Portland Vacations & Trips from $2,427

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Top destinations in Portland

A beach with clear turquoise water, a rocky coastline, and a small structure on a cliff.

Port Antonio

Port Antonio
A tropical beach with clear blue waters, sandy shore, and lush greenery.

Long Bay

Long Bay
A waterfall cascading over a rock formation into a clear pool of water.

Reach

Reach
A tropical beach with palm trees and a clear blue sky.

Buff Bay

Buff Bay
A sunset over a calm sea with a visible horizon line.

Hope Bay

Hope Bay

The Latest Portland Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Blue Berry Hills Villa

Blue Berry Hills Villa

Save 100% on your flight
$2,427
per person
Sep 25 - Oct 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Ocho Rios (OCJ)
No reviews

Best Places to Vacation in Portland

1. Book your ideal Port Antonio with a vacation package

Port Antonio, located in the beautiful parish of Portland, Jamaica, offers a vibrant and diverse outdoor vacation experience. With its stunning beaches, thrilling rafting opportunities, and picturesque horseback riding trails, this destination is a paradise for nature lovers. Immerse yourself in the local culture by enjoying live music and dancing, sampling delicious dining options, and savoring the world-renowned Jamaican coffee. Don't miss the chance to explore the enchanting waterfalls that dot the landscape. Whether you're seeking adventure or relaxation, Port Antonio offers a perfect blend of natural beauty and lively atmosphere for an unforgettable vacation.

  • Travelers tend to stay 3 days in Port Antonio

2. Discover Long Bay with our vacation deals

Long Bay in Portland, Jamaica, offers a unique and diverse outdoor vacation experience. The area boasts stunning natural beauty, with bar, waterfalls, islands, and a picturesque sea. Visitors can relax on the beautiful beach or explore the lush gardens. Long Bay is also a perfect destination for a romantic getaway or a luxurious vacation. With a variety of dining options, travelers can indulge in delicious local cuisine. Whether you're looking for adventure or relaxation, Long Bay has something to offer for every outdoor enthusiast.

  • The peak season is from January to March
  • The off-peak season is from October to December
  • Travelers tend to stay 3 days in Long Bay

3. Create memories in Buff Bay with a vacation package

Buff Bay in Portland, Jamaica offers a vibrant and picturesque atmosphere for outdoor vacation seekers. With its stunning natural beauty, visitors can explore lush rainforests, cascading waterfalls, and breathtaking beaches. The local atmosphere is laid-back and friendly, allowing travelers to immerse themselves in the warm and welcoming culture of Jamaica. Whether hiking through the Blue Mountains, swimming in the crystal-clear waters of the Rio Grande, or simply relaxing on the pristine beaches, Buff Bay provides an unforgettable outdoor experience for nature lovers and adventure enthusiasts alike.

  • The peak season is from January to March
  • The off-peak season is from April to June
  • Travelers tend to stay 1 day in Buff Bay

4. Explore Hope Bay with a vacation package

Hope Bay in Portland, Jamaica offers a serene and picturesque atmosphere for outdoor vacation seekers. Surrounded by lush green mountains and crystal-clear waters, visitors can enjoy a variety of activities such as hiking, bird watching, and exploring the pristine beaches. The local community is known for its warm hospitality, providing a genuine and authentic experience for travelers. Indulge in delicious Jamaican cuisine, immerse yourself in the vibrant reggae music scene, and relax in the laid-back island vibe. Hope Bay is the perfect destination for nature lovers looking to unwind and experience the true beauty of Jamaica.

  • Travelers tend to stay 3 days in Hope Bay

6. Experience Windsor Castle with a travel package

Windsor Castle in Portland, Jamaica offers a serene and tropical atmosphere for a beach vacation. With its crystal-clear turquoise waters, white sandy beaches, and lush green landscapes, it is the perfect destination for relaxation and rejuvenation. The local atmosphere exudes a laid-back and friendly vibe, with locals welcoming travelers with warm hospitality. Whether you're looking to laze on the beach, snorkel in the vibrant coral reefs, or indulge in delicious seafood, Windsor Castle offers a truly authentic Jamaican beach experience.

5. Find your perfect Boston Bay vacation

Boston Bay in Portland, Jamaica offers a vibrant and exciting atmosphere for outdoor vacation experiences. With a range of destination activities, including cruises, sailing, and water tours, visitors can immerse themselves in the beauty of the bay and its surrounding areas. Whether it's exploring the crystal-clear waters, enjoying a day or half-day cruise, or embarking on thrilling water adventures, Boston Bay provides endless opportunities for outdoor enthusiasts. With its stunning views and diverse range of activities, Boston Bay is the perfect destination for a memorable vacation in Jamaica.

  • The peak season is from January to March
  • The off-peak season is from September to November
  • Travelers tend to stay 1 day in Boston Bay

Find the Best Portland Vacation Packages

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

Ross Craig Long Bay Portland
Fully refundable
$122 nightly
$134 total
Sep 16 - Sep 17
Total with taxes and fees
8/10 Very Good! (223 reviews)
"First, I would like to say the property is beautiful and the view is breathtaking. It is the highlight of the entire property. I did not have any issues with the rooms. They were clean and comfortable. I will say, however, the air conditioning kept turning off. I’m not sure if it was on some kind ..."

Reviewed on Aug 13, 2026

Sea Cliff Resort
Jamaica Palace Hotel

Jamaica Palace Hotel

Williamsfield Port Antonio Portland
Fully refundableReserve now, pay when you stay
$138 nightly
$153 total
Aug 17 - Aug 18
Total with taxes and fees
8.2/10 Very Good! (347 reviews)
"It’s clean the staff is okay I don’t use anything bad to stay just not what I expected so it ac not the hotel but my expectations"

Reviewed on Aug 15, 2026

Jamaica Palace Hotel
Match Resort Hotel

Match Resort Hotel

Dolphin Bay Port Antonio
Fully refundableReserve now, pay when you stay
$94 nightly
$104 total
Sep 13 - Sep 14
Total with taxes and fees
8/10 Very Good! (237 reviews)
"Good afternoon, I was invited to a wedding in Portland and I wanted somewhere to stay so I went on Google and began to search and while searching what I saw was way over my budget. And then my friend send me match resort and when I check it out it was the perfect place. When I arrived there the customer ..."

Reviewed on Aug 7, 2026

Match Resort Hotel
See all 1,956 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.

Frequently asked questions

How much does a Portland vacation package cost?
Choose from any combination of car rentals, flights and hotels, and you can be vacationing in Portland from just $2,427. And the more you bundle, the more you save. Your dream vacation has never been so affordable.
How do I get a cheap travel package to Portland?
Imagine all the fun things you could do in Portland with a pile of extra cash in your pocket. Watch your savings stack up when you combine your flights, hotels and extras into a Portland vacation package. You have loads of choice when it comes to booking with Expedia too. In fact, you can select from over 550 air carriers and 1,000,000 hotel options around the world. Whether you're heading off with the whole family or adventuring alone, planning a getaway to Portland is better with a package.
How far in advance should I book my Portland vacation?
While prices fluctuate, we generally suggest booking your spot as soon as possible. Most international fares are available on Expedia up to 12 months in advance. If circumstances have left you booking last minute, you might still get lucky. Cheaper tickets to Portland occasionally appear in the weeks prior to departure.
What does an Expedia Portland travel package include?
With Expedia, you can select a combination of car rentals, flights and hotels to create your perfect Portland travel package. Once you've made your booking, you can add on fun stuff like day tours and activities. Don't forget, the more you bundle, the more deals you'll score!
What should I know before booking a Portland travel package?
Get set to save with an Expedia travel package. Combine your airfares, rental cars and hotels and enjoy great discounts. You're not limited to hotels, however. Book with us and choose from oceanfront condos, chalets in the middle of mountains and even houseboats and castles!
Can I choose my airline with a Portland Expedia vacation package?
Yes, you can. We have more than 550 airline partners across the globe, so opt for the carrier that suits your needs.
Does Expedia offer Book Now, Pay Later Portland vacation packages?
Your bank balance shouldn't prevent you from having an epic vacation, so Expedia has devised a plan to help. Thanks to our partnership with online lender Affirm, it's easy to book an unforgettable getaway that won't break the bank. Simply Book Now, Pay Later and take the financial strain out of planning for your journey.
If I'm not able to travel, can I cancel my Portland vacation package?
You sure can, and we're here to help. You may be able to cancel or amend your Portland vacation package at no cost if you booked in the last 24 hours. But you may be charged a fee by your airline, hotel or car rental company for older bookings. If your travel plans unexpectedly change, have a look at our Customer Service Portal for further information.

Stay near popular Portland attractions

Three boats docked at a calm, turquoise body of water surrounded by lush greenery.

Blue Lagoon

9.2/10 (229 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.
See properties
A woman walking on a sandy beach with turquoise water and lush green foliage.

Frenchman's Cove Beach

9.2/10 (164 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.
See properties
A turquoise coastal bay with clear waters, surrounded by lush green hills and a rocky coastline.

Boston Bay Beach

9.0/10 (132 reviews)
If a restful vacation is part of your travel plans, Boston Bay Beach might be the perfect place to seek out during your trip to Port Antonio. You can enjoy the restaurants while in the area.
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A large white colonial-style building with multiple towers and a staircase leading to the entrance, surrounded by lush greenery and a body of water.

Trident Castle

8.6/10 (77 reviews)
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.
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A beach with clear water, a sandy shore, and dense green foliage in the background.

Winnifred Beach

9.0/10 (117 reviews)
Discover a lovely vacation location, with white sands, crystal seas and friendly smiles, away from tourist hubs in Portland Parish.
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A beach with clear turquoise water, a large tree trunk in the sand, and a small island in the distance.

San San Beach

8.4/10 (47 reviews)
If a restful vacation is part of your travel plans, San San Beach might be the perfect place to seek out during your trip to Port Antonio. You can enjoy the restaurants while in the area.
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Portland Parish Church

8.2/10 (32 reviews)
Portland Parish Church is just one of the places to see in Titchfield Peninsula, so why not enjoy the other things to explore during your travels? Wander the waterfront and beaches in the area.
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Port Antonio Square

8.0/10 (99 reviews)
Learn about the local history of Titchfield Peninsula when you take a trip to Port Antonio Square. Wander the waterfront and beaches in the area.
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What to do in Portland

Kingston Blue Mountains Tour with Coffee Tasting

Kingston Blue Mountains Tour with Coffee Tasting

$90
per adult
100% of travellers recommend
Kingston Blue Mountains Tour with Coffee Tasting
Kingston Dub Club Sundays

Kingston Dub Club Sundays

$70
per adult
Kingston Dub Club Sundays
Walk Tours in Kingston.

Walk/Drive Tour of Downtown Kingston/Tivoli Gardens/Trench Town.

$60
per adult
100% of travellers recommend
Walk/Drive Tour of Downtown Kingston/Tivoli Gardens/Trench Town.
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.