Portland Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • Plan, book, travel with confidence

  • Better together

    Save up to CA $1,096 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 Haven Guesthouse

Blue Haven Guesthouse

2 out of 5
Price was CA $954, price is now CA $850 per person
CA $850
per person
Jun 23 - Jun 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Ocho Rios (OCJ)
No reviews
Luxury Oceanfront Villa Fully Staffed Pool Jacuzzi Movie Theatre

Luxury Oceanfront Villa Fully Staffed Pool Jacuzzi Movie Theatre

3 out of 5
Price was CA $10,138, price is now CA $8,083 per person
CA $8,083
per person
Jun 29 - Jul 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Ocho Rios (OCJ)
No reviews
Breathtaking Oceanfront Luxe Villa in Tower Isle Jacuzzi Pool Fully Staffed

Breathtaking Oceanfront Luxe Villa in Tower Isle Jacuzzi Pool Fully Staffed

2 out of 5
Price was CA $11,359, price is now CA $9,065 per person
CA $9,065
per person
Jun 29 - Jul 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Ocho Rios (OCJ)
No reviews
Luxury Oceanfront Villa Fully Staffed

Luxury Oceanfront Villa Fully Staffed

2 out of 5
Price was CA $8,475, price is now CA $7,018 per person
CA $7,018
per person
Jun 29 - Jul 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Ocho Rios (OCJ)
No reviews
4BR Seafront Villa in Boscobel Direct Sea Access Coastal Living

4BR Seafront Villa in Boscobel Direct Sea Access Coastal Living

2 out of 5
Price was CA $7,823, price is now CA $6,530 per person
CA $6,530
per person
Jun 29 - Jul 4
found 1 day ago
Roundtrip non-stop 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 $164 per night from Apr 15 to Apr 16
CA $164
CA $206 total
Apr 15 - Apr 16
includes taxes & fees
8.2/10 Very Good! (192 reviews)
Absolutely Disappointing Stay – Would Not Recommend During Easter break, my family and I stayed at Sea Cliffs Resort, and unfortunately, our experience was extremely disappointing from start to finish. Check-in was smooth, but that was the only positive part of our stay. As soon as we entered the ...

Reviewed on Apr 9, 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 $228 per night from Apr 25 to Apr 26
CA $228
CA $254 total
Apr 25 - Apr 26
includes taxes & fees
8.4/10 Very Good! (294 reviews)
Great hotel in a stunning property with really friendly staff at reception. Had an issue with bathroom shower which sprayed onto the wall and then the floor - apparently a result of bath/shower design so the staff couldn't help. Otherwise had a great stay with good food, although the restaurant was ...

Reviewed on Apr 10, 2026

Jamaica Palace Hotel
Geejam

Geejam

4.5 out of 5
San San, Port Antonio Port Antonio Portland
The price is CA $547 per night from Apr 26 to Apr 27
CA $547
CA $657 total
Apr 26 - Apr 27
includes taxes & fees
9.6/10 Exceptional! (86 reviews)
Food was unavailable when on menu, subs as well. Food quality was good but lacking flavor. Spa service not available when booked. Couldn’t see the studio and no follow up from staff about seeing or using it. Beautiful and quite definitely relaxing. Close to many thing to do.

Reviewed on Mar 27, 2026

Geejam
See all 1,859 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 $850. 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

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

Frenchman's Cove Beach

5/5(2 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.

Frenchman's Cove Beach
Blue Lagoon

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
Trident Castle - Port Antonio, JamaicaJa

Trident Castle

4/5(1 review)

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.