Portland Trips

Photo by Cathy Tracey

  • Plan, book, travel with confidence

  • Better together

    Save up to P 3,118 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 destinations in Portland

Winnifred Beach showing general coastal views as well as a small group of people
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Port Antonio

Port Antonio

Top hotels in Portland

Sea Cliff Resort

Sea Cliff Resort

3 out of 5
Ross Craig Long Bay Portland
Fully refundable
8.2/10 Very Good! (181 reviews)
Very disappointing stay. The resort looked nothing like the photos online and the condition of the place was really poor. It felt run down and not well maintained at all. For the price we paid, the standard was far below what we expected. The whole experience was very underwhelming and I would not ...

Reviewed on Mar 9, 2026

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Sea Cliff Resort
Jamaica Palace Hotel

Jamaica Palace Hotel

3.5 out of 5
Williamsfield Port Antonio Portland
Fully refundableReserve now, pay when you stay
The price is P9,518 per night from Apr 10 to Apr 11
P9,518
P10,589 total
Apr 10 - Apr 11
includes taxes & fees
8.4/10 Very Good! (285 reviews)
Beautifully kept grounds and hotel

Reviewed on Feb 25, 2026

Jamaica Palace Hotel
Geejam

Geejam

4.5 out of 5
San San, Port Antonio Port Antonio Portland
The price is P26,472 per night from Mar 11 to Mar 12
P26,472
P31,826 total
Mar 11 - Mar 12
includes taxes & fees
9.6/10 Exceptional! (83 reviews)
Geejam is a small piece of paradise for sure. Nestled along mountainside in a rain forest-like environment, it is impossible to be stressed here. Staff were amazing (kudos to Tishawney, Brian, Norton and Jada who ensured we were well taken care of) and the view of the ocean was impeccable. Geejam ...

Reviewed on Mar 3, 2026

Geejam
See all 1,855 properties in Portland
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 Portland vacation package cost?
We make it easy to travel somewhere new, with Portland packages starting from as little as . You'll have the flexibility to combine your preferred airlines, hotels and car rental. For the ultimate getaway, why not add a couple of tours and activities to your travel itinerary?
How do I get a cheap travel package to Portland?
Combining your flight and hotel with Expedia won't just save precious time — it'll save you a tidy sum too. A Portland vacation package makes it easy to arrange the perfect trip. With more than 550 airlines worldwide to pick from, finding flights that fit your busy schedule won't be hard. Not only that, we've got over 1,000,000 hotel options globally to select from. Now that's what you call choice. No matter who you are, Expedia can show you the world.
Where should I stay in Portland?
Make sightseeing a breeze by staying someplace near Portland's terrific attractions. Boston Bay Beach and Somerset Falls are two of the best in the area.
What are the top hotels in Portland?
If it's your first visit to Portland, lock in a room at Porty Hostel or Private Norse Hill Estate, 8 Acres. Both hotels offer comfortable beds and are favorites with many travelers.
How far in advance should I book my Portland vacation?
Search Expedia to compare international flights as soon as you know your travel dates. In many cases, you can purchase a seat up to 12 months before departure. If you can't find your preferred carrier, or you've left things to the last moment, don't stress. Cheap fares to Portland occasionally appear within weeks of the date of departure.
What does an Expedia Portland travel package include?
With Expedia, you can select a combination of car rentals, hotels and flights to build your ideal Portland package. Once you've made your booking, you can add on the fun things like tours and experiences. Remember, the more you bundle, the more deals you'll score!
What should I know before booking a Portland travel package?
Find deals that fit your budget with an Expedia package. Hotels, flights, rental cars — we have everything you need to plan your escape. You'll save a packet just by bundling your bookings. Whether you're going on a winter snow adventure or drinking cocktails on a beach, your perfect vacation is only clicks away.
Can I choose my airline with a Portland Expedia vacation package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines all over the world. Our packages give you the flexibility to pick from available flight, hotel or activity options that fit your needs.
If I'm not able to travel, can I cancel my Portland vacation package?
Yes, you can. We understand that even the best-laid plans can go awry, so we're happy to help if you have to make changes to your Portland vacation package. You may be able to change or cancel your itinerary at no cost if you've booked in the last 24 hours. Your hotel, airline or car rental company may impose a fee if your booking was made more than 24 hours ago. Take a look at our Customer Service Portal for more information. Also, check your itinerary for the nitty-gritty on change fees.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.