Portland Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top vacation destinations in Portland
Port Antonio
Buff Bay
Portland Hotel Deals
Sea Cliff Resort
Ross Craig Long Bay Portland
Fully refundable
CA $151
CA $190 total
Sep 26 - Sep 27
includes taxes & fees
8/10 Very good! (228 reviews)
"The view from our room at the cliffs edge was to die for!! Totally awesome and well worth our stay"
Reviewed on Aug 27, 2026
Jamaica Palace Hotel
Williamsfield Port Antonio Portland
Fully refundableReserve now, pay when you stay
CA $187
CA $209 total
Sep 3 - Sep 4
includes taxes & fees
8.2/10 Very good! (352 reviews)
"The property was well maintained but the room was extremely outdated. I had roaches on The bathroom and a lone lizard living in the room. The food was not good. The Jamaican breakfast was hit or miss good the first day then dry and flavorless the next day. The meal service was also extremely slow ..."
Reviewed on Aug 27, 2026
Match Resort Hotel
Dolphin Bay Port Antonio
Fully refundableReserve now, pay when you stay
CA $125
CA $139 total
Sep 25 - Sep 26
includes taxes & fees
8/10 Very good! (243 reviews)
"Great place, close to the attractions I wanted to do in Portland."
Reviewed on Aug 26, 2026
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 CA $5,846. 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.
Stay near popular Portland attractions
Blue Lagoon
9.2/10 (229 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.
Frenchman's Cove Beach
9.2/10 (164 reviews)
Why not spend a carefree afternoon at Frenchman's Cove Beach during your travels in Port Antonio? You can enjoy the restaurants while in the area.
Boston Bay Beach
9.0/10 (132 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.
Trident Castle
8.6/10 (77 reviews)
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.
Winnifred Beach
9.0/10 (117 reviews)
Discover a lovely vacation location, with white sands, crystal seas and friendly smiles, away from tourist hubs in Portland Parish.
San San Beach
8.4/10 (47 reviews)
If a restful vacation is part of your travel plans, San San Beach might be the perfect place to seek out during your trip to Port Antonio. You can enjoy the restaurants while in the area.
Portland Parish Church
8.2/10 (32 reviews)
Portland Parish Church is just one of the places to see in Titchfield Peninsula, so why not enjoy the other things to explore during your travels? Wander the waterfront and beaches in the area.
Port Antonio Square
8.0/10 (99 reviews)
Learn about the local history of Titchfield Peninsula when you take a trip to Port Antonio Square. Wander the waterfront and beaches in the area.
What to do in Portland
Kingston Blue Mountains Tour with Coffee Tasting
CA $126
per adult
100% of travellers recommend
Walk/Drive Tour of Downtown Kingston/Tivoli Gardens/Trench Town.
CA $84
per adult
100% of travellers recommend
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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.
