Portland Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

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

Top vacation destinations in Portland

A beach with clear turquoise water, a rocky coastline, and a small structure on a cliff.
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Port Antonio

Port Antonio
A tropical beach with palm trees and a clear blue sky.
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Buff Bay

Buff Bay

Top Portland Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Blue Berry Hills Villa

Blue Berry Hills Villa

3 out of 5
Price was CA $4,988, price is now CA $4,537 per person
CA $4,537
per person
Sep 18 - Sep 25
found 1 hour ago
Roundtrip flight included
Toronto (YYZ) to Ocho Rios (OCJ)
No reviews

Portland Hotel Deals

Sea Cliff Resort

Sea Cliff Resort

3 out of 5
Ross Craig Long Bay Portland
Fully refundable
The price is CA $167 per night from Jul 14 to Jul 15
CA $167
CA $211 total
Jul 14 - Jul 15
includes taxes & fees
8/10 Very good! (217 reviews)
"Beautiful property quiet and relaxing"

Reviewed on Jul 10, 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 CA $224 per night from Jul 27 to Jul 28
CA $224
CA $249 total
Jul 27 - Jul 28
includes taxes & fees
8.2/10 Very good! (328 reviews)
"I booked the hotel reading the reviews both good and bad and not sure what to expect. However, our experience was perfect. We stayed in room 30 and it was clean. The water pressure was great, the air-conditioning and everything worked fine. We had breakfast twice there and it was delicious. The facilities ..."

Reviewed on Jul 12, 2026

Jamaica Palace Hotel
Geejam

Geejam

4.5 out of 5
San San, Port Antonio Port Antonio Portland
The price is CA $514 per night from Jul 19 to Jul 20
CA $514
CA $619 total
Jul 19 - Jul 20
includes taxes & fees
9.4/10 Exceptional! (93 reviews)
"Geejam was a breath of fresh air after cancelling & leaving another property in Portland early & concluding our vacation here. The staff was very kind & hospitable. We definitely enjoyed the free breakfast daily & the food was good. We had a good time at dinner as well & drinks were made well. My ..."

Reviewed on Jun 28, 2026

Geejam
See all 1,933 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.
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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 $4,537. 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

Three boats docked at a calm, turquoise body of water surrounded by lush greenery.

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.
See properties

What to do in Portland

Walk Tours in Kingston.

Walk/Drive Tour of Downtown Kingston/Tivoli Gardens/Trench Town.

CA $72
per adult
100% of travellers recommend
Walk/Drive Tour of Downtown Kingston/Tivoli Gardens/Trench Town.
Shared horseback riding Punta Cana Beach

Shared horseback riding Punta Cana Beach

CA $135
per adult
Shared horseback riding Punta Cana Beach
Kingston: Story of Jamaican Music Tour including Entry Fees

Kingston: Rhythmic Story of Jamaican Music Tour

CA $128
per adult
100% of travellers recommend
Kingston: Rhythmic Story of Jamaican Music Tour
See all activities in Portland

Explore a world of travel with Expedia

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