Portland Holidays

Book a Hotel + Flight or Car together to unlock savings

Top destinations in Portland

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

Reach

Reach
A sunset over a calm sea with a visible horizon line.

Hope Bay

Hope Bay

Top hotels in Portland

Sea Cliff Resort

Sea Cliff Resort

Ross Craig Long Bay Portland
Fully refundable
3.086.561 ₫
3.884.303 ₫ total
27 Sept - 28 Sept
includes taxes & fees
8/10 Very good! (227 reviews)
"The stay was amazing. The views from the room, the sound of waves crashing at night was so refreshing. The quiet of the property really allows for reset, relaxation and reconnection that a hotel can’t provide. The staff were helpful and respectful at all times, zero complaints. Nitpicking - I wished ..."

Reviewed on 22 Aug 2026

Sea Cliff Resort
Jamaica Palace Hotel

Jamaica Palace Hotel

Williamsfield Port Antonio Portland
Fully refundableReserve now, pay when you stay
3.594.245 ₫
4.005.873 ₫ total
10 Sept - 11 Sept
includes taxes & fees
8.2/10 Very good! (351 reviews)
"After check-in we were taken up several stairs to the assigned room which was at the back of the hotel. We are OAP, 80 plus and 75! The room was like a sauna as no air conditioning had been turned on. The toilet could not be flushed as the toilet tank was empty! The TV had a 'million' channels, but ..."

Reviewed on 25 Aug 2026

Jamaica Palace Hotel
Match Resort Hotel

Match Resort Hotel

Dolphin Bay Port Antonio
Fully refundableReserve now, pay when you stay
2.871.220 ₫
3.184.445 ₫ total
10 Sept - 11 Sept
includes taxes & fees
8/10 Very good! (243 reviews)
"Great place, close to the attractions I wanted to do in Portland."

Reviewed on 26 Aug 2026

Match Resort Hotel
See all 1,971 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 holiday package cost?
We make it easy to travel somewhere new, with Portland packages starting from as little as . 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 holiday 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 1null000null000 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 favourites with many travellers.
How far in advance should I book my Portland holiday?
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 holiday is only clicks away.
Can I choose my airline with a Portland Expedia holiday 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 holiday 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 holiday 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.

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)
Why not spend a care-free afternoon at Blue Lagoon during your travels in Port Antonio? You can enjoy the restaurants while in the area.
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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 care-free afternoon at Frenchman's Cove Beach during your travels in Port Antonio? You can enjoy the restaurants while in the area.
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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 holiday is part of your travel plans, Boston Bay Beach might be the perfect place to visit 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)
If a restful holiday is part of your travel plans, Winnifred Beach might be the perfect place to visit during your trip to Port Antonio. You can enjoy the restaurants while in the area.
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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 holiday is part of your travel plans, San San Beach might be the perfect place to visit 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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