Portland Vacations & Trips from $601

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Your Portland Vacation

With a Portland vacation package, you can forget about the stress of planning and instead focus on experiencing all this exciting destination has to offer. Port Antonio, Long Bay and Happy Grove are a few of the most well-known cities here. Make sure your trip to Portland includes a stay in one or all of them! If you're ready to stop dreaming and start traveling, Expedia will help turn your Portland vacation into reality.

Top destinations in Portland

Port Antonio
FlightsFlightsHotelsHotels

Port Antonio

Port Antonio

The Latest Portland Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Ocho Rios Villa at The Palms

Ocho Rios Villa at The Palms

3 out of 5
per person
Jul 6 - Jul 13
Roundtrip flight included
Philadelphia (PHL) to Ocho Rios (OCJ)
10/10 Exceptional! (2 reviews)
All staff were professional, courteous and friendly. They all went out of their way to grant your requests. The ambience is very nice. The electrical outlets on the patio didn't always work. Had to be creative in getting plugs to stay in. They also need to upgrade from 110v to 220v. Just kidding, but they should have something for travelers from Europe. Internet service was pretty good. Everyone in my group were pleased and would return. The tour setup for us by the manager was fun!!!! Good people, fantastic accommodations. Recommended...

Reviewed on May 8, 2019

Fern Court Apartment With Oceanic View

Fern Court Apartment With Oceanic View

3.5 out of 5
per person
Jul 6 - Jul 13
Roundtrip flight included
Philadelphia (PHL) to Ocho Rios (OCJ)
8/10 Very Good! (8 reviews)
I was very impressed with how well this place was decorated. They had everything that I expected in the amenities list in the post. I think it’s also important to know that the property is in a gated community for your extra security which gave me a feel of exclusivity during my stay. The rooms have central air and the bathrooms are beautiful. I was really pleased and I think that you would be too. Thanks again guys one love!

Reviewed on Aug 21, 2019

Ocho Rios Villa at Coolshade III

Ocho Rios Villa at Coolshade III

2.5 out of 5
Save 100% on your flight
per person
Jul 6 - Jul 13
Roundtrip flight included
Philadelphia (PHL) to Ocho Rios (OCJ)
8.4/10 Very Good! (10 reviews)
Very quiet and nice place

Reviewed on May 31, 2022

Ocho Rios Ocean View Villa at The Palms

Ocho Rios Ocean View Villa at The Palms

4 out of 5
Save 100% on your flight
per person
Jun 17 - Jun 22
Roundtrip flight included
Newark (EWR) to Ocho Rios (OCJ)
6/10 (13 reviews)
Very nice, the did a little upgrading. Actually, it is very nice.

Reviewed on Jun 15, 2019

Whispering Seas

Whispering Seas

3.5 out of 5
Save 100% on your flight
per person
Jul 6 - Jul 10
Roundtrip flight included
Atlanta (ATL) to Ocho Rios (OCJ)
9/10 Wonderful! (129 reviews)
Lots of space. Clean great for families

Reviewed on Apr 7, 2024

Portland Essential Information

Language
English
Currency
Jamaican dollars
Closest Airport
Norman Manley Intl. Airport (KIN)
Top Sights
Blue Lagoon, Frenchmans Cove Beach and Boston Bay Beach

Portland Hotel Deals

Sea Cliff Resort
Sea Cliff Resort
3 out of 5
Ross Craig, Long Bay, Portland
Fully refundable
The price is $121 per night from May 15 to May 16
$121
$152 total
includes taxes & fees
May 15 - May 16
8/10 Very Good! (110 reviews)
"As a Jamaican national and native from Portland I was truly impressed with the property and my stay for the two nights. This trip was the pre celebration for my wifey birthday. The property is authentic and rustic and very secluded. Terrance helped to check us in and showed us great hospitality while ..."

Reviewed on May 1, 2024

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 $173 per night from May 14 to May 15
$173
$193 total
includes taxes & fees
May 14 - May 15
7.8/10 Good! (165 reviews)
"Peace, quiet and the feeling of being safe."

Reviewed on May 1, 2024

Jamaica Palace Hotel
Geejam
Geejam
4.5 out of 5
San San, Port Antonio, Port Antonio, Portland
The price is $380 per night from May 16 to May 17
$380
$458 total
includes taxes & fees
May 16 - May 17
9.6/10 Exceptional! (44 reviews)
"Absolutely worth every penny. Service is so amazing - they really know what they're doing. Room was very well laid out with a stunning view of the ocean. The whole resort is tucked away in the mountainside like it's always been there. Love the way the buildings have been built around the existing ..."

Reviewed on Apr 7, 2024

Geejam
See all 1,682 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly 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 $601. 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

Image for Blue Lagoon

Blue Lagoon

4.5/5(80 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
Image for Winnifred Beach

Winnifred Beach

4.5/5(28 reviews)

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

Winnifred Beach
Image for Somerset Falls

Somerset Falls

4.5/5(43 reviews)

The songs of tropical birds fill the air as you wind your way through a narrow gorge to secluded cascades with natural pool.

Somerset Falls

What to do in Portland

Image for Bamboo Rafting, Frenchman Cove, Boston Jerk Centre in Portland

Bamboo Rafting, Frenchman Cove, Boston Jerk Centre in Portland

$195
Per adult
Bamboo Rafting, Frenchman Cove, Boston Jerk Centre in Portland
Image for Private Bird watching Tour in Kingston Jamaica with Lunch

Private Bird watching Tour in Kingston Jamaica with Lunch

$180
Per adult
Private Bird watching Tour in Kingston Jamaica with Lunch
Image for Surfing and Motorized Canoeing Private Tour in Jamaica

Surfing and Motorized Canoeing Private Tour in Jamaica

$350
Per adult
Surfing and Motorized Canoeing Private Tour in Jamaica
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.