Portland Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Portland vacation deals
- Park Lane Apartments Mayfair Collection
Sept 22 - Sept 26Park Lane Apartments Mayfair Collection + Flight
London City Centre3 nights4.0 star property6.0/10 - (1 review)"Couldn’t get much hot water in the shower. Has an induction cooktop but no induction compatible cookware. Otherwise okay "Reviewed October 16, 2025Roundtrip • Toronto (YYZ) - London (LHR)YYZ - LGW • 1 stop LGW - YYZ • NonstopCA $2,428CA $1,408found 22 hours agoper traveller - Hotel Riu Plaza London The Westminster
Sept 15 - Sept 21Hotel Riu Plaza London The Westminster + Flight
London City Centre5 nights4.0 star property9.0/10 - Wonderful (1,907 reviews)Roundtrip • Montreal (YMQ) - London (LHR)YUL - LGW • Nonstop LGW - YUL • NonstopCA $3,080CA $1,985found 2 days agoper traveller - Hotel Riu Plaza London Victoria
Sept 15 - Sept 21Hotel Riu Plaza London Victoria + Flight
London City Centre5 nights4.0 star property9.0/10 - Wonderful (4,006 reviews)"Great hotel conveniently located near Victoria Station and many mayor attractions. Delicious buffet breakfast."Reviewed August 6, 2026Roundtrip • Montreal (YMQ) - London (LHR)YUL - LGW • Nonstop LGW - YUL • NonstopCA $3,159CA $2,044found 2 days agoper traveller - Miiro Templeton Garden
Sept 22 - Sept 27Miiro Templeton Garden + Flight
London City Centre4 nights4.0 star property9.6/10 - Exceptional (711 reviews)Roundtrip • Montreal (YMQ) - London (LHR)YUL - LHR • Nonstop LHR - YUL • NonstopCA $2,292CA $1,617found 1 day agoper traveller - Cleveland Residences Bloomsbury
Sept 13 - Sept 19Cleveland Residences Bloomsbury + Flight
London City Centre5 nights4.0 star property9.4/10 - Exceptional (152 reviews)"location, clean Good air conditioning and excellent overall"Reviewed August 2, 2026Roundtrip • Toronto (YTO) - London (LHR)YYZ - LHR • Nonstop LHR - YYZ • 1 stopCA $2,783CA $1,972found 10 hours agoper traveller
Discover the most popular places to visit in Portland
What to do in Portland
Pauls Walking Tours - Sundays at 10:00am
Guided E-Bike Tour of the Isle of Portland, Dorset
Portland Jurassic Coast Guided Mini Bus Excursions
Portland Hotel Deals
"Fantastically located with amazing views! The room was really clean, and the staff were incredibly friendly and welcoming. To top it off, they offered a really good breakfast spread with plenty of fresh food. Highly recommend staying here!"
"Very nice cottage in quiet location with room opening onto garden with lots of bird song. Snug with TV is very comfortable. Parking spot just outside cottage. Well appointed kitchen. Location is good for access to portland, but going elsewhere requires travelling through Weymouth which can be slow."
"Bed was not comfy as we had backache after second night , we turned mattress round was ok that night but the after that . The step into the shower was too high and we had to buy a step to get in it and also the floor surface was very slippy . Was ck an and tidy and overall not a bad place to stay and would recommend and return at some point "
Frequently Asked Questions
How much does a Portland vacation package cost?
You'll find cheap prices from CA $1,408 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.