Portland Holidays

Photo by Cathy Tracey

  • Plan, book, travel with confidence

  • Better together

    Save up to S$134 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 hotels in Portland

Sea Cliff Resort

Sea Cliff Resort

3 out of 5
Ross Craig Long Bay Portland
8.2/10 Very Good! (167 reviews)
My family and I had a wonderful stay at Sea Cliff Resort. From the moment we arrived, the manager, owner, and his son were warm, hospitable, and assisted us with everything we needed. Their kindness really made our stay feel special.Thank you were we all amazing, The ambiance is peaceful, and the ...

Reviewed on 9 Dec, 2025

Get rates
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 S$211 per night from 17 Dec to 18 Dec
S$211
17 Dec - 18 Dec
includes taxes & fees
8.2/10 Very Good! (259 reviews)
The room was clean. Breakfast and lunch was great. Thr staff was very friendly and accommodating.

Reviewed on 22 Nov, 2025

Jamaica Palace Hotel
Geejam

Geejam

4.5 out of 5
San San, Port Antonio Port Antonio Portland
The price is S$636 per night from 8 Jan to 9 Jan
S$636
8 Jan - 9 Jan, 2026
includes taxes & fees
9.6/10 Exceptional! (74 reviews)
It’s a given that Geejam is a beautifully appointed hotel but the real gem is the staff. Spent the last few days at Geejam while they navigated no power and limited internet but they worked to ensure our comfort. Special acknowledgement to Nadine and Brian who went above and beyond!

Reviewed on 17 Nov, 2025

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 holiday 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 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

Frenchman's Cove Beach

5/5(1 review)

Why not spend a care-free afternoon at Frenchman's Cove Beach during your travels in Port Antonio? You can enjoy the restaurants while in the area.

Frenchman's Cove Beach

What to do in Portland

Kingston Dub Club Sundays

Kingston Dub Club Sundays

S$84
per adult
Kingston Dub Club Sundays
displays at the bob marley museum in Jamaica

Kingston Tour & Bob Marley Museum Admission

S$105
per adult
74% of travellers recommend
Kingston Tour & Bob Marley Museum Admission
Deluxe Sunset and Saxophone Sail on Luxury Lady Grace Catamaran

Deluxe Sunset and Saxophone Sail on Luxury Lady Grace Catamaran

S$244
per adult
100% of travellers recommend
Deluxe Sunset and Saxophone Sail on Luxury Lady Grace Catamaran
See all activities 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.