Portland Vacations

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Find the Best Portland Vacation Packages

Portland Hotel Deals

The Aqua

The Aqua

Castletown Portland England
Fully refundableReserve now, pay when you stay
AED 529
AED 634 total
20 Sep - 21 Sep
includes taxes & fees
The Aqua
Heights Hotel

Heights Hotel

Yeates Road Portland England
AED 619
AED 743 total
6 Sep - 7 Sep
includes taxes & fees
8.4/10 Very Good! (718 reviews)
"Friendly staff, warm welcome, good food and incredible views"

Reviewed on 25 August 2026

Heights Hotel
Fairhaven Hotel

Fairhaven Hotel

Fairhaven Hotel, 37 Esplanade Weymouth England
Fully refundableReserve now, pay when you stay
AED 333
AED 400 total
27 Sep - 28 Sep
includes taxes & fees
8.4/10 Very Good! (863 reviews)
"Staff were great, room not as the pictures would suggest unless we ended up with the only one that hadn’t been renovated."

Reviewed on 24 August 2026

Fairhaven Hotel
See all 2,145 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 lively bars.
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A rocky coastline with waves crashing against the rocks.
Photo by Dan Weston

Portland Bill

9.0/10 (88 reviews)
Commune with nature and explore the great outdoors at Portland Bill during your travels in Portland. Stroll along the area's waterfront, or simply savor its lively bars.
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A rocky beach with waves crashing onto the shore and a cliff in the background.
Photo by Kye Carter

Church Ope Cove

8.4/10 (32 reviews)
Why not spend a carefree afternoon at Church Ope Cove during your travels in Portland? While you're here, you can savor the top-notch restaurants.
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Portland Harbour

9.0/10 (10 reviews)
Explore the waterfront in Portland with a trip to Portland Harbour. Stroll along the area's beautiful beaches, or simply savor its lively bars.
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Portland Castle

8.4/10 (7 reviews)
Portland Castle is just one of the places to see in Portland, so why not enjoy the other things to explore during your travels? Wander the area's beautiful beaches or simply enjoy one of its lively bars.
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Weymouth and Portland National Sailing Academy

9.2/10 (5 reviews)
Enjoy the collegiate vibe when you visit Weymouth and Portland National Sailing Academy, during your travels in Portland. Wander the area's beautiful beaches or simply enjoy one of its lively bars.
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The Olympic Rings Stone Sculpture

7.4/10 (6 reviews)
You can find out about the history of Portland with a visit to The Olympic Rings Stone Sculpture. While you're here, you can savor the top-notch restaurants.
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Verne High Angle Battery

8.6/10 (7 reviews)
You can learn about the history of Portland with a visit to Verne High Angle Battery. Stroll along the area's beautiful beaches, or simply savor its lively bars.
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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.

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