Portland Vacations & Trips

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to ￥45,448 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Portland Hotel Deals

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 Aug 20, 2025

Get rates
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 ￥26,978 per night from Aug 26 to Aug 27
￥26,978
￥29,970 total
Aug 26 - Aug 27
includes taxes & fees
8.2/10 Very Good! (244 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 Aug 7, 2025

Jamaica Palace Hotel
Geejam

Geejam

4.5 out of 5
San San, Port Antonio, Port Antonio, Portland
The price is ￥53,979 per night from Aug 26 to Aug 27
￥53,979
￥64,922 total
Aug 26 - Aug 27
includes taxes & fees
9.6/10 Exceptional! (71 reviews)
"Beautiful hotel"

Reviewed on Aug 20, 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 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

￥17,736
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

￥25,422
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

￥22,170
per adult
Bamboo Rafting, Frenchman Cove, Boston Jerk Centre in Portland
See all activities in Portland

Other vacations you might like

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