Portland Vacations & Trips

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Portland Hotel Deals

Sea Cliff Resort

Sea Cliff Resort

3 out of 5
Ross Craig, Long Bay, Portland
Fully refundable
8/10 Very Good! (148 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 Jul 22, 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 ￥25,353 per night from Aug 14 to Aug 15
￥25,353
￥28,183 total
Aug 14 - Aug 15
includes taxes & fees
8.2/10 Very Good! (237 reviews)
"The pool is amazing...well lit at night."

Reviewed on Jul 27, 2025

Jamaica Palace Hotel
Geejam

Geejam

4.5 out of 5
San San, Port Antonio, Port Antonio, Portland
The price is ￥58,223 per night from Aug 5 to Aug 6
￥58,223
￥70,015 total
Aug 5 - Aug 6
includes taxes & fees
9.6/10 Exceptional! (66 reviews)
"Secluded property with great views of ocean. Peaceful and nice rooms and vibes. I enjoyed the food and the owners and staff are great"

Reviewed on Jul 30, 2025

Geejam
See all 1,815 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 vacation 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 vacation 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 favorites with many travelers.
How far in advance should I book my Portland vacation?
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 vacation is only clicks away.
Can I choose my airline with a Portland Expedia vacation 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 vacation 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 vacation 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.

Discover the most popular places to visit in Portland

Blue Lagoon featuring boating and a lake or waterhole

Blue Lagoon

4.5/5(80 reviews)

This gorgeous teardrop-shaped bay is a famous movie location and changes color with the light of day: A picture-perfect location for a refreshing swim.

Blue Lagoon

Frenchman's Cove Beach

5/5(17 reviews)

Why not spend a carefree afternoon at Frenchman's Cove Beach during your travels in Drapers? You can enjoy the restaurants while in the area.

Frenchman's Cove Beach

Boston Bay Beach

4.5/5(34 reviews)

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

Boston Bay Beach

What to do in Portland

Blue Mountains Tour including Lunch

Blue Mountains Tour including Lunch

￥17,723
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

￥25,403
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

￥22,154
per adult
Bamboo Rafting, Frenchman Cove, Boston Jerk Centre in Portland
See all activities in Portland

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.