Portland Vacations

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    Save up to AEDĀ 5,000 when you book a flight and hotel together*

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Find the Best Portland Vacation Packages

Portland Hotel Deals

Heights Hotel

Heights Hotel

3 out of 5
Yeates Road Portland England
The price is AEDĀ 610 per night from Jul 26 to Jul 27
AEDĀ 610
AEDĀ 732 total
26 Jul - 27 Jul
includes taxes & fees
8.4/10 Very Good! (710 reviews)
"We've rarely felt less welcome. Desk staff were surly and seemed to resent our intrusion into their day by, you know, checking in. The breakfast staff next morning were also surly, though the woman serving in the CafƩ in the evening was cheery and pleasant. The advertised EV charging is a myth. There's ..."

Reviewed on 9 July 2026

Heights Hotel
The Aqua

The Aqua

3 out of 5
Castletown Portland England
Fully refundableReserve now, pay when you stay
The price is AEDĀ 521 per night from Jul 19 to Jul 20
AEDĀ 521
AEDĀ 625 total
19 Jul - 20 Jul
includes taxes & fees
The Aqua
Fairhaven Hotel

Fairhaven Hotel

3 out of 5
Fairhaven Hotel, 37 Esplanade Weymouth England
The price is AEDĀ 410 per night from Jul 19 to Jul 20
AEDĀ 410
AEDĀ 492 total
19 Jul - 20 Jul
includes taxes & fees
8.4/10 Very Good! (827 reviews)
"Always enjoy our stay, we have stayed in the Fairhaven 3 years on the trot and the staff are all very helpful and nice"

Reviewed on 12 July 2026

Fairhaven Hotel
See all 1,993 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.

Stay near popular Portland attractions

A coastal landscape with a prominent red and white lighthouse, rocky cliffs, and a white building with a green roof.

Portland Bill Lighthouse

9.2/10 (189 reviews)
Find out about the history of Portland when you spend time at Portland Bill Lighthouse. Wander the area's beautiful beaches or simply enjoy one of its top-notch restaurants.
See properties

Frequently asked questions

How much does a Portland vacation package cost?
You'll find cheap prices on Expedia for your Portland break. However, factors like the hotel choice, length of stay and season will determine how much your vacation to Portland costs.
What are the cheapest months to go to Portland?
Travel in the shoulder or low season and you're likely to score cheap Portland vacation packages. Bear in mind that school vacation periods and major events and festivals can have an impact on prices, so do a little research before booking.
How to find the best Portland package deals?
Begin your search for a Portland package deal by entering your travel dates and destination under our "Packages" tab. Then apply a few filters, like "Property type" and "Popular locations," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the perfect Portland package deal straight away, simply change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Portland getaway off to a flying start.
Is it cheaper to book a Portland vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll usually score a better deal than booking each component separately. And you'll still have the flexibility to create a tailored Portland vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Portland?
Land fantastic discounts by reserving your flights early with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for an impromptu Portland trip.
How to plan a trip to Portland?

  1. Choose your travel dates: What you want to do in Portland and your preferred season will help you decide when to go.
  2. Plan your budget wisely: On top of the cost of your accommodations, you'll need to consider other expenses. These include food, flights and transportation. Also, set aside some extra funds for unexpected costs that may come up during your trip to Portland.
  3. Decide how long to go away for: Now that you're more familiar with Portland, you can figure out the perfect length of your break. Pull together a rough itinerary and allocate enough time to get through everything on your must-do list.
  4. Combine your airfare and accommodations: After you've settled on your travel dates and duration, book the ideal Portland vacation package for you.