Surfside Vacations from $708

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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

Price found within the past 48 hours. Click for updated prices.
Chebeague Island Inn

Chebeague Island Inn

4 out of 5
Save 100% on your flight
per person
Sep 14 - Sep 18
found 19 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
8.8/10 Excellent! (71 reviews)
The location is perfect with the golf course right next door and sitting up on the hill overlooking the harbor. The restaurant serves wonderful meals, one of the best lobster bisque we’ve ever had. The wrap around porch is awesome with heaters. In saying all this, the inn needs some TLC. Our room had paint chipping on the walls and all around the shower. The shower head was awful. There isn’t a main door to the front desk and the one our driver brought us in was like we were walking into a shed, very weird . We will go back to the restaurant but we wouldn’t stay over.

Reviewed on Jun 20, 2025

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Save 100% on your flight
per person
Sep 14 - Sep 18
found 19 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.2/10 Wonderful! (1,533 reviews)
The beds were super comfortable! The entire staff was helpful and kind.

Reviewed on Jul 6, 2025

The Docent's Collection

The Docent's Collection

3.5 out of 5
Downtown Portland
Save 100% on your flight
per person
Sep 14 - Sep 18
found 19 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.6/10 Exceptional! (209 reviews)
Great place! Super convenient

Reviewed on Jul 4, 2025

Cliff House Maine

Cliff House Maine

4.5 out of 5
Save 100% on your flight
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Portland (PWM)
9.4/10 Exceptional! (1,003 reviews)
Everything about this location is five stars

Reviewed on Jul 6, 2025

Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
Save 100% on your flight
per person
Sep 14 - Sep 18
found 19 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.4/10 Exceptional! (585 reviews)
The property was lovely and convenient

Reviewed on Jun 28, 2025

Surfside Hotel Deals

Ocean Walk Hotel
Ocean Walk Hotel
2.5 out of 5
197 E. Grand Ave, Old Orchard Beach, ME
$239 nightly
The price is $261 total per night from Jul 8 to Jul 9
$261 total
Jul 8 - Jul 9
Total includes taxes and fees
8.6/10 Excellent! (355 reviews)
"It was great overall. We liked that they had beach chairs for guests to use, and the location was right on the beach. We were worried about the Murphy beds, but they were fine. The door to your room is a sliding one, and they are kind of hard to open. Also, I’m glad my mom brought shampoo, conditioner, ..."

Reviewed on Jun 21, 2025

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 Jul 13 to Jul 14
$168 total
Jul 13 - Jul 14
Total includes taxes and fees
7.8/10 Good! (1,006 reviews)
"Everything is good. Coffee and tea in lobby ."

Reviewed on Jul 5, 2025

Clarion Hotel Portland
Days Inn by Wyndham Airport/Maine Mall
Days Inn by Wyndham Airport/Maine Mall
2 out of 5
461 Maine Mall Rd, South Portland, ME
Fully refundableReserve now, pay when you stay
$129 nightly
The price is $141 total per night from Jul 8 to Jul 9
$141 total
Jul 8 - Jul 9
Total includes taxes and fees
7.8/10 Good! (1,022 reviews)
Great hotel, right across from the mall and close
"I stayed at this hotel with a number of years ago and then it was closed for a few years I think or repurposed. They have redone the place and it really looks nice. It’s clean and friendly. Breakfast was delicious. I will stay here again soon."

Reviewed on Jul 6, 2025

Days Inn by Wyndham Airport/Maine Mall
See all 2,827 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 $708. 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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.