Surfside Vacations from $728

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

Portland Harbor Hotel

4 out of 5
Downtown Portland
Save 100% on your flight
Price was $990, price is now $728 per person
$728
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9.2/10 Wonderful! (1,552 reviews)
This is a great place to stay, if it weren't for the hidden charges. Parking is an extra $45/night, and there is a $35 "service fee" added. This covers about 2/3 of a breakfast for two. overall it was well over $100 dollars more on top of the room rate. Very nice, but you pay for it.

Reviewed on Aug 31, 2025

Cliff House Maine

Cliff House Maine

4.5 out of 5
Save 100% on your flight
Price was $1,475, price is now $946 per person
$946
per person
Nov 1 - Nov 5
found 24 hours ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9.4/10 Exceptional! (1,002 reviews)
What’s not to love. It’s Cliff House!!

Reviewed on Aug 29, 2025

Admiral Peary Inn

Admiral Peary Inn

3 out of 5
Save 100% on your flight
Price was $1,595, price is now $1,110 per person
$1,110
per person
Oct 1 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Portland (PWM)
9.2/10 Wonderful! (30 reviews)
Pleasant stay, konstanz room was good sized and charming decorations. Quiet, only saw a few other people around the property. Area was very nice and walkable although i drove. Breakfast was at 830 although i didnt partake. Nice collection of books and games. Enjoyed sitting on the lawn in the evening. Owner offered me a muffin on my way out and it was amazing

Reviewed on Aug 31, 2025

River View Resort

River View Resort

2.5 out of 5
Save 100% on your flight
Price was $1,260, price is now $888 per person
$888
per person
Oct 10 - Oct 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Portland (PWM)
8.8/10 Excellent! (294 reviews)
It was a basic suite-like motel. Could use an upgrade. Very 70s

Reviewed on Mar 30, 2025

The Docent's Collection

The Docent's Collection

3.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $2,246, price is now $1,613 per person
$1,613
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9.6/10 Exceptional! (228 reviews)
We stayed at the property for three nights and paid extended hour for checking-out. Unfortunately, the system hotel created didn't work. the cleaning staffs kept knocking our door at 11am (normal check-out time). Even I told them that I paid for the extension hour to check out. They still kept coming back to knock the door multiple times.

Reviewed on Aug 31, 2025

Surfside Hotel Deals

Ocean Walk Hotel

Ocean Walk Hotel

2.5 out of 5
197 E. Grand Ave, Old Orchard Beach, ME
$142 nightly
The price is $155 total per night from Sep 14 to Sep 15
$155 total
Sep 14 - Sep 15
Total with taxes and fees
Ocean Walk Hotel
Clarion Hotel Portland

Clarion Hotel Portland

2.5 out of 5
1230 Congress St, Portland, ME
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $168 total per night from Sep 4 to Sep 5
$168 total
Sep 4 - Sep 5
Total with taxes and fees
Clarion Hotel Portland
Germaine Inn South Portland

Germaine Inn South Portland

2 out of 5
675 Main Street I-95, Rt 1-I95 ex 45-I295 Ex 3, South Portland, ME
Fully refundable
$85 nightly
The price is $93 total per night from Oct 1 to Oct 2
$93 total
Oct 1 - Oct 2
Total with taxes and fees
Germaine Inn South Portland
See all 2,723 properties in Surfside
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

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 $728. 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

Old Orchard Beach Pier

Old Orchard Beach Pier

4/5(644 reviews)

Explore the waterfront in Old Orchard Beach with a trip to Old Orchard Beach Pier. Amble around the area's beautiful beaches or attend a sporting event.

Old Orchard Beach Pier

Palace Playland

4/5(47 reviews)

You can enjoy the entertainment at Palace Playland during your travels to Old Orchard Beach. Amble around the area's beautiful beaches or attend a sporting event.

Palace Playland

Pirate's Cove

4.5/5(11 reviews)

Enjoy a round of golf in Old Orchard Beach at Pirate's Cove. Wander the beautiful beaches and picturesque gardens in the area.

Pirate's Cove

Things to do

Walk With Ghosts in Portland

Walk With Ghosts in Portland

$30
per adult
Walk With Ghosts in Portland
Maine Coastal Lighthouse:Two-hour bicycle tour

Maine Coastal Lighthouse:Two-hour bicycle tour

$75
per adult
Maine Coastal Lighthouse:Two-hour bicycle tour
West End Bakery Crawl for Ladies only

West End Bakery Crawl for Ladies only

$64
per adult
West End Bakery Crawl for Ladies only
See all activities in Old Orchard Beach
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.