent proximity to some of the best restaurants, including LB Kitchen, Fore Street, Central Provisions. Con’s: Couches could have benefited from some throw pillows - kinda weird without any. Bed wasn’t that comfortable - you sink in way too much. Parking was ok - just some weird communication before our arrival about where to park. Text messages from the..."Reviewed November 8, 2026Roundtrip • Atlanta (ATL) - Portland (PWM)ATL - PWM • 1 stop PWM - ATL • 1 stop$1,032$863found 2 hours agoper traveler - The Meadowmere Resort
Dec 18 - Dec 21The Meadowmere Resort + Flight
Ogunquit3 nights2.5 star property8.6/10 - Excellent (1,006 reviews)"We have stayed at the meadowmere in the past, but it’s been awhile. They have done A LOT of design changes and I loved it! The amenities are great for families. The color schemes are much better from the past visits and our room was so beautiful! So spacious, light and airy .. felt so refreshing."Reviewed November 9, 2026Roundtrip • Atlanta (ATL) - Portland (PWM)ATL - PWM • 1 stop PWM - ATL • 1 stop$1,027$877found 1 day agoper traveler
Surfside Hotel Deals
"my room was very clean and welcoming. The staff was very friendly and offered info on events and things that were happening in the area. They also allowed me to check in early."
"This was a quaint and cozy spot. Lovely and comfortable suite."
The Inn at SOHO Square
The Inn at SOHO Square
"This property is absolute garbage. The staff at the front desk were 0 help in any way. I called 7 times the night of our reservation to complain about the issues we found upon check in. Which had including bodily fluids, left around the room, holes in walls, water damage and mold. And that was just in one room. The staff at the front made sure to repeat over and over in old orchard You don't come for the room , you come for the location. To which we replied, ma'am , it's off season and the bare...
"Property was clean"
Frequently Asked Questions
How much does a Surfside vacation package cost?
We make it easy to explore the world, with Surfside packages starting from just $802. You'll have the flexibility to combine your preferred airlines, hotels and car rental. For the ultimate escape, why not add some tours and activities to your itinerary?
How do I get a cheap travel package to Surfside?
Browse and book everything in the one place with our Surfside vacation packages. You'll find deals on hotels, flights, tours and more that'll keep your hip pocket happy and your spirit of adventure alive. And, with more than 550 partner airlines and 1,000,000 hotels worldwide to select from, you'll have endless opportunities to mix and match all you want.
Where should I stay in Surfside?
With fascinating attractions like Old Orchard Beach Pier and Palace Playland in this neighborhood, look for a hotel located near either one. Dunegrass Golf Club is another sight in Surfside that lures the crowds.
What are the top hotels in Surfside?
Lock in a room at Family Friendly 2 Bedroom 1 Bath Oceanview Condo 189 East Grand Ave Unit 306. It's one of this neighborhood's most sought-after hotels. Another highly rated option in Surfside is Grandview One - Fourteen|steps To The Beach|communal Pool|bayley Vacation Rentals.
How far in advance should I book my Surfside vacation?
While not all airlines release tickets early, you can usually compare international fares on Expedia up to 12 months in advance. This is the time you'll nab some incredible bargains. If you're booking at the last minute, there's a chance you could get lucky. Low prices occasionally emerge only weeks before departure.
What does an Expedia Surfside travel package include?
Hotels, flights and car rentals — we connect you to the very best bargains. All you'll have to do is pick and choose your favorite combination. After you've made your booking, you can add on the exciting stuff like day tours and sightseeing activities. Our travel packages make it simple to customize an amazing Surfside getaway.
What should I know before booking a Surfside travel package?
You'll save plenty with an Expedia travel package. Bundle your flights, rental cars and hotels and enjoy fantastic discounts. You're not limited to hotels, though. We have island resorts, rural cottages and even castles and houseboats!
Can I choose my airline with a Surfside Expedia vacation package?
Yes — that's one of the best things about an Expedia package. You get to decide. We have more than 550 airline partners globally, so you have lots of choice when creating your Surfside adventure.
If I'm not able to travel, can I cancel my Surfside vacation package?
It's hard to predict what tomorrow might bring, so it's good to know that you can cancel or change your Surfside vacation package. If you booked in the last 24 hours, you may be entitled to a refund. If it's an older booking, your airline, hotel or car rental company may charge a fee. Visit our Customer Service Portal for more information.