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

FlightsFlightsHotelsHotels

Port Antonio

Port Antonio
FlightsFlightsHotelsHotels

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 $7,703, price is now CA $6,425 per person
CA $6,425
per person
Jul 30 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) 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 $164 per night from May 30 to May 31
CA $164
CA $206 total
May 30 - May 31
includes taxes & fees
8.2/10 Very Good! (201 reviews)
"Sea cliff's property was beautiful and my partner and I have an amazing time on the quiet property. The rooms were clean and the housekeeping came every morning. We do wish the air conditioner was more efficient and cooled the entire room, it only cooled one side. The lunch/dinner was great, it was ..."

Reviewed on May 26, 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 $254 per night from May 29 to May 30
CA $254
CA $282 total
May 29 - May 30
includes taxes & fees
8.4/10 Very Good! (303 reviews)
"I have stay here before and was very happy they could accommodate my family and I.. We booked another accommodation which was not as advertised… Breakfast is on point and with a wide choice. Room was clean and smells clean too… Great location to pop into town or to Boston beach… I will be back.."

Reviewed on May 19, 2026

Jamaica Palace Hotel
Geejam

Geejam

4.5 out of 5
San San, Port Antonio Port Antonio Portland
The price is CA $492 per night from Jun 4 to Jun 5
CA $492
CA $592 total
Jun 4 - Jun 5
includes taxes & fees
9.6/10 Exceptional! (90 reviews)
"Property and scenery was great . Awesome staff. Room and bathroom well decorated with pictures of music musicians in black and white also country folks. Food was delicious also property , pools and surroundings is well kept ."

Reviewed on May 14, 2026

Geejam
See all 1,896 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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 $6,425. 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

Blue Lagoon

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
Woman wades in the surf at Frenchman's Cove in Tobago; Port Antonio, Jamaica

Frenchman's Cove Beach

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.

Frenchman's Cove Beach
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

What to do in Portland

Kingston Dub Club Sundays

Kingston Dub Club Sundays

CA $89
per adult
Kingston Dub Club Sundays
Shared horseback riding Punta Cana Beach

Shared horseback riding Punta Cana Beach

CA $130
per adult
Shared horseback riding Punta Cana Beach
Kingston: Story of Jamaican Music Tour including Entry Fees

Kingston: Story of Jamaican Music Tour including Entry Fees

CA $123
per adult
100% of travellers recommend
Kingston: Story of Jamaican Music Tour including Entry Fees
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.