Portland Holidays

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    Save up to €185 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    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
Fully refundable
8/10 Very Good! (153 reviews)
"The views at the property are exceptional. It’s gives a cabin vibe. It’s a great choice if you want to unplug and relax. I went alone and I felt very peaceful. It’s a small property and the only thing to do onsite is really eat, relax and take in the views. I definitely also recommend that you only ..."

Reviewed on 20 Aug 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 €174 per night from 26 Aug to 27 Aug
€174
26 Aug - 27 Aug
includes taxes & fees
8.2/10 Very Good! (243 reviews)
"Always wanted to stay there. Property and pool was amazing. Rooms are ok, could use a little work. Breakfast was decent. Would return for a short stay"

Reviewed on 7 Aug 2025

Jamaica Palace Hotel
Geejam

Geejam

4.5 out of 5
San San, Port Antonio, Port Antonio, Portland
The price is €405 per night from 25 Aug to 26 Aug
€405
25 Aug - 26 Aug
includes taxes & fees
9.6/10 Exceptional! (71 reviews)
"Beautiful hotel"

Reviewed on 20 Aug 2025

Geejam
See all 1,828 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

Winnifred Beach which includes a beach as well as a small group of people

Winnifred Beach

Discover a lovely vacation location, with white sands, crystal seas and friendly smiles, away from tourist hubs in Portland Parish.

Winnifred Beach

Trident Castle

After visiting Trident Castle, make a plan to see the other sights and activities in Port Antonio. Wander the waterfront and beaches in the area.

Trident Castle

What to do in Portland

Blue Mountains Tour including Lunch

Blue Mountains Tour including Lunch

€104
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

€149
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

€130
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.