Portland Vacation Packages
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Your Portland Vacation
Prepare to experience Portland on your own terms with a custom Portland vacation package! Uncovering the treasures of this interesting city is made easier with a base in a neighborhood such as Winfrith Newburgh, which is great for nature, among lots of other things. A trip to Portland is a terrific opportunity to see the sights. Be sure to look around well-known attractions like Weymouth Beach, Chesil Beach and Weymouth Harbour. Stop daydreaming and start adventuring. Check out the wide range of options on Expedia today and finally put your Portland vacation plans into action!
Top Portland Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza London Victoria
London City Centre
CA $1,842
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to London (LHR)
9/10 Wonderful! (3,997 reviews)
The breakfast is a typical English breakfast with good balance of various fruits cereal bread and pastry.the room is clean but not friendly for guests who are not couples. One bed in the room is not the best when traveling without a spouse.
Reviewed on Aug 15, 2026
Park Lane Apartments Mayfair Collection
London City Centre
CA $2,260
per person
Oct 24 - Oct 30
found 16 hours ago
Roundtrip flight included
Toronto (YTO) to London (LHR)
6/10 (1 review)
Couldn’t get much hot water in the shower. Has an induction cooktop but no induction compatible cookware. Otherwise okay
Reviewed on Oct 16, 2025
Portland Beach Vacation
Get set to live out those beachy daydreams on your Portland vacation. Embark on a romantic stroll, soak up the spectacular coastal views and pick up pretty seashells on your trip to Portland. Only 0.97 kilometres from the centre of town, Church Ope Cove is the place to be for many travellers. Browse our Portland vacation packages and watch your travel budget stretch further!
Things You Should Know About Portland
- Check into one of our Portland beach hotels and experience this destination at its very best. Wander along the shoreline and marvel in the gorgeous sunsets right on your front door.
- Our cottages, like Heights Hotel and The Aqua, are popular with visitors of all types. Check out the amenities and get ready for your vacation in Portland!
- Some 12,700 people live in Portland. If you want recommendations about what to see and do around these parts, why not ask a couple of the friendly locals? Our Portland things to do page is also a handy source of information.
- Don't leave town without checking out Portland Harbour, Portland Bill and Weymouth and Portland National Sailing Academy. With the money you save through our Portland vacation deals, you can see more top sights like these.
Ready to book your vacation to Portland?
Portland Hotel Deals
The Aqua
Castletown Portland England
Fully refundableReserve now, pay when you stay
CA $199
CA $239 total
Aug 16 - Aug 17
includes taxes & fees
Heights Hotel
Yeates Road Portland England
CA $218
CA $261 total
Aug 16 - Aug 17
includes taxes & fees
Fairhaven Hotel
Fairhaven Hotel, 37 Esplanade Weymouth England
CA $153
CA $184 total
Aug 16 - Aug 17
includes taxes & fees
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
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.
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.
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.
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.
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.
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.
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.
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.
What to do in Portland
Portland Jurassic Coast Guided Mini Bus Excursions
CA $218
per adult
Guided E-Bike Tour of the Isle of Portland, Dorset
CA $242
per adult
Nordic Walking Tour of Weymouth’s Iconic Landmarks
CA $19
per adult
Frequently asked questions
How much does a Portland vacation package cost?
You'll find cheap prices from CA $1,842 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 many days is enough for Portland?
With a well-planned schedule, you can easily hit the main Portland attractions in a few days. But if you want to discover lesser-known spots or go on day tours, think about booking your Portland vacation for longer.
Is it worth booking a vacation package to Portland?
Portland has everything you need for the perfect getaway — walking trails, camping and watersports are just the start. Whether you want to check out sights like Weymouth and Portland National Sailing Academy and Portland Castle, or take the road less travelled, you'll have plenty to experience on your Portland vacation.
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?
- Choose your travel dates: What you want to do in Portland and your preferred season will help you decide when to go.
- 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.
- 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.
- Combine your airfare and accommodations: After you've settled on your travel dates and duration, book the ideal Portland vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
