Portland Holidays

Book a Hotel + Flight or Car together to unlock savings

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! (136 reviews)
"Friendly staff, clean property but most of all the location is just beautiful and breathtaking"

Reviewed on 24 May 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
8.2/10 Very Good! (231 reviews)
"Beautiful property, the gardens surrounding the property are immaculate. This is a classic old hotel with art work in abundance everywhere, classic period furnishings are priceless. The staff was very friendly and welcoming. Breakfast was sumptuous. We had dinner there twice and the food was delicious. ..."

Reviewed on 10 May 2025

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Jamaica Palace Hotel
Geejam
Geejam
4.5 out of 5
San San, Port Antonio, Port Antonio, Portland
The price is 10.321.745 ₫ per night from 25 Jun to 26 Jun
10.321.745 ₫
12.412.225 ₫ total
25 Jun - 26 Jun
includes taxes & fees
9.6/10 Exceptional! (64 reviews)
Geejam, Jamaica
"From arrival to departure the staff were amazing. We were also lucky enough to meet Steve one of the owners of the resort and he was great, took time to welcome all the guests at dinner individually. The food and drinks were great. All the staff were very friendly and attentive without being too ..."

Reviewed on 6 Apr 2025

Geejam
See all 1,823 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 1null000null000 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

Blue Lagoon showing boating and a lake or waterhole

Blue Lagoon

5/5(1 review)

Why not spend a care-free afternoon at Blue Lagoon during your travels in Port Antonio? You can enjoy the restaurants while in the area.

Blue Lagoon

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

Boston Bay Beach

If a restful holiday is part of your travel plans, Boston Bay Beach might be the perfect place to visit during your trip to Port Antonio. You can enjoy the restaurants while in the area.

Boston Bay Beach