
Portland Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- 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

Port Antonio
Top Portland Vacation Deals
Price found within the past 48 hours. Click for updated prices.




Casa Maria Hotel
Price was CA $1,964, price is now CA $1,606 per person
CA $1,606
per person
Nov 9 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Ocho Rios (OCJ)
6.6/10 (56 reviews)
No help was offered to get heavy luggage up the steep steps to the 2nd floor.
Reviewed on Jun. 22, 2025
Portland Hotel Deals

Sea Cliff Resort
Ross Craig, Long Bay, Portland
Fully refundable
The price is CA $147 per night from Aug 21 to Aug 22
CA $147
CA $185 total
Aug 21 - Aug 22
includes taxes & fees
8/10 Very Good! (152 reviews)
"My stay at Sea Cliff was relaxing. It's a beautiful property with relaxing views of the ocean from almost all the rooms. The bed was large and comfortable. The food was good we had breakfast included with our stay. The staff was warm and friendly. I felt like I was staying at a friend's house instead ..."
Reviewed on Aug. 10, 2025

Jamaica Palace Hotel
Williamsfield, Port Antonio, Portland
Fully refundableReserve now, pay when you stay
The price is CA $253 per night from Aug 20 to Aug 21
CA $253
CA $281 total
Aug 20 - Aug 21
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

Geejam
San San, Port Antonio, Port Antonio, Portland
The price is CA $545 per night from Aug 20 to Aug 21
CA $545
CA $656 total
Aug 20 - Aug 21
includes taxes & fees
9.6/10 Exceptional! (68 reviews)
"Gorgeous property. Very friendly staff."
Reviewed on Aug. 16, 2025
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
Discover the most popular places to visit in Portland

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.

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.
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.
What to do in Portland

Bob Marley Museum in Kingston & Blue Mountain Coffee Tour
CA $237
per adult

Bamboo Rafting, Frenchman Cove, Boston Jerk Centre in Portland
CA $207
per adult
Other vacations you might like
- Top destinations in Portland
- Vacations and getaways similar to Portland
- Best vacation destinations by month
- Expedia's Latest Trends
- January Vacations and Deals
- February Vacations and Deals
- March Vacations and Deals
- April Vacations and Deals
- May Vacations and Deals
- June Vacations and Deals
- July Vacations and Deals
- August Vacations and Deals
- September Vacations and Deals
- October Vacations and Deals
- November Vacations and Deals
- December Vacations and Deals
Expedia's Latest Trends
Hotels
- Best Hotels in Port Antonio
- Hotels in Tobago
- All Inclusive Resorts and Hotels in Saint Ann
- All Inclusive Resorts and Hotels in St. Croix Island
- All Inclusive Resorts and Hotels in Exuma
- Hotels in Bonaire
- All Inclusive Resorts and Hotels in La Altagracia
- Beach Hotel in Trelawny
- All Inclusive Resorts and Hotels in Puerto Plata
- All Inclusive Resorts and Hotels in Trelawny
- All Inclusive Resorts and Hotels in Bonaire
- All Inclusive Resorts and Hotels in Tobago
- All Inclusive Resorts and Hotels in Tortola
Flights
Activities
Packages
General
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.