Portland Holidays

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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.
Whispering Seas

Whispering Seas

3.5 out of 5
Save 100% on your flight
per person
29 Sept - 5 Oct
found 1 day ago
Return direct flight included
Montreal (YUL) to Ocho Rios (OCJ)
9/10 Wonderful! (157 reviews)
Amazing property and experience. I will be back.

Reviewed on 25 Jul, 2025

Lagardan Ocean View

Lagardan Ocean View

3 out of 5
Save 100% on your flight
per person
15 Sept - 21 Sept
found 1 day ago
Return direct flight included
Montreal (YUL) to Ocho Rios (OCJ)
10/10 Exceptional! (1 review)
Luxury Oceanfront Villa Fully Staffed Pool Jacuzzi Movie Theatre

Luxury Oceanfront Villa Fully Staffed Pool Jacuzzi Movie Theatre

2 out of 5
Save 100% on your flight
per person
15 Sept - 21 Sept
found 1 day ago
Return direct flight included
Montreal (YUL) to Ocho Rios (OCJ)
No reviews
Couples Tower Isle All Inclusive

Couples Tower Isle All Inclusive

4.5 out of 5
per person
29 Sept - 5 Oct
found 1 day ago
Return direct flight included
Montreal (YUL) to Ocho Rios (OCJ)
9.2/10 Wonderful! (1,010 reviews)
Pros: -The staff are kind and willing to help you with anything you need. The service was my favorite part of my stay at Couples Tower Isle. -The amenities they offer around the property are nice as well such as transportation, room service, the beach, spa, pools, jacuzzis, etc. -The private island is gorgeous. I went for a private island dinner for my birthday and they made sure I was taken care of. -Bartenders make good drinks! Cons: -I wasn't too pleased with the room. Although I had a great waterfront view, there were ants and a roach in my room during my stay. There also wasn't a door on the shower. It might've been the design, it just wasn't my favorite. -The food was good but not the best. I would've preferred a mix of American and Jamaican food, but there was mostly American food. The night they did have Jamaican food, it was delicious. -The shuttles are reliable, but you must book a driver through them to travel outside of the resort. Ubers aren't allowed. The same goes for the shopping center. They take you to 3 stores, but no other local places. -The demographic is mostly older couples. My partner and I are a couple in our early thirties, and we were one of the youngest couples there. This is also probably why the nightlife isn't the best on the resort.

Reviewed on 25 Jul, 2025

Top hotels in Portland

Sea Cliff Resort

Sea Cliff Resort

3 out of 5
Ross Craig, Long Bay, Portland
Fully refundableReserve now, pay when you stay
8/10 Very Good! (147 reviews)
"I recently booked several rooms over the past weekend as my family traveled to Jamaica for a funeral. We had a few mishaps on our part, but the staff was incredibly understanding and accommodating throughout. The rooms were clean, the staff was friendly, and Terrence went above and beyond to make ..."

Reviewed on 22 Jul, 2025

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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 S$262 per night from 11 Aug to 12 Aug
S$262
11 Aug - 12 Aug
includes taxes & fees
8.2/10 Very Good! (237 reviews)
"The pool is amazing...well lit at night."

Reviewed on 27 Jul, 2025

Jamaica Palace Hotel
LF Jungle Retreat

LF Jungle Retreat

3 out of 5
Lots 32-40, Willamsfield, Port Antonio
Fully refundableReserve now, pay when you stay
8.4/10 Very Good! (26 reviews)
"Amazing STAFFF"

Reviewed on 24 Jul, 2025

Get rates
LF Jungle Retreat
See all 1,850 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 S$1,155. 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 Drapers? You can enjoy the restaurants while in the area.

Frenchman's Cove Beach

What to do in Portland

Blue Mountains Tour including Lunch

Blue Mountains Tour including Lunch

S$154
per adult
Blue Mountains Tour including Lunch
Bob Marley Museum in Kingston & Blue Mountain Coffee Tour

Bob Marley Museum in Kingston & Blue Mountain Coffee Tour

S$220
per adult
Bob Marley Museum in Kingston & Blue Mountain Coffee Tour
Bamboo Rafting, Frenchman Cove and Boston Bay Private Day Tour

Bamboo Rafting, Frenchman Cove, Boston Jerk Centre in Portland

S$192
per adult
Bamboo Rafting, Frenchman Cove, Boston Jerk Centre in Portland
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.