Surfside Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $1,096 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in Surfside

Price found within the past 48 hours. Click for updated prices.
The Wolfeboro Inn

The Wolfeboro Inn

3.5 out of 5
Price was CA $989, price is now CA $807 per person
CA $807
per person
Apr 17 - Apr 20
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Portland (PWM)
8.2/10 Very Good! (544 reviews)
We had a very nice room. We were given a free upgrade. Staff was very accommodating. Property is right in the center of town within walking distance of restaurants, shops, the lake and X-country skiing. We had a great time.

Reviewed on Mar 1, 2026

84 Main

84 Main

4 out of 5
Price was CA $1,463, price is now CA $1,178 per person
CA $1,178
per person
Apr 2 - Apr 6
found 8 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
10/10 Exceptional! (52 reviews)
Very spacious and relaxing. Nice view of Kennebunk quaint ice rink and Main Street. Coffee shop at Street level was a fantastic add! Beds and bedding were comfortable. Will visit again! Nothing lacking with respect to amenities.

Reviewed on Dec 29, 2025

The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Downtown Portland
Price was CA $1,637, price is now CA $1,337 per person
CA $1,337
per person
May 18 - May 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.8/10 Exceptional! (86 reviews)
Location is excellent. Short walking distance to every good restaurant and shop. The property was very nice and clean. The kitchen is very well equipped. The gym is very good sized for the size of the apartment building with 13 units in it. The management’s communication was prompt and friendly and responded to all of our wishes. However, the place is advertised as a hotel, but don’t expect services as in a hotel. It resembles more a short term rental home - no cleaning service and no lobby. Otherwise everything was very nice in the apartment and we had a great time.

Reviewed on Jan 3, 2026

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was CA $1,473, price is now CA $1,206 per person
CA $1,206
per person
May 18 - May 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.2/10 Wonderful! (1,668 reviews)
Nice place, clean room, courteous staff, NO FREE PARKING! :(

Reviewed on Feb 28, 2026

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was CA $1,768, price is now CA $1,491 per person
CA $1,491
per person
May 18 - May 22
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.6/10 Exceptional! (161 reviews)
The whole was cozy! Well curated style and knowledgeable staff.

Reviewed on Jan 5, 2026

Surfside Hotel Deals

The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
157 High St Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $134 per night from Mar 16 to Mar 17
CA $134
CA $148 total
Mar 16 - Mar 17
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
Clean, quiet and comfortable. Exceptional team who were helpful and friendly. I actually hated to leave. Great stay!

Reviewed on Feb 28, 2026

The Westin Portland Harborview
Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $105 per night from Mar 5 to Mar 6
CA $105
CA $116 total
Mar 5 - Mar 6
includes taxes & fees
8/10 Very Good! (1,381 reviews)
Very clean and quiet. Optional breakfast which had very good portions. Only flaw i noticed was there were issues with the boiler. Hot water was scarce as they were at full capacity. Other than that i enjoyed my stay.

Reviewed on Mar 1, 2026

Clarion Hotel Portland Airport ME
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $155 per night from Mar 15 to Mar 16
CA $155
CA $224 total
Mar 15 - Mar 16
includes taxes & fees
9.2/10 Wonderful! (1,765 reviews)
Nice place, clean room, courteous staff, NO FREE PARKING! :(

Reviewed on Feb 28, 2026

Portland Harbor Hotel
See all 2,577 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
Family Vacations
Family 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 CA $807. 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 with rays through the pilings at low tide

Old Orchard Beach Pier

4/5(70 reviews)

After visiting Old Orchard Beach Pier, make a plan to see the other sights and activities in Old Orchard Beach. Amble around the area's beautiful beaches or attend a sporting event.

Old Orchard Beach Pier
Verlassener Rummel in Old Orchard Beach bei Sonnenschein, Maine

Palace Playland

4/5(4 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

Dunegrass Golf Club

Enjoy a round of golf in Old Orchard Beach at Dunegrass Golf Club. Amble around the area's beautiful beaches or attend a sporting event.

Dunegrass Golf Club

Things to do

Ultimate Portland Self-Guided Driving GPS Audio Tour

Ultimate Portland Self-Guided Driving GPS Audio Tour

CA $23
per traveller
100% of travellers recommend
Ultimate Portland Self-Guided Driving GPS Audio Tour
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.