Portland Vacation Packages

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Top vacation destinations in Portland

Winnifred Beach featuring general coastal views as well as a small group of people
FlightsFlightsHotelsHotels

Port Antonio

Port Antonio

Top Portland Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Lagardan Ocean View

Lagardan Ocean View

3 out of 5
per person
Sep 15 - Sep 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Ocho Rios (OCJ)
10/10 Exceptional! (1 review)
Top Brass Ocean View Vacation Rental

Top Brass Ocean View Vacation Rental

3 out of 5
per person
Sep 21 - Sep 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Ocho Rios (OCJ)
10/10 Exceptional! (1 review)
Ocho Rios Skyview Guest Apartment

Ocho Rios Skyview Guest Apartment

3.5 out of 5
per person
Sep 15 - Sep 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Ocho Rios (OCJ)
7.4/10 Good! (3 reviews)
Luxury Oceanfront Villa Fully Staffed Pool Jacuzzi Movie Theatre

Luxury Oceanfront Villa Fully Staffed Pool Jacuzzi Movie Theatre

2 out of 5
per person
Sep 15 - Sep 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Ocho Rios (OCJ)
No reviews
Luxury Oceanfront Villa in Tower Isle

Luxury Oceanfront Villa in Tower Isle

2 out of 5
per person
Sep 15 - Sep 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) 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 $146 per night from Aug 12 to Aug 13
CA $146
CA $184 total
Aug 12 - Aug 13
includes taxes & fees
8/10 Very Good! (149 reviews)
"Great stay good food"

Reviewed on Aug. 8, 2025

Sea Cliff Resort
Geejam

Geejam

4.5 out of 5
San San, Port Antonio, Port Antonio, Portland
The price is CA $543 per night from Aug 11 to Aug 12
CA $543
CA $654 total
Aug 11 - Aug 12
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
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 $253 per night from Aug 11 to Aug 12
CA $253
CA $281 total
Aug 11 - Aug 12
includes taxes & fees
8.2/10 Very Good! (242 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
See all 1,826 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 $1,260. 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

5/5(9 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
Winnifred Beach showing a sandy beach as well as a small group of people

Winnifred Beach

3.5/5(2 reviews)

Discover a lovely vacation location, with white sands, crystal seas and friendly smiles, away from tourist hubs in Portland Parish.

Winnifred Beach

Frenchman's Cove Beach

5/5(2 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

What to do in Portland

Blue Mountains Tour including Lunch

Blue Mountains Tour including Lunch

CA $164
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

CA $236
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

CA $206
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.