Portland Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Cathy Tracey

Top destinations in Portland

Epic view of the sun as it sets in Montego Bay, Jamaica.
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Hope Bay

Hope Bay

Top hotels in Portland

Sea Cliff Resort

Sea Cliff Resort

3 out of 5
Ross Craig Long Bay Portland
Fully refundable
The price is 3.115.178 ₫ per night from 29 Apr to 30 Apr
3.115.178 ₫
3.920.317 ₫ total
29 Apr - 30 Apr
includes taxes & fees
8.2/10 Very Good! (194 reviews)
Excellent place to relax and take in nature.

Reviewed on 17 Apr 2026

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 4.241.384 ₫ per night from 24 May to 25 May
4.241.384 ₫
4.718.210 ₫ total
24 May - 25 May
includes taxes & fees
8.4/10 Very Good! (296 reviews)
Ms. Moore - Operations Manager was accommodating as well as Georgia who was very helpful at the time of booking. Ensure what is advertised is accurate on this site. Omlettes were good. Would have liked more local fruits that were available in the area. Male server was exceptional...name starts with ...

Reviewed on 15 Apr 2026

Jamaica Palace Hotel
Geejam

Geejam

4.5 out of 5
San San, Port Antonio Port Antonio Portland
The price is 10.405.880 ₫ per night from 28 Apr to 29 Apr
10.405.880 ₫
12.513.400 ₫ total
28 Apr - 29 Apr
includes taxes & fees
9.6/10 Exceptional! (87 reviews)
Absolutely amazing. I highly recommend. Great good staff and the perfect location. We stayed in the Sandwood Villa and loved it. Akua our concierge was absolutely lovely and very helpful.

Reviewed on 13 Apr 2026

Geejam
See all 1,860 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

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 - Port Antonio, JamaicaJa

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
Meeresblick auf den Boston Beach von den Klippen an der Küste von Jamaika Portland

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

Explore a world of travel with Expedia