Portland Holidays

  • Plan, book, travel with confidence

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    Better together
    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy
    Plan, book, and manage your trip all in one place

Portland Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Blue-sky penthouse
Couples Tower Isle All Inclusive

Top hotels in Portland

Jamaica Palace Hotel
Jamaica Palace Hotel
3.5 out of 5
Williamsfield, Port Antonio, Portland
Fully refundable
The price is S$273 per night from 28 Apr to 29 Apr
S$273
includes taxes & fees
28 Apr - 29 Apr
8.2/10 Very Good! (215 reviews)
Tranquil Getaway
"This was my first time in Portland Parish, ao I wanted to stay close enough to town, so I could access the markets, restaurants, and other ammenities whenever needed. I read a lot of positive reviews about Jamaica Palace, so I decided to stay there. It was a lot more than I imagined. The old, colonial ..."

Reviewed on 18 Mar,2025

Jamaica Palace Hotel
Sea Cliff Resort
Sea Cliff Resort
3 out of 5
Ross Craig, Long Bay, Portland
Fully refundableReserve now, pay when you stay
The price is S$277 per night from 30 Mar to 31 Mar
S$277
includes taxes & fees
30 Mar - 31 Mar
8.2/10 Very Good! (132 reviews)
"Great property"

Reviewed on 12 Oct,2024

Sea Cliff Resort
Geejam
Geejam
4.5 out of 5
San San, Port Antonio, Port Antonio, Portland
The price is S$636 per night from 23 Apr to 24 Apr
S$636
includes taxes & fees
23 Apr - 24 Apr
9.6/10 Exceptional! (59 reviews)
"Love this area of Jamaica and we didn’t leave the hotel for x3 nights for dinner."

Reviewed on 15 Mar,2025

Geejam
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 holiday package cost?
We make it easy to travel somewhere new, with Portland packages starting from as little as S$1,978. 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 holiday 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 favourites with many travellers.
How far in advance should I book my Portland holiday?
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 holiday is only clicks away.
Can I choose my airline with a Portland Expedia holiday 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 holiday 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 holiday 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.

Popular places to visit

What to do in Portland

* 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.