Surfside Vacations from $429

Book a Hotel + Flight or Car together to unlock savings

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

Price found within the past 48 hours. Click for updated prices.
Portland Harbor Hotel
Cliff House Maine
The Docent's Collection - New Opening
Inn By The Sea
Kennebunkport Captains Collection

Surfside Hotel Deals

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street, Portland, ME
Fully refundableReserve now, pay when you stay
$165 nightly
The price is $183 total per night from Nov 30 to Dec 1
$183 total
Nov 30 - Dec 1
Total with taxes and fees
9.2/10 Wonderful! (1,656 reviews)
Amazing
Amazing location, unique hotel with beautiful decor and amenities

Reviewed on Oct 28, 2025

Portland Harbor Hotel
Clarion Hotel Portland

Clarion Hotel Portland

2.5 out of 5
1230 Congress St, Portland, ME
Fully refundableReserve now, pay when you stay
$83 nightly
The price is $92 total per night from Nov 5 to Nov 6
$92 total
Nov 5 - Nov 6
Total with taxes and fees
7.8/10 Good! (1,202 reviews)
The Clarion was excellent for my trip. Located close to airport and to downtown and priced reasonably.

Reviewed on Oct 27, 2025

Clarion Hotel Portland
Tru by Hilton Portland Airport Area

Tru by Hilton Portland Airport Area

2.5 out of 5
369 Maine Mall Road, South Portland, ME
Fully refundableReserve now, pay when you stay
$81 nightly
The price is $88 total per night from Nov 10 to Nov 11
$88 total
Nov 10 - Nov 11
Total with taxes and fees
8.8/10 Excellent! (1,572 reviews)
Location of hotel and quiet at night

Reviewed on Oct 29, 2025

Tru by Hilton Portland Airport Area
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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 $429. 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.

Discover the most popular places to visit in Surfside

Things to do

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.