Surfside Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$1,300 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
Price found within the past 48 hours. Click for updated prices.
  • 50-inch flat-screen TV with cable channels
    Jul 13 - Jul 16

    The Docent's Collection at 178 Middle Street + Flight

    Downtown Portland
    3 nights
    2.0 star property
    10/10 - Exceptional (23 reviews)
    "Beautiful, clean, modern room with modern amenities. Had everything you could need in an apartment even, and was so close to old for, everything was walking distance Staff with beyond friendly, helpful, assisting, and courteous. If I could give 6/5 stars instead I would have"
    Reviewed May 29, 2026
    Return • New York (LGA) - Portland (PWM)
    LGA - PWM • Direct PWM - LGA • Direct
    Save 100% on your flight
    S$1,217
    S$919
    per traveller
    found 12 hours ago
    The Docent's Collection at 178 Middle Street
  • Restaurant
    Jul 13 - Jul 16

    Portland Harbor Hotel + Flight

    Downtown Portland
    3 nights
    4.0 star property
    9.4/10 - Exceptional (1,757 reviews)
    "Staff was extremely gracious and helpful. From the valet to the front desk to the restaurant."
    Reviewed May 30, 2026
    Return • New York (LGA) - Portland (PWM)
    LGA - PWM • Direct PWM - LGA • Direct
    Save 100% on your flight
    S$1,344
    S$1,029
    per traveller
    found 12 hours ago
    Portland Harbor Hotel
  • Premium bedding, individually decorated, individually furnished
    Jul 13 - Jul 16

    Blind Tiger Portland - Danforth Street. + Flight

    West End
    3 nights
    3.5 star property
    9.6/10 - Exceptional (184 reviews)
    "The only real issue was the distance from all of the attractions and restaurants. "
    Reviewed May 15, 2026
    Return • New York (LGA) - Portland (PWM)
    LGA - PWM • Direct PWM - LGA • Direct
    Save 100% on your flight
    S$2,308
    S$1,787
    per traveller
    found 12 hours ago
    Blind Tiger Portland - Danforth Street.
  • Children’s activities
    Jul 13 - Jul 16

    Inn By The Sea + Flight

    Cape Elizabeth
    3 nights
    4.0 star property
    9.6/10 - Exceptional (317 reviews)
    "Very nice place, very cclean and friendly."
    Reviewed May 30, 2026
    Return • New York (LGA) - Portland (PWM)
    LGA - PWM • Direct PWM - LGA • Direct
    Save 100% on your flight
    S$2,119
    S$1,659
    per traveller
    found 12 hours ago
    Inn By The Sea
  • Living area
    Jul 13 - Jul 16

    The Docent's Collection at 121 Middle Street + Flight

    Downtown Portland
    3 nights
    3.5 star property
    9.6/10 - Exceptional (326 reviews)
    "The property is great. The amenities are quality- nothing is cheap… kitchen is stocked & utensils are not flimsy- bedding is nice. Some good touches like under mount lighting in the bathroom that comes on as you walk in- the temperature is easy to keep constant (which is rare in units) it’s very walkable and the parking is easy ($60 per night). Lots of good. The unit itself is very nice. My only complaint is that the furniture is stained and filthy… one chair had caked food and hair (a good..."
    Reviewed May 27, 2026
    Return • New York (LGA) - Portland (PWM)
    LGA - PWM • Direct PWM - LGA • Direct
    S$1,223
    S$991
    per traveller
    found 12 hours ago
    The Docent's Collection at 121 Middle Street

Top hotels in Surfside

Ocean Walk Hotel

Ocean Walk Hotel

2.5 out of 5
197 E. Grand Ave Old Orchard Beach ME
The price is S$191 per night from 1 Jun to 2 Jun
S$191
1 Jun - 2 Jun
includes taxes & fees
8.8/10 Excellent! (387 reviews)
"Cleaning good and quietly beautiful Service and amenities terrible"

Reviewed on 25 May, 2026

Ocean Walk Hotel
The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
157 High St Portland ME
The price is S$422 per night from 22 Jun to 23 Jun
S$422
22 Jun - 23 Jun
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
"we were here May 26-28th, our stay was fantastic. From the minute we pulled up valet was very attentive, the front desk staff was pleasant and helpful, our room immaculate and had a beautiful view of the bay. the rooms are quiet with the best beds. this was our first time in Portland , plenty to ..."

Reviewed on 31 May, 2026

The Westin Portland Harborview
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
25 HANCOCK STREET Portland ME
The price is S$391 per night from 7 Jun to 8 Jun
S$391
7 Jun - 8 Jun
includes taxes & fees
9.4/10 Exceptional! (1,222 reviews)
"Room was well organized. Bed was comfortable. Breakfast was okay and on the expensive side. All in all enjoyed it."

Reviewed on 30 May, 2026

Cambria Hotel Portland Downtown-Old Port
See all 2,658 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.

Frequently asked questions

How much does a Surfside holiday package cost?
We make it easy to explore the world, with Surfside packages starting from just . 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 holiday 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 neighbourhood, 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 neighbourhood's most sought-after hotels. Another highly rated option in Surfside is Grandview One - Fourteen|steps To The Beach|communal Pool|bayley Holiday Rentals.
How far in advance should I book my Surfside holiday?
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 favourite 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 holiday 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 holiday package?
It's hard to predict what tomorrow might bring, so it's good to know that you can cancel or change your Surfside holiday 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.

Things to do

Ultimate Portland Self-Guided Driving GPS Audio Tour

Ultimate Portland Self-Guided Driving GPS Audio Tour

S$22
per traveller
100% of travellers recommend
Ultimate Portland Self-Guided Driving GPS Audio Tour
Discover Maine's Coastal Charms: Half-Day Scenic Sail

Discover Maine's Coastal Charms: Half-Day Scenic Sail

S$329
per adult
Discover Maine's Coastal Charms: Half-Day Scenic Sail
Coastal Maine Sunset Sailing Experience - Public & Private

Coastal Maine Sunset Sailing Experience - Public & Private

S$189
per adult
Coastal Maine Sunset Sailing Experience - Public & Private
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.